[ CAS No. 69321-56-8 ] {[proInfo.proName]}

Name: 69321-56-8|5-Bromo-2-methylbenzene-1-sulfonyl chloride|97%
Brand: Ambeed
SKU: A682732
Price: 11.0 USD
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Quality Control of [ 69321-56-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 69321-56-8 ]

Product Details of [ 69321-56-8 ]

CAS No. :	69321-56-8	MDL No. :	MFCD06655596
Formula :	C₇H₆BrClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OYSAFEFFWRNQJF-UHFFFAOYSA-N
M.W :	269.54	Pubchem ID :	4962163
Synonyms :

Calculated chemistry of [ 69321-56-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.19
TPSA :	42.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.2
Log Po/w (XLOGP3) :	3.0
Log Po/w (WLOGP) :	3.77
Log Po/w (MLOGP) :	2.59
Log Po/w (SILICOS-IT) :	2.45
Consensus Log Po/w :	2.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.71
Solubility :	0.0531 mg/ml ; 0.000197 mol/l
Class :	Soluble
Log S (Ali) :	-3.56
Solubility :	0.0747 mg/ml ; 0.000277 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.18
Solubility :	0.0179 mg/ml ; 0.0000664 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.86

Safety of [ 69321-56-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 69321-56-8 ]

* 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 [ 69321-56-8 ]
Downstream synthetic route of [ 69321-56-8 ]

[ 69321-56-8 ] Synthesis Path-Upstream 1~1

1
[ 69321-56-8 ]
[ 62473-92-1 ]

Reference： [1] Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 10, p. 966 - 971
[2] Patent: WO2013/131408, 2013, A1,

[ 69321-56-8 ] Synthesis Path-Downstream 1~77

1
[ 106-38-7 ]
[ 69321-56-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With chlorosulfonic acid; In dichloromethane; at -5 - 20℃;	69.50 g (406.3 mmol) of 4-bromotoluene are initially charged in 250 ml of dichloromethane, and 175.33 g (1.50 mol) of chlorosulphonic acid are added dropwise at -5-5 C. With stirring, the reaction mixture is brought to room temperature overnight, 1000 ml of ice-water are added and the mixture is extracted with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and freed from the solvent under reduced pressure. This gives 89.54 g (95% pure, 78% of theory) of the title compound as a yellow liquid which is reacted further without further purification. log P[a]: 3.73; log P[b]: 3.74; GC-MS: EI mass (m/z): 270 (1Cl, 1Br) [M]+; 1H-NMR (CDCl3, 400 MHz): 8.19 (d, 1H), 7.73-7.72 (m, 1H), 7.31 (d, 1H), 2.73 (s, 3H); 1H-NMR (CD3CN, 400 MHz): 8.18 (d, 1H), 7.88-7.85 (m, 1H), 7.46 (d, 1H), 2.71 (s, 3H)
78%	With chlorosulfonic acid; In dichloromethane; at -5℃;	Stage 1: 5-Bromo-2-methylbenzenesulphonyl chloride 69.50 g (406.3 mmol) of 4-bromotoluene are initially charged in 250 ml of dichloromethane, and 175.33 g (1.50 mol) of chlorosulphonic acid are added dropwise at -5 C. With stirring, the reaction mixture is brought to room temperature overnight, 1000 ml of ice-water are added and the mixture is extracted with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and freed of the solvent under reduced pressure. This gives 89.54 g (95% pure, 78% of theory) of the title compound as a yellow liquid which is reacted further without further purification. log P[a]: 3.73; log P[b]: 3.74; GC-MS: EI mass (m/z): 270 (1Cl,1Br) [M]+; 1H NMR (CDCl3, 400 MHz): 8.19 (d, 1H), 7.73-7.72 (m, 1H), 7.31 (d, 1H), 2.73 (s, 3H); 1H NMR (CD3CN, 400 MHz): 8.18 (d, 1H), 7.88-7.85 (m, 1H), 7.46 (d, 1H), 2.71 (s, 3H)
70%	With chlorosulfonic acid; at 60℃; for 0.166667h;	[0396] Bromide (1.99 g, 11.61 mmol) was stirred vigorously and treated with chlorosulfonic acid (1.55 mL, 23.22 mmol). Once addition was complete, resulting red syrup was heated to 600C. Reaction TLC after 10 min showed no starting material and reaction was quenched by pouring onto ice. Product was extracted by washing with EtOAc (2 x 150 mL). Organic phase dried over Na2SO4, filtered and evaporated to yellow oil (2.2g, 70%).

