80565-30-6|4'-Chloro-[1,1'-biphenyl]-4-carbaldehyde| Ambeed

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Quality Control of [ 80565-30-6 ] Purity: 97% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 80565-30-6 ]

CAS No. :	80565-30-6
Formula :	C₁₃H₉ClO
M.W :	216.66
SMILES Code :	O=CC1=CC=C(C2=CC=C(Cl)C=C2)C=C1
MDL No. :	MFCD01631911
InChI Key :	UXCMNUUPBMYDLJ-UHFFFAOYSA-N
Pubchem ID :	592570

Safety of [ 80565-30-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 80565-30-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	62.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.27
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.06
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.82
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.53
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	4.33
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.2
Solubility	0.0136 mg/ml ; 0.0000629 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.12
Solubility	0.0163 mg/ml ; 0.0000754 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.49
Solubility	0.000708 mg/ml ; 0.00000327 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.74 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.52

Application In Synthesis of [ 80565-30-6 ]

* 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.

Downstream synthetic route of [ 80565-30-6 ]

[ 80565-30-6 ] Synthesis Path-Downstream 1~35

1
[ 34284-87-2 ]
[ 80565-30-6 ]
[ 98629-82-4 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 873 - 878.

2
[ 4885-02-3 ]
[ 2051-62-9 ]
[ 80565-30-6 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 873 - 878.

3
[ 80565-30-6 ]
[ 118395-73-6 ]
C₈₆H₉₇Cl₃N₁₀O₂₆ [ No CAS ]
oritavancin [ No CAS ]
C₉₉H₁₀₆Cl₄N₁₀O₂₆ [ No CAS ]
C₉₉H₁₀₆Cl₄N₁₀O₂₆ [ No CAS ]

References: [1]Journal of Antibiotics,1996,vol. 49,p. 575 - 581.
[2]Journal of Antibiotics,1996,vol. 49,p. 575 - 581.

4
[ 80565-30-6 ]
[ 118395-73-6 ]
C₈₆H₉₇Cl₃N₁₀O₂₆ [ No CAS ]
oritavancin [ No CAS ]
C₉₉H₁₀₆Cl₄N₁₀O₂₆ [ No CAS ]
C₁₁₂H₁₁₅Cl₅N₁₀O₂₆ [ No CAS ]

References: [1]Journal of Antibiotics,1996,vol. 49,p. 575 - 581.

5
[ 106-39-8 ]
[ 1122-91-4 ]
[ 80565-30-6 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 3841 - 3844.

6
[ 5452-35-7 ]
[ 80565-30-6 ]
[1-(4'-Chloro-biphenyl-4-yl)-meth-(E)-ylidene]-cycloheptyl-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 15 - 30.

7
[ 80565-30-6 ]
LY₂₆₄₈₂₆ triacetate [ No CAS ]
C₈₆H₉₅Cl₃N₁₀O₂₆ [ No CAS ]

References: [1]Journal of Antibiotics,1998,vol. 51,p. 560 - 569.

8
[ 1679-18-1 ]
[ 1122-91-4 ]
[ 80565-30-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In water; at 75℃; for 5h;	General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.
95%	With 1-phenylethanone-O-(4-chloro-phenyl)oxime; tetrabutylammomium bromide; potassium carbonate; palladium dichloride; In water; at 27℃; for 6h;Green chemistry;	General procedure: All the reactions were carried out in open atmosphere. A mixture of arylbromide (0.5 mmol), aryl boronic acid (0.55 mmol), K2CO3 (1 mmol), PdCl2(1 mol %), ligand (2 mol %), TBAB (0.5 mmol), and water (4 mL) was stirred atroom temperature for the indicated time in a 25 mL round bottom flask. Theprogress of the reaction was monitored using TLC (Merck silica gel 60F254plates) under UV light. After completion, the reaction mixture was diluted withbrine (10 mL) and extracted with ether (3 10 mL). The combined extract wasdried over anhydrous Na2SO4. After evaporation of ether under vacuum, theproduct was isolated by short-chromatography {silica gel (60-120 mesh), ethylacetate-hexane; 0.5:9.5}. The isolated products were confirmed by comparingtheir 1H and 13C NMR and mass spectral data with reported samples
94%	With palladium diacetate; sodium carbonate; In 1,2-dimethoxyethane; for 2.5h;Inert atmosphere; Reflux;	(b) A mixture of 4-chlorobenzeneboronic acid (19.4 g, 1 equiv), 4-bromobenzaldehyde (22.9 g, 1 equiv), palladium(II) acetate (1.4 g, 0.05 equiv) aqueous sodium carbonate (30.3 g in 144 ml solution, 2 equiv) and dimethoxyethane (500 ml) was stirred at reflux under argon for 2.5 h, then evaporated to low volume and diluted with dichloromethane. Workup continued as in (a) above to give identical material (25.2 g, 94%). 1H-NMR (CDCl3) delta 10.05 (1H, s), 7.96 (2H, d), 7.73 (2H,d), 7.57 (2H, d), 7.46 (2H, d); MS (AP+) found (M+1)=217, C13H935ClO requires 216.

