3141-24-0|2,3,5-Tribromothiophene| Ambeed

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Quality Control of [ 3141-24-0 ] Purity: 98% (stabilized with Cu+HQ+MgO) SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 3141-24-0 ]

CAS No. :	3141-24-0
Formula :	C₄HBr₃S
M.W :	320.83
SMILES Code :	BrC1=CC(Br)=C(Br)S1
MDL No. :	MFCD00014521
InChI Key :	SKDNDSLDRLEELJ-UHFFFAOYSA-N
Pubchem ID :	76592

Safety of [ 3141-24-0 ]

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

Computational Chemistry of [ 3141-24-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	5
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	47.42
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.24 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.36
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	4.34
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.04
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.	3.56
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	4.7
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.8

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.03
Solubility	0.00302 mg/ml ; 0.00000942 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.	-4.65
Solubility	0.00722 mg/ml ; 0.0000225 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	-4.2
Solubility	0.0202 mg/ml ; 0.000063 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.18 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	2.0
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<1.0
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)	3.04

Application In Synthesis of [ 3141-24-0 ]

* 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 [ 3141-24-0 ]

[ 3141-24-0 ] Synthesis Path-Downstream 1~35

1
[ 188290-36-0 ]
[ 3141-24-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With bromine; In chloroform; at 20 - 50℃;	Compound 25-2 (0443) To a solution of thiophene (84 g, 1.0 mol) in chloroform (34 mL) was added dropwise bromine at rt for 3 h. When the addition was complete, the mixture was stirred at rt overnight. The mixture was heated to 50 C. for 3 h. The reaction mixture was washed with 1M NaOH (aq. 100 mL), brine (100 mL×2) respectively. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to afford light yellow oil, which was solidified in methanol (100 mL). The solid was filtered and dried in vacuo to afford 25-2 (89 g, 56%).
	With tetrabutylammomium bromide; hydrogen bromide; dihydrogen peroxide; In water; at 25 - 75℃; for 10h;Large scale;	Thiophene was brominated to provide 2,3,5-tribromothiophene A according to the following procedure. A reactor was charged with a solution of aqueous hydrobromic acid (47.6%, 125.0 kg, 5 equiv). Thiophene (12.5 kg, purity 99%, 1 equiv) was added to it at 25- 30C. Tetrabutylammonium bromide (0.625 kg, 0.13 equiv) was added to the reaction mass. The reaction mass was heated to 50-55 C. 50%> Aqueous hydrogen peroxide solution (31.3 kg, 3.1 equiv) was added to the reaction mass over 10 h keeping the temperature in the range of 50-55 C. The reaction mass was then heated to 70-75C. After reaction completion, the reaction mass was cooled to 20-25 C and washed with 20%> sodium metabisulphite solution (17 L), 2 N sodium hydroxide solution (62 L) and the crude product was subjected to fractional distillation using a 2 ft wire-mesh packed column to afford 2,3,5-tribromothiophene A. The spectral properties of this molecule are consistent with commercially available material. ii. De-Bromination to prepare intermediate B
	With tetrabutylammomium bromide; hydrogen bromide; dihydrogen peroxide; In water; at 25 - 75℃;Large scale;	Bromination to prepare intermediate 7:[0149j Thiophene was brominated to provide 7 according to the following procedure. A reactor was charged with a solution of aqueous hydrobromic acid (47.6%, 125.0 kg, 5 equiv). Thiophene (12.5 kg, purity 99%, 1 equiv) was added to it at 25-30C. Tetrabutylammonium bromide (0.625 kg, 0.13 equiv) was added to the reaction mass. The reaction mass was heated to 50-55 C. 50% Aqueous hydrogen peroxide solution (31.3 kg, 3.1 equiv) was added to thereaction mass over 10 h keeping the temperature in the range of 50-55 C. The reaction mass was then heated to 70-75C. After reaction completion, the reaction mass was cooled to 20- 25 C and washed with 20% sodium metabisulphite solution (17 L), 2 N sodium hydroxide solution (62 L) and the crude product was subjected to fractional distillation to afford 2,3,5- tribromothiophene. The spectral properties of this molecule are consistent with commerciallyavailable material.

