[ CAS No. 97329-43-6 ] {[proInfo.proName]}

Name: 97329-43-6|1-Bromo-2-chloro-3-methylbenzene|98%
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SKU: A224345
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Quality Control of [ 97329-43-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 97329-43-6 ]

CAS No. :	97329-43-6	MDL No. :	MFCD07782165
Formula :	C₇H₆BrCl	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZAUOWBCSUDVVQT-UHFFFAOYSA-N
M.W :	205.48	Pubchem ID :	13348134
Synonyms :

Calculated chemistry of [ 97329-43-6 ]

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 :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.38
Log Po/w (XLOGP3) :	4.02
Log Po/w (WLOGP) :	3.41
Log Po/w (MLOGP) :	3.95
Log Po/w (SILICOS-IT) :	3.62
Consensus Log Po/w :	3.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.14
Solubility :	0.0149 mg/ml ; 0.0000725 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.72
Solubility :	0.0389 mg/ml ; 0.000189 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.26
Solubility :	0.0113 mg/ml ; 0.0000552 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.4

Safety of [ 97329-43-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 97329-43-6 ]

* 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.

Upstream synthesis route of [ 97329-43-6 ]
Downstream synthetic route of [ 97329-43-6 ]

[ 97329-43-6 ] Synthesis Path-Upstream 1~9

1
[ 97329-43-6 ]
[ 56961-27-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7631 - 7639
[2] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1984, vol. 38, # 8, p. 713 - 716

2
[ 627531-47-9 ]
[ 97329-43-6 ]

Reference： [1] Patent: US2008/194650, 2008, A1, . Location in patent: Page/Page column 24-25
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 36, p. 8363 - 8366

3
[ 134271-44-6 ]
[ 97329-43-6 ]

Reference： [1] Journal of Organometallic Chemistry, 1991, vol. 401, # 3, p. 261 - 272

4
[ 570-24-1 ]
[ 97329-43-6 ]

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

5
[ 95-46-5 ]
[ 97329-43-6 ]

Reference： [1] Journal of Biological Chemistry, 1915, vol. 20, p. 674
[2] Monatshefte fuer Chemie, 1934, vol. 64, p. 153,157

6
[ 958990-53-9 ]
[ 97329-43-6 ]

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

7
[ 591-17-3 ]
[ 97329-43-6 ]

Reference： [1] Monatshefte fuer Chemie, 1934, vol. 64, p. 153,157
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 331,346

8
[ 106-38-7 ]
[ 7782-50-5 ]
[ 97329-43-6 ]

Reference： [1] Monatshefte fuer Chemie, 1933, vol. 64, p. 153,158

9
[ 7553-56-2 ]
[ 100-39-0 ]
[ 97329-43-6 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1939, vol. <2> 152, p. 1,4, 6

[ 97329-43-6 ] Synthesis Path-Downstream 1~50

1
[ 570-24-1 ]
[ 97329-43-6 ]

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

2
[ 591-17-3 ]
[ 97329-43-6 ]

Reference： [1]Monatshefte fur Chemie,1934,vol. 64,p. 153,157

3
[ 95-46-5 ]
[ 97329-43-6 ]

Reference： [1]Journal of Biological Chemistry,1915,vol. 20,p. 674

4
[ 958990-53-9 ]
[ 97329-43-6 ]

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

5
[ 97329-43-6 ]
[ 56961-27-4 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7631 - 7639
[2]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 713 - 716

6
[ 134271-44-6 ]
[ 97329-43-6 ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 401,p. 261 - 272

7
[ 7553-56-2 ]
[ 100-39-0 ]
[ 97329-43-6 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1939,vol. <2> 152,p. 1,4, 6

8
[ 106-38-7 ]
[ 7782-50-5 ]
[ 97329-43-6 ]

Reference： [1]Monatshefte fur Chemie,1933,vol. 64,p. 153,158

Yield	Reaction Conditions	Operation in experiment
		By the procedure of Example 2, the following halo substituted toluene compounds: 2-bromo-3-chlorotoluene 3-bromo-2-chlorotoluene 2-chloro-3-iodotoluene 3-chloro-2-iodotoluene