With chlorosulfonic acid; In dichloromethane; at 0℃; for 4.0h;

General procedure: Chlorosulfonic acid (696 mg, 6.0 mmol) was added slowly to a cold solution (0 C) of 3-bromotoluene (170 mg, 1.0 mmol) (or 4-bromotoluene (170 mg, 1.0 mmol)), in CHCl3 (10 mL). The reaction was allowed to proceed for 4 h with stirring at 0 C prior to pouring onto crushed ice (250 g). The resulting mixture was extracted with CHCl3 (3 × 150 mL). The combined CHCl3 extracts were washed with water (3 × 100 mL) and dried with Na2SO4, and the solvent was removed in vacuum to yield the arylsulfonyl chloride product (6 or 7), which was used in next step without purification.

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468
[2]Patent: US2015/344499,2015,A1 .Location in patent: Paragraph 1055; 1056; 1057
[3]Patent: US2016/145235,2016,A1 .Location in patent: Paragraph 1672; 1673; 1674
[4]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 190
[5]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971
[6]Journal of the American Chemical Society,1940,vol. 62,p. 511,512
[7]Journal of the American Chemical Society,1940,vol. 62,p. 511,512
[8]Patent: US6369236,2002,B1 .Location in patent: Example 1a)
[9]European Journal of Medicinal Chemistry,2013,vol. 62,p. 597 - 604
[10]Patent: WO2013/131408,2013,A1 .Location in patent: Page/Page column 86

2
[ 69321-56-8 ]
[ 56919-16-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonia; In tetrahydrofuran; methanol; at 20℃; for 1.0h;	Ammonia in MeOH (25.00 ml; 7.00 mol/L; 175.00 mmol; 9.40 eq.) was added dropwise to a solution of <strong>[69321-56-8]5-bromo-2-methylbenzenesulfonyl chloride</strong> (5.00 g; 18.55 mmol; 1.00 eq.) in THF (50 ml) and the reaction was stirred 1 h at rt. Solid was filtered and washed twice with EtOAc. The filtrate was concentrated to dryness and dried under vacuum to give 5-bromo-2-methyl-benzenesulfonamide (4.94 g; 92 %) as a beige solid. 1
90%	With ammonium hydroxide; In 1,4-dioxane; at 0℃; for 6.0h;	General procedure: An aqueous solution of NH4OH (15 mL of 30% w/v) was added to a cold solution of the arylsulfonyl chloride (6 or 7, 268 mg, 1.0 mmol) in dioxane (10 mL) at 0 C with vigorous stirring, and the reaction was allowed to proceed for 6 h at 0 C with stirring. The insoluble material was removed by filtration, washed with water (3 × 10 mL). The organic layer was concentrated and recrystallized with 50% acetone in hexane to yield the product.

