1231160-83-0|1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione| Ambeed

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Quality Control of [ 1231160-83-0 ] Purity: 95% (stabilized with Cu+HQ+MgO) SDS Specification

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Product Details of [ 1231160-83-0 ]

CAS No. :	1231160-83-0
Formula :	C₁₄H₁₇Br₂NO₂S
M.W :	423.16
SMILES Code :	O=C1C2=C(Br)SC(Br)=C2C(N1CC(CC)CCCC)=O
MDL No. :	MFCD23703120
InChI Key :	AOZLCBYWDXFKCJ-UHFFFAOYSA-N
Pubchem ID :	58261078

Safety of [ 1231160-83-0 ]

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

Computational Chemistry of [ 1231160-83-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	5
Fraction Csp3	0.57
Num. rotatable bonds	6
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	93.65
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.62 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.58
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	5.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.7
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.	4.3
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	5.78
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.83

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.88
Solubility	0.000556 mg/ml ; 0.00000131 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.	-6.91
Solubility	0.0000525 mg/ml ; 0.000000124 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	-5.78
Solubility	0.000696 mg/ml ; 0.00000164 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	No
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.79 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	1.0
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)	3.6

Application In Synthesis of [ 1231160-83-0 ]

* 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 [ 1231160-83-0 ]

[ 1231160-83-0 ] Synthesis Path-Downstream 1~34

1
[ 1231160-82-9 ]
[ 1231160-83-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃;Inert atmosphere; Schlenk technique;	5-(2-ethylhexyl)-4,H-thieno[3,4-c]pyrrole-4,6(5H)-dione (0.27 g, 1.01 mmol) was dissolved in concentratedsulfuric acid (1.6 mL) and trifluoroacetic acid (3.4 mL). NBS (0.543 g,3.05 mmol) was added in one portion and the reaction mixturewasstirred at room temperature overnight. The resultant solution wasthen diluted with water (100 mL) and extracted with dichloromethane.The organic phase was washed with KOH solution,further dried over anhydrous magnesium sulfate and evaporated toafford the crude product as orange crystals. Purification by columnchromatography using silica gel and hexane/chloroform (3:2) gave1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (0.34 g, 79%) as pink solid. 1H NMR (400 MHz, CDCl3): delta 3.49(d, J 7.3 Hz, 2H), 1.81-1.76 (m, 1H), 1.35-1.27 (m, 8H), 0.93-0.88(t, 6H). 13C (100 MHz, CDCl3): delta 160.46, 134.46, 112.65, 42.26, 37.80,30.13, 28.13, 23.43, 22.54, 13.66, 9.95. Mp: 110.5-112 C. MALDITOF:calculated for C14H17Br2NO2S [M+H]+ 424.5344.
76.2%	With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃;	Compound 1 (1.40 g, 5.28 mmol) was dissolved in sulfuric acid (7.8 mL) and trifluoroaceticacid (26 mL). While stirring, NBS (2.81 g, 15.8 mmol) was added and the reaction mixturewas stirred at roomtemperature overnight. The mixture was poured into water and extractedwith dichloromethane. The organic phases were combined, washed with brine, and driedwithmagnesiumsulfate. The product was obtained by column chromatography using chloroform:hexane (2:1). Yield: 1.70 g (76.2%). 1H NMR (400 MHz, CDCl3): delta (ppm) 3.60 (d, 2H),1.37 (m, 9H), 0.90 (m, 6H).
75%	With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃;	To a solution of the 5-(2-ethylhexyl)thieno[3,4-c]pyrrole-4,6-dione (0.50 g, 1.88 mmol) in trifluoroacetic acid (5 mL) and conc.H2SO4 (2 mL) was added NBS (1.10 g, 6.18 mmol) in portions. Themixture was stirred at room temperature overnight. Then, waterwas added and the mixture was extracted with dichloromethanetwice. The organic phase was dried over Na2SO4. After removingsolvent under vacuum, the crude product was purified by silicacolumn to give the title compound as white powder with 75% yield.Mp: 104 C. FTIR (KBr) v/cm-1 2956, 2929, 1697, 1535, 1388, 1054,958,746, 680. 1H NMR (CDCl3, ppm): 3.52 (d, J 7.14 Hz, 2H),1.81e1.77 (m, 1H), 1.38-1.29 (m, 8H), 0.94-0.92 (m, 6H). 13C NMR(CDCl3, ppm): 160.87, 134.90, 113.13, 42.81, 38.36, 30.69, 28.72,24.00, 23.13, 14.26, 10.55. HRMS (ESI) (M+, C14H17Br2NO2S): calcd,420.9347; found, 420.9341.