10
[ 627531-47-9 ]
[ 97329-43-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In ethanol; water; at 70℃; for 2h;	Concentrated HCl was added to a solution of <strong>[627531-47-9]4-bromo-3-chloro-2-methyl-phenylamine</strong> (4.98 g, 22.60 mmol) in EtOH. NaNO2 (3.00 g, 43.50 mmol) was added and the resulting mixture was heated to 70 C. for 2 hours. Ethanol was distilled off and the residue was purified by column chromatography using hexanes as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 2.43 (s, 3H), 7.01 (t, J=7.91 Hz, 1H), 7.18 (d, J=7.62 Hz, 1H), 7.47 (d, J=7.91 Hz, 1H).

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8363 - 8366
[2]Patent: US2008/194650,2008,A1 .Location in patent: Page/Page column 24-25

11
[ 97329-43-6 ]
[ 1044256-89-4 ]

Yield	Reaction Conditions	Operation in experiment
82.1%	With N-Bromosuccinimide; dibenzoyl peroxide; In dichloromethane; for 12h;Reflux;	10.0 g of <strong>[97329-43-6]1-bromo-2-chloro-3-methylbenzene</strong>, 8.66 g of N-bromosuccinimide, and a small amount of bezoyl peroxide and 100 mL of methylene chloride were added to the reactor.After heating to reflux for 12 hours, the reaction mixture was cooled to room temperature and the bouillon was filtered off.The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane) to obtain 1-bromo-3- (bromomethyl) -2-chlorobenzene. (11.36 g, yield 82.1%)
46%	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux;	l-bromo-2-chloro-3-rnethylbenzene (10 g, 48.7 mmol) was dissolved in CCl4 (100 mL), and then N-bromosuccinimide (13.0 g, 73.0 mmol) and benzoyl peroxide (5.9 g, 24.3 mmol) were added. The mixture was stirred for 2 hours at reflux. The solid was removed by filtration, and the filtrate was washed with water and dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in DCM and purified on silica gel using 10% hexane/AcOEt to afford l-bromo-3-(bromomethyl)- 2-chlorobenzene (6.36 g, 46% yield); 1H NMR (400 MHz, CDCl3): delta 4.62 (s, 2H), 7.12 (t, J = 7.8 Hz, IH), 7.39 (dd, J = 1.6 Hz, J = 7.6 Hz, IH), 7.60 (dd, J = 1.6 Hz, J = 8.0 Hz, IH).
	With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 0.5h;Heating / reflux;	A solution of <strong>[97329-43-6]1-bromo-2-chloro-3-methyl-benzene</strong> (3.90 g, 19.00 mmol), NBS (3.60 g, 20.20 mmol) and a catalytic amount of AIBN (50 mg) in CCl4 was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The precipitate was washed with pentane. The solvent was distilled off and the residue was purified by column chromatography using pentane as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 4.62 (s, 2H), 7.14 (t, J=7.62 Hz, 1H), 7.39 (dd, J=7.62 Hz, 1H), 7.60 (dd, J=7.91 Hz, 1H).

Reference： [1]Patent: KR102006994,2019,B1 .Location in patent: Paragraph 0236-0239
[2]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 134
[3]Patent: US2008/194650,2008,A1 .Location in patent: Page/Page column 24-25

12
[ 14277-00-0 ]
[ 97329-43-6 ]
2,7-dimethyl-1-phenyl-1H-benzoimidazole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 680 - 686

13
[ 24544-04-5 ]
[ 97329-43-6 ]
[ 1227188-09-1 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 2241 - 2243

14
[ 97329-43-6 ]
[ 98-80-6 ]
[ 1334181-18-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8363 - 8366

15
[ 97329-43-6 ]
[ 98-80-6 ]
[ 19482-23-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8363 - 8366

