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Chemical Structure| 37882-75-0
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Product Details of [ 37882-75-0 ]

CAS No. :37882-75-0 MDL No. :MFCD03931117
Formula : C8H4O2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :UBKNFAFBINVTOP-UHFFFAOYSA-N
M.W : 196.25 Pubchem ID :361865
Synonyms :

Calculated chemistry of [ 37882-75-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 8
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.48
TPSA : 90.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 4.59
Consensus Log Po/w : 2.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.267 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (Ali) : -3.84
Solubility : 0.0283 mg/ml ; 0.000144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.602 mg/ml ; 0.00307 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 37882-75-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37882-75-0 ]

* 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 [ 37882-75-0 ]

[ 37882-75-0 ] Synthesis Path-Downstream   1~67

  • 1
  • [ 251-41-2 ]
  • [ 68-12-2 ]
  • [ 37882-75-0 ]
YieldReaction ConditionsOperation in experiment
75% [Preparation of Heteroacene Compound]; PREPARATIVE EXAMPLE 1; (1) Synthesis of Compound 2; Thienothiophene 1 could be synthesized using a process developed by Iddon et al (Lance S. Fuller, Brian Iddon, Kevin A. Smith J. Chem. Soc., Perkin Trans. 1, 1997, 3465-3470). The thienothiophene (about 3.35 g, about 24 mmol) was dissolved in about 50 ml of dry ether, and the solution was added in droplets to about 100 ml of a dry ether solution containing butyl lithium (about 21 ml of about 2.5 M in a hexane solution) cooled to about 0 C., after which the temperature was gradually increased and a stirring process was performed at about room temperature for about 2 hours. To the turbid solution, dimethylformamide (DMF, about 4.6 ml) was slowly added in droplets and then the mixture was stirred overnight. About 50 ml of a saturated solution of ammonium chloride was added thereto, and a precipitate was filtered and then washed several times with water and ether, thus obtaining a desired compound 2 (yield about 75%).1NMR (CDCl3) d 10.1 (s, 2H), 8.05 (s, 2H).
~ 75% (1) Synthesis of Compound 2; Thienothiophene 1 could be synthesized using a process developed by Iddon et al (Lance S. Fuller, Brian Iddon, Kevin A. Smith J. Chem. Soc., Perkin Trans. 1, 1997, 3465-3470). The thienothiophene (about 3.35 g, about 24 mmol) was dissolved in about 50 ml of dry ether, and the solution was added in droplets to about 100 ml of a dry ether solution containing butyl lithium (about 21 ml of about 2.5 M in a hexane solution) cooled to about 0C, after which the temperature was gradually increased and a stirring process was performed at about room temperature for about 2 hours. To the turbid solution, dimethylformamide (DMF, about 4.6 ml) was slowly added in droplets and then the mixture was stirred overnight. About 50 ml of a saturated solution of ammonium chloride was added thereto, and a precipitate was filtered and then washed several times with water and ether, thus obtaining a desired compound 2 (yield about 75%). 1NMR (CDCl3) d 10. 1 (s, 2H), 8.05 (s, 2H) .
75% Thienothiophene 1 is synthesized in a method developed by Iddon and the like (Reference: Lance S. Fuller, Brian Iddon, Kevin A. Smith J. Chem. Soc., Perkin Trans. 1, 1997, 3465-3470). Thienothiophene (3.35 g, 24 mmol) is dissolved in 50 mL of dry ether, and the solution is added in a dropwise fashion to 100 mL of a dry ether solution including butyl lithium (2.5 M in 21 mL of a hexane solution) cooled down to 0 C., and the mixture is slowly heated up to room temperature and stirred for 2 hours. Subsequently, dimethyl formamide (DMF; 4.6 mL) is added in a dropwise fashion to the opaque solution, and the obtained mixture is stirred overnight. Then, 50 mL of an ammonium chloride-saturated solution is added thereto, and a precipitate therein is filtered and several times washed with water and ether to obtain desired Compound 2 (A yield: 75%). (0246) 1NMR (CDCl3) d 10.1 (s, 2H), 8.05 (s, 2H).
