[ CAS No. 1271-48-3 ] {[proInfo.proName]}

Name: 1271-48-3|1,1'-Ferrocenedicarboxaldehyde|98%
Brand: Ambeed
SKU: A234870
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2D 3D

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Quality Control of [ 1271-48-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1271-48-3 ]

SDS Specification

Alternatived Products of [ 1271-48-3 ]

Product Details of [ 1271-48-3 ]

CAS No. :	1271-48-3	MDL No. :	MFCD02093629
Formula :	C₁₂H₁₀FeO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	242.05	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 1271-48-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.17
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.07
TPSA :	34.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.47
Log Po/w (WLOGP) :	2.04
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	0.74
Consensus Log Po/w :	1.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.0
Solubility :	2.4 mg/ml ; 0.00994 mol/l
Class :	Soluble
Log S (Ali) :	-1.79
Solubility :	3.89 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.86
Solubility :	33.6 mg/ml ; 0.139 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.28

Safety of [ 1271-48-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1271-48-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1271-48-3 ]
Downstream synthetic route of [ 1271-48-3 ]

[ 1271-48-3 ] Synthesis Path-Upstream 1~10

1
[ 102-54-5 ]
[ 68-12-2 ]
[ 1271-48-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 18 h; Inert atmosphere; Schlenk technique Stage #2: at 0 - 20℃; for 2 h; Inert atmosphere; Schlenk technique	The literature procedure [26b] for the preparation of 9 was modified as follows: To a room temperature solution of ferrocene (10 g, 0.054 mol) in dry hexane (200 mL) was added n-butyl lithium solution (67 mL, 1.6 M in hexanes, 0.10 mol) dropwise followed by addition of tetramethylene ethylenediamine (TMEDA) (14.7 g, 0.25 mol). No difference in yields was detected if the additions were made at -50 °C. After stirring the reaction mixture for 18 h at room temperature, dilithiated ferrocene has precipitated as an orange solid. The suspension was cooled to 0 °C, DMF (7.85 g, 0.11 mol, 8.3 mL) was added, and the stirring continued for further 2 h at room temperature.
56%	Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; Stage #2: at -78℃;	To a solution of ferrocene (6 g, 32 mmol) in hexane (100 mL) was addedtetramethylethylenediamine (TMEDA) (10.6 mL, 71 mmol) and n-butyllithium (46.4 mL,74 mmol) and the mixture stirred overnight at room temperature. The reaction was cooledto -78° C and a solution of DMF (5.5 mL, 71 mmol) in Et2O (100 mL) was added. Themixture was allowed to warm to room temperature and stirred for 4 h. The reaction wasquenched with brine (100 mL) and extracted with CH2Cl2( 100 mL). The organic phasewas dried over MgSO4 and the solvent removed in vacuo. The product was purified bycolumn chromatography on silica gel using hexane/ether followed by hexane/ether/ethylacetate. Yield 4.3 g, 56 percent.
48%	Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 20 h; Stage #2: at -78℃; for 2 h;	1 g (5.37 mmol) of ferrocene, dissolved in 12 ml of anhydrous ethyl ether, was treated with 7.2 ml (11.56 mmol) of n-BuLi (1.6M solution in hexane) and by addition of 1.74 ml (11.56 mmol) of N,N,N',N'-tetramethylethylenediamine. The reaction was left under argon and with stirring at ambient temperature for 20 hours. 1.33 ml (17.20 mmol) of DMF were added at -78° C. After stirring at -78° C. for 2 hours, the reaction mixture was hydrolyzed (15 ml of water). The aqueous phase was extracted with dichloromethane (3.x.15 ml). The resulting organic phase was dried over MgSO4 and was then concentrated. The residue was purified on silica gel with a pentane/ethyl acetate (50:50) mixture. [0152] 0.62 g (2.56 mmol, 48percent) of compound 1 was obtained in the form of a brown paste. [0153] 1H NMR (CDCl3): 4.62 (d, J=9 Hz, 4H, H2H3-H2'H3'), 4.83 (d, J=8.7 Hz, 4H, H1H4-H1'H4'), 9.89 (m, 2H, 2CHO) [0154] 13C NMR (CDCl3): 70.9 (C2H5), 74.20 (C3C4), 80.4 (C1), 192.9 (C6). [0155] MS: 185 (60), 243 (M+, 95).

3.363 g

Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 17 h;
Stage #2: at 20℃; for 0.5 h; Cooling with ice

To a dry Schlenk flask was added 3.100 g (16.6 mmol) of vacuum dried ferrocene and 12.0 mL of n-hexane,Stirred to a suspension; then 25.0 mL of n-butyllithium (1.6 M, 40.0 mmo1)Then, 6.0 mL of tetramethylethylenediamine (40.0 mmo1) was added dropwise over a period of about 60 min,The reaction was continued for 16 h at room temperature; the resulting mixture was filtered,The resulting orange-red powder was washed three times with 15.0 mL of n-hexane, i.e., about 15.0 mmo1 of 1,1'-bis-lithium ferrocene,To this was added 35.0 mL of n-hexane,Stirred to a suspension; another 12 mL of anhydrous ether was added 2.8 mL (36.0 mmo1) of dimethylformamide,The solution was added dropwise to the suspension (about 30 min) under ice-water bath cooling. After the dropwise addition, the ice-water bath was removed and allowed to warm to room temperature and stirred for about 30 minutes.Add 50.0 mL (4.0 M, 0.2 mol) of hydrochloric acid,Continue to react for 15 min after static, set stratification,The aqueous layer was extracted three times with 15.0 mL of dichloromethane,A dark red solid ferrocene dialdehyde was obtained 3.363 g.

Reference： [1] Journal of Organometallic Chemistry, 1993, vol. 463, # 1-2, p. 163 - 168
[2] Journal of Organometallic Chemistry, 2013, vol. 740, p. 61 - 69
[3] Journal of Organometallic Chemistry, 2009, vol. 694, # 13, p. 2020 - 2028
[4] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 10, p. 1551 - 1557
[5] European Journal of Inorganic Chemistry, 2014, vol. 2014, # 36, p. 6212 - 6219
[6] Journal of Organometallic Chemistry, 1991, vol. 412, # 3, p. 381 - 382
[7] Journal of Organometallic Chemistry, 2017, vol. 846, p. 251 - 262
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11445 - 11450[9] Angew. Chem., 2018, vol. 130, p. 11616 - 11621,6
[10] Patent: US2005/38234, 2005, A1, . Location in patent: Page/Page column 11
[11] Chemical Physics Letters, 2015, vol. 624, p. 47 - 52
[12] Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51
[13] Tetrahedron Asymmetry, 2015, vol. 26, # 23, p. 1307 - 1313
[14] Patent: CN105777817, 2016, A, . Location in patent: Paragraph 0105
[15] Patent: CN103665053, 2016, B, . Location in patent: Paragraph 0040-0044

2
[ 102-54-5 ]
[ 68-12-2 ]
[ 12093-10-6 ]
[ 1271-48-3 ]

Reference： [1] Journal of Organometallic Chemistry, 1993, vol. 463, # 1-2, p. 163 - 168
[2] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
[3] Organometallics, 2013, vol. 32, # 20, p. 5784 - 5797
[4] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
[5] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224
[6] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224

3
[ 2591-86-8 ]
[ 102-54-5 ]
[ 1271-48-3 ]

Reference： [1] Inorganica Chimica Acta, 2009, vol. 362, # 6, p. 2068 - 2070

4
[ 102-54-5 ]
[ 1271-48-3 ]

Reference： [1] New Journal of Chemistry, 2004, vol. 28, # 1, p. 134 - 144

5
[ 12093-10-6 ]
[ 68-12-2 ]
[ 1271-48-3 ]

Reference： [1] Chemical Communications, 1996, # 4, p. 527 - 528

6
[ 1293-65-8 ]
[ 68-12-2 ]
[ 1271-48-3 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2544 - 2547

7
[ 68-12-2 ]
[ 1271-48-3 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1992, # 8, p. 602 - 604

8
[ 1461-22-9 ]
[ 1271-48-3 ]

Reference： [1] Journal of Organometallic Chemistry, 1998, vol. 565, # 1-2, p. 115 - 124

9
[ 102-54-5 ]
[ 93-61-8 ]
[ 12093-10-6 ]
[ 1271-48-3 ]

Reference： [1] Chemistry and Industry (London, United Kingdom), [2] Chemistry and Industry (London, United Kingdom), 1957, p. 72 - 72
[3] , Gmelin Handbook: Fe: Org.Verb.A1, 2.5.7.7, page 161 - 162,

10
[ 1287-13-4 ]
[ 102-54-5 ]
[ 68-12-2 ]
[ 12093-10-6 ]
[ 1271-48-3 ]
[ 66507-25-3 ]

Reference： [1] Journal of Organometallic Chemistry, 1996, vol. 512, # 1-2, p. 219 - 224

[ 1271-48-3 ] Synthesis Path-Downstream 1~88

1
[ 1271-48-3 ]
triethyl phosphonoacetic acid [ No CAS ]
[ 168283-32-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium; In ethanol; at 0 - 20℃;	0.094 g (4.08 mmol) of sodium and 25 ml of absolute ethanol were introduced into a 50 ml three-necked round-bottomed flask equipped with a reflux condenser and under argon. After the sodium had been completely consumed, the solution was cooled to 0 C. and then 0.809 ml (4.08 mmol) of ethyl diethylphosphonoacetate and 0.470 g (1.94 mmol) of ferrocene-1,1'-carboxaldehyde 1, dissolved beforehand in 10 ml of absolute ethanol, were added. [0158] After returning to ambient temperature and evaporating, the residue was purified on silica gel with a cyclohexane/ethyl acetate (95:5) mixture. [0159] 0.560 g (1.46 mmol, 75%) of compound 2 was obtained in the form of red crystals. [0160] 1H NMR (CDCl3): 1.26 (t, J=7.15 and J=7.12 Hz, 6H, H9H10H11-H9'H10'H11'), 4.15 (q, J=7.14 and J=7.11 Hz, 4H, H7H8-H7'H8'), 4.31 (m, 4H, H2H3-H2'H3'), 4.38 (m, 4H, H1H4-H1'H4'), 5.91 (d, J=15.80 Hz, 2H, H6-H6'), 7.33 (d, J=15.79 Hz, 2H, H5-H5'). [0161] 13C NMR (CDCl3): 14.2 (C10), 60.1 (C9), 69.7 (C2H5), 72.2 (C3C4), 79.9 (C1), 116.2 (C7), 143.7 (C6), 166.9 (CB) [0162] MS: 382 (M?+, 85).

