[ CAS No. 25300-37-2 ] {[proInfo.proName]}

Name: 25300-37-2|2-Chloro-6-methylbenzene-1-sulfonyl chloride|95%
Brand: Ambeed
SKU: A169824
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3d Animation Molecule Structure of 25300-37-2

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Quality Control of [ 25300-37-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 25300-37-2 ]

SDS Specification

Alternatived Products of [ 25300-37-2 ]

Product Details of [ 25300-37-2 ]

CAS No. :	25300-37-2	MDL No. :	MFCD00051767
Formula :	C₇H₆Cl₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FJVZVTWCAGCLCS-UHFFFAOYSA-N
M.W :	225.09	Pubchem ID :	15725370
Synonyms :

Calculated chemistry of [ 25300-37-2 ] 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 :	49.5
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) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	2.94
Log Po/w (WLOGP) :	3.66
Log Po/w (MLOGP) :	2.43
Log Po/w (SILICOS-IT) :	2.42
Consensus Log Po/w :	2.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.0913 mg/ml ; 0.000406 mol/l
Class :	Soluble
Log S (Ali) :	-3.49
Solubility :	0.072 mg/ml ; 0.00032 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.95
Solubility :	0.0253 mg/ml ; 0.000112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 25300-37-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 25300-37-2 ]

* 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 [ 25300-37-2 ]

[ 25300-37-2 ] Synthesis Path-Downstream 1~43

Yield	Reaction Conditions	Operation in experiment
	2-Chlor-6-methyl-anilin;
		The following sulfonyl chlorides may be substituted for benzenesulfonyl chloride of Step One: ... 3-Chloro-4-fluorobenzenesulfonyl chloride 3-Chloro-2-fluorobenzenesulfonyl chloride 2-Chloro-6-methylbenzenesulfonyl chloride 5-Chlorothiophene-2-sulfonyl chloride ...
	2-Chlor-6-methylanilin;

aus 2-Chlor-6-methylanilin, Sandmeyer-Rkt.;

2
[ 61-80-3 ]
[ 25300-37-2 ]
2-chloro-<i>N</i>-(5-chloro-benzooxazol-2-yl)-6-methyl-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1807 - 1810

3
[ 25300-37-2 ]
[ 75-64-9 ]
N-(tert-butyl)-2-chloro-6-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; for 8h;

Reference： [1]Xu, Liang; Shu, Hong; Liu, Ying; Zhang, Suhong; Trudell, Mark L. [Tetrahedron, 2006, vol. 62, # 33, p. 7902 - 7910]

4
[ 299-26-3 ]
[ 25300-37-2 ]
2-chloro-N-[2-(1H-indol-3-yl)-1-methylethyl]-6-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane for 48h;

Reference： [1]Marshall, Daniel R.; Rodriguez, Gus; Thomson, David S.; Nelson, Richard; Capolina, Allison [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 2, p. 315 - 319]

5
[ 25300-37-2 ]
1-{1-[(2-chloro-6-methylphenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: (5-methoxy-1H-indol-4-ylmethyl)-dimethyl-amine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 2-chloro-6-methylbenzenesulfonyl chloride In N,N-dimethyl-formamide at 20℃;	162 Example 162; l-{l-[(2-Chloro-6-methylphenyl)sulfonyl]-5-methoxy-lH-indol-4-yl}-N,iV- dimethylmethanamine; To a solution of l-(5-methoxy-lH-indol-4-yl)-λ/,λ/-dimethylmethanamine (15 mg, 0.07 mmol; Intermediate 97) in DMF (1 mL) NaH (4 mg, 0.15 mmol) was added at rt. The reaction mixture was stirred at rt for 15 min and 2-chloro-5-methylbenzene-l-sulfonyl chloride (25 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at rt over night. The reaction was quenched by addition of water. Purification by preparative HPLC/UV (System B) afforded the title product (7 mg, 24%) as a white solid. MS (ESI+) for Ci9H2IClN2O3S m/z 394 (M+H)+.

Reference： [1]Current Patent Assignee: BENEVOLENTAI LIMITED - WO2008/3703, 2008, A1 Location in patent: Page/Page column 148

6
[ 25300-37-2 ]
2-Chloro-N-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-ylmethyl]-6-methyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]methyl amine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: 2-chloro-6-methylbenzenesulfonyl chloride In dichloromethane at 20℃;	34 Example 34 2-Chloro-N-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-ylmethyl]-6-methyl-benzenesulfonamide A solution of [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-yl]methyl amine hydrochloride (391 mg, 1 mmol) was suspended in dry dichloromethane (10 mL), and diisopropylethylamine (323 mg, 0,25 mmol) was added. The reaction mixture was stirred at room temperature for 15 min. 2-Chloro-6-methyl-benzenesulfonyl chloride (225 mg,1 mmol) was added and the reaction mixture was stirred at room temperature overnight. The solution was then washed with water, dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to yield 2-chloro-N-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-ylmethyl]-6-methyl-benzenesulfonamide which was purified by column chromatography using dichloromethane/methanol (98:2) (440mg, 81 % as a cream solid). 1H NMR (300 MHz, METHANOL-d4) δ ppm 2.70 (s, 3 H) 2.86 (dd, J=17.58, 6.15 Hz, 1 H) 3.37 (dd, J=17.58, 11.28 Hz, 1 H) 4.00 (d, J=16.05 Hz, 1 H) 4.06 (d, J=16.05 Hz, 1 H) 5.38 (dd, J=11.28, 6.15 Hz, 1 H) 7.08 (d, J=5.86 Hz, 2 H) 7.05 - 7.10 (m, 2 H) 7.14 - 7.23 (m, 3 H) 7.29 (d, J=7.47 Hz, 1H) 7.38 - 7.49 (m, 1 H) 7.41 (t, J=7.69 Hz, 1 H)