90%	With [2,6-(iPr)2C6H3-N=C(Ph)-C(Ph)(Me)-OH]PdCl2; sodium carbonate; In ethanol; water; at 60℃; for 2h;	General procedure: In a round bottle, palladium complexes (0.01 mol% mmol), aryl halides (1.0 mmol), arylboronic acid (1.2 mmol), base (2.0 mmol) and 4 ml of solvent were added with a magnetic stir bar. The reaction mixture was carried out at the described temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 ml), followed by extraction twice (2 × 5 ml) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20/1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR.
90%	With sodium hydroxide; In water; at 80℃; for 0.5h;Inert atmosphere; Green chemistry;	General procedure: 5 mL distilled water was taken in a 25 mL round bottom flask, equipped with a magnetic bar and a water condenser, and deoxygenated with nitrogen gas for 5 min. Aryl halide (1 mmol), arylboronic acid (1.2 mmol), NaOH (1.2 mmol) and Pd-gamma-Fe2O3 (20 mg) were added to it and allowed to stir at 80 C under nitrogen atmosphere. The progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was recovered using an external magnet. The reaction mixture was extracted with EtOAc (3 x 10 mL) and the combined organic layer was washed with water, brine solution and dried over anhydrous Na2SO4. The crude product was concentrated in a rotary evaporator and purified by column chromatography. The purified compounds were characterized by 1H and 13C NMR.
84%	With C26H18Cl2N6NiO2; potassium carbonate; In toluene; for 8h;Reflux;	General procedure: (1.0 mmol) and K2CO3 (2.0 mmol) in toluene (10 mL),1(0.5 mol%) were added. The resultant mixture was refluxed for 8 h, there action mixture was then cooled to room temperature, H2O(10 mL) added and the organic layer was extracted with EtOAc(3x20 mL). The solvent was stripped off and the remaining residue was purified by column chromatography (n-hexane-EtOAc) to yield the pure product. The products were confirmed by 1H NMR. For the double cross-coupling reaction the procedure was similar to that mentioned above where dibromide (1.0 mmol),arylboronic acid (2.0 mmol), 1 (1.0 mol%) and K2CO3 (4.0 mmol) in toluene (10 mL) were used.
80%	With 3,5-di-tert-butyl-2-hydroxybenzaldehyde; potassium carbonate; palladium dichloride; In ethanol; water; at 20℃; for 2h;	General procedure: To a round bottle with a magnetic stir bar, ligand (0.01% mmol), PdCl2 (0.01% mmol), aryl halides (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol) and 6 ml of solvent were added. The reaction mixture was conducted at room temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 mL), followed by extraction twice (2×5 mL) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The conversions rates were analyzed by gas chromatography, based on the peak area normalization method. The corrected factor was determined by samples against a standard of n-heptane. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20:1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux;	Example 83Synthesis of 4'-chlorobiphenyl-4-carbaldehyde (72)(72)[00224] Pd(PPh3)4 (1.16 g, 1.0 mmol) was added to a solution of 4-bromobenzaldehyde (1 85 g, 10.0 mmol) and A- chlorophenylboionic acid (1 56 g, 10 0 mmol) in 20 mL of 1,4-dioxane and 10 mL of 2M NaCO3 (20.0 mmol) under argon atmosphere Then the mixture was refluxed overnight The reaction was checked for completion by LC-MS The solvent was evaporated. The residue was extracted with ethyl acetate. The combined orgamc layer was dried over Na2SO4 and evaporated. The crude material was purified by flashing chromatography to give 4'- chlorobiphenyl-4-carbaldehyde £72} (0 735 g).
	With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate; In water; at 25℃;	A mixture of Compound 1A (5.13 g, 33 mmol), (4-chlorophenyl)boronic acid (5.52 g, 30 mmol), tetrabutylammonium bromide (9.66 g, 30 mmol), K2CO3 (8.28 g, 60 mmol), and Pd(PPh3)Cl2 (420 mg, 0.66 mmol) in water (240 mL) was stirred at 25 C overnight. The mixture was extracted with dichloromethane (200 mL x 2). The combined organic extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 2% v/v) to yield Compound IB: LC-MS (ESI) m/z: 217 [M+H]+. -NMR (CDCh, 400 MHz): d (ppm) 7.45 (d, J= 8.4 Hz, 2H), 7.56 (d, J= 8.4 Hz, 2H), 7.21 (d, J= 8.4 Hz, 2H), 7.95 (d, J= 8.4 Hz, 2H), 10.06 (s, 1H).

