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98-09-9

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98-09-9 Usage

Chemical Properties

Benzenesulfonyl chloride is a colorless oily liquid with a pungent odor. Insoluble in water, soluble in ethanol and ether. Can react with ammonia, amine and alcohol to produce benzenesulfonamide and benzene sulfonate respectively. It is toxic, irritates skin, eyes and mucous membranes, corrosive, and can cause burns. Oral LD50 1960mg/kg in rats.

Uses

Different sources of media describe the Uses of 98-09-9 differently. You can refer to the following data:
1. Intermediates of Liquid Crystals
2. Benzenesulfonyl chloride reacts with Grignard reagents to form oxindoles from N-unsubstituted indoles. It is widely used to check the assay of thiamine in different food products. It is involved in the synthesis of alpha-disulfones, sulfonamides and sulfoante esters as precursor. It is a derivatization reagent for the determination of various amines in waste water and surface water at the sub-ppb level by gas chromatography-mass spectrometry. It is common reagent used in Hinsberg test for detection and distinguishing the type of amines as primary, secondary and tertiary amines.
3. Benzenesulfonyl chloride may be used in thiamine assay for determination of thiamine in different food products.

General Description

A colorless to slightly yellow solid that melts at approximately 40°F. Very irritating to skin, eyes and mucous membranes. May emit toxic fumes when heated to high temperatures. Used to make dyes and other chemicals.

Air & Water Reactions

Insoluble and stable in cold water [Merck]. Decomposes in hot water to produce corrosive and toxic hydrochloric acid and benzenesulfonic acid. Rate of reaction decreases as temperature decreases.

Reactivity Profile

Benzenesulfonyl chloride is incompatible with strong oxidizing agents and bases, including amines. Corrodes metals in the presence of water due to slow formation of hydrochloric acid and benzenesulfonic acid [USCG, 1999]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

May be fatal if inhaled, swallowed or absorbed through skin. Contact may cause skin and eye burns. Irritating to eyes, skin and mucous membranes. INGESTION: May cause abdominal spasm and vomiting.

Safety Profile

Poison by intraperitoneal route. Adangerous storage hazard. It may explode in a sealedbottle. Explosive reaction with dimethyl sulfoxide. Reactsvigorously with methyl formamide. When heated todecomposition it emits toxic fumes of Cl- and SO

Potential Exposure

It is used as a chemical intermediate for benzenesulfonamides, thiophenol, glybuzole (hypoglycemic agent), N-2-chloroehtylamides, benzonitrile; for its esters-useful as insecticides, and miticides.

Shipping

UN2225 Benzene sulfonyl chloride, Hazard class: 8; Labels: 8—Corrosive material.

Purification Methods

Distil the sulfonyl chloride, then treat it with 3mole % each of toluene and AlCl3, and allow it to stand overnight. The sulfonyl chloride is distilled off at 1mm pressure and then carefully fractionally distilled at 10mm in an all-glass column. [Adams & Marvel Org Synth Coll Vol I 84 1941, Jensen & Brown J Am Chem Soc 80 4042 1958, Beilstein 11 IV 49.] It is TOXIC.

Incompatibilities

Violent reaction with strong oxidizers, dimethyl sulfoxide, and methyl formamide. It is very reactive with bases and many organic compounds. Incompatible with ammonia, aliphatic amines. Water contact forms hydrochloric and chlorosulfonic acids. Aqueous solutions of this chemical are strong acids that react violently with bases. Attacks metals in presence of moisture.

Check Digit Verification of cas no

The CAS Registry Mumber 98-09-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 98-09:
(4*9)+(3*8)+(2*0)+(1*9)=69
69 % 10 = 9
So 98-09-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H

98-09-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A10849)  Benzenesulfonyl chloride, 98%   