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971
[2]Patent: KR2019/137803,2019,A .Location in patent: Paragraph 0729-0731
[3]European Journal of Medicinal Chemistry,2013,vol. 62,p. 597 - 604
[4]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468
[5]Justus Liebigs Annalen der Chemie,1873,vol. 169,p. 21
[6]Patent: WO2013/131408,2013,A1 .Location in patent: Page/Page column 86

3
[ 69321-56-8 ]
[ 64732-38-3 ]

Reference： [1]Journal of the Chemical Society,1923,vol. 123,p. 2510
[2]Journal of the Chemical Society,1923,vol. 123,p. 2510

4
[ 56919-17-6 ]
[ 69321-56-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1873,vol. 169,p. 21

5
[ 69321-56-8 ]
[ 71-43-2 ]
[ 69321-57-9 ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3013,3016

6
[ 19947-75-2 ]
[ 69321-56-8 ]
5-Bromo-N-(3,4-dimethyl-isoxazol-5-yl)-2-methyl-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398

7
[ 69321-56-8 ]
[ 33084-49-0 ]
5-Bromo-N-(4-bromo-3-methyl-isoxazol-5-yl)-2-methyl-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398

9
sodium salt of/the/ 4-bromo-toluene-sulfonic acid-⁽²⁾ [ No CAS ]
[ 69321-56-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1873,vol. 169,p. 21

10
[ 69321-56-8 ]
[ 75-64-9 ]
[ 511529-00-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	In dichloromethane; for 16.0h;	[0400] A stirring suspension of intermediate 64 (1.22 g, 4.5 mmol) in DCM (25 mL) was treated with ter/-butylamine (1.4 mL, 13.6 mmol). After 16 h, reaction solvents were removed and resulting solids triturated with water. Solids were dried uner vacuum overnight (1.3 g, 94%).
73%	In chloroform; at 0 - 20℃;	Step 1) Formation of 5-Bromo-N-(tert-butyl)-2-methylbenzenesulfonamideTert-butylamine (16.25 g, 222.6 mmol) was added in dropwise to a solution of 5- Bromo-2-methylbenzenesulfonyl chloride (Tetrahedron, 2006, 62(33), 7902-7910, 30 g, 1 11.3 mmol) in dry HCCI3 (300 ml.) at O0C. The reaction mixture was stirred RT for 16 h. It was then concentrated under reduced pressure, diluted with water (500 ml.) and stirred for 15 min. The precipitate obtained was filtered, washed with water (200 ml.) and dried to give the title compound as a white solid (25 g, 73%). 1H NMR :(CDCI3, 400MHz) delta 8.17 (1 H, s), 7.56-7.55 (1 H, d), 7.19-7.18 (1 H, d),4.61 (1 H, brs), 2.60 (3H, s),1.27 (9H, s).

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 192
[2]Patent: WO2010/100144,2010,A1 .Location in patent: Page/Page column 139
[3]Tetrahedron,2006,vol. 62,p. 7902 - 7910

11
[ 69321-56-8 ]
6-bromo-2-tert-butyl-1,2-benzothiazol-3(2H)-one-1,1-dioxide [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 7902 - 7910

12
[ 69321-56-8 ]
[ 849067-20-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

13
[ 69321-56-8 ]
[ 849067-22-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

14
[ 69321-56-8 ]
[ 849067-24-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

15
[ 69321-56-8 ]
[ 849067-28-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

16
[ 69321-56-8 ]
3-acetylsulfamoyl-biphenyl-4-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

17
[ 69321-56-8 ]
[ 849067-29-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

18
[ 69321-56-8 ]
[ 849067-26-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

19
[ 69321-56-8 ]
N-acetyl-5-(4-methylsulfonylphenyl)-2-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

20
[ 69321-56-8 ]
3-acetylsulfamoyl-4'-fluoro-biphenyl-4-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

21
[ 69321-56-8 ]
[ 849067-40-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

22
[ 69321-56-8 ]
N-acetyl-2-methoxycarbonyl-5-(4-methylsulfonylphenyl)benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

23
[ 69321-56-8 ]
3-acetylsulfamoyl-2',4'-difluoro-biphenyl-4-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

24
[ 69321-56-8 ]
3-acetylsulfamoyl-4'-methanesulfonyl-biphenyl-4-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2459 - 2468

25
[ 69321-56-8 ]
[ 62473-92-1 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971
[2]Patent: WO2013/131408,2013,A1

26
[ 69321-56-8 ]
[ 524707-34-4 ]