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107-14-2 - Chloroacetonitrile, 98+% - A12825 - Alfa Aesar

A12825 Chloroacetonitrile, 98+%

CAS-Nummer
107-14-2
Synonyme

Größe Preis ($) Menge Verfügbarkeit
100g 21,01
500g 78,80
1kg 110,16
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Chloroacetonitrile, 98+%

MDL
MFCD00001885
EINECS
203-467-0

Chemische Eigenschaften

Formel
C2H2ClN
Molmasse
75.50
Siedepunkt
124-126°
Flammpunkt
56°(132°F)
Dichte
1.195
Brechungsindex
1.4230
Löslichkeit
Immiscible with water.

Anwendungen

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.

Bemerkungen

Incompatible with strong oxidizing agents and acids.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H301-H311-H331-H226-H411

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Flammable liquid and vapour. Toxic to aquatic life with long lasting effects.

Sicherheitshinweise: P210-P261-P273-P280-P301+P310-P303+P361+P353-P361-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
506028
Gefahrenklasse
6.1
Verpackungsgruppe
I
Harmonized Tariff Code
2926.90
TSCA
Yes
RTECS
AL8225000

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