2-[(2-chlorophenyl)methylidene]propanedinitrile

• ChemBase ID: 126749
• Molecular Formular: C10H5ClN2
• Molecular Mass: 188.6131
• Monoisotopic Mass: 188.01412585
• SMILES: Clc1ccccc1C=C(C#N)C#N
• Canonical SMILES: N#CC(=Cc1ccccc1Cl)C#N
• InChI: InChI=1S/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H
• InChIKey: JJNZXLAFIPKXIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-chlorophenyl)methylidene]propanedinitrile
• IUPAC Traditional name: CS gas
• Synonyms: Tear gas; CS gas; 2-[(2-Chlorophenyl)methylene]propanedinitrile; (o-Chlorobenzylidene)malononitrile; [(2-Chlorophenyl)methylene]propanedinitrile; 1-Chloro-2-(2,2-dicyanoethenyl)benzene; 2-(o-Chlorophenyl)-1,1-dicyanoethylene; NSC 542; NSC 637336; o-Chlorobenzylidenemalonic Nitrile; β,β-Dicyano-o-chlorostyrene; 2-Chlorobenzylidene MalononitrileDiscontinued controlled Chemical weapons precusor.

Database IDs

• CAS Number: 2698-41-1
• PubChem SID: 162221077
• PubChem CID: 17604
• Chemspider ID: 16644
• Wikipedia Title: CS_gas

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.7766051
• LogD (pH = 7.4): 2.7766051
• Log P: 2.7766051
• Molar Refractivity: 51.8976 cm^3
• Polarizability: 19.080103 Å^3
• Polar Surface Area: 47.58 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White crystalline powder; Colourless gas when burned
• Melting Point: 93°C, (366.15 K), (199.4 °F)
• Boiling Point: 310 °C, (583.15 K), (590 °F)
• Density: 1.04 g/cm^3
• Vapor Pressure: (mm Hg) 3.4 × 10^-5 at 20 °C

Safety Information

• NFPA704:
  

  1

  2

  0

DETAILS

Toronto Research Chemicals - C364545

The defining component of tear gas (CS gas).

REFERENCES

• Brone, B., et al.: Toxicol. App. Pharmacol., 231, 150 (2008)
• Alqasoumi, S., et al.: Bioorg. Med. Chem. Lett., 19, 6939 (2008)
• Jiang, H., et al.: Prepar. Biochem. Biotechnol., 39, 194 (2008)