45% The synthetic route of CNP2V2TT molecule is shown as Scheme 1 . To a solution of <strong>[251-41-2]thieno[3, 2-b]thiophene</strong> 1 (0.56 g, 4 mmol) and in dry Et2O 50 ml, n-butyl lithium in n-hexane (6 ml, 10 mmol, 1.6 M) was added dropwise under an argon atmosphere at 0 C. The stirring was continued for 2 h and subsequently DMF (?1 ml, 13 mmol) was added and stirred for additional 1 day at ambient temperature. The solution was quenched with diluted aqueous HCl under vigorous stirring. The precipitate was filtered and dried to give a yellow solid 2 (354 mg, 1.8 mmol, yield 45%), which was practically pure and can be used to the next reaction. 1H NMR (500 MHz, CDCl3) delta8.01 (s, 2H, Ar-H), 10.05 (s, 2H, CHO);
17% General procedure: To a solution of <strong>[251-41-2]thieno[3,2-b]thiophene</strong> 7 (0.5 g, 3.56 mmol) in THF (10 ml) an n-butyllithiumsolution (2.5 in hexanes, 3.1 ml, 7.84 mmol, 2.2 equiv.) was carefully added at -78 C under argon and thereaction mixture was slowly allowed to warm to 0 C within 2 h. Anhydrousdimethylformamide (1 ml, excess) was then added and the reaction was stirred room temperature overnight. The solutionwas poured into aq HCl (1N, 10 ml) and stirred for 20 min. After neutralisationby aq NaHCO3 (1N, 10 ml), the water phase was extracted withdichloromethane (3 x 30 ml). The combined organic portions were dried overanhydrous MgSO4 and the solvent was removed in vacuo. Thechromatography of the crude mixture on silicagel (hexane-ethyl acetate 6:1) yielded to dicarbaldehyde 8d (115mg, 17%) as a white amorphous solid

  • 2
  • [ 37882-75-0 ]
  • [ 104-13-2 ]
  • 2,5-Bis(4-butyl-β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 3
  • [ 37882-75-0 ]
  • [ 33228-45-4 ]
  • 2,5-Bis(4-hexyl-β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 4
  • [ 37882-75-0 ]
  • [ 4469-80-1 ]
  • 2,5-Bis(4-propoxy-β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 5
  • [ 37882-75-0 ]
  • [ 16245-79-7 ]
  • 2,5-Bis(4-octyl-β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 6
  • [ 37882-75-0 ]
  • 5-Butyl-2-triphenylphosphoniomethylthiophenchlorid [ No CAS ]
  • trans,trans-2,5-Bis(5-butyl-2-thienylvinyl)thieno<3,2-b>thiophen [ No CAS ]
  • 7
  • [ 37882-75-0 ]
  • (4-butylbenzyl)triphenylphosphonium bromide [ No CAS ]
  • [ 603-35-0 ]
  • trans,trans-2,5-Bis(4-butylstyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 8
  • [ 37882-75-0 ]
  • [ 104-94-9 ]
  • 2,5-Bis(4-methoxy-β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 9
  • [ 37882-75-0 ]
  • [ 62-53-3 ]
  • 2,5-Di(β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 10
  • [ 37882-75-0 ]
  • [ 156-43-4 ]
  • 2,5-Bis(4-ethoxy-β-azastyryl)thieno<3,2-b>thiophen [ No CAS ]
  • 11
  • [ 37882-75-0 ]
  • [ 14384-45-3 ]
  • 2,5-bis(4,4,5,5-tetramethyl-1-oxyl-3-oxideimidazoline-2-yl)thieno[3,2-b]thiophene [ No CAS ]
  • 13
  • [ 37882-75-0 ]
  • [ 769-31-3 ]
  • 5-[bis(3-methyl-1-azulenyl)methyl]-2-thieno[3,2-b]thiophenecarbaldehyde [ No CAS ]
  • 2,5-bis[bis(3-methyl-1-azulenyl)methyl]thieno[3,2-b]thiophene [ No CAS ]
  • 14
  • [ 37882-75-0 ]
  • [ 154678-31-6 ]
  • 5-[bis(3,6-di-tert-butyl-1-azulenyl)methyl]-2-thieno[3,2-b]thiophenecarbaldehyde [ No CAS ]