  • 98-09-9

  • 250g

  • 244.0CNY

  • Detail
  • Alfa Aesar

  • (A10849)  Benzenesulfonyl chloride, 98%   

  • 98-09-9

  • 1000g

  • 712.0CNY

  • Detail
  • Alfa Aesar

  • (A10849)  Benzenesulfonyl chloride, 98%   

  • 98-09-9

  • 5000g

  • 2765.0CNY

  • Detail
  • Aldrich

  • (108138)  Benzenesulfonylchloride  99%

  • 98-09-9

  • 108138-5G

  • 379.08CNY

  • Detail
  • Aldrich

  • (108138)  Benzenesulfonylchloride  99%

  • 98-09-9

  • 108138-100G

  • 464.49CNY

  • Detail
  • Aldrich

  • (108138)  Benzenesulfonylchloride  99%

  • 98-09-9

  • 108138-500G

  • 891.54CNY

  • Detail
  • Aldrich

  • (108138)  Benzenesulfonylchloride  99%

  • 98-09-9

  • 108138-1KG

  • 1,447.29CNY

  • Detail
  • Sigma-Aldrich

  • (12620)  Benzenesulfonylchloride  for HPLC derivatization

  • 98-09-9

  • 12620-100ML

  • 585.00CNY

  • Detail
  • Sigma-Aldrich

  • (12620)  Benzenesulfonylchloride  for HPLC derivatization

  • 98-09-9

  • 12620-500ML

  • 1,182.87CNY

  • Detail
  • Aldrich

  • (108111)  Benzenesulfonylchloride  96%

  • 98-09-9

  • 108111-25G

  • 362.70CNY

  • Detail
  • Aldrich

  • (108111)  Benzenesulfonylchloride  96%

  • 98-09-9

  • 108111-1KG

  • 1,019.07CNY

  • Detail

98-09-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzenesulfonyl Chloride

1.2 Other means of identification

Product number -
Other names Benzenesulfonyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Dyes,Intermediates,Pigments
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:98-09-9 SDS

98-09-9Synthetic route

benzenesulfonic acid
98-11-3

benzenesulfonic acid

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With trichloroacetonitrile; triphenylphosphine In dichloromethane for 1h; Heating;100%
With thionyl chloride99%
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; potassium chloride at 25℃; for 0.0333333h; Neat (no solvent);95%
phenyl thiobenzoate
884-09-3

phenyl thiobenzoate

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With N-chloro-succinimide; ammonium chloride In water; acetonitrile at 0℃; for 0.333333h; pH=0 - 2;100%
S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

A

thiophenol
108-98-5

thiophenol

B

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride In waterA 100%
B 100%
thiophenol
108-98-5

thiophenol

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With thionyl chloride; dihydrogen peroxide In water; acetonitrile at 25℃; for 0.0166667h;99%
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h;98%
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h;98%
diphenyldisulfane
882-33-7

diphenyldisulfane

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h;99%
With trichloroisocyanuric acid; tetrabutylammomium bromide; water In acetonitrile at 0 - 20℃; for 0.333333h;99%
With dihydrogen peroxide; trichlorophosphate In water at 25℃; for 0.5h; Micellar solution;96%
methyl carbamothioic acid S-phenyl ester
13509-39-2

methyl carbamothioic acid S-phenyl ester

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; N-chloro-succinimide In acetonitrile at 10℃;96.6%
S-phenyl thioacetate
934-87-2

S-phenyl thioacetate

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; N-chloro-succinimide In acetonitrile at 10℃; for 0.166667h;96.3%
Benzyl phenyl sulfide
831-91-4

Benzyl phenyl sulfide

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; iodosylbenzene for 0.0833333h;96%
With hydrogenchloride; iodosylbenzene for 0.0833333h; Chlorination; oxidation;96%
With 1,3-dichloro-5,5-dimethylhydantoin; acetic acid In dichloromethane; water at 0 - 5℃; Inert atmosphere;90%
With N-chloro-succinimide In dichloromethane; benzyl alcohol for 18h; Ambient temperature;62%
sodium phenylsulfonate
515-42-4

sodium phenylsulfonate

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; 18-crown-6 ether In acetone for 20h; Heating;94%
Stage #1: sodium phenylsulfonate With potassium phosphate; bis(trichloromethyl) carbonate In dichloromethane at 0 - 5℃; for 0.0833333h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 0.5h;
91%
With phosphorus pentachloride Man giesst in Wasser und destilliert das hierbei sich abscheidende Benzolsulfochlorid mit Wasser unter vermindertem Druck;
methoxymethyl phenyl sulfide
13865-50-4

methoxymethyl phenyl sulfide

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With water; chlorine In dichloromethane at 5 - 10℃; for 1h;94%
toluene-4-sulfonic acid phenyl ester
640-60-8

toluene-4-sulfonic acid phenyl ester

phenylboronic acid
98-80-6

phenylboronic acid

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With phenylchlorosulfate; C43H43NO3PPdS; sodium carbonate In acetone at 20 - 50℃; Inert atmosphere; Sealed tube;90%
S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