	With tetrabutylammomium bromide; dihydrogen peroxide; In water; at 50 - 75℃; for 10h;	Bromination to prepare intermediate 7 15 [0158j A reactor was charged with a solution of aqueous hydrobromic acid (47.6%, 125.0 kg, 5 equiv). Thiophene (12.5 kg, purity 99%, 1 equiv) was added to it at 25-30C. Tetrabutylammonium bromide (0.625 kg, 0.13 equiv) was added to the reaction mass. The reaction mass was heated to 50-55 C. 50% Aqueous hydrogen peroxide solution (31.3 kg, 3.1 equiv) was added to the reaction mass over 10 h keeping the temperature in the range of 50-20 55 C. The reaction mass was then heated to 70-75C. After reaction completion, the reaction mass was cooled to 20-25 C and washed with 20% sodium metabisulphite solution (17 L), 2 N sodium hydroxide solution (62 L) and the crude product was subjected to fractional distillation using a 2 ft wire-mesh packed column to afford 2,3,5-tribromothiophene. The spectral properties of this molecule are consistent with commercially available material.
52.6 kg		a, the chloroform 35L, thiophene and 16.8 kg 0.168kg copper bromide into reactor 1, stirred for 10 minutes, in a jacketed reactor was cooled to -5 water when the tank by the dropwise addition of 65.0kg of bromine was added dropwise 6 into the reactor 1. document.write(""); B, the drum to the reaction vessel 1 with air or oxygen after start of the reaction, after completion of bromine was slowly added dropwise, and then slowly heated to reflux for 1 reactor, the gas is condensed by the reflux condenser 8 into the reactor 1 at reflux, the reaction after 3.5 hours, cooled to 23 -25 ; document.write(""); C, the ethanol solution was added dropwise to the reactor tank 1 7 added dropwise 10L0.05mol / L sodium hydroxide, the decomposition of unreacted bromine and stirred for 30 minutes.document.write(""); d, the reaction mixture was washed into the autoclave 2 was added 35L of water, stir for 30 minutes, allowed to stand, the lower organic phase into the distillation still 3 atmospheric distillation, followed by distillation gas condenser 9, distillation condenser 10 after the condensation, the first fraction prior to recycling the solvent and the solvent recovery tank 4, and then distilled under reduced pressure to 15mmHg, followed after distillation gas condenser 9, distillation condenser 10 condensed, collecting 112 ~ 116 / 15mmHg into the product fraction collected tank 5 to give colorless liquid 52.6kg2,3,5- three bromothiophene product

References: [1]European Journal of Inorganic Chemistry,2001,p. 233 - 238.
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 861 - 870.
[3]Synthetic Communications,1988,vol. 18,p. 1763 - 1764.
[4]European Journal of Organic Chemistry,2008,p. 801 - 804.
[5]Chinese Journal of Chemistry,2014,vol. 32,p. 365 - 369.
[6]Organic Letters,2013,vol. 15,p. 4666 - 4669.
[7]Journal of the Chemical Society. Perkin transactions II,1982,p. 295 - 300.
[8]Journal of Photochemistry and Photobiology A: Chemistry,2010,vol. 212,p. 176 - 182.
[9]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 301.
[10]Chemistry Letters,2011,vol. 40,p. 93 - 95.
[11]Bulletin de la Societe Chimique de France,1955,p. 424.
[12]Journal of the Chemical Society. Perkin transactions I,1986,p. 1755 - 1758.
[13]Patent: WO2014/28341,2014,A1 .Location in patent: Paragraph 130-131.
[14]Patent: WO2014/28342,2014,A1 .Location in patent: Paragraph 0149.
[15]Patent: WO2014/28343,2014,A1 .Location in patent: Paragraph 0158.
[16]Patent: CN104529995,2016,B .Location in patent: Paragraph 0013-0017.

2
[ 3141-27-3 ]
[ 3141-24-0 ]

References: [1]Zeitschrift fur physikalische Chemie (Neue Folge),1981,vol. 127,p. 13 - 22.
[2]Chemische Berichte,1885,vol. 18,p. 1774.
[3]Chemische Berichte,1894,vol. 27,p. 2837.
[4]Arkiv foer Kemi,1957,vol. 11,p. 373,379, 380.