Reference： [1]Patent: US2005/38234,2005,A1 .Location in patent: Page column 11-12

2
[ 102-54-5 ]
[ 68-12-2 ]
[ 12093-10-6 ]
[ 1271-48-3 ]

Reference： [1]Journal of Organometallic Chemistry,1993,vol. 463,p. 163 - 168
[2]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224
[3]Organometallics,2013,vol. 32,p. 5784 - 5797
[4]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224
[5]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224
[6]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224

3
zinc(II) tetrahydroborate [ No CAS ]
[ 1271-48-3 ]
[ 1291-47-0 ]

Reference： [1]Organometallics,1996,vol. 15,p. 1065 - 1066

4
[ 1271-48-3 ]
[ 13292-87-0 ]
[ 1291-47-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane all manipulations under Ar atm.; to soln. of ferrocenyl compd. added equiv. amt. of soln. of B compd. in CH2Cl2, stirred at room temp. for 3 h; quenched with aq. NH4Cl, org. layer sepd., aq. layer extd. with CH2Cl2,combined org. extracts dried over anhyd. MgSO4, solvent removed in vac., chromy., elem. anal.;

Reference： [1]Kim, Dong-Hoo; Ryu, Eun-Sook; Cho, Chan Sik; Shim, Sang Chul; Kim, Hong-Seok; Kim, Tae-Jeong [Organometallics, 2000, vol. 19, p. 5784 - 5786][Organometallics]

5
[ 1271-48-3 ]
borane tetrahydrofuran [ No CAS ]
[ 1291-47-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran 6 equiv of borane, THF, reflux, 15 min;

Reference： [1]Routaboul, Lucie; Chiffre, Jérôme; Balavoine, Gilbert G.A.; Daran, Jean-Claude; Manoury, Eric [Journal of Organometallic Chemistry, 2001, vol. 637-639, p. 364 - 371]

6
[ 1271-48-3 ]
[ 1291-47-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium tetrahydroborate In dichloromethane; trifluoroacetic acid B-compd. addn. to stirred Fe-complex soln., mixt. stirring at 25°C for 1 h, diln. (CH2Cl2), quenching in aq. NaOH, org. layer sepn., drying over Na2SO4, solvent removal; residue flash chromy. (SiO2, Et2O/hexanes 1:9);

Reference： [1]Bhattacharyya, Sukanta [Journal of the Chemical Society. Perkin transactions I, 1996, # 12, p. 1381 - 1383]

7
[ 1271-48-3 ]
[ 25895-60-7 ]
[ 1291-47-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate In tetrahydrofuran; ammonium hydroxide; dichloromethane addn. of BF3*OEt2 to a stirred soln. of the 1,1'-diacylferrocene in THF at 25°C, addn. of NaBH3CN over 10 min, stirring (1 h), diln. withCH2Cl2, addn. of aq. NH3 to pH 10; layer sepn., drying (Na2SO4), concn., flash chromy. (SiO2; hexanes/Et2O);

Reference： [1]Bhattacharyya, Sukanta [Journal of the Chemical Society, Dalton Transactions, 1996, p. 4617 - 4620]

8
[ 102-54-5 ]
[ 68-12-2 ]
[ 1271-48-3 ]

Yield	Reaction Conditions	Operation in experiment
85%		The literature procedure [26b] for the preparation of 9 was modified as follows: To a room temperature solution of ferrocene (10 g, 0.054 mol) in dry hexane (200 mL) was added n-butyl lithium solution (67 mL, 1.6 M in hexanes, 0.10 mol) dropwise followed by addition of tetramethylene ethylenediamine (TMEDA) (14.7 g, 0.25 mol). No difference in yields was detected if the additions were made at -50 C. After stirring the reaction mixture for 18 h at room temperature, dilithiated ferrocene has precipitated as an orange solid. The suspension was cooled to 0 C, DMF (7.85 g, 0.11 mol, 8.3 mL) was added, and the stirring continued for further 2 h at room temperature.
56%		To a solution of ferrocene (6 g, 32 mmol) in hexane (100 mL) was addedtetramethylethylenediamine (TMEDA) (10.6 mL, 71 mmol) and n-butyllithium (46.4 mL,74 mmol) and the mixture stirred overnight at room temperature. The reaction was cooledto -78 C and a solution of DMF (5.5 mL, 71 mmol) in Et2O (100 mL) was added. Themixture was allowed to warm to room temperature and stirred for 4 h. The reaction wasquenched with brine (100 mL) and extracted with CH2Cl2( 100 mL). The organic phasewas dried over MgSO4 and the solvent removed in vacuo. The product was purified bycolumn chromatography on silica gel using hexane/ether followed by hexane/ether/ethylacetate. Yield 4.3 g, 56 %.
48%		1 g (5.37 mmol) of ferrocene, dissolved in 12 ml of anhydrous ethyl ether, was treated with 7.2 ml (11.56 mmol) of n-BuLi (1.6M solution in hexane) and by addition of 1.74 ml (11.56 mmol) of N,N,N',N'-tetramethylethylenediamine. The reaction was left under argon and with stirring at ambient temperature for 20 hours. 1.33 ml (17.20 mmol) of DMF were added at -78 C. After stirring at -78 C. for 2 hours, the reaction mixture was hydrolyzed (15 ml of water). The aqueous phase was extracted with dichloromethane (3×15 ml). The resulting organic phase was dried over MgSO4 and was then concentrated. The residue was purified on silica gel with a pentane/ethyl acetate (50:50) mixture. [0152] 0.62 g (2.56 mmol, 48%) of compound 1 was obtained in the form of a brown paste. [0153] 1H NMR (CDCl3): 4.62 (d, J=9 Hz, 4H, H2H3-H2'H3'), 4.83 (d, J=8.7 Hz, 4H, H1H4-H1'H4'), 9.89 (m, 2H, 2CHO) [0154] 13C NMR (CDCl3): 70.9 (C2H5), 74.20 (C3C4), 80.4 (C1), 192.9 (C6). [0155] MS: 185 (60), 243 (M+, 95).

3.363 g

Reference： [1]Journal of Organometallic Chemistry,1993,vol. 463,p. 163 - 168
[2]Journal of Organometallic Chemistry,2013,vol. 740,p. 61 - 69
[3]Journal of Organometallic Chemistry,2009,vol. 694,p. 2020 - 2028
[4]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 1551 - 1557
[5]European Journal of Inorganic Chemistry,2014,vol. 2014,p. 6212 - 6219
[6]Dalton Transactions,2019,vol. 48,p. 17147 - 17152
[7]Journal of Organometallic Chemistry,1991,vol. 412,p. 381 - 382
[8]Journal of Organometallic Chemistry,2017,vol. 846,p. 251 - 262
[9]Angewandte Chemie - International Edition,2018,vol. 57,p. 11445 - 11450
Angew. Chem.,2018,vol. 130,p. 11616 - 11621,6
[10]Patent: US2005/38234,2005,A1 .Location in patent: Page/Page column 11
[11]Chemical Physics Letters,2015,vol. 624,p. 47 - 52
[12]Inorganica Chimica Acta,2015,vol. 438,p. 42 - 51
[13]Tetrahedron Asymmetry,2015,vol. 26,p. 1307 - 1313
[14]Patent: CN105777817,2016,A .Location in patent: Paragraph 0105
[15]Patent: CN103665053,2016,B .Location in patent: Paragraph 0040-0044

9
[ 1271-48-3 ]
(η(5)-MeC5H4)(CO)2Mn=C(OEt)CH3 [ No CAS ]
(C₆H₇)(CO)2Mn(CO(C₂H₅)CHCH((C₅H₄)Fe(C₆H₅O))) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,1999,p. 739 - 742

10
[ 1271-48-3 ]
[ 133186-66-0 ]
[ 154988-02-0 ]

Reference： [1]Organometallics,1994,vol. 13,p. 1224 - 1234

11
[ 62217-21-4 ]
[ 1271-48-3 ]
[ 154987-99-2 ]

Reference： [1]Organometallics,1994,vol. 13,p. 1224 - 1234

12
[ 1271-48-3 ]
1,1'-diacetylruthenocene [ No CAS ]
[3.3](1,1')ferrocenoruthenocenophane-2,14-diene-1,16-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With ethanol; sodium In ethanol mixt. of Ru and Fe complexes and Na in ethanol stirred at 60°C for 6 h under N2; product filtered off, washed with water, ethanol, and ether, dried; elem. anal.;

Reference： [1]Kamiyama, Shin-ichi; Kasahara, Akira; Izumi, Taeko; Shimizu, Iwao; Watabe, Hiroyuki [Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 7, p. 2079 - 2082]

13
[(5-bromothiophen-2-yl)methyl]triphenylphosphonium bromide [ No CAS ]
[ 1271-48-3 ]
1,1'-bis[2-(5-bromo-2-thienyl)ethenyl]ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With Na In methanol N2-atmosphere; refluxing (overnight); H2O addn., extg. (CH2Cl2), drying (MgSO4), evapn., chromy. (SiO2, CH2Cl2/ hexane = 1 : 4), toluene addn., refluxing (2 h, I2), crystn. (hexane) ; elem. anal.;

Reference： [1]Thomas, K. R. Justin; Lin, Jiann T.; Lin, Kuan-Jiuh [Organometallics, 1999, vol. 18, # 25, p. 5285 - 5291]

14
[ 108-89-4 ]
[ 1271-48-3 ]
[ 222165-10-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With lithium diisopropylamide In tetrahydrofuran stirring (room temp., 30 min), ferrocene addn., stirring (room temp., 4 h); H2O and CH2Cl2 addn., evapn., pyridine and POCl3 addn., stirring (room temp., 1.5 h), evapn., H2O addn., 4 M NaOH addn., filtering, chromy. (SiO2, Et2O / MeOH = 1 : 1); elem. anal.;

Reference： [1]Lee, In Su; Chung, Young Keun; Mun, Junho; Yoon, Choon Sup [Organometallics, 1999, vol. 18, # 24, p. 5080 - 5085]

15
[ 16940-66-2 ]
[ 1271-48-3 ]
[ 100-46-9 ]
[ 402751-14-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	In not given
70%	In acetonitrile condensation of iron complex with amine in acetonitrile at room temp., reaction with NaBH4 in methanol;
70%	In acetonitrile under N2; Fe-contg. compd. was reacted with amine (2 equiv.) in MeCN at room temp. followed by redn. with NaBH4 in MeOH;

Reference： [1]Santacruz-Juarez, Ericka; Cruz-Huerta, Jorge; Hernandez-Ahuactzi, Iran Fernando; Reyes-Martinez, Reyna; Tlahuext, Hugo; Morales-Rojas, Hugo; Hoepfl, Herbert [Inorganic Chemistry, 2008, vol. 47, # 21, p. 9804 - 9812]
[2]Lai, Siu-Wai; Drew, Michael G.B.; Beer, Paul D. [Journal of Organometallic Chemistry, 2001, vol. 637-639, p. 89 - 93]
[3]Wong, Wallace W. H.; Curiel, David; Lai, Siu-Wai; Drew, Michael G. B.; Beer, Paul D. [Dalton Transactions, 2005, # 4, p. 774 - 781]

16
[ 1271-48-3 ]
[ 42890-76-6 ]
[ 149-73-5 ]
bis-1,1'-[(2S,4S)-(hydroxymethyl)-2-dioxane-1,3]-ferrocene [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1998,vol. 565,p. 115 - 124

17
[ 4784-77-4 ]
[ 1271-48-3 ]
[ 592531-41-4 ]

Reference： [1]Journal of Organometallic Chemistry,2003,vol. 675,p. 105 - 112

18
[ 1271-48-3 ]
[ 504-63-2 ]
[ 656236-44-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With p-toluenesulfonic acid In benzene under N2 or Ar; 1,3-propanediol (406 mmol) and acid (6.6 mmol) added to soln. of Fe compd. (41 mmol) in benzene, mixt. refluxed for 24 h in the darkness; chromy. (SiO2, hexane/10% Et3N); elem. anal.;
63%	With p-toluenesulfonic acid monohydrate In toluene ligand, molecular sieves, p-MeC6H4SO3H*H2O were added to soln. of Fe-complex in toluene, stirred for 24 h at 60°C under Ar; cooled, K2CO3 was added, filtered, column chromy. with hexane:ethyl acetate; elem. anal.;

Reference： [1]Connell, Arthur; Holliman, Peter J.; Butler, Ian R.; Male, Louise; Coles, Simon J.; Horton, Peter N.; Hursthouse, Michael B.; Clegg, William; Russo, Luca [Journal of Organometallic Chemistry, 2009, vol. 694, # 13, p. 2020 - 2028]
[2]Hartinger, Christian G.; Nazarov, Alexey A.; Chevchenko, Vladimir; Arion, Vladimir B.; Galanski, Markus; Keppler, Bernhard K. [Dalton Transactions, 2003, # 15, p. 3098 - 3102]

19
[ 1271-48-3 ]
[ 24621-61-2 ]
1,1'-bis[(R)-(-)-4-methyl-1,3-dioxane-2-yl]ferrocene [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 3098 - 3102

