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A12825 Chloroacetonitrile, 98+%

CAS Number
107-14-2
Synonyms

Stock No. Size Price ($) Quantity Availability
A12825-22 100g 23.60
A12825-36 500g 88.70
A12825-A1 1kg 142.00
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Chloroacetonitrile, 98+%

MDL
MFCD00001885
EINECS
203-467-0

Chemical Properties

Formula
C2H2ClN
Formula Weight
75.50
Boiling Point
124-126°
Flash Point
56°(132°F)
Density
1.195
Refractive Index
1.4230
Storage & Sensitivity
Ambient temperatures.
Solubility
Immiscible with water.

Applications

Chloroacetonitrile is used in the electrochemical synthesis of cyanoacetic acid with carbon dioxide. It is involved in phase-transfer-catalyzed Darzen's condensation reaction with cyclohexanone. It is also used as an eluent additive in thermospray liquid chromatography/mass spectrometry. Further, it is used to prepare polysubstituted pyrido[1,2-a]benzimidazole by reacting with other reactant such as malononitrile, aromatic aldehyde and pyridine.

Notes

Incompatible with strong oxidizing agents and acids.

Literature 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 ß-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.

Hoseini, S. J.; Nasrabadi, H.; Fath, R. H.; Moradi, Z.; Rashidi, M. Oxidative Addition of Propargyl Halides, Chloroacetonitrile, and Ethyl Chloroacetate to a Dimethylplatinum(II) Complex: Kinetic and DFT Studies. Organometallics 2014, 33 (7), 1689-1699.

Kimura, S. Y.; Komaki, Y.; Plewa, M. J.; Marinas, B. J. Chloroacetonitrile and N,2-Dichloroacetamide Formation from the Reaction of Chloroacetaldehyde and Monochloramine in Water. Environ. Sci. Technol. 2013, 47 (21), 12382-12390.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H301-H311-H331

Flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled.

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P270-P271-P280-P301+P310-P303+P361+P353-P304+P340-P311-P312-P330-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
506028
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2926.90
TSCA
Yes
RTECS
AL8225000

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