29150-63-8|Benzo[1,2-b:3,4-b':5,6-b'']trithiophene| Ambeed

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Quality Control of [ 29150-63-8 ] Purity: 96% SDS Specification

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Product Details of [ 29150-63-8 ]

CAS No. :	29150-63-8
Formula :	C₁₂H₆S₃
M.W :	246.37
SMILES Code :	C12=C(C=CS3)C3=C(C=CS4)C4=C1C=CS2
MDL No. :	MFCD22381057
InChI Key :	DKSAJSCNXULKER-UHFFFAOYSA-N
Pubchem ID :	44225674

Safety of [ 29150-63-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 29150-63-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	15
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	72.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.72 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.83
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	4.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.33
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.	4.06
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	7.04
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.24
Solubility	0.0014 mg/ml ; 0.00000569 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.	-6.5
Solubility	0.0000783 mg/ml ; 0.000000318 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	-5.24
Solubility	0.00142 mg/ml ; 0.00000578 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	No
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	Yes
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.	-4.27 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	0.0
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	0.0 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)	2.36

Application In Synthesis of [ 29150-63-8 ]

* 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 [ 29150-63-8 ]

[ 29150-63-8 ] Synthesis Path-Downstream 1~35

1
[ 106032-17-1 ]
[ 29150-63-8 ]
[ 122357-57-7 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 4203 - 4205.
[2]Journal of Organic Chemistry,1989,vol. 54,p. 4203 - 4205.

2
[ 113201-28-8 ]
[ 29150-63-8 ]

References: [1]Organic Letters,2004,vol. 6,p. 273 - 276.
[2]Journal of Organic Chemistry,1989,vol. 54,p. 4203 - 4205.

4
[ 29150-63-8 ]
[ 211737-28-9 ]
2,5,8-tris(5-hexyl-2-thienyl)benzo[1,2-b:3,4-b':5,6-b'']trithiophene [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 273 - 276.

5
[ 29150-63-8 ]
[ 655249-04-0 ]
2,5,8-tris[5-(5-hexyl-2-thienyl)-2-thienyl]benzo[1,2-b:3,4-b':5,6-b'']trithiophene [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 273 - 276.

6
[ 351014-15-8 ]
[ 29150-63-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium sulfide nonahydrate; In 1-methyl-pyrrolidin-2-one; at 190℃; for 12h;Inert atmosphere;	50mL round bottom flask was added compound 2 (0.94g, 2mmol), sodium sulfide nonahydrate (2.67g, 12mmol) and N- methylpyrrolidinone (20mL), 190 under nitrogen for 12 hours.After the reaction was cooled to room temperature, poured into aqueous ammonium chloride solution, filtered, the cake washed with petroleum ether and subjected to silica gel column chromatography eluent, to give a white solid 3 (0.33g, 67% yield).
62%	With sodiumsulfide nonahydrate; In 1-methyl-pyrrolidin-2-one; at 180 - 190℃; for 38h;	Synthesis Example 3 Synthesis of benzo[1,2-b:3,4-b':5,6-b"]trithiophene (Scheme 1-(2)) [Show Image] In a 30 mL round-bottom flask, sodium sulfide nonahydrate (7.74 g, 32.2 mmol) and NMP (138 mL) were placed and stirred for 15 minutes. Subsequently, 1,3,5-trichloro-2,4,6-tris(trimethylsilylethynyl)benzene (3.0 g, 6.38 mmol) obtained in Synthesis Example 2 was added and heated at 180-190C for 38 hours. After completion of the reaction, the reaction mixture was poured into a saturated aqueous ammonium chloride solution (700 mL) and a precipitated solid substance was obtained by filtration. The resultant solid substance was extracted with chloroform (210 mL), washed with saturated saline solution and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure and purification was performed by column chromatography (hexane, butch, Rf = 0.5) to obtain a white solid substance (814 mg, 62%). 1H-NMR(270MHz,CDCl3)δ7.64(d,J=5.4Hz,3H)7.54(d,J=5.4Hz,3H); 13C-NMR(99.5MHz,CDCl3)δ131.94, 131.55, 125.11, 122.44; M.S.(70eV,EI)m/z=246(M+); m.p.156.7-157.7C
60%	With sodiumsulfide nonahydrate; In 1-methyl-pyrrolidin-2-one; at 185 - 195℃; for 12h;	Under nitrogen atmosphere, sodium sulfide nonahydrate (1.54 g, 6.42 mmol) was added to anhydrous NMP (40 ml) and the mixture was stirred for ten minutes. To this mixture, 1,3,5-trichloro-2,4,6-tris[(trimethylsilyl)ethinyl]benzene (Compound 100)(500 mg, 1.07 mmol) was added, followed by heating at 185C to 195C for 12 hours. Upon completion of the reaction, the mixture was poured into water (400 ml) and precipitated solid was collected by filtration. The solid thus obtained was dissolved in chloroform (200 ml), and the resulting solution was washed with saturated saline. The solution was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. Solid thus obtained was purified by a column chromatography (silica gel and hexane), thereby white crystalline Compound 104 was obtained (156 mg, yield: 60%). 1H-NMR (270 MHz, CDCl3) δ7.64 (d, J=5.4 Hz, 3H) 7.54 (d, J=5.4 Hz, 3H), M.S. (70eV, EI) m/z=246 (M+)