20
[ 1271-48-3 ]
[ 37868-93-2 ]
[ 632367-09-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With CoCl₂ In toluene under N2 atm. mixt. 1,1'-carbonyldipyrazole, 1,1'-ferrocenedicarbaldehyde, and CoCl2 in toluene was heated at reflux for 5 h; react. mixt. was cooled to room temp., water was added and stirred for 30 min, aq. layer was extd. with CH2Cl2, org. fractions were dried over MgSO4, filtered and evapd. in vacuo, residue was chromed. on silica; elem. anal.;

Reference： [1]Reger, Daniel L.; Brown, Kenneth J.; Gardinier, James R.; Smith, Mark D. [Organometallics, 2003, vol. 22, # 24, p. 4973 - 4983]

21
[ 1271-48-3 ]
[ 540-63-6 ]
[ 193818-58-5 ]

Reference： [1]Chemical Communications,2003,p. 888 - 889
[2]New Journal of Chemistry,2004,vol. 28,p. 1584 - 1589
[3]Dalton Transactions,2013,vol. 42,p. 1196 - 1209
[4]Dalton Transactions,2013,vol. 42,p. 5056 - 5067

22
[ 1271-48-3 ]
[ 870-63-3 ]
[ 592531-53-8 ]

Reference： [1]Journal of Organometallic Chemistry,2003,vol. 675,p. 105 - 112

23
[ 1271-48-3 ]
[ 4392-24-9 ]
[ 592531-50-5 ]

Yield	Reaction Conditions	Operation in experiment
49%	With tin(ll) chloride In dichloromethane; water under Ar; PhCHCHCH2Br dissolved in distd. CH2Cl2 added to stirred soln. of SnCl22H2O and CuCl22H2O (molar ratio 1:1:0.05) in water at ambient temp.; Fe complex (0.25 equiv.) in distd. CH2Cl2 added dropwise; 3 h; monitored by TLC; extd. with CH2Cl2; org. layer washed with aq. NaHCO3, water and brine; dried (MgSO4); concd. under reduced pressure; purified by column chromy. (silica gel, ethyl acetate-petroleum ether); elem. anal.;

Reference： [1]Debroy, Paromita; Roy, Sujit [Journal of Organometallic Chemistry, 2003, vol. 675, # 1-2, p. 105 - 112]

24
[ 1271-48-3 ]
[ 50917-72-1 ]
[ 852631-39-1 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1977 - 1981

25
[ 109-97-7 ]
[ 1271-48-3 ]
[ 863413-54-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With trifluoroacetic acid at 20℃; for 0.5h; Inert atmosphere;
40%	With triethylamine; trifluoroacetic acid In neat (no solvent) mixt. of pyrrole and Fe complex flushed with Ar for 5 min; treated with trifluoroacetic acid; stirred at 25°C for 25 min; Et3N added; excess pyrrole removed under reduced pressure; oil dissolved in ethyl acetate; washed with water; dried (Na2SO4); solvent removed under reduced pressure; purified by column chromy. (silica, hexane-ethyl acetate 4:1);crystd. from Et2O-hexane;

Reference： [1]Benniston, Andrew C.; Sirbu, Dumitru; Turta, Constantin; Probert, Michael R.; Clegg, William [European Journal of Inorganic Chemistry, 2014, vol. 2014, # 36, p. 6212 - 6219]
[2]Koszarna, Beata; Butenschoen, Holger; Gryko, Daniel T. [Organic and Biomolecular Chemistry, 2005, vol. 3, # 14, p. 2640 - 2645]

26
[ 1271-48-3 ]
[ 852631-39-1 ]
2,17-diaza[4,4]ferrocenophane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1977 - 1981

27
[ 1271-48-3 ]
[ 20439-47-8 ]
(CHNC₆H₁₀NCHC₅H₄FeC₅H₄)3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In neat (no solvent, solid phase) at 20℃; for 0.166667h; Milling;
13%	In dichloromethane Fe complex added to a soln. of (1R,2R)-diaminocyclohexane in CH2Cl2, stirred for 45 min at room temp.; evapd., recrystd. (EtOAc); elem. anal.;
	With molecular sieve In dichloromethane ferrocenedialdehyde and diamine in CH2Cl2 in the presence of molecular sieve at room temp. for 1 d; filtered, filtrate concd., pptd. by addn. of diethyl ether; elem. anal.;

Reference： [1]Gúnka, Piotr A.; Kasprzak, Artur; Krzyzanowski, Maurycy; Kunde, Tom; Pausch, Tobias; Schmidt, Bernd M. [Chemical Science, 2022, vol. 13, # 10, p. 2877 - 2883]
[2]Kuhnert, Nikolai; Burzlaff, Nicolai; Patel, Chirag; Lopez-Periago, Ana [Organic and Biomolecular Chemistry, 2005, vol. 3, # 10, p. 1911 - 1921]
[3]Hong, Bog Ki; Lee, In Su; Shin, Dong Mok; Chung, Young Keun [Chemical Communications, 2004, # 8, p. 936 - 937]

28
[ 1271-48-3 ]
[ 61251-99-8 ]
[ 947488-98-4 ]

Yield	Reaction Conditions	Operation in experiment
82.5%	With hydrogenchloride In ethanol byproducts: H2O; (under inert atm.); ligand in EtOH treated with Fe-complex, HCl added, refluxed for 6 h, cooled to room temp.; filtered, flash chromy. with hexane:acetone 5:1, recrystd. from petroleum ether, solvent evapd. in vac., ppt. dried in vac. dessicator over CaCl2; elem. anal.;

Reference： [1]Akhter, Zareen; Nigar, Asifa; Razzaq, Muhammad Y.; Siddiqi, Humaira M. [Journal of Organometallic Chemistry, 2007, vol. 692, # 16, p. 3542 - 3546]

29
[ 1271-48-3 ]
[ 108-42-9 ]
[ 936024-81-6 ]

Yield	Reaction Conditions	Operation in experiment
89.9%	With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux;	General procedure: Ferrocene-1,1-dicarbaldehyde (0.22 g, 0.90 mmol), aromatic amine (2.14 mmol), and 75 mL xylene were sequentially added to a 150 mL three-neck round bottom flask. When the ferrocene-1,1-dicarbaldehyde was completely dissolved with stirring vigorously, 0.2 g basic Al2O3 (1.96 mmol) was added. The reaction mixture was heated to reflux for 8 h and then filtered. Solvent was evaporated and the product was washed with solvent, affording a corresponding product in a certain yield.

Reference： [1]Chemical Physics Letters,2015,vol. 624,p. 47 - 52
[2]Polyhedron,2007,vol. 26,p. 1037 - 1044

30
[ 1271-48-3 ]
[ 104-94-9 ]
[ 936024-79-2 ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 3443 - 3453
[2]Polyhedron,2007,vol. 26,p. 1037 - 1044
[3]Dalton Transactions,2009,p. 8399 - 8405

31
[ 932013-08-6 ]
[ 1271-48-3 ]
(O(C₆H₂(CH₃)NHC₂H₅)2CC₆H₄CONNCHC₅H₄)2Fe [ No CAS ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 7190 - 7201

32
[ 1271-48-3 ]
[ 63126-47-6 ]
Fe(C₅H₄CH₂NC₄H₇CH₂OCH₃)2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14030 - 14031
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 7823 - 7829

33
[ 1271-48-3 ]
[ 98-86-2 ]
[ 57-13-6 ]
(4R,4aS,5R,8aS)-hexahydro-4,5-(ferroce-1,1'-diyl)-8a-phenylpyrimido[4,5-d]pyrimidine-2,7(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With chloro-trimethyl-silane In acetonitrile Ar; soln. of urea, ketone, and TMSCl added to soln. of 1,1'-diformylferrocene and FeCl3*6H2O (3:2:2:1:0.2 molar ratio), mixt. refluxed for 15 h; cooled to room temp., quenched (water), filtered off, dried, chromd. (SiO2, DCM/MeOh=25/1), recrystd. (EtOH), elem. anal.;

Reference： [1]Csámpai; Györfi; Túrós; Sohár [Journal of Organometallic Chemistry, 2009, vol. 694, # 22, p. 3667 - 3673]

34
[ 1271-48-3 ]
[ 1009-61-6 ]
[ 57-13-6 ]
(4R,4aS,5R,8aS)-hexahydro-4,5-(ferroce-1,1'-diyl)-8a-(4-methoxyphenyl)pyrimido[4,5-d]pyrimidine-2,7(1H,3H)-dione [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 3667 - 3673

35
[ 1271-48-3 ]
[ 104-94-9 ]
1,1'-bis[(4-methoxyphenylimino)methyl]ferrocene [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 3183 - 3191

36
[ 1271-48-3 ]
[ 63-68-3 ]
C₂₂H₂₆FeN₂O₄S₂^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 345 - 360,16

37
[ 1271-48-3 ]
[ 71-00-1 ]
C₂₄H₂₂FeN₆O₄^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 345 - 360,16

38
[ 1271-48-3 ]
[ 107-95-9 ]
C₁₈H₁₈FeN₂O₄^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 345 - 360,16

39
[ 867-13-0 ]
[ 1271-48-3 ]
[ 168283-32-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium; In ethanol; at 0 - 20℃; for 1h;Inert atmosphere; Schlenk technique;	After dissolving sodium (0.18 g, 8.16 mmol) in absolute ethanol (50 mL; caution, hydrogen is evolved), one equivalent of triethyl phosphonoacetate (1.62 mL, 8.16 mmol) followed by a solution of 9 (0.94 g, 3.88 mmol) in absolute ethanol (25 mL) was added dropwise at 0 C. The mixture was allowed to warm up to room temperature and stirred for 1 h. Removal of the solvent followed by column chromatography (hexane:ether v/v 1:1) gave analytically pure 10 (Rf = 0.35) as a dark red crystalline solid in 80% (1.27 g, 3.1 mmol) yield w.r.t. 9, m.p. 92-93 C. 1H NMR (CDCl3) delta/ppm: 7.39 (d, J = 15.8 Hz, 2H, Cp-CH=CH), 5.96 (d, J = 15.8 Hz, 2H, Cp-CH=CH), 4.44 (pt, J = 1.8 Hz, 4H, 2* C5H4), 4.36 (pt, J = 1.8 Hz, 4H, 2* C5H4), 4.21 (q, J = 7.1 Hz, 4H, -CH2-CH3), 1.32 (t, J = 7.1 Hz, 6H, CH2-CH3). 13C{1H} NMR (CDCl3) delta/ppm: 166.9 (C=O), 143.7 (Cp-CH=CH), 116.2 (Cp-CH=CH) 79.9 (Cipso),72.2 (Cp), 69.7 (Cp), 60.1 (CH2), 14.2 (CH3). IR, neat, numax/cm-1: 3180, 2978, 2902, 1706, 1626, 1120, 1066.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 740,p. 61 - 69

40
[ 1271-48-3 ]
1,1'-dihydroxymethylferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tetrahydroborate; In tetrahydrofuran; at 20℃; for 0.583333h;Inert atmosphere; Schlenk technique;	To a stirred mixture of NaBH4 (350 mg, 8.8 mmol) in dry THF (15 mL), 1 g (4.12 mmol) of solid 1,1'-ferrocenedicarboxaldehyde, 9, was added in small portions. The mixture was stirred at room temperature for 15 min and two more portions of NaBH4 (each 200 mg, 5.3 mmol) was added within 10 min of each other. Thereafter the reaction is filtered through a pad of Celite and the Celite-residue washed with THF (3 * 20 mL). Caution: Quenching with water or dilute acid before filtering severely lowers yields. The Celite with remainder of the reaction residue still on it was suspended in THF (100 mL) and water (10 mL) was added. This suspension was stirred for 5 min, filtered, and the organic layer was separated and dried over MgSO4. The combined THF fractions were evaporated to dryness to obtain the product, 1, as yellow crystals.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 740,p. 61 - 69
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 11445 - 11450
Angew. Chem.,2018,vol. 130,p. 11616 - 11621,6
[3]Russian Journal of General Chemistry,2016,vol. 86,p. 338 - 343
Zh. Obshch. Khim.,2016,vol. 86,p. 338 - 343,6