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 5553 - 5566.
[2]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 578 - 584.
[3]Green Chemistry,2016,vol. 18,p. 967 - 973.
[4]ChemMedChem,2016,p. 2194 - 2204.
[5]RSC Advances,2016,vol. 6,p. 89621 - 89626.
[6]Applied Organometallic Chemistry,2012,vol. 26,p. 701 - 706.
[7]Applied Organometallic Chemistry,2012,vol. 26,p. 425 - 429.
[8]Tetrahedron Letters,2014,vol. 55,p. 3038 - 3040.
[9]Chemical Communications,2008,p. 6318 - 6320.
[10]Patent: US9266841,2016,B2 .Location in patent: Page/Page column 14.
[11]Chinese Journal of Chemistry,2014,vol. 32,p. 1225 - 1232.
[12]Journal of Organometallic Chemistry,2013,vol. 729,p. 95 - 102.
[13]Journal of Organometallic Chemistry,2018,vol. 871,p. 96 - 102.
[14]Inorganica Chimica Acta,2016,vol. 449,p. 127 - 132.
[15]Chemistry Letters,2019,vol. 48,p. 547 - 550.
[16]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 15 - 30.
[17]Dalton Transactions,2006,vol. 6,p. 1322 - 1330.
[18]Tetrahedron,2008,vol. 64,p. 4637 - 4643.
[19]Patent: WO2008/140973,2008,A1 .Location in patent: Page/Page column 69.
[20]Chinese Journal of Chemistry,2012,vol. 30,p. 1543 - 1547.
[21]Patent: WO2019/104011,2019,A1 .Location in patent: Paragraph 00293-00295.

9
[ 80565-30-6 ]
[ 256349-90-3 ]
C₉₀H₉₇Cl₃N₁₀O₂₇ [ No CAS ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 12608 - 12609.

10
[ 80565-30-6 ]
C₇₈H₉₇ClN₁₀O₂₈ [ No CAS ]
C₉₁H₁₀₆Cl₂N₁₀O₂₈ [ No CAS ]

References: [1]Journal of Antibiotics,2001,vol. 54,p. 455 - 459.

11
[ 80565-30-6 ]
[ 354123-15-2 ]
C₁₀₁H₁₀₈Cl₂N₁₀O₂₈ [ No CAS ]

References: [1]Journal of Antibiotics,2001,vol. 54,p. 455 - 459.

12
[ 21700-74-3 ]
[ 1122-91-4 ]
[ 80565-30-6 ]

References: [1]Synthesis,2001,p. 2231 - 2233.

13
[ 80565-30-6 ]
C₆₈H₇₉Cl₂N₉O₂₅ [ No CAS ]
C₈₁H₈₈Cl₃N₉O₂₅ [ No CAS ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 12722 - 12723.

14
[ 80565-30-6 ]
[ 15996-82-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.