16
[ 3744-02-3 ]
[ 97329-43-6 ]
[ 1354491-90-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tributyltin methoxide;tris-(o-tolyl)phosphine; palladium dichloride; In toluene; at 100℃; for 5h;Inert atmosphere;	Preparation of l-(2-chloro-3-methylphenyl)propan-2-one: A Smith process vial was charged with l-bromo-2-chloro-3 -methylbenzene (528 mg, 2.57 mmol, 1 eq.), tributylmethoxytin (1.11 mL, 1.5 eq.), 4-methylpent-4-en-2-one (0.42 mL, 1.5 eq.), PdCl2 (23 mg, 5%) and tri(o-tolyl)phosphine (79 mg, 10%), toluene (1 mL) was added and mixture sparged with nitrogen for 10 minutes and then heated in oil bath at 100 C for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with brine, dried (MgS04), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to l -(2-chloro-3-methylphenyl)propan-2- one (375 mg, 80% yield). 1H-NMR: 400 MHz, (CDC13) delta : 7.19-7.02 (m, 3H), 3.82(s, 2H), 2.38(s, 3H), 2.18 (s, 3H).

Reference： [1]Patent: WO2012/3497,2012,A1 .Location in patent: Page/Page column 306-307

17
[ 538-32-9 ]
[ 97329-43-6 ]
[ 156726-03-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3844 - 3846

18
[ 97329-43-6 ]
[ 100-52-7 ]
[ 4269-05-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; potassium hydrogencarbonate; DL-Pro-NHMe; In tert-Amyl alcohol; at 120℃; for 24h;Inert atmosphere;	General procedure: A mixture of arylaldehyde (0.1 g, 1 mmol), dihaloarene (0.565 g, 2 mmol), Pd(OAc)2 (0.022 g, 10.0 mol%), N-phenylpicolinamide (L7, 0.019 g, 15.0 mol%) and potassium hydrogen carbonate (0.5 g, 5 mmol) in tert-amyl alcohol (5.0 ml) was taken in 100.0 ml round bottom flask under N2 atmosphere and stirred for 120C for 24 h. Progress of the reaction was monitored continuously by TLC with ethyl acetate: hexane (2:3) eluent system. After completion of reaction, crude was poured into crushed ice and then filter the reaction mixture. Filtrate then extracted with ethyl acetate (3 times). Organic layer was separated, dried (over anhydrous Na2SO4) and evaporated under reduced pressure and purified by column chromatography to obtain desired product. Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found exactly similar as reported in the literature (References of above compound are mentioned in Supplementary data).

Reference： [1]Tetrahedron,2019,vol. 75,p. 236 - 245

19
[ 52289-54-0 ]
[ 97329-43-6 ]
3-methoxy-1,5-dimethyl-9H-fluoren-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; potassium hydrogencarbonate; DL-Pro-NHMe; In tert-Amyl alcohol; at 120℃; for 24h;Inert atmosphere;	General procedure: A mixture of arylaldehyde (0.1 g, 1 mmol), dihaloarene (0.565 g, 2 mmol), Pd(OAc)2 (0.022 g, 10.0 mol%), N-phenylpicolinamide (L7, 0.019 g, 15.0 mol%) and potassium hydrogen carbonate (0.5 g, 5 mmol) in tert-amyl alcohol (5.0 ml) was taken in 100.0 ml round bottom flask under N2 atmosphere and stirred for 120C for 24 h. Progress of the reaction was monitored continuously by TLC with ethyl acetate: hexane (2:3) eluent system. After completion of reaction, crude was poured into crushed ice and then filter the reaction mixture. Filtrate then extracted with ethyl acetate (3 times). Organic layer was separated, dried (over anhydrous Na2SO4) and evaporated under reduced pressure and purified by column chromatography to obtain desired product. Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found exactly similar as reported in the literature (References of above compound are mentioned in Supplementary data).

Reference： [1]Tetrahedron,2019,vol. 75,p. 236 - 245

20
[ 97329-43-6 ]
[ 1044256-91-8 ]

Yield	Reaction Conditions	Operation in experiment
46%		A mixture of <strong>[97329-43-6]1-bromo-2-chloro-3-methylbenzene</strong> (1.0 g, 4.87 mmol), NBS (1.3 g, 7.3 mmol), and benzoyl peroxide (11 mg, 0.05 mmol) in carbon tetrachloride (10 mL) was heated at 80 C. for 18 hours. The mixture was concentrated, then dichloromethane (10 mL) and water (10 mL) were added. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was re-dissolved in ethanol (10 mL) and NH4OH (10 mL, 4.87 mmol) was added. Then the mixture was stirred at room temperature for 2 hours. The mixture was concentrated and purified by prep-TLC (normal phase, silica gel, dichloromethanemethanol=20:1) to give (3-bromo-2-chlorophenyl)methanamine (500 mg, 46% yield) as a yellow solid. LCMS (ESI) [M+H]+=220.0

