27139-97-5|2-Bromo-4-chloro-1-methylbenzene| Ambeed

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Quality Control of [ 27139-97-5 ] Purity: 98% SDS Specification

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Product Details of [ 27139-97-5 ]

CAS No. :	27139-97-5
Formula :	C₇H₆BrCl
M.W :	205.48
SMILES Code :	CC1=CC=C(Cl)C=C1Br
MDL No. :	MFCD00060650
Boiling Point :	No data available
InChI Key :	CSUUXPHPCXHYGY-UHFFFAOYSA-N
Pubchem ID :	609898

Safety of [ 27139-97-5 ]

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

Computational Chemistry of [ 27139-97-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	44.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.44
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.	3.41
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.	3.95
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	3.62
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.32
Solubility	0.00992 mg/ml ; 0.0000483 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.	-4.01
Solubility	0.0199 mg/ml ; 0.000097 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	-4.26
Solubility	0.0113 mg/ml ; 0.0000552 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	Low
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.	-4.5 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<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)	1.39

Application In Synthesis of [ 27139-97-5 ]

* 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 [ 27139-97-5 ]

[ 27139-97-5 ] Synthesis Path-Downstream 1~35

1
[ 106-43-4 ]
[ 27139-97-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	With bromine; iron; for 3.5h;	Example 1 (Scheme 1); 2-Bromo-4-chlorotoluene (4). To a flask containing p-chlorotoluene (10.00 g, 79.00 mmol) and iron filings (4.41 g, 79.00 mmol) was added molecular bromine (5.06 mL, 98.73 mmol) via a drip funnel; the reac- tion was left to stir for 3.5 hours, after which the mixture was filtered and the product purified by distillation (b. p. 80°C at 2 mm Hg). 6.71 g of bromoderivative (4) were obtained as a transparent oil with a yield of 40percent. 1H NMR (CDC13) (read. ); MS m/z 206 (100, M++H), 169,125, 99, 89, 73; Anal. (C7H6BrCl) compliant with the expected structure.

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1705 - 1708.
[2]Patent: WO2005/97797,2005,A2 .Location in patent: Page/Page column 11.
[3]Journal of the Chemical Society,1914,vol. 105,p. 1910.
[4]Patent: US2778857,1954, .

2
[ 95-46-5 ]
[ 27139-97-5 ]

References: [1]Journal of the Chemical Society,1914,vol. 105,p. 1910.

3
[ 27139-97-5 ]
[ 5306-98-9 ]

References: [1]Patent: US2778857,1954, .

4
[ 27139-97-5 ]
[ 936-08-3 ]

References: [1]Journal of the Chemical Society,1904,vol. 85,p. 1269.
[2]Collection of Czechoslovak Chemical Communications,1975,vol. 40,p. 3530 - 3544.

5
[ 119-32-4 ]
[ 27139-97-5 ]

References: [1]Journal of the Chemical Society,1904,vol. 85,p. 1269.

6
[ 7745-87-1 ]
[ 27139-97-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1975,vol. 40,p. 3530 - 3544.

7
[ 7745-91-7 ]
[ 27139-97-5 ]

References: [1]Tetrahedron,1988,vol. 44,p. 6525 - 6536.

8
[ 27139-97-5 ]
[ 16807-37-7 ]
[ 80568-32-7 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 220 - 227.

9
[ 27139-97-5 ]
[ 80568-44-1 ]
[ 80568-45-2 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 220 - 227.

10
[ 27139-97-5 ]
C₉H₁₂BrNO₂Zn [ No CAS ]
2-(5-Chloro-2-methyl-phenyl)-furan-3-carboxylic acid diethylamide [ No CAS ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 2437 - 2440.
[2]Tetrahedron Letters,1993,vol. 34,p. 2437 - 2440.

11
[ 27139-97-5 ]
C₉H₁₂BrNOSZn [ No CAS ]
[ 148839-44-5 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 2437 - 2440.

12
[ 815-24-7 ]
[ 27139-97-5 ]
[ 63076-55-1 ]

References: [1]Journal of Organic Chemistry,1977,vol. 42,p. 3394 - 3399.