  • 2,5-bis[bis(3,6-di-tert-butyl-1-azulenyl)methyl]thieno[3,2-b]thiophene [ No CAS ]
  • 15
  • [ 37882-75-0 ]
  • [ 68629-94-7 ]
  • C22H16O8S6 [ No CAS ]
  • 16
  • [ 37882-75-0 ]
  • (4,5-Bis-methylsulfanyl-[1,3]dithiol-2-yl)-phosphonic acid diethyl ester [ No CAS ]
  • 2,5-bis-(4,5-bis-methylsulfanyl-[1,3]dithiol-2-ylidenemethyl)-thieno[3,2-<i>b</i>]thiophene [ No CAS ]
  • 17
  • [ 37882-75-0 ]
  • (4,5-bis-pentylsulfanyl-[1,3]dithiol-2-yl)-phosphonic acid diethyl ester [ No CAS ]
  • 2,5-bis-(4,5-bis-pentylsulfanyl-[1,3]dithiol-2-ylidenemethyl)-thieno[3,2-<i>b</i>]thiophene [ No CAS ]
  • 18
  • [ 82014-59-3 ]
  • [ 37882-75-0 ]
  • 19
  • [ 6267-14-7 ]
  • [ 37882-75-0 ]
  • 20
  • 2,3-dihydro-thieno[3,2-<i>b</i>]thiophen-3-ol [ No CAS ]
  • [ 37882-75-0 ]
  • 21
  • (thiophen-3-ylsulfanyl)-acetyl chloride [ No CAS ]
  • [ 37882-75-0 ]
  • 22
  • [ 37882-75-0 ]
  • [ 719284-05-6 ]
  • 2,5-bis(2'-(1'',2'',3'',4'',5''-pentamethylruthenocenyl)ethenyl)thieno[3,2-b]thiophene [ No CAS ]
  • 23
  • [ 3140-93-0 ]
  • [ 37882-75-0 ]
  • C16H10Br2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
(2) Synthesis of Compound 3; 2,3-Dibromothiophene (about 2.42 g, about 10 mmol) was dissolved in about 100 ml of an about 5:1 solution of ether and THF and then cooled to about -78 C. Butyl lithium (11 mmol) was slowly added in droplets thereto and then the mixture was stirred for about 30 min. The solution was slowly added in droplets to the solution (about -78 C.) of the compound 2 (about 0.99 g, about 5 mmol) in about 100 ml of THF and stirred, and the temperature was gradually increased to about room temperature. About 100 ml of a saturated solution of ammonium chloride was added thereto and thus the reaction was terminated. Thereafter, about 200 ml of ether was added and the organic layer was separated. The separated organic layer was washed with brine, dried over MgSO4 and then concentrated, thus obtaining yellow oil, which was then purified through silica chromatography (hexane:ethylacetate=about 5:1), thereby yielding a desired diol compound.1NMR (CDCl3) d 7.32 (d, 2H), 7.18 (s, 2H), 6.97 (dd, 2H), 6.42 (d, 2H), 2.76 (d, 2H).
(2) Synthesis of Compound 3; 2,3-Dibromothiophene (about 2.42 g, about 10 mmol) was dissolved in about 100 ml of an about 5:1 solution of ether and THF and then cooled to about -78C. Butyl lithium (11 mmol) was slowly added in droplets thereto and then the mixture was stirred for about 30 min. The solution was slowly added in droplets to the solution (about -78C) of the compound 2 (about 0.99 g, about 5 mmol) in about 100 ml of THF and stirred, and the temperature was gradually increased to about room temperature. About 100 ml of a saturated solution of ammonium chloride was added thereto and thus the reaction was terminated. Thereafter, about 200 ml of ether was added and the organic layer was separated. The separated organic layer was washed with brine, dried over MgSO4 and then concentrated, thus obtaining yellow oil, which was then purified through silica chromatography (hexane:ethylacetate = about 5:1), thereby yielding a desired diol compound. 1NMR (CDCl3) d 7.32 (d, 2H), 7.18 (s, 2H), 6.97 (dd, 2H), 6.42 (d, 2H), 2.76 (d, 2H).
