[(chlorosulfonyl)imino]methanone

• ChemBase ID: 123298
• Molecular Formular: CClNO3S
• Molecular Mass: 141.5336
• Monoisotopic Mass: 140.92874155
• SMILES: S(=O)(=O)(N=C=O)Cl
• Canonical SMILES: O=C=NS(=O)(=O)Cl
• InChI: InChI=1S/CClNO3S/c2-7(5,6)3-1-4
• InChIKey: WRJWRGBVPUUDLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(chlorosulfonyl)imino]methanone
• IUPAC Traditional name: chlorosulfonyl isocyanate
• Synonyms: sulfurisocyanatidic chloride; N-Carbonylsulfamyl chloride; Chloropyrosulfonyl isocyanate; Sulfuryl chloride isocyanate; Chlorosulfonyl isocyanate; CSI; N-Carbonylsulfamyl chloride; Chlorosulfonyl isocyanate; N-碳酰氨磺酰基氯; 氯磺酰异氰酸酯

Database IDs

• CAS Number: 1189-71-5
• EC Number: 214-715-2
• MDL Number: MFCD00011608
• Beilstein Number: 1237247
• PubChem SID: 162217651; 24848531; 24855894
• PubChem CID: 70918
• Chemspider ID: 64080
• Wikipedia Title: Chlorosulfonyl_isocyanate

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.35053393
• LogD (pH = 7.4): -0.35053393
• Log P: -0.35053393
• Molar Refractivity: 22.2194 cm^3
• Polarizability: 9.62044 Å^3
• Polar Surface Area: 63.57 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chlorocarbons; MeCN; decomp. in water
• Apperance: colorless liquid
• Melting Point: -44 °C; -44 °C(lit.)
• Boiling Point: 107 °C; 107 °C(lit.)
• Density: 1.626 g/cm^3; 1.626 g/mL at 25 °C(lit.)
• Refractive Index: 1.447; n20/D 1.447(lit.)
• Vapor Pressure: 5.57 psi ( 20 °C)

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 14-22-34-42
• Safety Statements: 23-26-30-36/37/39-45
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• Main Hazard: toxic, corrosive; hydrolyzes violently
• GHS Hazard statements: H302-H314-H334
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ABCB1(5243), FPR1(2357)

Product Information

• Purity: ≥99.0% (AT); 98%; 99.0-100.3% (w/w) (T)
• Grade: Lonza quality; purum
• Impurities: ≤1.00% chloropropylsulfonyl isocyanate
• Linear Formula: ClSO2NCO

DETAILS

Sigma Aldrich - 142662

Application
Employed in a regio- and diastereoselective introduction of a protected amino group in a synthesis of chiral, polyhydroxylated piperidines.1 Generation of ureas from amino groups in a synthesis of benzimidazolones.2
Synthetically versatile reagent for the preparation of amides, lactams, and triazocinones.
Packaging
1 kg in glass bottle
25, 100 g in glass bottle

Sigma Aldrich - 691399

Packaging
1 kg in PVC coated
10 kg in comp drum

Sigma Aldrich - 26391

Other Notes
The most reactive isocyanate known. Review1,2