3
[ 3141-24-0 ]
[ 109-72-8 ]
[ 60-29-7 ]
[ 872-31-1 ]

References: [1]Arkiv foer Kemi,1957,vol. 11,p. 373,379, 380.

4
[ 3141-24-0 ]
[ 109-72-8 ]
[ 118833-77-5 ]

References: [1]Arkiv foer Kemi,1957,vol. 11,p. 317,322.

5
[ 3141-24-0 ]
[ 925-90-6 ]
[ 3140-93-0 ]
[ 3140-92-9 ]

References: [1]Arkiv foer Kemi,1958,vol. 12,p. 115,120.

6
[ 3141-24-0 ]
[ 872-31-1 ]

References: [1]Chinese Journal of Chemistry,2014,vol. 32,p. 365 - 369.
[2]Organic Letters,2013,vol. 15,p. 4666 - 4669.
[3]Journal of the Chemical Society. Perkin transactions II,1982,p. 295 - 300.
[4]Bulletin de la Societe Chimique de France,1955,p. 424.
[5]Acta Chemica Scandinavica (1947),1959,vol. 13,p. 1045.
[6]Acta Chemica Scandinavica (1947),1956,vol. 10,p. 1020,1021.
Arkiv foer Kemi,1957,vol. 11,p. 317,321.
[7]Journal of the Chemical Society. Perkin transactions I,1986,p. 1755 - 1758.
[8]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 889 - 891.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1046 - 1048.

7
[ 3141-24-0 ]
[ 3140-93-0 ]
[ 3140-92-9 ]

References: [1]Justus Liebigs Annalen der Chemie,1934,vol. 512,p. 136,156.
[2]Justus Liebigs Annalen der Chemie,1934,vol. 512,p. 136,156.
[3]Organometallics,2016,vol. 35,p. 3234 - 3239.

8
[ 3141-24-0 ]
[ 3140-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In dimethyl sulfoxide; at 15 - 25℃; for 2h;Large scale;	Selective de-bromination of A provided 2,4 dibromothiophene B according to the following procedure. Dimethyl sulfoxide (DMSO, 330 L) was charged to reactor. 2,3,5- tribromothiophene A (33 kg, 1.0 equiv) was charged to the reaction mass under stirring. The reaction mass was cooled to 15-20C. Sodium borohydride (7.8 kg, 2.0 equiv) was charged lot wise to the reaction mass in 2. Oh maintaining temperature 15 to 20 C. The reaction mass was heated to 20 to 25C and maintained until the reaction was completed. The reaction mass was quenched in water (660 L) at 10 to 15 C and the product was extracted into toluene (5 x 165 L). The combined organic layer was washed with water (165 L). The organic layer was dried over anhydrous sodium sulfate (8.0 kg) and concentrated under reduced pressure below 50 C to yield 2,4 dibromothiophene B. The spectral properties of this molecule are consistent with commercially available material. iii.
	With sodium tetrahydroborate; In dimethyl sulfoxide; at 15 - 25℃;Large scale;	ii. De-Bromination to prepare intermediate 8: [0151j Selective de-bromination of 7 provided 8 according to the following procedure.Dimethyl sulfoxide (DMSO, 330 L) was charged to reactor. <strong>[3141-24-0]2,3,5-tribromothiophene</strong> (33 kg, 1.0equiv) was charged to the reaction mass under stirring. The reaction mass was cooled to15-20 C. Sodium borohydride (7.8 kg, 2.0 equiv) was charged lot wise to the reaction mass in2.0 h maintaining temperature 15 to 20 C. The reaction mass was heated to 20 to 25C andmaintained until the reaction was completed. The reaction mass was quenched in water (660 L) at 10 to 15 C and the product was extracted into toluene (5 x 165 L). The combined organic layer was washed with water (165 L). The organic layer was dried over anhydrous sodium sulfate (8.0 kg) and concentrated under reduced pressure below 50 C to yield 2,4 dibromothiophene. The spectral properties of this molecule are consistent with commerciallyavailable material.
	With sodium tetrahydroborate; In dimethylsulfoxide-d6; at 10 - 25℃;	2. De-Bromination to prepare intermediate 8 [0159j Dimethyl sulfoxide (DMSO, 330 L) was charged to reactor. <strong>[3141-24-0]2,3,5-tribromothiophene</strong> (33 kg, 1.0 equiv) was charged to the reaction mass under stirring. The reaction mass was cooledto 15-20C. Sodium borohydride (7.8 kg, 2.0 equiv) was charged lot wise to the reaction mass in2.Oh maintaining temperature 15 to 20 C. The reaction mass was heated to 20 to 25C and maintained until the reaction was completed. The reaction mass was quenched in water (660 L) at 10 to 15 C and the product was extracted into toluene (5 x 165 L). The combined organic layer was washed with water (165 L). The organic layer was dried over anhydrous sodiumsulfate (8.0 kg) and concentrated under reduced pressure below 50 C to yield 2,4 dibromothiophene. The spectral properties of this molecule are consistent with commercially available material.

