2-chloroacetonitrile

• ChemBase ID: 109955
• Molecular Formular: C2H2ClN
• Molecular Mass: 75.49698
• Monoisotopic Mass: 74.98757675
• SMILES: ClCC#N
• Canonical SMILES: ClCC#N
• InChI: InChI=1S/C2H2ClN/c3-1-2-4/h1H2
• InChIKey: RENMDAKOXSCIGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloroacetonitrile
• IUPAC Traditional name: chloroacetonitrile
• Synonyms: Chloroacetonitrile; CHLOROACETONITRILE; 氯乙腈

Database IDs

• CAS Number: 107-14-2
• EC Number: 203-467-0
• MDL Number: MFCD00001885
• Beilstein Number: 506028
• PubChem SID: 24892453; 162095693
• PubChem CID: 7856

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.37194696
• LogD (pH = 7.4): 0.37194696
• Log P: 0.37194696
• Molar Refractivity: 16.3762 cm^3
• Polarizability: 6.175021 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 124-126 °C(lit.); 124-126°C
• Flash Point: 118.4 °F; 48 °C; 56°C(132°F)
• Density: 1.193 g/mL at 25 °C(lit.); 1.195
• Refractive Index: 1.4230; n20/D 1.422(lit.); n20/D 1.423
• Vapor Pressure: 1.78 psi ( 20 °C)
• Vapor Density: 3 (vs air)

Safety Information

• RTECS: AL8225000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2668; UN2668
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; I
• Risk Statements: 23/24/25-51/53; R:23/24/25-51/53
• Safety Statements: 1/2-45-61; 45-61; S:45-61
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H226-H411; H301-H311-H331-H411
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P361-P405-P501A; P261-P273-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2668 6.1/PG 2

Product Information

• Purity: ≥99.0% (GC); 98+%; 99%
• Grade: purum
• Linear Formula: ClCH2CN

DETAILS

MP Biomedicals - 05213167

MP Biomedicals Rare Chemical collection

Sigma Aldrich - C19651

Packaging
5, 100, 500 g in glass bottle

REFERENCES

• Forms cyanomethyl esters with carboxylic acids, e.g. in the presence of Et₃N, which are a useful protection method; the esters are readily cleaved by Na₂S in aqueous acetone: Synth. Commun., 22, 693 (1992).
• Good yields of ?-hydroxy nitriles have been obtained by Reformatsky-type reaction with aldehydes and ketones using Zn and TMS chloride: Tetrahedron Lett., 31, 2205 (1990). See Bromoacetonitrile, A13933.
• In the presence of base, Darzens condensation with aldehydes and ketones, under conventional or phase-transfer conditions, gives glycidonitriles (cyano epoxides), readily converted to the homologated carboxylic acids, esters or aldehydes with loss of cyanide: J. Chem. Soc., Chem. Commun., 988 (1974); Coll. Czech. Chem. Commun., 53, 822 (1988).
• Ritter reaction with tertiary alcohols yields 2-chloroacetamides which, on treatment with thiourea, provides a high-yield conversion of tertiary alcohols to the corresponding amines: Synthesis, 1709 (2000):
  
• For use in vicarious nucleophilic substitution of hydrogen in nitro-substituted hetereocycles, see 2-Nitrothiophene, A17464.