15
[ 80565-30-6 ]
[ 74-89-5 ]
[ 304693-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	With molecular sieve; magnesium sulfate; In tetrahydrofuran; ethanol; at 20℃; for 16h;	Intermediate A2-N-Methyl-4-(4-chlorophenyl)benzylamine A mixture of Intermediate A1 (3.5 g, 1 equiv), methylamine (32.3 ml of a 2M solution in THF, 4 equiv) and anhydrous magnesium sulphate (4.47 g, 2 equiv) was stirred at room teperature for 16 h, then filtered, the solid washed thoroughly with ethyl acetate, and the combined filtrates evaporated to a white solid (3.7 g).This imine intermediate was suspended in ethanol (100 ml), cooled in ice and sodium borohydride (0.61 g, 1 equiv) added portionwise.The ice bath was removed, and the mixture stirred for 45 min at room temperature then at 50 C. for 1 h.The solvent was removed in vacuo, water was added to the residue, and the product extracted into dichloromethane.Drying and evaporation of the solvent gave a white solid (3.56 g).1H-NMR (CDCl3) delta 7.51 (4H, d), 7.40 (4H, d), 3.79 (2H, s), 2.48 (3H, s); MS (APCI+) found (M+1)=232, C14H1435ClN requires 231.
	With sodium tetrahydroborate; magnesium sulfate; In tetrahydrofuran; at 20℃; for 16h;	A mixture of Intermediate A1 (3.5 g, 1 equiv), methylamine (32.3 ml of a 2M solution in THF, 4 equiv) and anhydrous magnesium sulphate (4.47 g, 2 equiv) was stirred at room teperature for 16 h, then filtered, the solid washed thoroughly with ethyl acetate, and the combined filtrates evaporated to a white solid (3.7 g). This imine intermediate was suspended in ethanol (100 ml), cooled in ice and sodium borohydride (0.61 g, 1 equiv) added portionwise. The ice bath was removed, and the mixture stirred for 45 min at room temperature then at 50C. for 1 h. The solvent was removed in vacuo, water was added to the residue, and the product extracted into dichloromethane. Drying and evaporation of the solvent gave a white solid (3.56 g). 1H-NMR (CDCl3) ? 7.51 (4H, d), 7.40 (4H, d), 3.79 (2H, s), 2.48 (3H, s); MS (APCI+) found (M+1)=232, C14H1435ClN requires 231
3.7 g	With magnesium sulfate; In tetrahydrofuran; at 20℃; for 16h;	N-Methyl-4-(4-chlorophenyl)benzylamine A mixture of Intermediate A1 (3.5 g, 1 equiv), methylamine (32.3 ml of a 2M solution in THF, 4 equiv) and anhydrous magnesium sulphate (4.47 g, 2 equiv) was stirred at room temperature for 16 h, then filtered, the solid washed thoroughly with ethyl acetate, and the combined filtrates evaporated to a white solid (3.7 g). This imine intermediate was suspended in ethanol (100 ml), cooled in ice and sodium borohydride (0.61 g, 1 equiv) added portionwise. The ice bath was removed, and the mixture stirred for 45 min at room temperature then at 50 C. for 1 h. The solvent was removed in vacuo, water was added to the residue, and the product extracted into dichloromethane. Drying and evaporation of the solvent gave a white solid (3.56 g). 1H-NMR (CDCl3) delta 7.51 (4H, d), 7.40 (4H, d), 3.79 (2H, s), 2.48 (3H, s); MS (APCI+) found (M+1)=232, C14H1435ClN requires 231.

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.
[2]Patent: US2004/167142,2004,A1 .Location in patent: Page/Page column 8.
[3]Patent: US2004/167142,2004,A1 .Location in patent: Page/Page column 8.
[4]Patent: US9266841,2016,B2 .Location in patent: Page/Page column 14; 15.

16
[ 80565-30-6 ]
[ 410077-88-2 ]
des-(N-methyl-D-leucyl)-N'-[p-(p-chlorophenyl)benzyl]eremomycin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1340 - 1347.

17
[ 80565-30-6 ]
[ 5748-41-4 ]

References: [1]Russian Journal of General Chemistry,2014,vol. 84,p. 782 - 788.
Zh. Obshch. Khim.,2014,vol. 84,p. 782 - 788,7.
[2]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 437 - 448.

18
[ 80565-30-6 ]
[ 345268-61-3 ]
C₈₈H₉₂Cl₃N₉O₂₇ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3027 - 3031.

19
[ 80565-30-6 ]
[ 64-19-7 ]
(3-{4-[(2S,3R,4S,5S,6R)-3-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-3,5-dimethoxy-phenyl}-propyl)-carbamic acid 2-trimethylsilanyl-ethyl ester [ No CAS ]
C₄₃H₆₁ClN₂O₁₂Si*C₂H₄O₂ [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 6585 - 6594.

20
[ 80565-30-6 ]
[ 64-19-7 ]
2C₆₇H₇₇Cl₂N₉O₂₅*3C₂HF₃O₂ [ No CAS ]
C₈₀H₈₆Cl₃N₉O₂₅*2C₂H₄O₂ [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 6585 - 6594.