benzenesulfenyl chloride
931-59-9

benzenesulfenyl chloride

A

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 115℃; for 24h; Mechanism;A n/a
B 88.7%
chloroamine-T
127-65-1

chloroamine-T

thiophenol
108-98-5

thiophenol

A

N-chloro-N-(4-methylbenzenesulfonyl)benzenesulfinamide

N-chloro-N-(4-methylbenzenesulfonyl)benzenesulfinamide

B

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With N-chloro-succinimide In water; acetonitrile at 35℃; for 0.25h; Solvent; Temperature; Reagent/catalyst;A 78%
B 17%
thiophenol
108-98-5

thiophenol

A

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With potassium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water at 20℃; for 10h; Reagent/catalyst;A 22%
B 68%
dibenzyl disulphide
150-60-7

dibenzyl disulphide

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; iodosylbenzene for 0.0833333h;56%
sulfinothioyldibenzene

sulfinothioyldibenzene

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; iodosylbenzene for 0.0833333h; Chlorination; oxidation;56%
aniline
62-53-3

aniline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
Stage #1: aniline With hydrogenchloride; acetic acid
Stage #2: With sodium nitrite In water at -10 - -5℃; for 0.75h;
Stage #3: With hydrogenchloride; sulfur dioxide; acetic acid; copper(l) chloride In water at 10℃; for 0.5h;
53%
With hydrogenchloride; sodium nitrite In acetic acid
Stage #1: aniline With hydrogenchloride; sodium nitrite
Stage #2: With sulfur dioxide; copper(l) chloride In acetone
methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

A

Methyl phenyl sulfone
3112-85-4

Methyl phenyl sulfone

B

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With hydrogenchloride; iodosylbenzene for 0.0833333h;A 47%
B 4%
With hydrogenchloride; iodosylbenzene for 0.0833333h; Chlorination; oxidation;A 47%
B 4%
N-chloro-succinimide
128-09-6

N-chloro-succinimide

Benzyl phenyl sulfide
831-91-4

Benzyl phenyl sulfide

benzyl alcohol
100-51-6

benzyl alcohol

A

Succinimide
123-56-8

Succinimide

B

benzyl chloride
100-44-7

benzyl chloride

C

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
In dichloromethane for 18h; Product distribution; Ambient temperature;A n/a
B n/a
C 42%
nitrostyrene
5153-67-3

nitrostyrene

benzene diazonium chloride
100-34-5

benzene diazonium chloride

A

(2-nitro-1-(phenylsulfonyl)ethyl)benzene
87015-49-4

(2-nitro-1-(phenylsulfonyl)ethyl)benzene

B

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With sulfur dioxide In acetic acid; acetone at 15 - 20℃;A 35%
B n/a
benzene
71-43-2

benzene

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid at 20℃; Cooling with ice;34%
With chlorosulfonic acid; sulfuric acid
With chlorosulfonic acid; sodium chloride
N-chloro-succinimide
128-09-6

N-chloro-succinimide

ethanol
64-17-5

ethanol

Benzyl phenyl sulfide
831-91-4

Benzyl phenyl sulfide

A

Succinimide
123-56-8

Succinimide

B

ethyl benzenesulfinate
1859-03-6

ethyl benzenesulfinate

C

benzyl chloride
100-44-7

benzyl chloride

D

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
In dichloromethane for 18h; Product distribution; Ambient temperature;A n/a
B 30%
C n/a
D n/a
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With thionyl chloride; tris(bipyridine)ruthenium(II) dichloride hexahydrate In water; acetonitrile at 20℃; for 20h; Sealed tube; Irradiation;30%
benzene diazonium chloride
100-34-5

benzene diazonium chloride

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

A

4-benzenesulfonyl-4-phenyl-butan-2-one
62692-46-0

4-benzenesulfonyl-4-phenyl-butan-2-one

B

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With sulfur dioxide In acetic acid; acetoneA 14%
B n/a
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

A

N,N,N',N'-tetramethylbenzidine
366-29-0

N,N,N',N'-tetramethylbenzidine

B

4-fluoro-N,N-dimethylaniline
403-46-3

4-fluoro-N,N-dimethylaniline

C

2-fluoro-N,N-dimethylaniline
393-56-6

2-fluoro-N,N-dimethylaniline

D

1-chloro-2-(dimethylamino)benzene
698-01-1

1-chloro-2-(dimethylamino)benzene

E

4-(methylamino)benzaldehyde
556-21-8

4-(methylamino)benzaldehyde

F

4,4'-methylene-bis(N,N-dimethylaniline)
101-61-1

4,4'-methylene-bis(N,N-dimethylaniline)