2,3-dibromothiophene (2.42 g, 10 mmole) is dissolved in 100 mL of a mixed solution of ether and THF in a ratio of 5:1, and the obtained solution is cooled down to -78 C. Subsequently, butyl lithium (11 mmole) is slowly added thereto in a dropwise fashion, and the obtained mixture is stirred for 30 minutes. This solution is slowly added in a dropwise fashion to the other solution that Compound 2 (0.99 g, 5 mmole) is dissolved in 100 mL of THF (-78 C.), and the obtained mixture is heated up to room temperature. Then, 100 mL of an ammonium chloride-saturated solution is added thereto to complete a reaction, 200 mL of ether is added thereto to separate an organic layer. The separated organic layer is washed with brine, dried with MgSO4, and concentrated to obtain yellow oil. This material is purified with a silica chromatography (hexane:ethyl acetate=5:1) to obtain a desired diol compound. (0249) 1NMR (CDCl3) d 7.32 (d, 2H), 7.18 (s, 2H), 6.97 (dd, 2H), 6.42 (d, 2H), 2.76 (d, 2H). (0250) The diol compound (1.4 g, 2.7 mmole) is dissolved in 150 mL of dichloromethane, and Znl2 (2.75 g, 8.6 mmole) and NaCNBH3 (2.4 g, 37.66 mmole) are slowly added thereto. The mixture is stirred at room temperature for 24 hours and passed through a Celite pad. A filtrate therefrom is respectively washed with an ammonium chloride-saturated solution and water, dried with MgSO4, and concentrated under a reduced pressure to obtain yellow oil. This material is purified with a silica chromatography to obtain desired Compound 3 (A yield: 80%). (0251) 1NMR (CDCl3) d 7.17 (d, 2H), 6.98 (s, 2H), 6.94 (d, 2H), 4.34 (s, 4H)
  • 24
  • [ 37882-75-0 ]
  • Br(1-)*C59H52N2P(1+) [ No CAS ]
  • C49H40N2OS2 [ No CAS ]
  • 25
  • [ 37882-75-0 ]
  • (1,3-benzodithiol-2-yl)tributylphosphonium tetrafluoroborate [ No CAS ]
  • [ 1297473-19-8 ]
  • 26
  • [ 37882-75-0 ]
  • [ 1449-46-3 ]
  • [ 84466-16-0 ]
  • 27
  • [ 37882-75-0 ]
  • (4-butylbenzyl)triphenylphosphonium bromide [ No CAS ]
  • [ 1361012-89-6 ]
  • 28
  • [ 251-41-2 ]
  • [ 93-61-8 ]
  • [ 37882-75-0 ]
  • 29
  • [ 37882-75-0 ]
  • [ 1419111-53-7 ]
  • [ 1361012-90-9 ]
  • 30
  • [ 37882-75-0 ]
  • ((4-n-Octylphenyl)methyl)triphenylphosphonium bromide [ No CAS ]
  • [ 1361012-91-0 ]
  • 31
  • [ 37882-75-0 ]
  • [ 500530-72-3 ]
  • [ 1431984-44-9 ]
YieldReaction ConditionsOperation in experiment
78% With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere; General procedure: To a solution of dicarbaldehyde 8a (36 mg, 0.26 mmol) anddiethyl 4-(tert-butylthio)-benzylphosphonate29 (165 mg, 0.52 mmol, 2.0 equiv.) in THF (20 ml)a solution of t-BuOK (113 mg, 1.0mmol, 3.8 equiv.) in THF (10 ml) was carefully added under argon and thereaction mixture was stirred at room temperature overnight. Then it was pouredinto water (25 ml), yellow material was filtered off using the sintered glass,washed with ethanol (20 ml) and dried in vacuo. The crude mixture afforded theproduct 2a (57 mg, 48%) as a yellow amorphous solid. The synthesis of 2b from dicarbaldehyde 8d (44 mg, 0.315 mmol) wascarried out following the same procedure as for the synthesis of 2ausing diethyl 4-(tert-butylthio)benzylphosphonate2 9 (200 mg, 0.63 mmol, 2.0 equiv.), THF (20 ml)and a solution of t-BuOK (113 mg, 1.0mmol, 3.2 equiv.) in THF (10 ml) to provide the product 2d (125 mg, 78%) as a yellow amorphous. 1H NMR (300 MHz, CDCl3): 1.30 (18 H, s), 6.93 (2 H, d, J = 16.1), 7.07 (1 H, d, J = 16.1), 7.16 (1 H, s), 7.24 (1 H, d, J = 16.1), 7.32 (1 H, s), 7.43 (4 H, d, J = 7.9), 7.51 (4 H, 2 x d, J = 7.9). 13C NMR (75 MHz, CDCl3): 31.15 (q), 46.38 (s), 46.45 (s), 122.46 (d), 122.61 (d), 123.68 (d), 124.01 (d), 126.41 (2 x d), 128.19 (d), 128.26 (d), 131.97 (s), 132.29 (s), 137.26 (s), 137.88 (s), 137.92 (2 x d), 140.48 (s) , 143.36 (s). IR (CHCl3): 3011 w, 2964 s, 2940 w, 2925 w, 2899 w, 2862 w, 2361 w, 2342 w, 1634 w, 1591 w, 1488 w, 1472 w, 1457 w, 1402 w, 1365 m, 1166 m, 1015 w, 961 m, 947 w, 865 w, 834 m, 620 w, 551 w, 528 w cm-1. UV/Vis (CH3CN): lambdamax (log epsilon) = 318 (4.79). EI MS: 464 (M+?, 30), 408 (24), 352 (100), 318 (15), 286 (29), 184 (13), 57 (54), 41 (57). HR EI MS: calcd for C28H32S3 464.1666, found 464.1672.