21
[ 80565-30-6 ]
[ 64-19-7 ]
2C₆₈H₇₉Cl₂N₉O₂₅*3C₂HF₃O₂ [ No CAS ]
C₈₁H₈₈Cl₃N₉O₂₅*2C₂H₄O₂ [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 6585 - 6594.

22
[ 80565-30-6 ]
[ 141-43-5 ]
[ 817168-46-0 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8917 - 8920.

23
[ 7005-37-0 ]
[ 80565-30-6 ]
2-[4-(4-Chloro-phenyl)-phenyl]-1H-benzoimidazole-5-carboxylic Acid Amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1873 - 1885.

24
[ 106-39-8 ]
[ 128376-64-7 ]
[ 80565-30-6 ]

References: [1]Synthetic Communications,2007,vol. 37,p. 667 - 674.

25
[ 1122-91-4 ]
[ 195062-61-4 ]
[ 80565-30-6 ]

References: [1]Synthetic Communications,2007,vol. 37,p. 667 - 674.

26
[ 106-39-8 ]
[ 80565-30-6 ]

References: [1]Synthetic Communications,2007,vol. 37,p. 667 - 674.
[2]Synthesis,2001,p. 2231 - 2233.

27
[ 1122-91-4 ]
LiPh₂InH₂ [ No CAS ]
[ 80565-30-6 ]

References: [1]Synthetic Communications,2007,vol. 37,p. 667 - 674.

28
[ 80565-30-6 ]
[ 817168-37-9 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8917 - 8920.

29
[ 80565-30-6 ]
4-(4'-chloro-biphenyl-4-yl)-morpholine-2,3-dione [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8917 - 8920.

30
[ 80565-30-6 ]
[ 283170-27-4 ]

References: [1]Tetrahedron,2002,vol. 58,p. 6585 - 6594.

31
[ 80565-30-6 ]
[ 304693-35-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.
[2]Patent: US9266841,2016,B2 .

32
[ 80565-30-6 ]
1-(N-Methyl-N-(4-(4-chlorophenyl)benzyl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(1-methylpyrazol-4-ylmethyl)pyrimidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.

33
[ 80565-30-6 ]
1-(N-(4-(4-chlorophenyl)benzyl)amino-carbonylmethyl)-2-(4-fluorobenzyl)thio-5-(1-methyl-4-pyrazolylmethyl)-pyrimidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.

34
[ 80565-30-6 ]
1-(4-(4-chlorophenyl)benzylamino-carbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-methoxy-5-pyrimidylmethyl)-pyrimidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.

35
[ 80565-30-6 ]
1-(N-methyl-N-(4-(4-chlorophenyl)-benzyl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-methoxy-5-pyrimidylmethyl)pyrimidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 51 - 55.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 80565-30-6 ]

Aryls

A120968 [40137-29-9]

4-Chloro-2-methylbenzaldehyde

Similarity: 0.92

A300364 [104-88-1]

4-Chlorobenzaldehyde

Similarity: 0.92

A141934 [134-85-0]

4-Chlorobenzophenone

Similarity: 0.90

A121760 [90-98-2]

4,4-Dichlorobenzophenone

Similarity: 0.90

A407114 [101349-71-7]

4-Chloro-3-methylbenzaldehyde

Similarity: 0.89

Chlorides

A120968 [40137-29-9]

4-Chloro-2-methylbenzaldehyde

Similarity: 0.92

A300364 [104-88-1]

4-Chlorobenzaldehyde

Similarity: 0.92

A141934 [134-85-0]

4-Chlorobenzophenone

Similarity: 0.90

A121760 [90-98-2]

4,4-Dichlorobenzophenone

Similarity: 0.90

A407114 [101349-71-7]

4-Chloro-3-methylbenzaldehyde

Similarity: 0.89

Aldehydes

A120968 [40137-29-9]

4-Chloro-2-methylbenzaldehyde

Similarity: 0.92

A300364 [104-88-1]

4-Chlorobenzaldehyde

Similarity: 0.92

A103016 [587-04-2]

3-Chlorobenzaldehyde

Similarity: 0.89

A407114 [101349-71-7]

4-Chloro-3-methylbenzaldehyde

Similarity: 0.89

A707079 [103426-20-6]

3-Chloro-5-methylbenzaldehyde

Similarity: 0.89

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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

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CAS No.: 80565-30-6

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