41
[ 1271-48-3 ]
[ 109-89-7 ]
1,1′-bis((N,N-diethylamino)methyl)ferrocene [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

42
[ 123-75-1 ]
[ 1271-48-3 ]
1,1′-bis((pyrrolidin-1-yl)methyl)ferrocene [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

43
[ 110-89-4 ]
[ 1271-48-3 ]
1,1′-bis((piperidin-1-yl)methyl)ferrocene [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

44
[ 1271-48-3 ]
[ 103-49-1 ]
1,1′-bis((N,N-dibenzylamino)methyl)ferrocene [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

45
[ 1271-48-3 ]
[ 13214-66-9 ]
1,1′-bis((N-(4-phenylbutyl)amino)methyl)ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 1,1'-ferrocenyldicarboxaldehyde; 4-phenyl-1-butylamine In dichloromethane at 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;

46
[ 1271-48-3 ]
[ 13214-66-9 ]
[ 394654-26-3 ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

47
[ 1271-48-3 ]
[ 109-73-9 ]
bis((N-(n-butyl)imino)methyl)ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; acetonitrile at 20℃; for 2.25h; Schlenk technique; Inert atmosphere;
	In methanol at 20℃; for 12h;

Reference： [1]Dwadnia, Nejib; Allouch, Fatima; Pirio, Nadine; Roger, Julien; Cattey, Helene; Fournier, Sophie; Penouilh, Marie-Josee; Devillers, Charles H.; Lucas, Dominique; Naoufal, Daoud; Ben Salem, Ridha; Hierso, Jean-Cyrille [Organometallics, 2013, vol. 32, # 20, p. 5784 - 5797]
[2]Yoon, Jisoo; Jadhav, Jyoti Ramesh; Kim, Jun Myung; Cheong, Minserk; Kim, Hong-Seok; Kim, Joohoon [Chemical Communications, 2014, vol. 50, # 57, p. 7670 - 7672]

48
[ 1271-48-3 ]
[ 109-73-9 ]
N-(n-butyl)-2-aza[3]ferrocenophane [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

49
[ 1271-48-3 ]
[ 100-46-9 ]
[ 244272-22-8 ]

Reference： [1]Organometallics,2013,vol. 32,p. 5784 - 5797

50
[ 1271-48-3 ]
[ 1615713-70-6 ]

Yield	Reaction Conditions	Operation in experiment
49%		To a solution of ferrocene 1,1'-dicarboxaldehyde(400 mg, 1.65 mmol) in acetonitrile (20 mL) at 0 C was added slowly asolution of KMnO4 (800 mg, 5.06 mmol) in water (13 mL). Afterstirring for 15 min a solution of aq. NaOH (2 mL, 20% w/v) was added andstirred for a further 5 minutes. The reaction mixture was filtered throughCelite and washed with aq. NaOH (3 mL, 10% w/v). The filtrate was washed withEt2O (3 x 30 mL) to remove the unreacted starting material andslowly acidified to pH 3 with a solution of aq. HCl (10 %). Extraction with chloroform(3 x 40 mL) with further drying over Na2SO4 and evaporationof the solvent gave the desired compound 1as an orange solid (210 mg, 49 % yield). 1H-NMR(400 MHz, acetonitrile-d3, delta): 9.87 (s, 1 H), 4.83 (s, 2 H), 4.81 (s,2 H), 4.65 (s, 2 H), 4.53 (s, 2 H). 13CNMR (101 MHz, acetonitrile-d3, delta): 193.21, 170.77, 80.58, 74.56, 72.79,71.60, 70.95. FTIR (cm-1): 624 (w), 718 (m), 747 (vs), 785 (vw), 816 (m), 834 (s), 836 (s), 879(vw), 912 (vw), 1032 (s), 1051 (vw sh), 1151 (s), 1212 (vw), 1244 (s), 1262(vs), 1295 (vw), 1332 (vw), 1372 (m), 1396 (m), 1455 (w), 1472(m), 1529 (vw), 1630 (s, sh), 1640 (vs), 1673 (m), 1690 (m), 1717 (s), 2533(vw, br), 2615 (w, br) 2865 (w, br), 2939 (m, br), 3111 (w, br). HRMS (ASAP, m/z): found [M + H]+259.0047, [M - OH]+ 240.9942, calcd for C12H11FeO3259.0052. Elemental Anal. (%) Calcd. for C12H10FeO3:C, 55.85; H, 3.91; N, 0.00. Found: C, 56.10; H, 3.89; N, 0.00.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3777 - 3780

51
[ 1271-48-3 ]
[ 67-64-1 ]
1'-[(E)-3-oxo-but-1-enyl]ferrocenecarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		To a solution of ferrocene 1,1'-dicarboxaldehyde(500 mg, 2.07 mmol) in acetone (20 mL) at 0 C was added slowly (1h) a solution of KMnO4(1.30 g, 8.23 mmol) in water (21 mL). After stirringfor 15 min a solution of aq. NaOH (3 mL, 20%) was added and the solution was stirredfor a further 5 minutes. The reaction mixture was filtered through Celite andwashed with aq. NaOH (6 mL, 10%). The filtrate was washed with Et2O(3 x 40 mL) to remove the unreacted starting material and slowly acidified topH 2 with a solution of aq. HCl (10 %). The precipitate formed was collected byfiltration, washed with distilled water and dried to give the desired compound 2 as an orange solid (370mg, 60 % yield).Some more impure compound (ca. 50 mg) could be obtained by extracting thefiltrate with ethylacetate. 1H-NMR (400 MHz, acetone-d6,delta): 7.35 (d, J = 16.2 Hz, 1 H), 6.30 (d,J = 16.2 Hz, 1 H), 4.75 (ap t, J = 1.9 Hz, 2 H), 4.67 (ap t, J = 1.7 Hz, 2 H), 4.50 (ap t, J = 1.7 Hz, 2 H), 4.45 (ap t, J = 1.9 Hz, 2 H), 2.25 (s, 3 H). 13C NMR (101 MHz, acetone-d6,delta): 197.51, 171.03, 143.04, 127.10, 81.34, 74.54, 73.32, 73.13, 72.40, 70.80, 26.84. FTIR(cm-1): 717 (m), 739(vw), 783 (w), 821 (m), 869 (vw, sh), 910 (vw, sh), 931 (vw, sh), 966 (m), 1030(m), 1049 (w), 1145 (s), 1185 (vw), 1264 (vs), 1281(w, sh), 1361 (m), 1398 (w,sh), 1471 (s), 1524 (w), 1626 (vs), 1667 (s), 1705 (s), 1750 (vw), 2633 (w,br), 2934 (m, v br), 3440 (w, br). HRMS (ESI, m/z): found [M + H]+ 299.0367, [M + Na]+321.0182, [2M + Na]+ 619.0499, calcd for C15H15FeO3299.0371. Anal. (%) Calcd for C15H14FeO3:C, 60.43; H, 4.73; N, 0.00. Found: C, 60.50; H, 4.92; N, 0.00.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3777 - 3780

52
[ 1271-48-3 ]
[ 1642167-65-4 ]
(Z,Z)-1,1'-bis[(1-paratoluoyloxy-4-vinyl)benzene]ferrocene [ No CAS ]
(E,E)-1,1'-bis[(1-paratoluoyloxy-4-vinyl)benzene]ferrocene [ No CAS ]
(E,Z)-1,1'-bis[(1-paratoluoyloxy-4-vinyl)benzene]ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		Under an argon atmosphere, butyllithium (1.6 M, 5.6 mL, 8.96 mmol) was slowly added to a solution of 4-toluoyloxybenzyltriphenylphosphoniumbromide (20, 5 g, 8.82 mmol) in THF (80 mL) at -78 C. The resultingsolution was allowed to warm at room temperature. A solution of ferrocene-1,1'-dicarbaldehyde [59] (19, 0.95 g, 4.41 mmol) in THF (15 mL) was added dropwise and the reaction mixture was stirred overnight. Ice-cold water (500 mL) was added and the mixture was stirred for an additional hour. The aqueous layer was extracted with ethyl acetate; the combined organic layers were washed with waterand dried over MgSO4. After evaporating the solvent, 47% of a crude mixture of EE/EZ/ZZ isomers was obtained. The EE isomer was isolated by chromatography (heptane/EtOAc: 9/1), yield 25%. 1H-NMR delta (ppm): 3.41 (s, 6H, CH3), 4.28 (t, 4H, Fc-H), 4.48 (d, 4H, Fc-H), 6.63 (d, 2H, 3J = 15.09Hz, =CH), 6.81 (d, 2H, 3J = 15.09 Hz, =CH), 7.11 (d, 4H, Ar-H), 7.28 (d, 4H, Ar-H), 7.41 (d, 4H,Ar-H), 8.09 (d, 4H, Ar-H); 13C-NMR delta (ppm): 22.3 (CH3), 67.9, 68.1, 70.4 (Fc-C), 121.7, 124.1,124.5, 125.1, 127.2, 127.7, 131.3, 143.5, 148.0 (Ar-C), 164.3 (C=O); C42H34FeO4 (MW 657.18). HRMS (ESI): m/z 658.17693 [M]+, calculated mass 658.18018 (sigma = 4.8 ppm).

Reference： [1]Molecules,2014,vol. 19,p. 7850 - 7868

53
[ 1271-48-3 ]
[ 876-31-3 ]
1,1′-ferrocenyldi[2-(4-cyanophenyl)acrylonitrile] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With piperidine; In neat (no solvent); at 20℃; for 0.333333h;Sealed tube;	General procedure: The general procedure for synthesizing 1,1?-ferrocenyldiacrylonitriles was developed from that described by Imrie et al. [15]. Compound 1 (1 eq.) and substituted phenylacetonitriles (2.2 eq.) were mixed in a Pyrex tube fitted with a ground-glass joint. The compounds were thoroughly ground with a glass rod. One to two drops of piperidine was added into the Pyrex tube and the mixture was further ground at RT until a melt was formed. The Pyrex tube was sealed and placed in a shaker for approximately 20 min. To evaporate the remaining piperidine (boiling point 106 C) and water formed as a by-product, the samples were first dried in open air, and thereafter under a vacuum line. The products were further purified by silica gel chromatography. The formation of the products was determined using IR or NMR spectroscopy (1H and 13C). In solid-state IR spectra, formation of the products was characterized by the disappearance of the sharp carbonyl absorption at approximately 1650 cm-1 and the appearance of a strong nitrile absorption at approximately 2200 cm-1. 1H and 13C NMR spectra showed the disappearance of the carbonyl resonance and the appearance of alkene resonance peaks. Pure compounds were further analyzed by mass spectrometry, microanalysis, and X-ray diffraction.

Reference： [1]Journal of Coordination Chemistry,2014,vol. 67,p. 1905 - 1922

54
[ 1271-48-3 ]
[ 2338-75-2 ]
1,1′-ferrocenyldi[2-(4-{trifluoromethyl}phenyl)acrylonitrile] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With piperidine; In neat (no solvent); at 20℃; for 0.333333h;Sealed tube;	General procedure: The general procedure for synthesizing 1,1?-ferrocenyldiacrylonitriles was developed from that described by Imrie et al. [15]. Compound 1 (1 eq.) and substituted phenylacetonitriles (2.2 eq.) were mixed in a Pyrex tube fitted with a ground-glass joint. The compounds were thoroughly ground with a glass rod. One to two drops of piperidine was added into the Pyrex tube and the mixture was further ground at RT until a melt was formed. The Pyrex tube was sealed and placed in a shaker for approximately 20 min. To evaporate the remaining piperidine (boiling point 106 C) and water formed as a by-product, the samples were first dried in open air, and thereafter under a vacuum line. The products were further purified by silica gel chromatography. The formation of the products was determined using IR or NMR spectroscopy (1H and 13C). In solid-state IR spectra, formation of the products was characterized by the disappearance of the sharp carbonyl absorption at approximately 1650 cm-1 and the appearance of a strong nitrile absorption at approximately 2200 cm-1. 1H and 13C NMR spectra showed the disappearance of the carbonyl resonance and the appearance of alkene resonance peaks. Pure compounds were further analyzed by mass spectrometry, microanalysis, and X-ray diffraction.

