Acetamidine Hydrochloride

Title: Acetamidine Hydrochloride
CAS Registry Number: 124-42-5
CAS Name: Ethanimidamide hydrochloride
Additional Names: ethanamidine hydrochloride; a-amino-a-iminoethane hydrochloride; ethenylamidine hydrochloride; acediamine hydrochloride
Manufacturers' Codes: SN-4455
Molecular Formula: C2H7ClN2
Molecular Weight: 94.54
Percent Composition: C 25.41%, H 7.46%, Cl 37.50%, N 29.63%
Literature References: Prepd by passing HCl into a soln of acetonitrile in abs alcohol, then passing NH3 into the reaction mixture: Pinner, Ber. 16, 1654 (1883); 17, 178 (1884); Dox, Org. Synth. coll. vol. I, 5 (New York, 2nd ed., 1941). See also Fargher, J. Chem. Soc. 117, 674 (1920). Review: Shriner, Neumann, Chem. Rev. 35, 351-425 (1944).
Properties: Long prisms from alcohol, somewhat deliquescent, mp 174° (Fargher); mp 164-166° (Dox). Very sol in water. Sol in alcohols. Practically insol in acetone, ether. Should be stored in a closed container and in a cool place. If alkali is added to an aq soln, the free base is liberated.
Melting point: mp 174° (Fargher); mp 164-166° (Dox)
Derivative Type: Free base
Molecular Formula: C2H6N2
Molecular Weight: 58.08
Percent Composition: C 41.36%, H 10.41%, N 48.23%
Properties: uv max: 224 nm (e 4000). pK1 (25°): 12.1. Has a strong alkaline reaction and on slight warming dissociates into ammonia and acetic acid.
pKa: pK1 (25°): 12.1
Absorption maximum: uv max: 224 nm (e 4000)
CAUTION: Irritates mucous membranes, skin. Avoid tasting, swallowing, inhalation of the dust, skin contact.
Use: In the synthesis of imidazoles, pyrimidines, triazines.
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