G

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

H

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With zirconium(IV) chloride; N-fluorobis(benzenesulfon)imide In chloroform for 5h; Reflux;A n/a
B n/a
C n/a
D n/a
E n/a
F n/a
G n/a
H 6%
N,N-Dichlorobenzenesulfonamide
473-29-0

N,N-Dichlorobenzenesulfonamide

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
at 200℃;
1,2-bis(phenylsulfonyl)ethane
599-94-0

1,2-bis(phenylsulfonyl)ethane

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With chlorine
diphenyl sulphone
127-63-9

diphenyl sulphone

A

chlorobenzene
108-90-7

chlorobenzene

B

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride at 160 - 170℃;
With chlorine at 120 - 130℃;
N,N-dimethylbenzenesulfonamide
14417-01-7

N,N-dimethylbenzenesulfonamide

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid at 130 - 150℃;
1-indoline
496-15-1

1-indoline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-benzenesulfonyl-2,3-dihydro-1H-indole
81114-41-2

1-benzenesulfonyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 1h;100%
With potassium trimethylsilonate In water at 20℃; for 0.5h; Concentration; Inert atmosphere;97%
With dmap; triethylamine In dichloromethane at 0 - 20℃;96%
isobutylamine
78-81-9

isobutylamine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-(iso-butyl)benzenesulfonamide
23705-39-7

N-(iso-butyl)benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -25 - 20℃; Inert atmosphere;100%
With N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 1h;80%
With picoline In dichloromethane at 20℃; for 1h;71%
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-(2-methoxyphenyl)benzenesulfonamide
21226-32-4

N-(2-methoxyphenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine for 12h; Ambient temperature;100%
With sodium hydroxide at 20℃; for 1h; Addition;85%
51%
4-nitro-aniline
100-01-6

4-nitro-aniline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-(4-nitrophenyl)benzenesulfonamide
1829-81-8

N-(4-nitrophenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 24h;100%
With pyridine In dichloromethane at 20℃;92%
With pyridine for 13h; Ambient temperature;83%
aniline
62-53-3

aniline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-phenylbenzenesulfonamide
1678-25-7

N-phenylbenzenesulfonamide

Conditions
ConditionsYield
With pyridine at 0 - 25℃;100%
With pyridine at 20℃;98%
With Fe3O4-supported (diisopropylamino)acetamide In dichloromethane at 25℃;98%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

ethyl 4-benzoate
89113-18-8

ethyl 4-benzoate

Conditions
ConditionsYield
Stage #1: benzenesulfonyl chloride; p-aminoethylbenzoate With pyridine for 18h;
Stage #2: With ammonia In methanol at 90℃; for 0.5h; Microwave irradiation;
100%
With pyridine In tetrahydrofuran at 20℃; for 1.5h;100%
With pyridine at 5 - 20℃; for 1h; sulfonylation;70%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

o-toluidine
95-53-4

o-toluidine

N-o-tolyl-benzenesulfonamide
18457-86-8

N-o-tolyl-benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;100%
86%
With pyridine for 4h; Heating;81%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

benzylamine
100-46-9

benzylamine

N-benzylbenzenesulfonamide
837-18-3

N-benzylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane 1) 0 deg C, 1 h, 2) room temperature;100%
With sodium hydroxide In water at 25℃; for 2h; pH 9.6;99.9%
With Fe3O4-supported (diisopropylamino)acetamide In dichloromethane at 25℃;98%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

3,4-dimethoxyaniline
6315-89-5

3,4-dimethoxyaniline

N-(3,4-dimethoxyphenyl)benzenesulfonamide
62035-67-0

N-(3,4-dimethoxyphenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.0833333h;100%
With pyridine; dmap In tetrahydrofuran Ambient temperature;65%
With potassium hydroxide at 30 - 40℃; zuletzt bei 75grad;
With sodium hydroxide In acetone
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;100%
With tungsten(VI) chloride; sodium iodide In acetonitrile for 16h; Ambient temperature;97%
With Silphos; iodine In acetonitrile for 10h; Heating;96%
cyclohexylamine
108-91-8

cyclohexylamine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-cyclohexylbenzenesulfonamide
3237-31-8