References: [1]Journal of Chemical Research - Part S,1996,p. 150 - 151.
[2]Journal of Organic Chemistry,1988,vol. 53,p. 417 - 420.
[3]Journal of Photochemistry and Photobiology A: Chemistry,2010,vol. 212,p. 176 - 182.
[4]Arkiv foer Kemi,1957,vol. 11,p. 317,322.
[5]Journal of the Chemical Society. Perkin transactions I,1987,p. 1777 - 1780.
[6]Patent: WO2014/28341,2014,A1 .Location in patent: Paragraph 0132.
[7]Patent: WO2014/28342,2014,A1 .Location in patent: Paragraph 0151.
[8]Patent: WO2014/28343,2014,A1 .Location in patent: Paragraph 0159.
[9]Organometallics,2016,vol. 35,p. 3234 - 3239.

9
[ 3141-24-0 ]
[ 858000-09-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1934,vol. 512,p. 136,156.

10
[ 3141-24-0 ]
[ 7311-68-4 ]

References: [1]Acta Chemica Scandinavica (1947),1956,vol. 10,p. 1020,1021.
Arkiv foer Kemi,1957,vol. 11,p. 317,321.

11
[ 3141-24-0 ]
[ 116277-69-1 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 3030.

12
[ 3141-24-0 ]
[ 52431-30-8 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 3030.

13
[ 3141-24-0 ]
tribromo-[3]thienylmercury ⁽¹⁺⁾; chloride [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1936,vol. 522,p. 35,38.

14
[ 3141-24-0 ]
[ 3958-03-0 ]

References: [1]Chemische Berichte,1894,vol. 27,p. 2837.

15
[ 3141-24-0 ]
[ 7311-68-4 ]
[ 6324-10-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1934,vol. 512,p. 136,156.

16
[ 1003-09-4 ]
[ 3141-26-2 ]
[ 3141-24-0 ]
[ 3141-25-1 ]
[ 3958-03-0 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2119 - 2122.

17
[ 3141-24-0 ]
[ 2009-97-4 ]
(2Z,5E,7Z)-5,7,8-Tribromo-2-methyl-[1,4]oxathiocine-3-carboxylic acid ethyl ester [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1991,vol. 63,p. 161 - 170.

18
[ 3141-24-0 ]
[ 355-43-1 ]
[ 188290-36-0 ]
[ 128032-25-7 ]

References: [1]Journal of Fluorine Chemistry,1990,vol. 46,p. 137 - 159.

19
[ 3141-24-0 ]
[ 124-38-9 ]
[ 7311-68-4 ]

References: [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 4514 - 4525.
[2]Journal of the Chemical Society. Perkin transactions I,1994,p. 2735 - 2744.
[3]Journal of the Chemical Society. Perkin transactions I,1986,p. 233 - 244.
[4]Archiv der Pharmazie,1998,vol. 331,p. 405 - 411.

20
[ 3141-24-0 ]
[ 1807-68-7 ]
[ 139081-02-0 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1991,vol. 63,p. 161 - 170.

21
[ 3141-24-0 ]
[ 75-36-5 ]
[ 7209-12-3 ]
[ 80775-52-6 ]
[ 3958-03-0 ]
[ 80775-47-9 ]