31161-46-3|(5-Bromothiophen-2-yl)(phenyl)methanone| Ambeed

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Quality Control of [ 31161-46-3 ] Purity: 97% (stabilized with Cu+HQ+MgO) SDS Specification

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Product Details of [ 31161-46-3 ]

CAS No. :	31161-46-3
Formula :	C₁₁H₇BrOS
M.W :	267.14
SMILES Code :	O=C(C1=CC=C(Br)S1)C2=CC=CC=C2
MDL No. :	MFCD03086026
InChI Key :	DHPVOIIUHSEYJY-UHFFFAOYSA-N
Pubchem ID :	298604

Safety of [ 31161-46-3 ]

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

Computational Chemistry of [ 31161-46-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	61.89
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.31 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.48
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	4.3
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.74
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.	2.78
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	4.72
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.	-4.65
Solubility	0.00592 mg/ml ; 0.0000221 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.	-4.96
Solubility	0.0029 mg/ml ; 0.0000108 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	-4.99
Solubility	0.00277 mg/ml ; 0.0000104 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.	-4.88 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<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)	2.42

Application In Synthesis of [ 31161-46-3 ]

* 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 [ 31161-46-3 ]

[ 31161-46-3 ] Synthesis Path-Downstream 1~35

1
[ 1003-09-4 ]
[ 98-88-4 ]
[ 31161-46-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With aluminum (III) chloride; In carbon disulfide; for 2.46h;	Example 13c; (5-bromothien-2-yl)(phenyl)methanone.; To a mixture of benzoyl chloride (2.81 g, 20.0 mmol) and 2-bromothiophene (3.42 g, 21.0 mmol) in carbon disulfide (120 mL) aluminum chloride (5.34 g, 40.0 mmol), was added in portions over 10 min with vigorous magnetic stirring. The reaction was next allowed to stir for 2.5 h before being quenched with 100 mL 1 M HCl(aq). The organics were separated, the aqueous layer extracted with carbon disulfide (3 x 50 mL), and the combined organics washed with water (3 x 100 mL) and dried over MgSO4. After filtration, the organics were concentrated in vacuo and the residue chromatographed on a silica gel column (hexane : ether = 9 : 1) to yield <n="30"/>5.14 g (96 %) of yellow crystals, mp 41-43 C ; 1H NMR (CDCl3): δ 7.84 (d, 2H, 3J = 8.0 Hz), 7.62 (t, IH, 3J =7.2 Hz), 7.52 (t, 2H, 3J = 7.5 Hz), 7.40 (d, 2H, 3J = 3.5 Hz), 7.15 (d, 2H, 3J = 4.0 Hz).
92.7%	With aluminium trichloride; In dichloromethane;	EXAMPLE 1 Preparation of the 5-benzoyl-α-methyl-2-thiopheneacetic acid. 3.420 kg of benzoyl chloride are slowly added to a suspension of 3.250 kg of aluminum trichloride in 12 kg of methylene chloride, between 10 and 20 C. At the end the mixture is stirred for 10 minutes and then 3.600 kg of 2-bromothiophene are slowly added between 0 and 5 C. The mixture is stirred for 1 hour at 15 C. and then it is poured into a mixture of ice, water and hydrogen chloride. The organic phase is separated and dry concentrated and the residual product is crystallized from sec-butanol and dried. 5.500 kg of 5-benzoyl-2-bromothiophene with m.p. 73-75 C. and HPLC purity>99% are obtained. Yield equal to 92.7%,
	With sodium hydroxide;tin(IV) chloride; In hexane; dichloromethane; water;	PREPARATION 1 5-Benzoyl-2-bromothiophene 2-Bromothiophene (9.7 ml., 0.1 mole), benzoyl chloride (11.6 ml., 0.1 mole) and stannic chloride (11.5 ml., 0.1 mole) were combined in 100 ml. of methylene chloride and stirred at room temperature for 4 hours. The reaction mixture was cooled to room temperature, water (65 ml.) was added and the two phase system stirred for 20 minutes. Ether (165 ml.) was added, the organic phase was separated, back-washed with 20 ml. of 1 N sodium hydroxide and twice with 20 ml. of water, and concentrated to an oil (20.8 g.) which crystallized on standing. The crude was melted by warming with 25 ml. of hexane (two phases formed) and cooled to yield purified crystalline 5-benzoyl-2-bromothiophene (16.5 g., m/e 266/268).

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 13476 - 13477.
[2]Patent: WO2007/50049,2007,A1 .Location in patent: Page/Page column 27-29.
[3]Patent: US5650522,1997,A .
[4]Recueil des Travaux Chimiques des Pays-Bas,1949,vol. 68,p. 5,29.
[5]Patent: US4282246,1981,A .
[6]Chemistry - A European Journal,2010,vol. 16,p. 1911 - 1928.
[7]Organic Letters,2019.

2
[ 31161-46-3 ]
[ 6921-34-2 ]
1-(5-bromo-[2]thienyl)-1,2-diphenyl-ethylene [ No CAS ]

References: [1]Journal of the Chemical Society,1954,p. 1690,1695.

3
[ 135-00-2 ]
[ 31161-46-3 ]

References: [1]Journal of the American Chemical Society,1937,vol. 59,p. 2699,2700.

4
[ 31161-46-3 ]
[ 61464-23-1 ]

References: [1]Organic Letters,2019.
[2]Journal of the Chemical Society. Perkin transactions I,1985,p. 275 - 282.

5
[ 162607-17-2 ]
[ 98-88-4 ]
[ 31161-46-3 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 3057 - 3060.
[2]Russian Chemical Bulletin,2004,vol. 53,p. 364 - 369.

Yield	Reaction Conditions	Operation in experiment
52%		EXAMPLE 3 Reaction and post-treatment were carried out in the same manner as in Example 1, except that 10.6 g (0.065 mole) of 2-bromothiophene and 6.1 g (0.05 mole) of benzoic acid were substituent for the thiophene and the suberic acid monomethyl ester, to obtain 6.95 g of 2-benzoyl-5-bromothiophene. Yield: 52%.

8
5-benzoyl-<2>thienylmercury(1+) chloride [ No CAS ]
[ 31161-46-3 ]

References: [1]Journal of the American Chemical Society,1937,vol. 59,p. 2699,2700.

9
[ 31161-46-3 ]
[ 171290-94-1 ]
5,5'''-bis(phenylcarbonyl)-2,2':5',2'':5'',2'''-quaterthiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 15h;	Example 13d; 5,5" '-bis(phenylcarbonyl)-2,2 ':5 ',2 ' ':5 ",2 " '-quaterthiophene (DPCO- 4T, 2).; A mixture of 2-bromo-5-benzoylthiohene (1.07 g, 4.00 mmol), 5,5'- bis(tributylstannyI)-2,2'-dithiophene (1.49 g, 2.00 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.0693 g, 0.0600 mmol) was degassed with nitrogen three times before 20 mL anhydrous DMF was added. The reaction mixture was heated to 80 C for 15 h with stirring. A deep red precipitate formed and upon cooling and was collected by filtration, then washed with hexanes (3 x 10 mL) and methanol (3 x 10 mL). Gradient sublimation (2x) afforded an orange-red crystalline material (0.689 g, 64 %) with some crystals suitable for x-ray diffraction, mp 307-310 C; 1H NMR (DMSO): δ 7.85 (2H), 7.84 (2H), 7.67 (4H), 7.59 (2H), 7.53 (2H), 7.48 (IH), 7.44 (IH); Anal. Calcd for C30H18O2S4: C 66.88, H 3.37. Found: C 66.93, H 3.42; MS (EI): m/z (%) 538.0 (100) [M+].

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 13476 - 13477.
[2]Patent: WO2007/50049,2007,A1 .Location in patent: Page/Page column 27; 29.
[3]Chemistry - A European Journal,2010,vol. 16,p. 1911 - 1928.

10
[ 31161-46-3 ]
phenyl-thiophen-2-yl-methanol [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 275 - 282.

11
[ 31161-46-3 ]
[ 16821-78-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 275 - 282.

12
[ 31161-46-3 ]
[ 135-00-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 275 - 282.

13
[ 31161-46-3 ]
[ 98215-99-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 275 - 282.

14
[ 31161-46-3 ]
[ 6861-51-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 275 - 282.

15
[ 31161-46-3 ]
[ 101607-13-0 ]

References: [1]Journal of the Chemical Society,1954,p. 1690,1695.

16
[ 31161-46-3 ]
copper(l) cyanide [ No CAS ]
[ 79505-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	In quinoline; water;	PREPARATION 2 5-Benzoyl-2-cyanothiophene 5-Benzoyl-2-bromothiophene (8 g., 30 mmoles) and cuprous cyanide (3.2 g., 36 mmoles) were combined in 75 ml. of quinoline and refluxed for 3 hours. The reaction mixture was cooled to room temperature and solids removed by filtration with 15 ml. of quinoline and 15 ml. of water wash. The combined filtrate and washings were poured into approximately 300 g. of ice, acidified with conc. hydrochloric acid and product extracted into 300 ml. of ether. The ether extract was back-washed with 150 ml. of water, filtered from insolubles and concentrated to yield solid 5-benzoyl-2-cyanothiophene (5.7 g., m.p. 85-89 C., m/e 213).

References: [1]Patent: US4282246,1981,A .

17
[ 1003-09-4 ]
[ 31161-46-3 ]
[ 27132-23-6 ]
[ 98-88-4 ]
sodium methyl diethylmalonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride; In N-methyl-acetamide; methylene chloride,between;	EXAMPLE 1 Preparation of the 5-benzoyl-α-methyl-2-thiopheneacetic acid. 3.420 kg of benzoyl chloride are slowly added to a suspension of 3.250 kg of aluminum trichloride in 12 kg of methylene chloride,between 10 and 20 C. At the end the mixture is stirred for 10 minutes and then 3.600 kg of 2-bromothiophene are slowly added between 0 and 5 C. The mixture is stirred for 1 hour at 15 C and then it is poured into a mixture of ice, water and hydrogen chloride. The organic phase is separated and dry concentrated and the residual product is crystallized from sec-butanol and dried. 5.500 kg of 5-benzoyl-2-bromothiophene with m.p. 73-75 C and HPLC purity > 99% are obtained. Yield equal to 92.7%. 260 of methyl diethylmalonate are slowly added, maintaining the temperature between 10 and 20 C, to a suspension of 54 g of sodium hydride at 60% in 600 g of dimethylformamide. At the end the mixture is stirred for 2 hours at 20 C in order to complete the formation of the sodium methyl diethylmalonate.

References: [1]Patent: EP748802,1996,A1 .

18
[ 31161-46-3 ]
[ 326798-98-5 ]
[ 326799-09-1 ]

References: [1]Journal of Organometallic Chemistry,2000,vol. 612,p. 172 - 175.

19
[ 31161-46-3 ]
[ 326798-96-3 ]
[ 326799-03-5 ]

References: [1]Journal of Organometallic Chemistry,2000,vol. 612,p. 172 - 175.

20
[ 31161-46-3 ]
[ 326798-96-3 ]
[ 326799-06-8 ]

References: [1]Journal of Organometallic Chemistry,2000,vol. 612,p. 172 - 175.

21
[ 31161-46-3 ]
tri-n-butylstannylferrocene [ No CAS ]
[ 271782-75-3 ]

References: [1]Journal of Organometallic Chemistry,2000,vol. 598,p. 348 - 352.
[2]Journal of Organometallic Chemistry,2000,vol. 598,p. 348 - 352.

22
[ 31161-46-3 ]
[ 12291-11-1 ]
[ 400736-14-3 ]

References: [1]Journal of Organometallic Chemistry,2001,vol. 637-639,p. 723 - 726.

23
[ 31161-46-3 ]
[ 1144114-45-3 ]
[ 1187424-89-0 ]

References: [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3672 - 3679.

24
[ 31161-46-3 ]
[ 98-80-6 ]
[ 13858-68-9 ]

References: [1]Journal of Chemical Research,2009,p. 745 - 749.
[2]Organic Letters,2019.

25
[ 31161-46-3 ]
[ 73183-34-3 ]
[ 1220107-42-5 ]

References: [1]Organic Letters,2020,vol. 22,p. 3273 - 3278.
[2]Organic Letters,2021,vol. 23,p. 2320 - 2325.
[3]Chemistry - A European Journal,2010,vol. 16,p. 1911 - 1928.

26
[ 31161-46-3 ]
[ 41842-35-7 ]
[ 1322616-80-7 ]
[ 67513-10-4 ]
5,5'-Dibenzoyl-[2,2']bithienyl [ No CAS ]