Reference： [1]Journal of Coordination Chemistry,2014,vol. 67,p. 1905 - 1922

55
[ 1271-48-3 ]
[ 140-53-4 ]
1,1′-ferrocenyldi[2-(4-chlorophenyl)acrylonitrile] [ No CAS ]
C₂₀H₁₄ClFeNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%; 10%	With piperidine; In neat (no solvent); at 20℃; for 0.333333h;Sealed tube;	General procedure: The general procedure for synthesizing 1,1?-ferrocenyldiacrylonitriles was developed from that described by Imrie et al. [15]. Compound 1 (1 eq.) and substituted phenylacetonitriles (2.2 eq.) were mixed in a Pyrex tube fitted with a ground-glass joint. The compounds were thoroughly ground with a glass rod. One to two drops of piperidine was added into the Pyrex tube and the mixture was further ground at RT until a melt was formed. The Pyrex tube was sealed and placed in a shaker for approximately 20 min. To evaporate the remaining piperidine (boiling point 106 C) and water formed as a by-product, the samples were first dried in open air, and thereafter under a vacuum line. The products were further purified by silica gel chromatography. The formation of the products was determined using IR or NMR spectroscopy (1H and 13C). In solid-state IR spectra, formation of the products was characterized by the disappearance of the sharp carbonyl absorption at approximately 1650 cm-1 and the appearance of a strong nitrile absorption at approximately 2200 cm-1. 1H and 13C NMR spectra showed the disappearance of the carbonyl resonance and the appearance of alkene resonance peaks. Pure compounds were further analyzed by mass spectrometry, microanalysis, and X-ray diffraction.

Reference： [1]Journal of Coordination Chemistry,2014,vol. 67,p. 1905 - 1922

56
[ 1271-48-3 ]
[ 459-22-3 ]
1,1′-ferrocenyldi[2-(4-fluorophenyl)acrylonitrile] [ No CAS ]
C₂₀H₁₄FFeNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%; 24%	With piperidine; In neat (no solvent); at 20℃; for 0.333333h;Sealed tube;	General procedure: The general procedure for synthesizing 1,1?-ferrocenyldiacrylonitriles was developed from that described by Imrie et al. [15]. Compound 1 (1 eq.) and substituted phenylacetonitriles (2.2 eq.) were mixed in a Pyrex tube fitted with a ground-glass joint. The compounds were thoroughly ground with a glass rod. One to two drops of piperidine was added into the Pyrex tube and the mixture was further ground at RT until a melt was formed. The Pyrex tube was sealed and placed in a shaker for approximately 20 min. To evaporate the remaining piperidine (boiling point 106 C) and water formed as a by-product, the samples were first dried in open air, and thereafter under a vacuum line. The products were further purified by silica gel chromatography. The formation of the products was determined using IR or NMR spectroscopy (1H and 13C). In solid-state IR spectra, formation of the products was characterized by the disappearance of the sharp carbonyl absorption at approximately 1650 cm-1 and the appearance of a strong nitrile absorption at approximately 2200 cm-1. 1H and 13C NMR spectra showed the disappearance of the carbonyl resonance and the appearance of alkene resonance peaks. Pure compounds were further analyzed by mass spectrometry, microanalysis, and X-ray diffraction.

Reference： [1]Journal of Coordination Chemistry,2014,vol. 67,p. 1905 - 1922

57
[ 1271-48-3 ]
[ 62-53-3 ]
C₂₄H₂₀FeN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.9%	With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux;	General procedure: Ferrocene-1,1-dicarbaldehyde (0.22 g, 0.90 mmol), aromatic amine (2.14 mmol), and 75 mL xylene were sequentially added to a 150 mL three-neck round bottom flask. When the ferrocene-1,1-dicarbaldehyde was completely dissolved with stirring vigorously, 0.2 g basic Al2O3 (1.96 mmol) was added. The reaction mixture was heated to reflux for 8 h and then filtered. Solvent was evaporated and the product was washed with solvent, affording a corresponding product in a certain yield. Compound 1 was synthesized according to the general procedure above. After the reaction was completed, the reaction mixture was concentrated to give red oil product which was washed with petroleum ether and dichloromethane, giving a red needle crystalline solid in 89.9% yield. m.p. 92-93C. 1H NMR (500 MHz, CDCl3): 8.325 (s, 2H, CH N ), 7.333 (t, J = 8 Hz, 4H, Ar-H), 7.204 (t, J = 7.5 Hz,2H, Ar-H), 7.132 (t, J = 7.5 Hz, 4H, Ar-H), 4.890 (t, J = 2 Hz, 4H, Cp-H), 4.556 (t, J = 4 Hz, 2H, Cp-H). MS (ESI): m/z = 393.1 (M+H)+. Elem. Anal. Calcd for C24H20N2Fe: C, 73.48; H, 5.14; N, 7.14. Found: C, 73.29; H, 5.26; N, 7.09.

Reference： [1]Chemical Physics Letters,2015,vol. 624,p. 47 - 52
[2]Patent: CN105777817,2016,A .Location in patent: Paragraph 0105

58
[ 1271-48-3 ]
[ 536-90-3 ]
C₂₆H₂₄FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.3%	With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux;	General procedure: Ferrocene-1,1-dicarbaldehyde (0.22 g, 0.90 mmol), aromatic amine (2.14 mmol), and 75 mL xylene were sequentially added to a 150 mL three-neck round bottom flask. When the ferrocene-1,1-dicarbaldehyde was completely dissolved with stirring vigorously, 0.2 g basic Al2O3 (1.96 mmol) was added. The reaction mixture was heated to reflux for 8 h and then filtered. Solvent was evaporated and the product was washed with solvent, affording a corresponding product in a certain yield.

Reference： [1]Chemical Physics Letters,2015,vol. 624,p. 47 - 52

59
[ 1271-48-3 ]
[ 372-39-4 ]
C₂₄H₁₆F₄FeN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49.9%	With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux;	General procedure: Ferrocene-1,1-dicarbaldehyde (0.22 g, 0.90 mmol), aromatic amine (2.14 mmol), and 75 mL xylene were sequentially added to a 150 mL three-neck round bottom flask. When the ferrocene-1,1-dicarbaldehyde was completely dissolved with stirring vigorously, 0.2 g basic Al2O3 (1.96 mmol) was added. The reaction mixture was heated to reflux for 8 h and then filtered. Solvent was evaporated and the product was washed with solvent, affording a corresponding product in a certain yield.

Reference： [1]Chemical Physics Letters,2015,vol. 624,p. 47 - 52

60
[ 1271-48-3 ]
[ 99-09-2 ]
C₂₄H₁₈FeN₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45.2%	With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux;	General procedure: Ferrocene-1,1-dicarbaldehyde (0.22 g, 0.90 mmol), aromatic amine (2.14 mmol), and 75 mL xylene were sequentially added to a 150 mL three-neck round bottom flask. When the ferrocene-1,1-dicarbaldehyde was completely dissolved with stirring vigorously, 0.2 g basic Al2O3 (1.96 mmol) was added. The reaction mixture was heated to reflux for 8 h and then filtered. Solvent was evaporated and the product was washed with solvent, affording a corresponding product in a certain yield.

Reference： [1]Chemical Physics Letters,2015,vol. 624,p. 47 - 52

61
[ 934-32-7 ]
[ 1271-48-3 ]
C₂₆H₂₀FeN₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.5%	With aluminum oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux;	General procedure: Ferrocene-1,1-dicarbaldehyde (0.22 g, 0.90 mmol), aromatic amine (2.14 mmol), and 75 mL xylene were sequentially added to a 150 mL three-neck round bottom flask. When the ferrocene-1,1-dicarbaldehyde was completely dissolved with stirring vigorously, 0.2 g basic Al2O3 (1.96 mmol) was added. The reaction mixture was heated to reflux for 8 h and then filtered. Solvent was evaporated and the product was washed with solvent, affording a corresponding product in a certain yield.

Reference： [1]Chemical Physics Letters,2015,vol. 624,p. 47 - 52

62
[ 1271-48-3 ]
(acetylcyclopentadienyl)tricarbonylmanganese [ No CAS ]
1,1'-[{(CO)₃Mn(η⁵-C₅H₄)COCH=CH(η⁵-C₅H₄)}₂Fe] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In ethanol; at 20℃;Inert atmosphere; Schlenk technique;	A solution of 1,1'-ferrocenyl dialdehyde (24 mg, 0.1 mmol) in ethanol (10 ml) was taken in a round bottomed flask and acetyl cymantrene (56 mg, 0.2 mmol) was added under stirring condition. Ethanolic solution of sodium hydroxide was then added to the reaction mixture dropwise and stirred for 3-4 h at room temperature under inert atmosphere. The reaction was continuously monitored by TLC and on disappearance of the reactants the solution was dried under vacuum and the residue was dissolved in dichloromethane solvent and subjected to chromatographic work-up using column chromatography. Elution with dichloromethane/hexane (40:60 v/v) solvent mixture separated the violet colored compound [{(eta5-C5H4)Mn(CO)3COCH=CH (eta5-C5H4)}2Fe] (2) along with trace amount of the reactants. {Yield: 46 mg (65%)} 2: Anal. calcd. (found): C, 55.01 (55.18); H, 2.87 (2.81). IR(nuCO, cm-1, CH2Cl2): 2021 (vs), 1925 (vs br), 1648 (s), 1591 (s). 1H NMR (delta, CDCl3): 4.44 (t, eta5-C5H4, 4H), 4.47 (t, eta5-C5H4, 4H), 4.82 (t, eta5-C5H4, 4H), 5.45 (t, eta5-C5H4, 4H), 6.43 (d, J = 15 Hz, CH=, 2H), 7.57 (d, J = 15 Hz, =CH, 2H). 13C NMR (delta, CDCl3): 70.76 (eta5-C5H4), 73.42 (eta5-C5H4), 79.86 (eta5-C5H4), 83.77 (eta5-C5H4), 86.67 (eta5-C5H4), 93.42 (eta5-C5H4), 118.60 (=CH), 144.43 (CH=), 185.31 (-C=O). UV-Visible (lambda (nm), CH2Cl2) = 304, 334, 374 (sh), 505. MS (ESI): m/z 699 (M + 1)+.

Reference： [1]Journal of Molecular Structure,2015,vol. 1085,p. 162 - 172

63
[ 1271-48-3 ]
[ 2213-43-6 ]
C₂₂H₃₀FeN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With magnesium sulfate; In dichloromethane; at 20℃;Schlenk technique; Inert atmosphere;	General procedure: General procedure: in a Schlenk tube, under argon,were added 115 mg (0,47 mmol) of 1,10-ferrocenedicarboxaldehyde,625 mg (5,19 mmol) of anhydrous magnesiumsulphate MgSO4 and 10 ml of anhydrousdichloromethane. To the red suspension was then added12 equiv of the specific hydrazine using a syringe. Thereaction mixture was then stirred at room temperatureovernight. The crude material was purified by flashchromatography on silica gel. 2d: reaction with 626 mL of 1-aminopiperidine to yield189 mg of 2d (yield = 98%). 1H (300 MHz, CDCl3): 7.37 (s,2H, CH), 4.52 (t, J = 1.9 Hz, 4H, Cp), 4.23 (t, J = 1.9 Hz, 4H,Cp), 3.02 (m, 8H, CH2), 1.75 (m, 8H, CH2), 1.52 (m, 4H, CH2).13C (300 MHz, CDCl3): 135.8 (s, CH), 83.2 (s, quat. Cp), 70.0(s, subst. Cp), 67.6 (s, subst. Cp), 52.7 (s, CH2), 25.3 (s, CH2),24.2 (s, CH2). HR MS (ESI+): 407.1892 (100%, 407.1898 forC22H31FeN4: M + 1).