  • 32
  • [ 37882-75-0 ]
  • [ 129806-51-5 ]
  • [ 1429623-05-1 ]
YieldReaction ConditionsOperation in experiment
61% To a solution of 7 (0.55g, 1.31mmol) in dry THF (20mL) at -30C, n-BuLi (0.85mL, 1.36mmol) 1.6M in hexaneswas added under argon atmosphere. The solution turned to dark green and was stirred at this temperature for 45min. Then, a suspension of 5 (0.28 g, 1.41mmol) in dry THF (14mL) was slowly added via a syringe and the mixture was stirred for one further hour. A solution of saturated NH4Cl (60mL) was then added and the aqueous phase was extracted with AcOEt (4×50mL). The resulting organic layer was dried over MgSO4 and evaporated. The crude product was purified by flash column chromatography (silicagel) using CH2Cl2 as eluent, affording 8a (0.33g, 0.8mmol, 61%) as a dark red solid. Found: C 72.91, H 3.73. C25H16O2S2 requires C 72.79, H 3.91%. Mp 213-217C. IR (KBr, cm-1): 1660 (C=O), 1581 (C=C, Ar), 1556 (C=C, Ar). 1H NMR (300MHz, CDCl3): delta 9.91 (s, 1H, -CHO), 7.92-7.83 (m, 3H, phenyl-H+TT-H), 7.81-7.76 (m, 2H, phenyl-H), 7.56-7.42 (m, 6H, phenyl-H), 7.18 (d, J=1.9Hz, 1H, pyranylidene-H), 7.13 (s, 1H, TT-H), 6.50 (d, J=1.9Hz, 1H, pyranylidene-H), 6.15 (s, 1H, pyranylidene=C-H). 13C NMR (75MHz, CDCl3): delta 182.6, 154.4, 152.1, 151.3, 147.0, 143.2, 136.9, 132.8, 132.6, 131.3, 130.0, 129.5, 129.0, 128.8, 128.7, 125.2, 124.6, 116.6, 108.4, 107.4, 102.6. HRMS (MALDI+): found 412.0594 [M+]. C25H16O2S2 requires 412.0586; found 413.0638 [M+H]+. C25H17O2S2 requires 413.0665.
