ISOPROPYLSULFONYL CHLORIDE

ISOPROPYLSULFONYL CHLORIDE Property

Melting point:

-47°C

Boiling point:

74-75 °C/19 mmHg (lit.)

Density 

1.27 g/mL at 25 °C (lit.)

vapor density 

4 (vs air)

vapor pressure 

15.5 mm Hg ( 25 °C)

refractive index 

n20/D 1.453(lit.)

Flash point:

187 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetontrile (Slightly), Chloroform (Slightly)

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

1.270

Water Solubility 

Reacts with water.

Sensitive 

Lachrymatory

BRN 

1747497

CAS DataBase Reference

10147-37-2(CAS DataBase Reference)

Safety

Hazard Codes 

C

Risk Statements 

34-R34

Safety Statements 

26-28-36/37/39-45-S45-S36/37/39-S28-S26

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

13-19-21

Autoignition Temperature

865 °F

Hazard Note 

Lachrymatory/Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

P405Store locked up.

ISOPROPYLSULFONYL CHLORIDE Chemical Properties,Usage,Production

Chemical Properties

Clear pale yellow-greenish liquid

Uses

2-Propanesulfonyl chloride is used as a pharmaceutical intermediate. Reductive cleavage of a secondary alcohol to methylene has been achieved by reduction of the 2-propanesulfonyl ester with lithium triethylborohydride.

Uses

2-Propanesulfonyl chloride (isopropylsulfonyl chloride) can be used as a reactant to prepare:

• 1-Isopropylsulfonyl-2-amine benzimidazole by reacting with 2-aminobenzimidazole via N-sulfonylation reaction in the presence of a base.
• Bis(isopropylsulfonyl)disulfide, a sulfurizing agent, used to synthesize phosphorothioate oligonucleotide analogs.

General Description

The solvolysis of 2-propanesulfonyl chloride by an addition-elimination (association-dissociation) pathway was studied.

Synthesis

The general procedure for the synthesis of isopropylsulfonyl chloride from isopropyl mercaptan is as follows: a solution of isopropyl mercaptan (1 eq.) and isopropanol (2 eq.) was stirred in dichloromethane (0.15 M). Subsequently, N-bromosuccinimide (4 eq.) or N-chlorosuccinimide (3.5 eq.) was added in batches at room temperature (when N-bromosuccinimide was used) or at 0 °C (when N-chlorosuccinimide was used). The reaction mixture was stirred at room temperature until the starting material was undetectable by thin layer chromatography (TLC) (about 1 hour). After completion of the reaction, the reaction mixture was diluted with cold saturated sodium bicarbonate solution and extracted with ethyl acetate (four times). The organic extracts were combined, dried with sodium sulfate and subsequently concentrated under vacuum to give the crude product. Finally, pure isopropylsulfonyl chloride was purified by silica gel column chromatography or radial chromatography using a hexane/ethyl acetate/acetone solvent mixture as eluent to give pure isopropylsulfonyl chloride.

References

[1] Chemistry Letters, 1992, # 8, p. 1483 - 1486
[2] Tetrahedron Letters, 2017, vol. 58, # 23, p. 2244 - 2247
[3] Journal fuer Praktische Chemie (Leipzig), 1979, vol. 321, p. 279 - 292
[4] Journal fuer Praktische Chemie (Leipzig), 1969, vol. 311, p. 596 - 603
[5] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1992, vol. 334, # 3, p. 251 - 256