Reference： [1]Comptes Rendus Chimie,2015,vol. 18,p. 801 - 807

64
[ 1271-48-3 ]
[ 57-14-7 ]
C₁₆H₂₂FeN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With magnesium sulfate; In dichloromethane; at 20℃;Schlenk technique; Inert atmosphere;	General procedure: General procedure: in a Schlenk tube, under argon,were added 115 mg (0,47 mmol) of 1,10-ferrocenedicarboxaldehyde,625 mg (5,19 mmol) of anhydrous magnesiumsulphate MgSO4 and 10 ml of anhydrousdichloromethane. To the red suspension was then added12 equiv of the specific hydrazine using a syringe. Thereaction mixture was then stirred at room temperatureovernight. The crude material was purified by flashchromatography on silica gel. 2a: reaction with 430 mL of N,N-dimethylhydrazine toyield 120 mg of 2a as a red solid (yield = 77%). 1H (300 MHz,CDCl3): 7.00 (s, 2H, CH), 4.44 (t, J = 1.8 Hz, 4H, Cp), 4. 14 (t,J = 1.8 Hz, 4H, Cp), 2.81 (s, 12H, CH3). 13C (300 MHz, CDCl3):133.6 (s, CH), 83.5 (s, quat. Cp), 69.6 (s, subst. Cp), 67.3 (s,subst. Cp), 43.2 (s, CH3). HR MS (ESI+): 327.1266 (100%,327.1272 for C16H23Fe N4: M + H).

Reference： [1]Comptes Rendus Chimie,2015,vol. 18,p. 801 - 807

65
[ 1271-48-3 ]
[ 530-50-7 ]
C₃₆H₃₀FeN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With magnesium sulfate; In dichloromethane; at 20℃;Schlenk technique; Inert atmosphere;	General procedure: General procedure: in a Schlenk tube, under argon,were added 115 mg (0,47 mmol) of 1,10-ferrocenedicarboxaldehyde,625 mg (5,19 mmol) of anhydrous magnesiumsulphate MgSO4 and 10 ml of anhydrousdichloromethane. To the red suspension was then added12 equiv of the specific hydrazine using a syringe. Thereaction mixture was then stirred at room temperatureovernight. The crude material was purified by flashchromatography on silica gel. 2b: reaction with 940 mL of, N,N-diphenylhydrazine toyield 237 mg of 2b (yield = 87%). 1H (300 MHz, CDCl3): 7.40(m, 8H, Ph), 7.22-7.16 (m, 12H, Ph), 7.00 (s, 2H, CH), 4.56 (t,J = 1.8 Hz, 4H, Ph), 4.30 (t, J = 1.8 Hz, 4H, Cp). 13C (300 MHz,CDCl3): 144.0 (s, quat. Ph), 135.5 (s, CH), 129.8 (s, Ph), 124.1(s, Ph), 122.5 (s, Ph), 82.9 (s, quat. Cp), 70.3 (s, subst. Cp),67.7 (s, subst. Cp). HR MS (ESI): 574.1826 (100%,574.1821 for C36H30FeN4: M).

Reference： [1]Comptes Rendus Chimie,2015,vol. 18,p. 801 - 807

66
[ 1271-48-3 ]
[ 614-31-3 ]
C₃₈H₃₄FeN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With magnesium sulfate; In dichloromethane; at 20℃;Schlenk technique; Inert atmosphere;	General procedure: General procedure: in a Schlenk tube, under argon,were added 115 mg (0,47 mmol) of 1,10-ferrocenedicarboxaldehyde,625 mg (5,19 mmol) of anhydrous magnesiumsulphate MgSO4 and 10 ml of anhydrousdichloromethane. To the red suspension was then added12 equiv of the specific hydrazine using a syringe. Thereaction mixture was then stirred at room temperatureovernight. The crude material was purified by flashchromatography on silica gel. 2c: reaction with 1 mL of N,N-phenylbenzylhydrazineto yield 286 mg of 2c (yield = 84%). 1H (300 MHz, CDCl3):7.40-7.30 (m, 8H, Ph), 7.20-7.08 (m, 12H, Ph), 6.96 (s, 2H,CH), 4.98 (s, 4H, CH2), 4. 36 (t, J = 1.8 Hz, 4H, Cp), 4.15 (t,J = 1.8 Hz, 4H, Cp). 13C (300 MHz, CDCl3): 147.7 (s, quat. Ph),136.2 (s, quat. Ph), 132.0 (s, CH), 129.1 (s, Ph), 128.9 (s, Ph), 127.2 (s, Ph), 126.2 (s, Ph), 120.2 (s, Ph), 114.3 (s, Ph), 83.6(s, quat. Cp), 70.2 (s, subst. Cp), 67.9 (s, subst. Cp), 49.8 (s,CH2). HR MS (ESI): 603.2198 (100%, 603.2212 forC38H35FeN4: M + 1).

Reference： [1]Comptes Rendus Chimie,2015,vol. 18,p. 801 - 807

67
[ 1271-48-3 ]
[ 3182-95-4 ]
C₃₀H₃₂FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 10h; Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;	1 General procedures for the synthesis of C2-symmetric ferrocenyl amino alcohols General procedure: Method A, for compound, 1-4 and 8: A mixture offerrocenedicarboxaldehyde (1.00 g, 4.13 mmol) and amino alcohol(12.4 mmol) in previously dried CH2Cl2 (250 ml) containing molecularsieves (4 Å, 5.00 g) was refluxed under argon for 10 h. Themixture was filtered through Celite 545. The solvent was removedunder reduced pressure and the residue was re-dissolved in drymethanol (150 ml). Solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions at 0 C. After stirring for 1 h, the reaction wasquenched by addition of a saturated solution of NH4Cl (250 ml)and extracted with CH2Cl2 (3 30 ml). The combined organicextracts were dried over Na2SO4 and evaporated. The subsequentpurification by column chromatography yielded the desiredferrocenyl amino alcohols.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

68
[ 1271-48-3 ]
[ 20989-17-7 ]
C₂₈H₂₈FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 10h; Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;	2 General procedures for the synthesis of C2-symmetric ferrocenyl amino alcohols General procedure: Method A, for compound, 1-4 and 8: A mixture offerrocenedicarboxaldehyde (1.00 g, 4.13 mmol) and amino alcohol(12.4 mmol) in previously dried CH2Cl2 (250 ml) containing molecularsieves (4 Å, 5.00 g) was refluxed under argon for 10 h. Themixture was filtered through Celite 545. The solvent was removedunder reduced pressure and the residue was re-dissolved in drymethanol (150 ml). Solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions at 0 C. After stirring for 1 h, the reaction wasquenched by addition of a saturated solution of NH4Cl (250 ml)and extracted with CH2Cl2 (3 30 ml). The combined organicextracts were dried over Na2SO4 and evaporated. The subsequentpurification by column chromatography yielded the desiredferrocenyl amino alcohols.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

69
[ 1271-48-3 ]
[ 7533-40-6 ]
C₂₄H₃₆FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 10h; Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;	3 General procedures for the synthesis of C2-symmetric ferrocenyl amino alcohols General procedure: Method A, for compound, 1-4 and 8: A mixture offerrocenedicarboxaldehyde (1.00 g, 4.13 mmol) and amino alcohol(12.4 mmol) in previously dried CH2Cl2 (250 ml) containing molecularsieves (4 Å, 5.00 g) was refluxed under argon for 10 h. Themixture was filtered through Celite 545. The solvent was removedunder reduced pressure and the residue was re-dissolved in drymethanol (150 ml). Solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions at 0 C. After stirring for 1 h, the reaction wasquenched by addition of a saturated solution of NH4Cl (250 ml)and extracted with CH2Cl2 (3 30 ml). The combined organicextracts were dried over Na2SO4 and evaporated. The subsequentpurification by column chromatography yielded the desiredferrocenyl amino alcohols.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

70
[ 1271-48-3 ]
[ 248279-49-4 ]
C₂₄H₃₆FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 10h; Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;	4 General procedures for the synthesis of C2-symmetric ferrocenyl amino alcohols General procedure: Method A, for compound, 1-4 and 8: A mixture offerrocenedicarboxaldehyde (1.00 g, 4.13 mmol) and amino alcohol(12.4 mmol) in previously dried CH2Cl2 (250 ml) containing molecularsieves (4 Å, 5.00 g) was refluxed under argon for 10 h. Themixture was filtered through Celite 545. The solvent was removedunder reduced pressure and the residue was re-dissolved in drymethanol (150 ml). Solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions at 0 C. After stirring for 1 h, the reaction wasquenched by addition of a saturated solution of NH4Cl (250 ml)and extracted with CH2Cl2 (3 30 ml). The combined organicextracts were dried over Na2SO4 and evaporated. The subsequentpurification by column chromatography yielded the desiredferrocenyl amino alcohols.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

71
[ 1271-48-3 ]
[ 2799-17-9 ]
C₁₈H₂₄FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform for 1.5h; Reflux; Inert atmosphere; Schlenk technique;	6 2.3. General procedures for the synthesis of C2-symmetric ferrocenylamino alcohols General procedure: Method B, for compound, 5-7: The procedure for the preparationof ferrocenyl-substituted b-amino alcohols was used for 5-7.A mixture of ferrocenedicarboxaldehyde (484 mg, 2 mmol) andamino alcohol (4.2 mmol) were dissolved in dry chloroform(25 ml) and the solution was refluxed under argon for 1.5 h. Then,the solution was allowed to cooling to room temperature and thesolvent was evaporated under reduced pressure. The residue wasre-dissolved in dry methanol (40 ml). The methanolic solutionwas cooled to 0 C and solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions. After stirring for further 1 h at 0 C and 1.5 h atroom temperature, the reaction was terminated by addition of10% aqueous NaOH (40 ml) and extracted with CH2Cl2(2 25 ml). The combined organic layers were dried over MgSO4,evaporated and the residue was chromatographed over a silicacolumn.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

72
[ 1271-48-3 ]
[ 2549-14-6 ]
C₂₈H₂₈FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; for 1.5h;Reflux; Inert atmosphere; Schlenk technique;	General procedure: Method B, for compound, 5-7: The procedure for the preparationof ferrocenyl-substituted b-amino alcohols was used for 5-7.A mixture of ferrocenedicarboxaldehyde (484 mg, 2 mmol) andamino alcohol (4.2 mmol) were dissolved in dry chloroform(25 ml) and the solution was refluxed under argon for 1.5 h. Then,the solution was allowed to cooling to room temperature and thesolvent was evaporated under reduced pressure. The residue wasre-dissolved in dry methanol (40 ml). The methanolic solutionwas cooled to 0 C and solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions. After stirring for further 1 h at 0 C and 1.5 h atroom temperature, the reaction was terminated by addition of10% aqueous NaOH (40 ml) and extracted with CH2Cl2(2 25 ml). The combined organic layers were dried over MgSO4,evaporated and the residue was chromatographed over a silicacolumn.