  • 33
  • [ 37882-75-0 ]
  • [ 1429623-07-3 ]
  • 34
  • [ 37882-75-0 ]
  • [ 1429622-94-5 ]
  • 35
  • [ 37882-75-0 ]
  • [ 1429622-96-7 ]
  • 36
  • [ 37882-75-0 ]
  • [ 1429622-97-8 ]
  • 37
  • [ 37882-75-0 ]
  • [ 1429622-99-0 ]
  • 38
  • [ 37882-75-0 ]
  • 2-((5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)thieno[3,2-b]-thiophen-2-yl)methylene)malononitrile [ No CAS ]
  • 39
  • [ 37882-75-0 ]
  • (Z)-2-(5-((5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)-thieno[3,2-b]thiophen-2-yl)methylene)thiophen-2(5H)-ylidene)-malononitrile [ No CAS ]
  • 40
  • [ 37882-75-0 ]
  • (2,6-Di-tert-butyl-4H-pyran-4-yl)tributylphosphonium perchlorate [ No CAS ]
  • 5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)thieno[3,2-b]-thiophene-2-carbaldehyde [ No CAS ]
  • 41
  • [ 37882-75-0 ]
  • [ 769-42-6 ]
  • [ 1566578-25-3 ]
  • 42
  • [ 37882-75-0 ]
  • [ 32479-73-5 ]
  • [ 1566579-00-7 ]
  • 43
  • [ 37882-75-0 ]
  • [ 3158-63-2 ]
  • [ 1566578-97-9 ]
  • 44
  • [ 37882-75-0 ]
  • [ 5217-47-0 ]
  • [ 1566578-37-7 ]
  • 45
  • [ 37882-75-0 ]
  • [ 140-29-4 ]
  • C24H14N2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With potassium tert-butylate; tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; methanol; tert-butyl alcohol; at 20℃; for 10h; To a solution of compound 2 (100 mg, 0.5 mmol) and benzylcyanide (113 mg, 1.1 mmol) in 20 ml THF, a solvent of potassium tert-butoxide (1 mg/ml) in 20 ml tert-butoxide was added dropwise within 5 min, then 4 drops (?0.2 ml) of tetra-n-butylammonium hydroxide (1 M in methanol) were added. The mixture stirred at ambient temperature for 10 h. The orange precipitate was collected by filtration and washed with methanol. The material was further purified by three sublimations to afford CNP2V2TT as a red solid (36 mg, 0.076 mmol, yield 18%). CNP2V2TT exhibits poor solubility in commonly used organic solvent. Anal. Calcd for C24H14N2S2: C, 73.07; H, 3.58. N, 7.10; Found: C, 72.94; H 3.91, N 7.08.
  • 46
  • [ 37882-75-0 ]
  • [(9-octyl-9H-carbazol-3-yl)methyl]triphenyl-phosphonium bromide [ No CAS ]
  • (E)-5-(2-(9-octyl-9H-carbazol-3-yl)vinyl)thieno[3,2-b]thiophene-2-carbaldehyde [ No CAS ]
  • (Z)-5-(2-(9-octyl-9H-carbazol-3-yl)vinyl)thieno[3,2-b]thiophene-2-carbaldehyde [ No CAS ]
  • 47
  • [ 37882-75-0 ]
  • 3,4-dihexylthienylmethylphosphonate diethyl [ No CAS ]
  • (E,E)-2,5-bis[2-(3,4-dihexyl-2-thienylvinyl)]thieno[3,2-b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere; General procedure: In a round-bottomed flask, under an argon atmosphere, thecorresponding phosphonate (2 eq) and the corresponding dialdehyde(1 eq) were dissolved in dry THF. tBuOK (8 eq) was addedand the mixture was stirred overnight at room temperature. Afterconsumption of the dialdehyde (monitored by TLC), the crudeproduct was extracted with diethyl ether. The organic phase wasdried over MgSO4, concentrated in vacuo and purified by chromatographycolumn (silica gel, hexane).
  • 48
  • [ 37882-75-0 ]
  • (E,E)-2,5-bis[2-(5-formyl-3,4-dihexyl-2-thienylvinyl)]thieno[3,2-b]thiophene [ No CAS ]
  • 49
  • [ 37882-75-0 ]
  • C50H60N4S4 [ No CAS ]
  • 50
  • [ 37882-75-0 ]
  • 2,5-bis((2-bromopyridin-3-yl)methyl)thieno[3,2-b]thiophene [ No CAS ]
  • 51
  • [ 37882-75-0 ]
  • 3,3'-(thieno[3,2,b]thiophen-2,5-diylbis(methylene))dipicolinealdehyde [ No CAS ]
  • 52
  • [ 37882-75-0 ]
  • 2,5-bis((3-bromopyridin-4-yl)methyl)thieno[3,2-b]thiophene [ No CAS ]
  • 53
  • [ 37882-75-0 ]
  • 4,4'-(thieno[3,2-b]thiophene-2,5-diylbis(methylene))dinicotinaldehyde [ No CAS ]
  • 54
  • [ 13534-89-9 ]
  • [ 37882-75-0 ]