References: [1]Patent: CN103288848,2016,B .Location in patent: Paragraph 0126-0127.
[2]Organic Letters,2009,vol. 11,p. 2473 - 2475.
[3]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 36.
[4]Patent: EP2147923,2010,A1 .Location in patent: Page/Page column 18.
[5]Angewandte Chemie - International Edition,2016,vol. 55,p. 6270 - 6274.
Angew. Chem.,2016,vol. 128,p. 6378 - 6382,5.
[6]Patent: WO2017/98455,2017,A1 .Location in patent: Page/Page column 6; 7.
[7]Journal of Materials Chemistry A,2021,vol. 9,p. 3333 - 3340.
[8]European Journal of Organic Chemistry,2017,vol. 2017,p. 5966 - 5974.

7
[ 1174223-25-6 ]
[ 29150-63-8 ]

References: [1]Organic Letters,2009,vol. 11,p. 3230 - 3233.
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 13594 - 13598.
Angew. Chem.,2015,vol. 127,p. 13798 - 13802,5.

8
[ 29150-63-8 ]
[ 1174223-26-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-Bromosuccinimide; In dichloromethane; acetic acid; at 20℃; for 48h;Inert atmosphere; Darkness;	Example 4 Synthesis of 2,5,8-Tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (33) [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flask, benzo[1,2-b:4,5-b':5.6-b"]trithiophene (800 mg, 3.25 mmol) obtained in Synthesis Example 3, methylene chloride (22.7 mL) and acetic acid (5.7 mL) were added. Under light exclusion conditions, NBS (1.73 g, 9.74 mmol) was added little by little and stirred at room temperature 48 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration and washed with ethanol (50 mL) and THF (20 mL) to obtain a light purple solid substance (1.2 g, 76%). 1H-NMR(270MHz,CDCl3)δ7.51(s,3H);M.S.(70eV,EI)m/z=484(M+)
52%	With N-Bromosuccinimide; In chloroform; for 12h;Inert atmosphere; Reflux;	General procedure: Under a nitrogen gas stream to IC-7-3 (14.5 g, 60.33 mmol) obtained in Step 2 and NBS (11.81 g, 66.36 mmol) in 200 ml of chloroform was refluxed for 12 hours. After the reaction was terminated by using MgSO4 and the organic layer was separated with methylene chloride to remove the water from the organic layer. After removing the solvent in water is removed, the organic layer was purified by column chromatography (Hexane: MC = 15: 1 (v / v)) to obtain the IC-7-2 (11.75 g, yield 61%). Instead of IC-7-3 (14.5 g, 60.33 mmol) and NBS (11.81 g, 66.36 mmol) the IC-12-3 (20 g, 81.18 mmol) and NBS (47.68To g, 267.89 mmol), and performs the same procedure of the Preparation Example 7 step 3 to obtain a IC-15-2 (20.39 g, yield 52%).

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 6270 - 6274.
Angew. Chem.,2016,vol. 128,p. 6378 - 6382,5.
[2]Patent: WO2017/98455,2017,A1 .Location in patent: Page/Page column 7.
[3]Journal of Materials Chemistry A,2021,vol. 9,p. 3333 - 3340.
[4]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070.
[5]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 39.
[6]Organic Letters,2009,vol. 11,p. 3230 - 3233.
[7]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016.
[8]Patent: KR101609027,2016,B1 .Location in patent: Paragraph 0205; 0206; 0316-0318.

9
[ 29150-63-8 ]
[ 1260140-90-6 ]