Reference： [1]Inorganica Chimica Acta,2015,vol. 438,p. 42 - 51

73
[ 1271-48-3 ]
[ 5856-63-3 ]
C₂₀H₂₈FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform for 1.5h; Reflux; Inert atmosphere; Schlenk technique;	8 2.3. General procedures for the synthesis of C2-symmetric ferrocenylamino alcohols General procedure: Method B, for compound, 5-7: The procedure for the preparationof ferrocenyl-substituted b-amino alcohols was used for 5-7.A mixture of ferrocenedicarboxaldehyde (484 mg, 2 mmol) andamino alcohol (4.2 mmol) were dissolved in dry chloroform(25 ml) and the solution was refluxed under argon for 1.5 h. Then,the solution was allowed to cooling to room temperature and thesolvent was evaporated under reduced pressure. The residue wasre-dissolved in dry methanol (40 ml). The methanolic solutionwas cooled to 0 C and solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions. After stirring for further 1 h at 0 C and 1.5 h atroom temperature, the reaction was terminated by addition of10% aqueous NaOH (40 ml) and extracted with CH2Cl2(2 25 ml). The combined organic layers were dried over MgSO4,evaporated and the residue was chromatographed over a silicacolumn.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

74
[ 23364-44-5 ]
[ 1271-48-3 ]
C₄₀H₃₆FeN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 10h; Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;	5 General procedures for the synthesis of C2-symmetric ferrocenyl amino alcohols General procedure: Method A, for compound, 1-4 and 8: A mixture offerrocenedicarboxaldehyde (1.00 g, 4.13 mmol) and amino alcohol(12.4 mmol) in previously dried CH2Cl2 (250 ml) containing molecularsieves (4 Å, 5.00 g) was refluxed under argon for 10 h. Themixture was filtered through Celite 545. The solvent was removedunder reduced pressure and the residue was re-dissolved in drymethanol (150 ml). Solid NaBH4 (0.79 g, 20.8 mmol) was addedin small portions at 0 C. After stirring for 1 h, the reaction wasquenched by addition of a saturated solution of NH4Cl (250 ml)and extracted with CH2Cl2 (3 30 ml). The combined organicextracts were dried over Na2SO4 and evaporated. The subsequentpurification by column chromatography yielded the desiredferrocenyl amino alcohols.

Reference： [1]Ak, Bünyamin; Aydemir, Murat; Durap, Feyyaz; Meriç, Nermin; Baysal, Akin [Inorganica Chimica Acta, 2015, vol. 438, p. 42 - 51]

75
[ 1271-48-3 ]
[ 2549-14-6 ]
(R)-bis[N-(2-hydroxy-2-phenyl)ethyl]-1,1'-ferrocenylmethyldiamine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2015,vol. 26,p. 1307 - 1313

76
[ 1271-48-3 ]
[ 140-53-4 ]
1,1'-ferrocenyldi[2-(4-chlorophenyl)acrylonitrile] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With piperidine; In melt; at 20℃; for 0.0833333h;Milling;	General procedure: The general procedure for the synthesis and characterization of 1,1?-ferrocenyl-diacrylonitriles is displayed in Scheme 1 and has been previously reported [20]. In brief, 1,1?-ferrocenedicarboxaldehyde and substituted phenylacetonitriles (2.2 Eq.) were mixed in a Pyrex tube fitted with a ground glass joint. The compounds were thoroughly ground in the open air with a glass rod in the presence of 1-2 drops of piperidine to form a melt. The melt was first dried in open air, followed by drying under a vacuum line. The dry products were purified by means of silica gel chromatography. Formation of the products was determined by use of IR or NMR spectroscopy (1H- and 13C-NMR). In the solid-state IR spectra, the formation of the products was characterized by the disappearance of the sharp carbonyl absorption band at approximately 1650cm-1 and the appearance of a strong nitrile absorption band at approximately 2200cm-1. The 1H- and 13C-NMR spectra showed the disappearance of the carbonyl resonance (?10ppm) and the appearance of alkene resonance peaks (?7.4ppm). Pure compounds were further analyzed by melting point determination (DSC), mass spectrometry, microanalysis, and X-ray diffraction. 4.2.2 1,1?-Ferrocenyldi[-2(4-chlorophenyl)acrylonitrile] (para-Cl catalyst) The general procedure for synthesis of this catalyst is described in Section 4.2 and involves the use of 1,1?-ferrocenyldicarboxaldehyde (145.0 mg, 0.60 mmol) and 4-chlorophenylacetonitrile (200.0 mg, 1.32 mmol). Upon grinding the two substances in the presence of a drop of piperidine (0.05 ml), the solid mixture transformed into a brown paste, which eventually turned into a red solid. The reaction completion was monitored by using preparative TLC plates with a solvent system of hexane/dichloromethane (1:1). The red paste was dried, then purified by means of column chromatography in hexane and dichloromethane (1:1) solution to obtain the product as a red solid and 87.0 mg of the recovered starting 1,1?-ferrocenedicarboxaldehyde. Characterization of the red solid gave the para-Cl catalysts (153.0 mg, 52%) m.p. 238 C; IR (cm-1) 3087, 3050, 2209, 1898, 1649, 1598, 1493, 1456, 1411, 1374, 1329, 1305, 1251, 1186, 1094, 1037, 997, 917, 827, 815, 774, 745, 540, 499, 489, 437, 396; 1H-NMR spectra (CDCl3) 7.22 (4H, s, ArH), 7.18 (4H, s, ArH), 7.15 (2H, s, CH), 5.06 (4H, s, C5H4), 4.56 (4H, s, C5H4); 13C-NMR spectra (CDCl3) 140.1, 129.1, 126.0, 79.3, 72.7, 71.5; HR-MS (C28H18Cl2FeN2) ES: [M] + m/z calc. 508.0196, found 508.0199.

Reference： [1]Journal of Solid State Chemistry,2016,vol. 235,p. 202 - 211

77
[ 1271-48-3 ]
[ 2338-75-2 ]
1,1'-ferrocenyldi[2-(4-{trifluoromethyl}phenyl)acrylonitrile] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With piperidine; In melt; at 20℃; for 0.0833333h;Milling;	General procedure: The general procedure for the synthesis and characterization of 1,1?-ferrocenyl-diacrylonitriles is displayed in Scheme 1 and has been previously reported [20]. In brief, 1,1?-ferrocenedicarboxaldehyde and substituted phenylacetonitriles (2.2 Eq.) were mixed in a Pyrex tube fitted with a ground glass joint. The compounds were thoroughly ground in the open air with a glass rod in the presence of 1-2 drops of piperidine to form a melt. The melt was first dried in open air, followed by drying under a vacuum line. The dry products were purified by means of silica gel chromatography. Formation of the products was determined by use of IR or NMR spectroscopy (1H- and 13C-NMR). In the solid-state IR spectra, the formation of the products was characterized by the disappearance of the sharp carbonyl absorption band at approximately 1650cm-1 and the appearance of a strong nitrile absorption band at approximately 2200cm-1. The 1H- and 13C-NMR spectra showed the disappearance of the carbonyl resonance (?10ppm) and the appearance of alkene resonance peaks (?7.4ppm). Pure compounds were further analyzed by melting point determination (DSC), mass spectrometry, microanalysis, and X-ray diffraction. 4.2.3 1,1?-Ferrocenyldi[-2(4-{trifluoromethyl}phenyl)acrylonitrile] (para-CF3 catalyst)T he general procedure for synthesis of this catalyst is described in Section 4.2 and involves the use of 1,1?-ferrocenyldicarboxaldehyde (145.0 mg, 0.60 mmol) and 4-(trifluoromethyl)phenylacetonitrile (244.0 mg, 1.32 mmol). Upon grinding a deep red paste was formed, which was dried to obtain a red solid. The reaction completion was monitored by use of preparative TLC plates with a solvent system of hexane/diethyl ether (1:1) and the product was then purified by means of column chromatography with a solvent system of hexane/diethyl ether (1:1) to obtain red crystals as the product (268.0 mg, 78%) and 31.0 mg of the recovered starting 1,1?-ferrocenedicarboxaldehyde. Product m.p. 252 C; IR (cm-1) 3059, 2924, 2216, 1617, 1593, 1456, 1421, 1324, 1255, 1157, 1111, 1070, 1000, 925, 824, 729, 667, 642, 621, 584, 477, 421; 1H-NMR spectra (CDCl3) 7.40 (8H, q, J 5 Hz, ArH), 7.31 (2H, s, CH), 5.12 (4H, s, C5H4), 4.62 (4H, s, C5H4); 13C-NMR spectra (CDCl3) 141.4, 125.9, 124.8, 107.3, 79.1, 77.2, 73.1, 72.9; HR-MS (C30H18F6FeN2) ES: [M]+ m/z calc. 576.0724, found 576.0717.

Reference： [1]Journal of Solid State Chemistry,2016,vol. 235,p. 202 - 211

78
[ 1271-48-3 ]
[ 876-31-3 ]
1,1'-ferrocenyldi[2-(4-cyanophenyl)acrylonitrile] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With piperidine; In melt; at 20℃; for 0.0833333h;Milling;	General procedure: The general procedure for the synthesis and characterization of 1,1?-ferrocenyl-diacrylonitriles is displayed in Scheme 1 and has been previously reported [20]. In brief, 1,1?-ferrocenedicarboxaldehyde and substituted phenylacetonitriles (2.2 Eq.) were mixed in a Pyrex tube fitted with a ground glass joint. The compounds were thoroughly ground in the open air with a glass rod in the presence of 1-2 drops of piperidine to form a melt. The melt was first dried in open air, followed by drying under a vacuum line. The dry products were purified by means of silica gel chromatography. Formation of the products was determined by use of IR or NMR spectroscopy (1H- and 13C-NMR). In the solid-state IR spectra, the formation of the products was characterized by the disappearance of the sharp carbonyl absorption band at approximately 1650cm-1 and the appearance of a strong nitrile absorption band at approximately 2200cm-1. The 1H- and 13C-NMR spectra showed the disappearance of the carbonyl resonance (?10ppm) and the appearance of alkene resonance peaks (?7.4ppm). Pure compounds were further analyzed by melting point determination (DSC), mass spectrometry, microanalysis, and X-ray diffraction. 4.2.1 1,1?-Ferrocenyldi[-2(4-cyanophenyl)acrylonitrile] (para-CN catalyst) The general procedure for the synthesis of this catalyst is described in Section 4.2 and involves the use of 1,1?-ferrocenyldicarboxaldehyde (145.0 mg, 0.60 mmol) and 4-cyanophenylacetonitrile (188.0 mg, 1.32 mmol). Upon grinding, a deep maroon paste was formed which was dried to obtain a maroon solid. Reaction completion was monitored by use of preparative TLC plates with a solvent system of hexane/diethyl ether (1:1). The final product was then purified by means of column chromatography with a solvent system of hexane/diethyl ether (1:1) to obtain dark maroon crystals (219.0 mg, 74%) as the desired product and 37.0 mg of the recovered starting (1,1?-ferrocenedicarboxaldehyde). Product d.p. ca. 325 C; IR (cm-1) 3182, 2926, 2852, 2213, 1608, 1587, 1510, 1452, 1417, 1371, 1319, 1251, 1180, 1035, 996, 918, 830, 819, 542, 501, 486, 456, 425; 1H-NMR spectra (CDCl3) 7.55 (4H, d, J 8.4 Hz, ArH), 7.47 (4H, d, J 8.5 Hz, ArH), 7.34 (2H, s, CH), 5.08 (4H, s, C5H4), 4.65 (4H, s, C5H4); 13C-NMR spectra (CDCl3) 132.7, 125.3, 77.2, 73.7, 72.2; HR-MS (C30H18FeN4) ES: [M + H+] m/z calc. 491.0959, found 491.0969.