  • thieno[3,2-b]thiophene-2,5-diylbis((2-bromopyridin-3-yl)methanol) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; at -78 - 24℃; for 12h; Thienothiophene dicarbaldehyde (5 g, 25.48 mmol) is dissolved in 250 mL of dry diethylether and dry tetrahydrofuran and then, cooled down to -78 C. 42.12 mL of lithium diisopropylamine (a 2.0 M hexane solution) is slowly added thereto in a dropwise fashion, and 2,3-dibromopyridine (13.3 g, 56.16 mmol) is added thereto. The temperature is slowly increased, and the mixture is stirred at room temperature (24 C.) for 12 hours. Then, 100 mL of an ammonium chloride-saturated solution is added thereto, and an extract is obtained by using chloroform and several times washed with water. The extract is dried with magnesium sulfate and filtered, and the chloroform solvent is removed to obtain a compound 1a. (a yield of 75%)
  • 55
  • [ 13534-90-2 ]
  • [ 37882-75-0 ]
  • thieno[3,2-b]thiophene-2,5-diylbis((3-bromopyridin-4-yl)methanol) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; at -78 - 24℃; for 12h; Thienothiophene dicarbaldehyde (5 g, 25.48 mmol) is dissolved in 250 mL of dry diethylether and dry tetrahydrofuran (THF) and then, cooled down to -78 C. Then, 42.12 mL of diisopropylamine (a 2.0 M hexane solution) is slowly added thereto in a dropwise fashion, and 2,3-dibromopyridine (13.3 g, 56.16 mmol) is added thereto. The mixture is slowly heated and stirred at room temperature (24 C.) for 12 hours. Subsequently, 100 mL of an ammonium chloride-saturated solution is added thereto, and an extract is obtained by using chloroform and several times washed with water. The obtained extract is dried with magnesium sulfate and then, filtered, and the chloroform solvent is removed to obtain a compound 2a. (a yield of 75%)
  • 56
  • 3,4-bis(hexyloxy)aniline [ No CAS ]
  • [ 37882-75-0 ]
  • [ 134-81-6 ]
  • 2,5-bis(1-(3,4-bis(hexyloxy)phenyl)-4,5-diphenyl-1H-imidazol-2-yl)thieno[3,2-b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With ammonium acetate; In acetic acid; at 110℃; for 12h; General procedure: To the solution of benzaldehyde (1 equiv) and aniline (1.5 equiv) in glacial AcOH, benzil (1 equiv) and NH4OAc (5 equiv) were added. The mixture was stirred at 110 C for 12 h. The solution was poured intocopious amount of water and extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and the solvent was removed undervacuum. The product was purified by chromatography (silica gel,hexanes/EtOAc).
  • 57
  • 3,4-bis(hexyloxy)aniline [ No CAS ]
  • [ 37882-75-0 ]
  • C72H76N4O4S2 [ No CAS ]
  • 58
  • [ 37882-75-0 ]
  • (5-bromoselenophen-2-yl)(tert-butyl)dimethylsilane [ No CAS ]
  • C28H38Br2O2S2Se2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% 9.3 g (29 mmol, 2eq.) of the S1 compound is put in 500 ml of dry tetrahydrofuran to prepare a cool solution (-78 C.), lithium diisopropylamide (2.0 M in THF/heptane/ethylbenzene, 15 mL, 2.1 eq.) is added thereto, and the reaction mixture is fervently stirred at -78 C. for 2 hours. Subsequently, <strong>[37882-75-0]thieno[3,2-B]thiophene-2,5-dialdehyde</strong> (2.8 g, 1 eq.) is added thereto, the mixture is stirred at room temperature all through night, and a sat. sodium bicarbonate solution is added thereto. Then, the solution is diluted with dichloromethane and several times cleaned with water, and an organic layer therefrom is dried with magnesium and evaporated to obtain a brown solid. Subsequently, the brown solid is recrystallized with a mixed solvent of ethylacetate/hexane/chloroform to obtain 6.7 g of an S2 compound as an ivory solid. The yield is 56.0%. 1H-NMR (300 MHz, CDCl3): delta 7.34 (s, 2H), 7.21 (s, 2H), 6.35 (s, 2H), 2.76 (d, J=2.1 Hz, 2H), 0.92 (m, 18H) 0.26 (m, 12H); 13C-NMR (125.8 MHz, CDCl3): 152.0, 148.4, 146.0, 140.3, 138.7, 118.3, 110.5, 71.0, 26.9, 17.4
  • 59
  • [ 37882-75-0 ]
  • [ 1033611-93-6 ]
  • 60
  • [ 37882-75-0 ]
  • [ 1033611-95-8 ]
  • 61
  • [ 37882-75-0 ]