13
[ 27139-97-5 ]
[ 33924-45-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 24h;Reflux;	Take a 500 ml double-necked round bottom bottle and place it in a stirrer and a reflux tube. After drying, it is filled with nitrogen. First, add compound A-3 (20.548 g, 1.0 equivalent) and NBS (N-bromosuccinimide). , 19.5778 g, 1.1 eq.), and AIBN (azobisisobutyronitrile, 0.821 g, 0.5 molpercent), followed by the addition of carbon tetrachloride (250 ml) and stirred for 10 minutes, finally heated to reflux and reacted After 24 hours; after the temperature was warmed, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), and the obtained extract was sequentially dried over magnesium sulfate, filtered and dried. Purification (ethyl acetate / hexanes, 1/10) afforded Intermediate 1-3 (23.604 g, yield 83percent).
80%	With bromine; at 190℃; for 3h;Irradiation;	In a three-necked round-bottom 500 ml flask equipped with a reflux condenser, thermometer, dropping funnel with pressure-equalizing, and magnetic stirring bar, 41.3 ml (128 g, 0.80 mmol) of bromine were added dropwise to 164 g (0.80 mol) of <strong>[27139-97-5]2-bromo-4-chlorotoluene</strong> under exposure to 500 W lamp for 3 h at 19O0C. The resulting mixture was cooled to room temperature. Fractional distillation gave a colorless liquid, b.p. 1 1 1-1 15C/7 mm Hg. Yield 182 g (80%).Anal. calc. for C7H5Br2Cl: C, 29.56; H, 1.77. Found: C, 29.76; H, 1.89.1H NMR (CDCl3): delta 7.44 (d, J= 1.7 Hz, IH, 2-H), 7.36 (dd, J= 6.0 Hz, J= 1.7 Hz, IH, 4-H), 7.18 (d, J= 6.0 Hz, IH, 5-H), 4.69 (s, 2H, CH2).
75%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 90℃; for 24h;	(b) into a 500mL three-neck bottle add 50g of compound 3, 50g of NBS (i.e. N-bromosuccinimide), 0.3g of BetaRho0 (i.e. dibenzoyl peroxide) and 300mL of carbon tetrachloride, the external temperature is raised at 90 C and the reaction is carried out for 24h (at this time, TLC showed complete reaction); pour the reaction solution into 500mL of ice water, adjust the pH at 10 with 2N (equivalent concentration) sodium hydroxide solution, layered extraction, combined organic phase, wash once with 5% sodium bicarbonate (mass concentration, the same below) solution, dry and then spin dry, separated by column chromatography and then obtained 52 g of compound 4 (yield is 75%)

75%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 90℃; for 24h;	(b) 50 g of compound 3, 50 g of NBS (ie N-bromosuccinimide), 0.3 g of BPO (ie dibenzoyl peroxide) and 300 mL of carbon tetrachloride were added to a 500 mL three-necked flask, and the external temperature was raised to At 90 C, the reaction was carried out for 24 h (at this time, TLC showed complete reaction);Pour the reaction solution into 500 mL of ice water, adjust the pH to 10 with 2N (equivalent concentration) sodium hydroxide solution, extract the layers, combine the organic phases, and wash with 5% sodium bicarbonate (mass concentration, the same below) solution. After drying, it was spin-dried, and column chromatography was carried out to obtain 52 g of Compound 4 (yield: 75%) (the nuclear magnetic spectrum of Compound 4 is shown in Fig. 3, and the specific resolution is: 1H NMR (400 MHz, CDCl3) delta (ppm): 7.58 ( d, J = 2.0 Hz, 1H), 7.38 (d, J = 4.0 Hz, 1H), 7.28 (d, J = 4.0 Hz, 1H), 4.55 (s, 1H))
64%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 4h;Heating / reflux;	2-Bromo-4-chlorobenzylbromide (5b). To the bromoderivative (6.71 g, 32.68 mmol) (4) dissolved in CCl4 were added N-bromosuccinimide (NBS) (5.82 g, 32.68 mmol), a,a'-azoisobutyronitrile (AIBN) (107.2 mg, 0.65 mmol) and after heating at reflux for 4 hours, the reaction mix- ture was cooled and filtered on Gooch. The filtrate was washed with aqueous sodium thiosulphate solution and then the organic phase was anhydrified on anhydrous sodium sulphate and the solvent evapo- rated. The crude reaction product was purified by flash chromatogra- phy, using n-hexane as the eluent. 6.00 g of product (5b) are thus obtained as a colourless oil with a yield of 64%. ¹H NMR (CDCIs) 8 7.58 (d, 1H, J = 1.75 Hz), 7.38 (d, 1H, J = 8.51 Hz), 7.28 (m, 1H), 4.55 (s, 2H); MS m/z 284 (M+), 205 (100), 169,124, 89; Anal. (C7H5Br2CI) C, H, N compliant with the expected structure.
182 g (80%)	With bromine;	2-Bromo-4-chlorobenzyl bromide In a three-necked round-bottom 500 ml flask equipped with a reflux condenser, thermometer, dropping funnel with pressure-equalizing, and magnetic stirring bar, 41.3 ml (128 g, 0.80 mmol) of bromine were added dropwise to 164 g (0.80 mol) of <strong>[27139-97-5]2-bromo-4-chlorotoluene</strong> under exposure to 500 W lamp for 3 h at 190 C. The resulting mixture was cooled to room temperature. Fractional distillation gave a colorless liquid, b.p. 111-115 C./7 mm Hg. Yield 182 g (80%). Anal. calc. for C7H5Br2Cl: C, 29.56; H, 1.77. Found: C, 29.76; H, 1.89. 1H NMR (CDCl3): delta 7.44 (d, J=1.7 Hz, 1H, 2-H), 7.36 (dd, J=6.0 Hz, J=1.7 Hz, 1H, 4-H), 7.18 (d, J=6.0 Hz, 1H, 5-H), 4.69 (s, 2H, CH2).
	With N-Bromosuccinimide;	1) Preparation of 4-[3-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile 109.2Compound 109.2 was prepared as described for example 1.2, by reacting compound 1.1, instead of 2-bromobenzyl bromide, with 2-bromo-1-bromomethyl-4-chlorobenzene (prepared by N-bromosuccinimide bromination from <strong>[27139-97-5]2-bromo-4-chloro-1-methylbenzene</strong>; 1H NMR: 7.82, d, 1H; 7.65, s, 1H, 7.5, d, 1H, 4.72, s, 2H). 4-[3-(2-Bromo-4-chlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile was obtained. (Molecular weight 498.99 (C20H14BrClF3N3O2); retention time Rt=2.30 min. [B]; MS (ESI): 541.04 (MH++CH3CN).