References: [1]Dyes and Pigments,2017,vol. 137,p. 117 - 125.
[2]Advanced Functional Materials,2011,vol. 21,p. 718 - 728.
[3]Molecular Crystals and Liquid Crystals,2016,vol. 635,p. 87 - 93.
[4]Polymer,2011,vol. 52,p. 2559 - 2564.
[5]Dyes and Pigments,2017,vol. 137,p. 50 - 57.
[6]Journal of the American Chemical Society,2010,vol. 132,p. 7595 - 7597.
[7]Macromolecules,2012,vol. 45,p. 6906 - 6914,9.
[8]Chemistry - An Asian Journal,2013,vol. 8,p. 168 - 177.
[9]Patent: WO2014/29014,2014,A1 .Location in patent: Paragraph 00111.
[10]Chemistry - A European Journal,2018,vol. 24,p. 13523 - 13534.
[11]Chemistry of Materials,2019,vol. 31,p. 4629 - 4638.

2
[ 1231160-83-0 ]
1-bromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With hydrogenchloride; zinc; In ethanol; acetic acid; for 1h;Reflux;	,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (2.6 g, 5 mmol) was placed in a three neck round-bottom flask equipped with a water condenser with ethanol (35 mL), acetic acid (10 mL) and three drops of 1 M HC1. The mixture was heated until the starting material was fully dissolved. At this point, zinc (310 mg, 5 mmol) was added in one portion. Mixture was refluxed for one hour after which an aliquot was taken for GC analysis and NMR, indicating reaction completion. After cooling, the solution was filtered through fritted glass to eliminate remaining Zn particles and solvent was evaporated under vacuum. Product was obtained by silica chromatography (1.lg, 52%), using a 100% hexane to 100% CHC13 gradient.Spectral data: 1H NMR (300 MHz, CDC13): deltaH0.88 (t, 3H, 6.8Hz), 0.9 (t, 3H, 7.4Hz), 1.2-1.4 (m, 8H), 1.72-1.84 (m, 1H), 3.5 (d, 2H, 7.2Hz), 7.72 (s, 1H).

References: [1]Patent: WO2011/28827,2011,A2 .Location in patent: Page/Page column 102-103.

3
[ 1231160-83-0 ]
5,5’-bis(2-ethylhexyl)-4H,4’H-1,1’-bi(thieno[3,4-c]pyrrole)-4,4’,6,6’(5H,5’H)-tetraone [ No CAS ]

References: [1]Patent: WO2011/28827,2011,A2 .

4
[ 1231160-83-0 ]
3,3'-dibromo-5,5'-bis(2-ethylhexyl)-4H,4'H-[1,1'-bithieno[3,4-c]pyrrole]-4,4',6,6'(5H,5'H)-tetraon [ No CAS ]

References: [1]Patent: WO2011/28827,2011,A2 .

5
[ 1231160-83-0 ]
1,1'-(thiophene-2,5-diyl)bis(5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione) [ No CAS ]

References: [1]Patent: WO2011/28827,2011,A2 .

6
[ 1231160-83-0 ]
(4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)trimethylstannane [ No CAS ]
1,3-bis(4,8-diethylhexyloxybenzo[1,2-b;3,4-b]dithiophene)-5-(2-ethylhexyl)thieno[3,4-c]pyrrole-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(o-tolyl)phosphine;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 110℃; for 2h;Inert atmosphere;	In a glove box, 2-trimethyltin-4,8-diethylhexyloxybenzo[l,2-b;3,4-b]dithiophene (1.0 g, 1.64 mmol), l,3-dibromo-5-(2-ethylhexyl)thieno[3,4-c]pyrrole-4,6-dione (0.33 g, 0.78 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.018 g, 0.020 mmol) and tris(o-tolyl)phosphine (0.024 g, 0.080 mmol) were weighted out into a flame dried 50 mL Schlenk flask. Reaction flask was removed from the glove box and 10 mL of deoxygenated toluene were added via syringe. The mixture was evacuated and refilled with argon five times. The reaction flask was immersed into a preheated to 110C oil bath and was left stirring under an argon stream for 2 hours. The oil bath was removed and after cooling to room temperature, the final mixture was poured into 40 mL of methyl tert-butyl ether (MTBE) and extracted with it (3x50 mL). The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgS04). After the product was filtered, the solvent was removed by rotary evaporation. The product was first passed thru a flash silica gel chromatography column with hexanes/ chloroform (gradient), and then thru a biobeads SX-1 column with chloroform. It was obtained as an orange waxy in appearance solid paste (0.40 g, 60%). Spectral data: 1H NMR (300 MHz, CDC13): deltaH8.76 (s, 2H), 7.47 (d, 2H), 7.42 (d, 2H), 4.32 (d, 4H), 4.20 (d, 4H), 3.63 (d, 2H), 1.25-1.94 (bm, 55H), 0.86-1.08 (bm, 30H).

References: [1]Patent: WO2011/28827,2011,A2 .Location in patent: Page/Page column 53.