N-cyclohexylbenzenesulfonamide

Conditions
ConditionsYield
With picoline In dichloromethane at 20℃; for 1h;100%
With pyridine In dichloromethane at 0 - 20℃;85%
With pyridine
tert-butylamine
75-64-9

tert-butylamine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-tert-butylbenzenesulfonamide
2512-24-5

N-tert-butylbenzenesulfonamide

Conditions
ConditionsYield
In chloroform at 0℃;100%
With hydrogenchloride In dichloromethane at 0 - 20℃; for 0.666667h;97%
With triethylamine In dichloromethane at 20℃;95%
piperidin-2-one
675-20-7

piperidin-2-one

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one
7744-25-4

1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one

Conditions
ConditionsYield
Stage #1: piperidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran; hexane at -78℃; for 4h; Inert atmosphere;
100%
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h;94%
With n-butyllithium 1.) THF, hexane, -60 deg C, 20 min, 2.) THF, hexane, from -60 deg C to 0 deg C, 2.5 h; Yield given. Multistep reaction;
indole
120-72-9

indole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-benzenesulfonylindole
40899-71-6

1-benzenesulfonylindole

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0 - 20℃; for 3h;100%
Stage #1: indole With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice bath;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃;
100%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane99%
pyrrole
109-97-7

pyrrole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-phenylsulfonylpyrrole
16851-82-4

N-phenylsulfonylpyrrole

Conditions
ConditionsYield
With potassium hydroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 1h;100%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 20℃; Inert atmosphere; Cooling;99%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 18.5h;98%
5,6-methylenedioxyindole
267-48-1

5,6-methylenedioxyindole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

5-(benzenesulfonyl)-[1,3]dioxolo[4,5-f]indole
100587-74-4

5-(benzenesulfonyl)-[1,3]dioxolo[4,5-f]indole

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; Cooling with ice;100%
With n-butyllithium 1.) THF, hexane, from -70 deg C to 0 deg C, 45 min, 2.) from -70 deg C to room temperature, 2 h; Multistep reaction;
5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

5-chloro-1-(phenylsulfonyl)-1H-indole
78329-47-2

5-chloro-1-(phenylsulfonyl)-1H-indole

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Reflux;100%
Stage #1: 5-chloro-1H-indole With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran for 1h;
96%
Stage #1: 5-chloro-1H-indole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
96.3%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

4-hydroxybenzaldehyde benzenesulfonate ester
13493-50-0

4-hydroxybenzaldehyde benzenesulfonate ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;99%
With triethylamine In dichloromethane at 20℃; for 2h;98%
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

3-methyl-3-butenyl-1-benznesulfonate
90545-36-1

3-methyl-3-butenyl-1-benznesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 4h;100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4.33333h;
4-methyl-5-nitrophenol
2042-14-0

4-methyl-5-nitrophenol

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

4-benzenesulfonyloxy-2-nitrotoluene
92059-54-6

4-benzenesulfonyloxy-2-nitrotoluene

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h;100%
2-(3-methoxyanilino)acetaldehyde diethyl acetal
32431-44-0

2-(3-methoxyanilino)acetaldehyde diethyl acetal

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-(2,2-diethoxyethyl)-N-(3-methoxyphenyl)-benzene-sulfonamide
99546-93-7

N-(2,2-diethoxyethyl)-N-(3-methoxyphenyl)-benzene-sulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane 1.) 0 deg C, 1 h, 2.) 25 deg C, overnight;100%
1-benzenesulfonamido-2,4-diaminonaphthalene
85218-98-0

1-benzenesulfonamido-2,4-diaminonaphthalene

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1,2,4-tris(benzenesulfonamido)naphthalene
85218-99-1

1,2,4-tris(benzenesulfonamido)naphthalene

Conditions
ConditionsYield
With pyridine for 10h;100%
N-(5-hexen-1-yl)aniline
105971-30-0

N-(5-hexen-1-yl)aniline

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-(hex-5-enyl)-N-phenylbenzenesulfonamide
157099-71-3

N-(hex-5-enyl)-N-phenylbenzenesulfonamide

Conditions
ConditionsYield
In pyridine for 10h; Heating;100%
R-(+)-4-methyl-6-(tert-butyldimethylsiloxy)-1-hexanol
87921-27-5

R-(+)-4-methyl-6-(tert-butyldimethylsiloxy)-1-hexanol

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

R-(+)-4-methyl-6-(tert-butyldimethylsiloxy)-1-hexyl benzenesulphonate
87921-28-6

R-(+)-4-methyl-6-(tert-butyldimethylsiloxy)-1-hexyl benzenesulphonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 3h; Ambient temperature;100%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