References: [1]Patent: CN109651423,2019,A .Location in patent: Paragraph 0099-0106.
[2]Patent: WO2007/70041,2007,A1 .Location in patent: Page/Page column 91.
[3]Patent: CN108409659,2018,A .Location in patent: Paragraph 0018; 0032.
[4]Patent: CN108707112,2018,A .Location in patent: Paragraph 0013; 0023-0024; 0027.
[5]Journal of the American Chemical Society,2011,vol. 133,p. 9282 - 9285.
[6]Journal of Medicinal Chemistry,2005,vol. 48,p. 1705 - 1708.
[7]Patent: WO2005/97797,2005,A2 .Location in patent: Page/Page column 11-12.
[8]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 57 - 64.
[9]Patent: US2007/135595,2007,A1 .
[10]Patent: US2009/215728,2009,A1 .Location in patent: Page/Page column 40.
[11]Patent: WO2009/158426,2009,A1 .

14
[ 106-43-4 ]
amalgamated aluminium [ No CAS ]
[ 57310-39-1 ]
[ 27139-97-5 ]

References: [1]Journal of the Chemical Society,1914,vol. 105,p. 1910.

Yield	Reaction Conditions	Operation in experiment
148 g (72%)		2-Bromo-4-chlorotoluene In a 3000 ml beaker 142 g (1.00 mol) of melted 2-methyl-4-chloroaniline were slowly added to 1200 ml of 23percent aqueous HBr. This mixture was stirred for 20 min using a mechanical stirrer, cooled to -5° C.; and then a solution of 70.0 g (1.00 mol) of NaNO2 in 400 ml of water was added dropwise for 1.5 h at this temperature. The diazonium reagent obtained was added in several portions to a solution of 144 g (1.00 mol) of CuBr in 400 ml of 47percent HBr at 0° C. The resulting mixture was warmed to 70° C., stirred for 30 min at this temperature, and, then, cooled to room temperature. The product was extracted with 3*500 ml of methyl-tert-butyl ether; and the combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave colorless oil, b.p. 81-84° C./7 mm Hg. Yield 148 g (72percent). Anal. calc. for C7H6BrCl: C, 40.92; H, 2.94. Found: C, 41.00; H, 2.99. 1H NMR (CDCl3): delta 7.45 (d, J=1.8 Hz, 1H, 2-H), 7.34 (dd, J=6.0 Hz, J=1.8 Hz, 1H, 4-H), 7.12 (d, J=6.0 Hz, 1H, 5-H), 2.43 (s, 3H, Me).

16
[ 95-46-5 ]
amalgamated aluminium [ No CAS ]
[ 27139-97-5 ]
[ 62356-27-8 ]

References: [1]Journal of the Chemical Society,1914,vol. 105,p. 1910.

17
[ 75-97-8 ]
[ 27139-97-5 ]
2-(5-chloro-2-methyl-phenyl)-3,3-dimethyl-butan-2-ol [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 581 - 590.

18
[ 27139-97-5 ]
1-bromo-5-chloro-4-iodo-2-methylbenzene [ No CAS ]