| Identification | More | [Name]
ISOPROPYLSULFONYL CHLORIDE | [CAS]
10147-37-2 | [Synonyms]
2-PROPANESULFONYL CHLORIDE
2-PROPANESULPHONYL CHLORIDE
ISOPROPYLSULFONYL CHLORIDE
ISOPROPYLSULPHONYL CHLORIDE
PROPANE-2-SULFONYL CHLORIDE
Isopropylsulphonyl choride
1-Methylethanesulfonic acid chloride
1-Methylethanesulfonyl chloride
Propane-2-sulfonic acid chloride | [EINECS(EC#)]
233-415-2 | [Molecular Formula]
C3H7ClO2S | [MDL Number]
MFCD00007453 | [Molecular Weight]
142.6 | [MOL File]
10147-37-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear pale yellow-greenish liquid | [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.)
| [Fp ]
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 Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [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 Information | Back Directory | [Chemical Properties]
Clear pale yellow-greenish liquid | [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.
| [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. | [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 |
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