2-chloroethane-1-sulfonyl chloride

• ChemBase ID: 34711
• Molecular Formular: C2H4Cl2O2S
• Molecular Mass: 163.02296
• Monoisotopic Mass: 161.93090573
• SMILES: S(=O)(=O)(CCCl)Cl
• Canonical SMILES: ClCCS(=O)(=O)Cl
• InChI: InChI=1S/C2H4Cl2O2S/c3-1-2-7(4,5)6/h1-2H2
• InChIKey: VHCSBTPOPKFYIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloroethane-1-sulfonyl chloride
• IUPAC Traditional name: 2-chloroethanesulfonyl chloride
• Synonyms: 2-Chloro-1-ethanesulfonyl chloride; 2-Chloroethanesulfonyl chloride; Ethanesulfonyl chloride, 2-chloro-; 2-Chloroethane sulfochloride; 2-Chloroethanesulfonyl chloride; 2-Chloroethylsulfonyl chloride; 2-氯-1-乙烷磺酰氯; 2-氯乙烷磺酰氯

Database IDs

• CAS Number: 1622-32-8
• EC Number: 216-594-1
• MDL Number: MFCD00007461
• Beilstein Number: 1751202
• PubChem SID: 160998018; 24858246
• PubChem CID: 15385
• Chemspider ID: 14644
• Wikipedia Title: 2-Chloroethanesulfonyl_chloride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6217018
• LogD (pH = 7.4): 0.6217018
• Log P: 0.6217018
• Molar Refractivity: 29.5703 cm^3
• Polarizability: 12.602846 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 203°C; 203°C; 84-86 °C/15 mmHg(lit.)
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.56 g/mL at 25 °C(lit.); 1.560
• Refractive Index: 1.4915; n20/D 1.493(lit.); n20/D 1.494
• Vapor Pressure: 15 mmHg ( 84 °C)

Safety Information

• Storage Warning: Moisture Sensitive; TOXIC BY INHALATION, CORROSIVE
• RTECS: KI8060000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3390; UN3390
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Risk Statements: 22-26-34
• Safety Statements: 26-28-36/37/39-45; 9-23-26-28-36/37/39-45
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314-H330; H301-H330-H314-H318
• GHS Precautionary statements: P260-P280-P284-P301 + P310-P305 + P351 + P338-P310; P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3390 6.1/PG 1

Product Information

• Purity: ≥97.0% (AT); 95%; 96%; 98%
• Grade: purum
• Linear Formula: ClCH2CH2SO2Cl

DETAILS

Sigma Aldrich - 302325

Packaging
5, 25 g in glass bottle

REFERENCES

• In the presence of a base, converts alcohols to vinyl sulfonates: J. Am. Chem. Soc., 68, 1797 (1946); Angew. Chem. Int. Ed., 4, 300 (1965). These electrophilic alkenes readily undergo conjugate addition reactions with various nucleophiles:
  
• Reaction with pentafluorophenol, in the presence of Et₃N, gives PFP vinylsulfonate, which can be converted to a sulfonamide via tin-mediated radical addition of alkyl halides to the olefinic bond, followed by displacement of the PFP group with an amine: Org. Lett., 42549 (2002).