7
[ 104-75-6 ]
[ 1231160-83-0 ]

References: [1]Advanced Functional Materials,2011,vol. 21,p. 718 - 728.
[2]Chemistry - An Asian Journal,2013,vol. 8,p. 168 - 177.
[3]Molecular Crystals and Liquid Crystals,2016,vol. 635,p. 87 - 93.

8
[ 1231160-83-0 ]
[ 1286745-60-5 ]

References: [1]Advanced Functional Materials,2011,vol. 21,p. 718 - 728.
[2]Molecular Crystals and Liquid Crystals,2016,vol. 635,p. 87 - 93.

9
[ 1231160-83-0 ]
[ 54663-78-4 ]
[ 1286745-51-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 72℃; for 48h;Inert atmosphere;	General procedure: Monomers were synthesized via Stille coupling reaction between 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole- 4,6(5H)-dione as the acceptor unit and 2-(tributylstannyl)thiophene, 2-(tributylstannyl)-3,4-ethylenedioxythiophene, and tributyl(3,3-didecyl-3,4-dihydro-2H-thieno [3,4-b] [1,4]dioxepin-6-yl)stannane as the donor units (Scheme 1 ). The acceptor (1 eq), the donor (2.2 eq) and 5% mol of Pd(PPh3)2Cl2 were dissolved in freshly distilled THF (50mL) and stirrred under Ar atmophere. The mixture was heated to reflux and the reflux was continued for 48hat 72C. The progress of reaction was controlled by thin layer chromatography. After the reaction was stopped, THF was removed under reduced pressure. The reaction product was extracted with DCM, washed three times with brine, and dried on anhydrous MgSO4. Further purification was achieved by column chromatography. Synthesis route to monomers was shown in Scheme 1. TAT was obtained as a green solid with a yield of 82% by using a Hex:EtOAc (25:1) eluent. m.p: 130-133?C. 1H NMR (400?MHz, CDCl3, delta (ppm)): 7.94 (d, J?=?3.7?Hz, 2H), 7.35 (d, J?=?5.1?Hz 2H), 7.04 (t, J?=?3.8?Hz, 2H), 3.47 (d, J?=?7.3?Hz, 2H), 1.70-1.81 (m, 1H), 1.11-1.40 (m, 8H), 0.72-0.92 (m, 6H); 13C NMR (100?MHz, CDCl3, delta (ppm)): 162.9, 136.5, 132.5, 129.9, 128.6, 128.5, 128.4, 42.5, 38.3, 30.6, 28.6, 23.9, 23.1, 14.1, 10.4. HRMS calculated for C22H23NO2S3, [M+H]+: 430.0969. Found for C22H23NO2S3, [M+H]+: 430.0968.
58.2%	With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In toluene; at 90℃;	Compound 2 (0.59 g, 1.4 mmol), 2-(tributylstannyl)thiophene (1.2 g, 3.1 mmol), Pd2(dba)3(0.088 g, 0.096 mmol), and P(o-tol)3 (0.046 g, 0.15 mmol) were dissolved in toluene(23 mL). The mixture was heated overnight at 90C. The reaction mixture was extractedwith dichloromethane and water. The organic phases were combined, washed with brine, anddried with magnesium sulfate. The yellow solid product was obtained by recrystallizationfrom methanol. Yield: 0.35 g (58.2%). 1H NMR (400 MHz, CDCl3): delta (ppm) 8.21 (d, 2H),7.95 (d, 2H), 7.33 (t, 2H), 3.60 (d, 2H), 1.37 (m, 9H), 0.9 (m, 6H).

References: [1]Journal of Materials Chemistry A,2013,vol. 1,p. 1785 - 1793.
[2]Advanced Functional Materials,2011,vol. 21,p. 718 - 728.
[3]Dyes and Pigments,2018,vol. 158,p. 175 - 182.
[4]Molecular Crystals and Liquid Crystals,2016,vol. 635,p. 87 - 93.

10
[ 4282-29-5 ]
[ 1231160-83-0 ]

References: [1]Advanced Functional Materials,2011,vol. 21,p. 718 - 728.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 9608 - 9618.
[3]Molecular Crystals and Liquid Crystals,2016,vol. 635,p. 87 - 93.
[4]Chemistry of Materials,2019,vol. 31,p. 4629 - 4638.

11
[ 104-75-6 ]
[ 4282-29-5 ]
[ 1231160-83-0 ]

References: [1]Macromolecules,2012,vol. 45,p. 6906 - 6914,9.

12
[ 6007-85-8 ]
[ 1231160-83-0 ]

References: [1]Chemistry - An Asian Journal,2013,vol. 8,p. 168 - 177.
[2]Chemistry of Materials,2019,vol. 31,p. 4629 - 4638.

13
[ 6165-68-0 ]
[ 1231160-83-0 ]
[ 1286745-51-4 ]