Reference： [1]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP1911747, 2008, A1 Location in patent: Page/Page column 48

7
[ 25300-37-2 ]
[ 908602-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / CH₂Cl₂ / 8 h / 0 - 20 °C 2: 65 percent / H₅IO₆; CrO₃; Ac₂O / acetonitrile / 10 h / 20 °C

Reference： [1]Xu, Liang; Shu, Hong; Liu, Ying; Zhang, Suhong; Trudell, Mark L. [Tetrahedron, 2006, vol. 62, # 33, p. 7902 - 7910]

8
[ 288321-54-0 ]
[ 25300-37-2 ]
C₃₀H₄₁ClN₄O₁₀S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (2E)-3-[(3-{4-[(2S)-2-amino-2-(methoxycarbonyl)ethyl]phenoxy}propoxy)amino]-2-aza-3-[(tert-butoxy)carbonylamino]prop-2-enoate; 2-chloro-6-methylbenzenesulfonyl chloride With N-ethyl-N,N-diisopropylamine Stage #2: Stage #3: With lithium hydroxide

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US6344484, 2002, B1 Location in patent: Page column 68

9
[ 123-91-1 ]
2-oxo-2-hydroxymethyl-4-methyl-1.3.2-dioxaphosphorinane [ No CAS ]
[ 25300-37-2 ]
[ 4743-40-2 ]
2-Oxo-4-methyl-2-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]-1,3,2-dioxaphosphorinan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran; water; ethyl acetate	43 Preparation and Separation of the Two Diastereomers of 2-Oxo-4-methyl-2-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]-1,3,2-dioxaphosphorinan (Compounds 139 and 140) EXAMPLE 43 Preparation and Separation of the Two Diastereomers of 2-Oxo-4-methyl-2-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]-1,3,2-dioxaphosphorinan (Compounds 139 and 140) A solution of 12.65 g of 2-(hydroxymethyl)-2-oxo-4-methyl-1,3,2-dioxaphosphorinan, (Example 21), was prepared by dissolving the phosphorinan in a mixture of 40 ml of p-dioxane, 30 ml of ether, and 20 ml of THF with stirring and gentle heating on a steam bath. When all of the phosphorinan had dissolved, 11.8 ml of triethylamine was added to the cooled (room temperature) phosphorinan solution. The phosphorinan/base solution was then added dropwise to a solution of 16.4 g of 2-chloro-6-methylbenzenesulfonyl chloride in 70 ml of ether over 50 minutes. The addition caused a mild exotherm and the reaction was allowed to stir overnight at room temperature. The reaction solution was gravity filtered and the filter cake was rinsed with 75 ml of ethyl acetate, the combined filtrates concentrated, the concentrate partitioned between 300 ml of ethyl acetate and 100 ml of water, the phases separated, the organic phase rewashed with an additional 100 ml of water, dried with magnesium sulfate, filtered and concentrated to yield 18.2 g of the crude desired product as an off white solid. Phosphorus NMR indicated two diastereomers were present. The product was purified by flash chromatographing 7.4 g of the crude reaction product, dissolved in 12 ml of methylene chloride, on Merck silica gel (230-400 mesh) eluding with blends of hexanes and ethyl acetate. Similar fractions were combined and concentrated to yield the two diastereomers: isomer A, 3.05 g, mp 113°-114° C. (Compound 139) and isomer B, 1.46 g, mp 76.5°-78° C. (Compound 140).
	With triethylamine In tetrahydrofuran; water; ethyl acetate	43 Preparation and Separation of the Two Diastereomers of 2-Oxo-4-methyl-2-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]-1,3,2-dioxaphosphorinan (Compounds 139 and 140) Example 43 Preparation and Separation of the Two Diastereomers of 2-Oxo-4-methyl-2-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]-1,3,2-dioxaphosphorinan (Compounds 139 and 140) A solution of 12.65 g of 2-(hydroxymethyl)-2-oxo-4-methyl-1,3,2-dioxaphosphorinan, (Example 21), was prepared by dissolving the phosphorinan in a mixture of 40 ml of p-dioxane, 30 ml of ether, and 20 ml of THF with stirring and gentle heating on a steam bath. When all of the phosphorinan had dissolved, 11.8 ml of triethylamine was added to the cooled (room temperature) phosphorinan solution. The phosphorinan/base solution was then added dropwise to a solution of 16.4 g of 2-chloro-6-methylbenzenesulfonyl chloride in 70 ml of ether over 50 minutes. The addition caused a mild exotherm and the reaction was allowed to stir overnight at room temperature. The reaction solution was gravity filtered and the filter cake was rinsed with 75 ml of ethyl acetate, the combined filtrates concentrated, the concentrate partitioned between 300 ml of ethyl acetate and 100 ml of water, the phases separated, the organic phase rewashed with an additional 100 ml of dried with magnesium sulfate, filtered and concentrated to yield 18.2 g of the crude desired product as an off white solid. Phosphorus NMR indicated two diastereomers were present. The product was purified by flash chromatographing 7.4 g of the crude reaction product, dissolved in 12 ml of methylene chloride, on Merck silica gel (230-400 mesh) eluding with blends of hexanes and ethyl acetate. Similar fractions were combined and concentrated to yield the two diastereomers: isomer A, 3.05 g, mp 113°-114° C. (Compound 139) and isomer B, 1.46 g, mp 76.5°-78° C. (Compound 140).