L-proline
147-85-3

L-proline

N-benzenesulfonyl-L-proline
88425-46-1

N-benzenesulfonyl-L-proline

Conditions
ConditionsYield
With sodium carbonate In water for 5h;100%
With sodium carbonate In water for 4h;100%
With sodium carbonate In water at -5 - 20℃; for 4h; Inert atmosphere;100%
5-Hydroxy-2-methylpyridine
1121-78-4

5-Hydroxy-2-methylpyridine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

5-(benzenesulfonyloxy)-2-methylpyridine
173913-74-1

5-(benzenesulfonyloxy)-2-methylpyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0℃; for 2h;95%
With triethylamine
L-phenylalanine
63-91-2

L-phenylalanine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

Nα-benzenesulfonyl-L-phenylalanine
40279-95-6

Nα-benzenesulfonyl-L-phenylalanine

Conditions
ConditionsYield
With sodium carbonate In water for 5h;100%
With sodium carbonate In water for 4h;100%
With sodium hydroxide for 2h; Ambient temperature; pH=10;
With sodium hydroxide for 2.5h; Ambient temperature;
With N-ethyl-N,N-diisopropylamine; sodium hydroxide In acetone at 0 - 20℃; for 6h; Inert atmosphere;
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

5-(4-methylphenoxy)tetrazole
4612-90-2

5-(4-methylphenoxy)tetrazole

NI-(benzenesulfonyl)(4-methylphenoxy)imidoyl azide

NI-(benzenesulfonyl)(4-methylphenoxy)imidoyl azide

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 20℃; Ring cleavage;100%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

5-(2,6-dimethoxy-phenoxy)-2H-tetrazole

5-(2,6-dimethoxy-phenoxy)-2H-tetrazole

NI-(benzenesulfonyl)(2,6-dimethoxyphenoxy)imidoyl azide

NI-(benzenesulfonyl)(2,6-dimethoxyphenoxy)imidoyl azide

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 20℃; Ring cleavage;100%
(+/-)-trans-2-butyl-5-heptylpyrrolidine
116558-84-0

(+/-)-trans-2-butyl-5-heptylpyrrolidine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

(2R,5R)-1-Benzenesulfonyl-2-butyl-5-heptyl-pyrrolidine
95513-29-4, 95587-13-6, 95587-18-1, 129446-24-8

(2R,5R)-1-Benzenesulfonyl-2-butyl-5-heptyl-pyrrolidine

Conditions
ConditionsYield
With sodium hydroxide In chloroform Substitution;100%

98-09-9Relevant articles and documents

-

Wittmann et al.

, p. 734 (1969)

-

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng

supporting information, p. 8338 - 8342 (2021/10/25)

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao

, (2021/09/20)

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Proline-Based Allosteric Inhibitors of Zika and Dengue Virus NS2B/NS3 Proteases

Millies, Benedikt,Von Hammerstein, Franziska,Gellert, Andrea,Hammerschmidt, Stefan,Barthels, Fabian,G?ppel, Ulrike,Immerheiser, Melissa,Elgner, Fabian,Jung, Nathalie,Basic, Michael,Kersten, Christian,Kiefer, Werner,Bodem, Jochen,Hildt, Eberhard,Windbergs, Maike,Hellmich, Ute A.,Schirmeister, Tanja

, p. 11359 - 11382 (2019/12/24)

The NS2B/NS3 serine proteases of the Zika and Dengue flaviviruses are attractive targets for the development of antiviral drugs. We report the synthesis and evaluation of a new, proline-based compound class that displays allosteric inhibition of both proteases. The structural features relevant for protease binding and inhibition were determined to establish them as new lead compounds for flaviviral inhibitors. Based on our structure-activity relationship studies, the molecules were further optimized, leading to inhibitors with submicromolar IC50 values and improved lipophilic ligand efficiency. The allosteric binding site in the proteases was probed using mutagenesis and covalent modification of the obtained cysteine mutants with maleimides, followed by computational elucidation of the possible binding modes. In infected cells, antiviral activity against Dengue virus serotype 2 using prodrugs of the inhibitors was observed. In summary, a novel inhibitor scaffold targeting an allosteric site shared between flaviviral NS2B/NS3 proteases is presented whose efficacy is demonstrated in vitro and in cellulo.

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