  • C26H16Br2N2S4 [ No CAS ]
  • 62
  • [ 37882-75-0 ]
  • C28H16N4S4 [ No CAS ]
  • 63
  • [ 37882-75-0 ]
  • C28H18N2O2S4 [ No CAS ]
  • 64
  • [ 37882-75-0 ]
  • [ 123784-08-7 ]
  • C26H16Br2N2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Compound 1 (20.1 g, 83.8 mmol) is dissolved in 1.6 L of dry tetrahydrofuran (THF), the solution is slowly added in a dropwise fashion to LDA (a 2 M solution, 52.4 ml, 104.8 mmol) cooled down to -78C., and the obtained mixture is stirred for 2 hours. Subsequently, <strong>[37882-75-0]thieno[3,2-b]thiophene-2,5-dicarbaldehyde</strong> (8.2 g, 41.9 mmol) is slowly added in a dropwise fashion to the solution which becomes opaque, and the obtained mixture is slowly heated up and stirred for 12 hours. 100 mL of a chloride-saturated aqueous solution is added thereto, and a THF layer therein is dried with MgSO4. A precipitate produced by adding ethylacetate thereto is filtered to obtain Compound 1 . (Yield: 86%). 1H-NMR (300 MHz, THF-d4): delta 8.47 (d, J=4.2 Hz, 1H), 7.74 (m, 2H), 7.54 (s, 1H), 7.18 (m, 2H), 6.26 (d, J=3.6 Hz, 1H), 5.90 (d, J=3.6 Hz, 1H)
  • 65
  • [ 37882-75-0 ]
  • C8H3BrF2S2 [ No CAS ]
  • C24H10Br2F4O2S6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Compound 2 (8.0 g, 28.6 mmol) is dissolved in dry tetrahydrofuran (THF, 700 mL), the solution is cooled down to -78C., LDA (a 2 M solution, 15 ml, 30.0 mmol) is slowly added thereto in a dropwise fashion, and the mixture is stirred at -78C. for 2 hours. Subsequently, <strong>[37882-75-0]thieno[3,2-b]thiophene-2,5-dicarbaldehyde</strong> is added in a dropwise fashion to the solution which becomes opaque, and the mixture is slowly heated up to room temperature and stirred for 12 hours. 100 mL of a sodium bicarbonate-saturated aqueous solution is added thereto, and the obtained mixture is extracted with dichloromethane and washed with water. The resultant is dried with MgSO-4 and concentrated under a reduced pressure and then, dissolved in 50 mL of a mixed solvent of EA/CHCl3 (EA:CHCl3=1:5), and a precipitate obtained by adding hexane thereto is filtered to obtain Compound 3 as yellow powder. (Yield: 81%). 1H-NMR (300 MHz, CDCl3): delta 7.22 (m, 2H), 6.86 (d, J=5.7 Hz, 1H), 6.37 (s, 1H), 2.75 (s, 1H)
  • 66
  • [ 37882-75-0 ]
  • [ 343239-58-7 ]
  • C56H38N2S2 [ No CAS ]
  • 67
  • [ 37882-75-0 ]
  • [ 18646-81-6 ]
YieldReaction ConditionsOperation in experiment
77% 2 g of <strong>[37882-75-0]thieno[3,2-b]thiophene-2,5-dicarbaldehyde</strong> (0.0102 mol) were placed in a 100-mL round-bottom flask. Then a two-fold molar excess of the prepreparedTollens reagent (40 mL, 0.042 mol) was added. The reaction mixture was kept for 2 days at room temperature with activestirring. After that, hydrochloric acid (10 mL, 5 M) was added to the mixture and left to be stirred for 1 h. The precipitate wasfiltered off, five times washed with distilled water (100 mL each portion), and transferred into a cylindrical vessel. Then50 mL of DMF were added into the vessel and heated under vigorous stirring for 2 h. The precipitate was filtered off and thefiltrate was evaporated on a rotary evaporator to reduce the initial liquid volume to 10-15 mL. 5-10 mL of a KMnO4 solutionin DMF (0.01 M) were added to the obtained concentrated solution until it acquired the steady purple color. The excess ofpermanganate and MnO2 formed were removed by adding 5-10 mL of formic acid and 5-10 mL of concentrated HCl at 60-70 C. A yellow precipitate formed was filtered off and purified by recrystallization from DMF at -15 C. The yield was1.8 g (77%). NMR spectra (DMSO-d6) were recorded with a working frequency of 500.13 Hz; the 8.16 ppm signal fullycoincides with the literature data.
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