Reference： [1]Patent: US2018/282282,2018,A1 .Location in patent: Paragraph 0459; 0460

21
[ 97329-43-6 ]
N-(3-bromo-2-chlorobenzyl)-2,2-diethoxyacetimidamide [ No CAS ]

Reference： [1]Patent: US2018/282282,2018,A1

22
[ 97329-43-6 ]
7-bromo-8-chloroisoquinolin-3-amine [ No CAS ]

Reference： [1]Patent: US2018/282282,2018,A1

23
[ 7463-35-6 ]
[ 97329-43-6 ]

Reference： [1]Patent: US2008/194650,2008,A1

24
[ 125328-80-5 ]
[ 97329-43-6 ]

Reference： [1]Patent: US2008/194650,2008,A1

25
[ 97329-43-6 ]
[ 73183-34-3 ]
[ 915070-53-0 ]
2-(2-chloro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; at 85℃; for 12h;Inert atmosphere;	To a stirred solution of <strong>[97329-43-6]1-bromo-2-chloro-3-methylbenzene</strong> (2 g, 9.73 mmol) in 1,4-dioxane (15 mL), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (3.7 g, 14.6 mmol) and potassium acetate (2.86 g, 29.1 mmol) were added. The reaction mixture was degassed with argon for 10 min. Then Pd(PPh3)2Cl2 (1.02 g, 1.45 mmol) was added and heated at 85 C. with stirring for 12 h. The color of the reaction mixture changed from yellow to red and finally to black. Progress of the reaction was monitored by TLC, which showed consumption of starting material. The reaction mixture was cooled to room temperature and filtered through celite, followed by ethyl acetate wash (100 mL). The filtrate was concentrated to dryness under reduced pressure to afford mixtures of product (1.5 g, 60% pure in LCMS) as a red colored oil, which was used directly for the next step.

Reference： [1]Patent: US2019/77792,2019,A1 .Location in patent: Paragraph 0502-0504

26
2-amino-3-bromo-6-chloropyrazine [ No CAS ]
[ 97329-43-6 ]
[ 73183-34-3 ]
6-chloro-3-(2-chloro-3-methylphenyl)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.28 g		To a stirred solution of 3-bromo-6-chloropyrazin-2-amine (0.3 g, 1.43 mmol) in THF:H2O (20 ml, 9:1), and mixture of boronic acid and ester (0.3 g, crude), sodium carbonate (0.46 g, 4.31 mmol) were added. The reaction mixture was degassed with argon for a 10 minutes and Pd(PPh3)4 (0.16 g, 0.14 mmol) was added. The reaction mixture was degassed again with argon and heated at 80 C. with stirring for 12 h. Progress of the reaction was monitored by TLC, which showed complete consumption of starting material. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was diluted with water (20 mL) and the extracted with EtOAc (3*20 mL). The combined organic layer was washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography [silica gel (100-200 mesh), gradient 4% to 6% ethyl acetate in hexane] to give 6-chloro-3-(2-chloro-3-methylphenyl)pyrazin-2-amine (0.28 g, 76%) as a yellow solid. MS (ESI+ve): 253.92 1H-NMR (400 MHz; DMSO-d6): delta 7.82 (s, 1H), 7.44-7.46 (d, J=7.20 Hz, 1H), 7.32-7.36 (t, J=7.6 Hz, 1H), 7.20-7.22 (d, J=6.8 Hz, 1H), 6.51 (bs, 2H), 2.40 (s, 3H).

Reference： [1]Patent: US2019/77792,2019,A1 .Location in patent: Paragraph 0502; 0505-0508

27
[ 97329-43-6 ]
(3aR,5r,6aS)-2-(4-amino-5-(2-chloro-3-methylphenyl)pyrimidin-2-yl)-5-methyloctahydrocyclopenta[c]pyrrol-5-amine hydrogen chloride salt [ No CAS ]