Reference： [1]Journal of Solid State Chemistry,2016,vol. 235,p. 202 - 211

79
[ 1293-65-8 ]
[ 68-12-2 ]
[ 1271-48-3 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 2544 - 2547

80
[ 1122-54-9 ]
[ 1271-48-3 ]
1,1′-bis(4,2′:6′,4″-terpyridin-4′-yl)ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.8%	With ammonium hydroxide; potassium hydroxide; In ethanol; at 20℃;	1,1?-Ferrocenedicarboxaldehyde (0.20g, 0.83mmol) was dissolved in EtOH (70mL). 4-Acetylpyridine (0.45g, 3.63mmol) and KOH (0.23g, 4.13mmol) were added to the solution. Aqueous NH3 (32%, 6.36mL) was slowly added to the reaction mixture which was then stirred at room temperature overnight. The solid that formed was collected by filtration, washed with EtOH (3×20mL) and H2O (3×20mL) and dried in vacuo. Compound 1 was isolated as a red powder (0.24g, 0.37mmol, 44.8%). Decomp >300C. 1H NMR (500MHz, CDCl3, 298K) delta/ppm 8.60 (m, 4H, HA2), 7.67 (m, 4H, HA3), 7.41 (m, 2H, HB3), 4.85 (m, 2H, HCp), 4.59 (m, 2H, HCp). IR (nu/cm-1) 3032 (w), 1612 (m), 1596 (s), 1559 (m), 1541 (m), 1431 (m), 1411 (m), 1398 (m), 1261 (w), 1226 (w), 1067 (w), 1036 (w), 994 (m), 892 (w), 827 (s), 764 (w), 741 (w), 679 (w), 649 (m), 629 (s), 597 (w), 570 (m), 508 (m), 475 (m). MALDI-MS (alpha-cyano-4-hydroxycinnamic acid matrix) m/z 649.52 [M+H]+ (calc. 649.18). Found C 70.44, H 4.65, N 12.38; calculated for C40H28FeN62H2O C 70.18, H 4.71, N 12.28.

Reference： [1]Inorganic Chemistry Communications,2016,vol. 70,p. 118 - 120

81
[ 1271-48-3 ]
5-(4-methylphenyl)isoxazole-3-carbohydrazonamide [ No CAS ]
1,1'-bis[N'-methylene-5-(4-methylphenyl)isoxazole-3-carbohydrazonamide]ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With acetic acid; In methanol; for 1h;Reflux;	General procedure: A mixture of 2 mmol of carbohydrazonamide 1, 2 mmol of the corresponding aldehyde (or 1 mmol of diformylferrocene), 30 mL of anhydrous methanol, and 3 drops of glacial acetic acid was refluxed for 1 h. The hot solution was filtered, cooled, and maintained for 10-15 h at 0-5C. The resulting compounds 2-23 were separated by filtration on a glass porous filter, washed with a small amount (5-10 mL) of cold methanol, and dried in air. The condensation of carbohydrazonamide 1 with 1,1'-diacetylferrocene was carried out in benzene at refluxat a ratio of 1 : diacetylferrocene = 2 : 1. The product was isolated in a similar manner, but washed with cold benzene

Reference： [1]Russian Journal of General Chemistry,2016,vol. 86,p. 2059 - 2066
Zh. Obshch. Khim.,2016,vol. 86,p. 1495 - 1502,7

82
[ 1271-48-3 ]
[ 53348-04-2 ]
C₂₆H₁₈FeN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In nitrobenzene; at 55℃; for 15h;Inert atmosphere; Schlenk technique;	To a solution of <strong>[53348-04-2]9,10-diaminophenanthrene</strong> (62.5 mg,0.3 mmol) and 1,10-ferrocene dicarboxaldehyde (72.6 mg,0.3 mmol) in nitrobenzene (20 mL) was added acetic acid(0.5 mL). The resulting mixture was stirred at 55 C for 15 hand then neutralized to pH 7 with a NaHCO3 solution. ThenH2O (50 mL) was added and the solution was extracted withCHCl3 (2 x 50 mL). The organic layer was added to a suspension ofchloromethyltriphenylphosphonium chloride (104.2 mg, 0.3 mmol)and potassium tert-butoxide (33.7 mg, 0.3 mmol) in dry THF(4 mL) under nitrogen of 0 C. The mixture was warmed to refluxtemperature for 2 h. After cooling to room temperature, water(5 mL) was added and the mixture extracted with hexane. Thesolvent was removed under reduced pressure and the residual oilwas purified by silica gel column chromatography using hexane-dichloromethane (4:1) as the eluent. HC=CFcIP was obtained asan orange-red solid. 76.5% (98 mg) yield. m.p. 65 C. Anal. Calc.,C27H18FeN2: C, 76.07; H, 4.26; N, 6.57. Found: C, 76.01; H, 4.19;N, 6.51. IR (KBr, cm1): 3108 (w), 3045 (w), 1587 (m), 1568 (m),1549 (w), 1448 (w), 1265 (w), 887 (w). TOF-MS: 427 [M+H]+. 1HNMR (DMSO-d6): delta 9.58 (s, 1H, H-16b), 7.92 (t, 2H, H-6b, 12b orH-7b,11b, 3J 7.6), 7.77 (d, 2H, H-8b, 10b or H-5b,13b, 3J 7.6), 7.60(d, 2H, H-8b, 10b or H-5b, 3J 7.6), 7.41 (t, 2H, H-6b, 12b orH-7b,11b, 3J 7.6), 4.96 (s, 2H, H-Cp), 4.81 (s, 2H, H-Cp), 4.69 (s,2H, H-Cp), 4.58 (s, 2H, H-Cp), 3.08 (s, 1H, H-12a). 13C NMR(DMSO-d6): delta 152.14 (Ar), 129.90 (Ar), 126.84 (Ar), 125.00 (Ar),123.02 (Ar), 121.00 (Ar), 80.69 (C=C), 78.54 (C=C), 75.63 (CACp),72.99 (CACp), 70.99 (CACp), 69.73 (CACp).

Reference： [1]Polyhedron,2016,vol. 119,p. 575 - 583

83
[ 1271-48-3 ]
[ 118-93-4 ]
1,1'-bis[(E)-3-(2-hydroxyphenyl)-3-oxopropenyl]ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25.8%		General procedure: In a typical procedure, 1.39 mmol of 2?-hydroxyacetophenone (for 1 and 3) or 2?-hydroxy-4?-methoxyacetophenone (for 2 and 4) were dissolved in 40 ml of methanol. To this solution, 4 equivalent of potassium hydroxide were added and stirred for 15 min at room temperature. Then, 1.40 mmol of the appropriate ferrocenecarboxaldehyde derivative, (i.e. 1-ferrocenecarboxaldehyde for 1 and 2 or 1,1-ferrocenedicarboxaldehyde for 3 and 4) were added. The mixture was stirred during three days at room temperature. Then, methanol was evaporated in vacuum (rotary evaporator) and the crude reaction mixture was submitted to column chromatography (silica gel 60, Ethyl acetate: Hexane = 3:10 v/v).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 437 - 441

84
[ 552-41-0 ]
[ 1271-48-3 ]
1,1'-bis[(E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxopropenyl]ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30.3%		General procedure: In a typical procedure, 1.39 mmol of 2?-hydroxyacetophenone (for 1 and 3) or 2?-hydroxy-4?-methoxyacetophenone (for 2 and 4) were dissolved in 40 ml of methanol. To this solution, 4 equivalent of potassium hydroxide were added and stirred for 15 min at room temperature. Then, 1.40 mmol of the appropriate ferrocenecarboxaldehyde derivative, (i.e. 1-ferrocenecarboxaldehyde for 1 and 2 or 1,1-ferrocenedicarboxaldehyde for 3 and 4) were added. The mixture was stirred during three days at room temperature. Then, methanol was evaporated in vacuum (rotary evaporator) and the crude reaction mixture was submitted to column chromatography (silica gel 60, Ethyl acetate: Hexane = 3:10 v/v).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 437 - 441

85
[ 1271-48-3 ]
4,4-difluoro-8-(4-aminophenyl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
1,1′-(ferrocen-1,1′-diyl)-bis-(N-(4-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacen-8-yl)phenyl)methanimine) [ No CAS ]

Reference： [1]Dalton Transactions,2017,vol. 46,p. 1124 - 1133

86
[ 1271-48-3 ]
[ 1730-25-2 ]
1,1'-bis(1-hydroxy-3-butenyl)ferrocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.5%	In tetrahydrofuran; at 20℃;Inert atmosphere; Cooling with ice; Schlenk technique;	To a dry Schlenk flask was added 3.100 g (16.6 mmol) of vacuum dried ferrocene and 12.0 mL of n-hexane,Stirred to a suspension; then 25.0 mL of n-butyllithium (1.6 M, 40.0 mmo1)Then, 6.0 mL of tetramethylethylenediamine (40.0 mmo1) was added dropwise over a period of about 60 min,The reaction was continued for 16 h at room temperature; the resulting mixture was filtered,The resulting orange-red powder was washed three times with 15.0 mL of n-hexane, i.e., about 15.0 mmo1 of 1,1'-bis-lithium ferrocene,To this was added 35.0 mL of n-hexane,Stirred to a suspension; another 12 mL of anhydrous ether was added 2.8 mL (36.0 mmo1) of dimethylformamide,The solution was added dropwise to the suspension (about 30 min) under ice-water bath cooling. After the dropwise addition, the ice-water bath was removed and allowed to warm to room temperature and stirred for about 30 minutes.Add 50.0 mL (4.0 M, 0.2 mol) of hydrochloric acid,Continue to react for 15 min after static, set stratification,The aqueous layer was extracted three times with 15.0 mL of dichloromethane,A dark red solid ferrocene dialdehyde was obtained 3.363 g. Addition hydrolysis reaction: Dissolve 3.363 g of ferrocene aldehyde in 200.0 mL of anhydrous tetrahydrofuran250 mL of dry Schlenk vials,Under the protection of dry nitrogen,Under ice-cooling, 15.0 mL (2.0 M solution in tetrahydrofuran) was slowly added dropwise to a solution of allylmagnesium bromide(Industrial grade reagent), dropwise to the room temperature and stir the reaction overnight,After the end of the reaction, the filtrate was added with 2 plastic dropper saturated ammonium chloride solution, the volatile solvent was removed under reduced pressure,Re-dissolved in dichloromethane, washed with saturated brine and deionized water,After drying, the volatile solvent is removed,To give 3.995 g 1,1'-bis (1-hydroxy-3-butenyl) ferrocene in a yield of73.5% (relative to the raw material ferrocene),

Reference： [1]Patent: CN103665053,2016,B .Location in patent: Paragraph 0040-0044

87
[ 1271-48-3 ]
[ 536-74-3 ]
[ 103-49-1 ]
C₅₆H₄₈FeN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With (S)-[AuCl2(eta2-C,N-C6H4CH(Me)NMe2)]; at 40℃; for 48h;Inert atmosphere; Schlenk technique; Enzymatic reaction;	To a dry nitrogen flushed schlenk flask was added ferrocene-1-1?-dicarbaldehyde (0.12 g,0.5 mmol) dibenzylamine (190 muL, 1 mmol), phenylacetylene (131 muL, 1.2 mmol), and(S)-[AuCl2(eta2-C,N-C6H4CH(Me)NMe2)] 4 (2 mg, 1 mol %). The mixture was stirred at 40 C for 48 h, then extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo.The product was purified by column chromatography on silica gel using hexane/EtOACeluent.

Reference： [1]Journal of Organometallic Chemistry,2017,vol. 846,p. 251 - 262

88
[ 1271-48-3 ]
[ 3281-08-1 ]
[Fe(Cp(2-(quinolin-8-yloxy)acetohydrazide))]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetic acid; In methanol; for 0.833333h;Reflux;	General procedure: A solution of ferrocenecarboxaldehyde (0.86 g, 4 mmol) in dry MeOH(5 mL) containing AcOH (0.1 mL) was added dropwise to a stirred solution of 2-(quinolin-8-yloxy)acetohydrazide (0.87 g, 4 mmol) indry MeOH (15 mL). The reaction mixture was refluxed for 50 min andthen cooled in an ice-bath for 30 min. The resulting yellow precipitate was collected by filtration and washed several times with MeOH,followed by recrystallisation from CH2Cl2/MeOH (1:4, v:v) to give 1.

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 491 - 496

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P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1271-48-3 ] {[proInfo.proName]}

Quality Control of [ 1271-48-3 ]

Related Doc. of [ 1271-48-3 ]

Product Details of [ 1271-48-3 ]

Calculated chemistry of [ 1271-48-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1271-48-3 ]

Application In Synthesis of [ 1271-48-3 ]

[ 1271-48-3 ] Synthesis Path-Upstream 1~10

[ 1271-48-3 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry