935-99-9|1-(2-Bromo-5-chlorophenyl)ethanone| Ambeed

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Quality Control of [ 935-99-9 ] Purity: 97% SDS Specification

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Product Details of [ 935-99-9 ]

CAS No. :	935-99-9
Formula :	C₈H₆BrClO
M.W :	233.49
SMILES Code :	CC(C1=CC(Cl)=CC=C1Br)=O
MDL No. :	MFCD11847057
InChI Key :	BCQAWQMDMPBDBW-UHFFFAOYSA-N
Pubchem ID :	12486617

Safety of [ 935-99-9 ]

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

Computational Chemistry of [ 935-99-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	49.35
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.1
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	2.92
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.31
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.	3.08
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	3.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.46
Solubility	0.0801 mg/ml ; 0.000343 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.94
Solubility	0.268 mg/ml ; 0.00115 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.21
Solubility	0.0145 mg/ml ; 0.0000619 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	No
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.	-5.65 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	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	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)	1.47

Application In Synthesis of [ 935-99-9 ]

* 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 [ 935-99-9 ]

[ 935-99-9 ] Synthesis Path-Downstream 1~35

1
[ 7677-24-9 ]
[ 935-99-9 ]
[ 71095-32-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1979,p. 829 - 837.

3
[ 455957-87-6 ]
[ 75-16-1 ]
[ 935-99-9 ]

Yield	Reaction Conditions	Operation in experiment
		Methylmagnesium bromide (4.26 mL of a 1.4M solution in tetrahydrofuran/toluene, 5.97 mmol) was added dropwise to a stirred solution of 2-bromo-5-chloro-N-methoxy-N-methylbenzamide (3-1) (0.554 g, 1.99 mmol) in tetrahydrofuran (20 mL) at approximately 0° C. After 1 h, 1N hydrochloric acid (5 mL) was added and the resulting biphasic mixture was stirred vigorously for about 10 min. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0-10percent ethyl acetate/hexanes as eluent) provided 3-3 (0.44 g) as a colorless oil.

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7509 - 7513.
Angew. Chem.,2013,vol. 125,p. 7657 - 7661,5.
[2]Patent: US2003/225060,2003,A1 .Location in patent: Page 36-38.

4
[ 935-99-9 ]
[ 455957-88-7 ]

Yield	Reaction Conditions	Operation in experiment
		Trimethylborate (1.74 mL, 15.4 mmol) was added to a stirred solution of (S)-(-)-alpha,alpha-diphenyl-2-pyrrolidinemethanol (3.24 g, 12.8 mol) in tetrahydrofuran (350 mL) at room temperature. After 1.25 h, borane-methyl sulfide complex (70.4 mL of a 2M solution in tetrahydrofuran, 0.141 mol) was added slowly and a gentle effervesence was observed. The resulting solution was cooled to approximately 0° C. and a solution of <strong>[935-99-9]1-(2-bromo-5-chlorophenyl)ethanone</strong> (3-3) (30.0 g, 0.128 mmol) in tetrahydrofuran (150 mL) was then added uniformly over 1 h. After the addition, the resulting mixture was allowed to warm to ambient temperature and aged overnight. The reaction mixture was concentrated under reduced pressure to approximately one quarter of its original volume, poured into 1N hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (9percent ethyl acetate/hexanes as eluent) afforded 3-4 as a colorless solid (25.8 g; 98:2 S/R enantiomeric ratio).

References: [1]Patent: US2003/225060,2003,A1 .Location in patent: Page 37-38.

5
[ 935-99-9 ]
[ 149-73-5 ]
C₁₀H₁₂BrClO₂ [ No CAS ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 9298 - 9300.

6
[ 935-99-9 ]
[ 103-81-1 ]
[ 1315568-05-8 ]

References: [1]Synthesis,2011,p. 1547 - 1554.

7
[ 935-99-9 ]
[ 1260857-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; bromine; In tetrahydrofuran; at 0 - 20℃; for 3.5h;Inert atmosphere;	General procedure: The title compd was prepared as per Scheme 3 (steps a-b). Step a: To a solution of 2?-bromoacetophenone 46 (100 g, 0.50 mol), in THF (100 mL) at 0 °C was added AlCl3 (3.37 g, 0.025 mol) followed by dropwise addition of Br2 (28.3 mL, 0.552 mol) over 90 min. The mixture was then allowed to warm to rt and stirred for 2 h whereupon it was quenched by addition of water (500 mL) and extracted with EtOAc (3×300 mL). (Note: the first extract is denser than water due to concentration.)The combined organic layer washed with brine(2×400 mL), dried (MgSO4), filtered and concentrated in vacuo toobtain 2-bromo-(2?-bromoacetophenone) as yellow oil (215.4 g) and was used as crude. The 2-bromo-(2?-bromoacetophenone) (176.9 g, 0.414 mol) thus obtained was dissolved in ethanol (1.8 L) and 1-cyclopropylthiourea 20 (48 g, 0.414 mol) and the mixture refluxed for 2 h then allowed to cool to rt and the mixture concentrated to ?150 mL whereupon diethyl ether (2.2 L) was added with rapid stirring resulting in a precipitate that was filtered and air-dried to obtain the HBr salt ofthe desired product (145 g). This salt was then suspended in DCM (1.1L) and washed with saturated NaHCO3 (2×900 mL) to free base the product. The organic layer was dried (Na2SO4), filtered and concentrated to obtain 48 as an off-white solid (101 g, 83percent). LCMS(Method B) m/z 296 (M+1). HPLC purity > 98percent (254 nm). 1H NMR(CDCl3) delta: 7.69 ? 7.62 (m, 2H), 7.35 ? 7.29 (m, 1H), 7.19 ? 7.11 (m,1H), 6.91 (s, 1H), 6.56 (bs, 1H), 2.60 ? 2.53 (m, 1H), 0.72 ? 0.65 (m,2H), 0.62 ? 0.56 (m, 2H). Step b: A mixture of 48 (1g, 3.39mmol), aq 2M K2CO3 (5.1mL, 10.2mmol), 6-methoxypyridine-3-boronic acid (1.04g, 6.78mmol) and toluene (30mL) was degassed with Ar for 10min. Pd2(dba)3 (0.31g, 0.34mol) and S-Phos (0.28g, 0.68mmol) were then added and the mixture heated to 85°C for 90min. After allowing the mixture to cool to rt the reaction mixture was diluted with EtOAc (100mL) and washed with brine (50mL). The aq layer was further extracted with EtOAc (2*50mL) and then the combined extracts dried (MgSO4), filtered and concentrated in vacuo. The crude (brown viscous oil) was purified by flash chromatography using 20-50percent EtOAc in cyclohexane to obtain 50 as yellow solid (0.99g, 90percent). LCMS (Method B) m/z 324 (M+1). HPLC purity>98percent (254nm). 1H NMR (CDCl3) delta: 7.73 (d, J=2.6Hz, 1H), 7.55 (d, J=8.5Hz, 1H), 7.12 (dd, J=2.6, 8.5Hz, 1H), 7.00 (bs, 1H), 2.59 - 2.55 (m, 1H), 0.74 - 0.69 (m, 2H), 0.63 - 0.59 (m, 2H).

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7509 - 7513.
Angew. Chem.,2013,vol. 125,p. 7657 - 7661,5.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5169 - 5180.

8
[ 935-99-9 ]
(Z)-N'-[1-(2,5-dibromophenyl)ethylidene]-4-methylbenzenesulfonohydrazide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7509 - 7513.
Angew. Chem.,2013,vol. 125,p. 7657 - 7661,5.

9
[ 935-99-9 ]
5-chloro-3-methyl-1-tosyl-1H-indazole [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7509 - 7513.
Angew. Chem.,2013,vol. 125,p. 7657 - 7661,5.

10
[ 21739-93-5 ]
[ 935-99-9 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7509 - 7513.
Angew. Chem.,2013,vol. 125,p. 7657 - 7661,5.

11
[ 935-99-9 ]
[ 77287-34-4 ]
N-[1-(2-bromo-5-chlorophenyl)ethyl]formamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With formic acid; at 180℃; for 33h;	General procedure: Typical procedure for the preparation of formamides 2: A mixture of 1-(2-bromophenyl)ethanone (1a) (4.0 g, 20 mmol), HCONH2 (9.3 mL), and HCO2H (6.2 mL) was heated at 180 °C for 33 h. After cooling to room temperature, water (50 mL) was added and the mixture was extracted with AcOEt (330 mL). The combined extracts were washed with water (20 mL), satd aq NaHCO3 (320 mL), and then brine (20 mL), dried (Na2SO4), and concentrated by evaporation. The residue was purified by column chromatography on silica gel to afford 2a (2.9 g, 73percent); a yellow oil; Rf 0.10 (AcOEt/hexane 1:2); IR (neat) 3280, 1660 cm-1; 1H NMR (500 MHz) delta 1.53 and 1.55 (2d, J=6.9 Hz each, combined 3H), 5.07-5.13 and 5.42-5.48 (2m, combined 1H), 5.97 (br 1H), 7.14 and 7.17 (2t, J=7.4 Hz each, combined 1H), 7.29-7.35 (m, 2H), 7.56 and 7.58 (2d, J=7.4 Hz each, combined 1H), 8.18 and 8.20 (2s, combined 1H); 13C NMR delta 21.00, 22.42, 47.97, 51.04, 122.43, 122.82, 126.89, 127.78, 128.17, 128.90, 129.20, 133.27, 133.40, 141.49, 141.89, 160.16, 164.29. Anal. Calcd for C9H10BrNO: C, 47.39; H, 4.42; N, 6.14. Found: C, 47.27; H, 4.68; N, 6.01.