Acetamidine

Acetamidine
Names
IUPAC name
Ethanimidamide[1]
Other names
Identifiers
3D model (JSmol)
605302
ChEBI
ChEMBL
ChemSpider
323199
UNII
  • InChI=1S/C2H6N2/c1-2(3)4/h1H3,(H3,3,4)
    Key: OQLZINXFSUDMHM-UHFFFAOYSA-N
  • CC(=N)N
Properties
C2H6N2
Molar mass 58.084 g·mol−1
Appearance Colorless crystalline solid[2]
Melting point 66 °C (151 °F; 339 K)
Hazards
GHS labelling:
GHS08: Health hazard
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acetamidine is an organic compound with the chemical formula CH3C(NH)NH2. Its structural formula is H3C−C(=NH)−NH2. It is a colorless crystalline solid. It is a nitrogen analog of acetic acid H3C−C(=O)−OH, where the carbonyl oxygen =O is replaced by imino group =NH, and the hydroxyl group −OH is replaced by amino group −NH2.

Acetamidine also refers to the group of compounds called acetamidines, whose formula is H3C−C(=NR)−NR'R", where R, R' and R" are typically hydrogen, halogen or organyl.

Acetamidine is usually available as its hydrochloride salt, acetamidinium chloride ([CH3C(NH2)2]+Cl−).[3]

Structure

In the molecule of acetamidine, nonhydrogen atoms and hydrogen atoms attached to the nitrogen atoms are coplanar, thus, the molecule is trigonal planar at the nonmethyl carbon atom. The rotational barrier of the methyl group is very small. Crystals of acetamidine are tetragonal, with these parameters: a = 10.964 Å, c = 5.701 Å, Z = 8 and V = 685.3 Å3, with P42/n space group. The molecules are connected by a hydrogen bond by =NH and −NH2 groups.[2]

Uses

Acetamidine (and other acetamidines) is used for the synthesis of heterocycles such as quinazoline, pyrrole, imidazole, purine, pyrimidine, triazine, and their derivatives, which play an important role in biochemistry and medicinal chemistry.[4]

Reactions

The free base of acetamidine is hygroscopic. It decomposes into ammonia and acetonitrile at high temperatures, and produces acetamidinium carbonate [CH3C(NH2)2]2CO3 during one day at room temperature when stored in air. Because of that, it is unsuitable as a starting material for synthesis and the use of an acetamidinium salt is necessary. Acetamidinium cation forms salts with various counterions, such as sulfate, hydrogensulfate, formate, acetate, oxalate, chloride, perchlorate, nitrate, and dinitromethanide.[3]

Structure of the acetamidinium cation

References

  1. ^ a b c PubChem. "Acetamidine". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-03-15.
  2. ^ a b Norrestam, R.; Mertz, S.; Crossland, I. (15 November 1983). "Structure of acetamidine, C2H6N2, at 108 K". Acta Crystallographica Section C Crystal Structure Communications. 39 (11): 1554–1556. doi:10.1107/S0108270183009245.
  3. ^ a b Jalový, Zdeněk; Matyáš, Robert; Ottis, Jan; Růžička, Aleš; Šimůnek, Petr; Polášek, Miroslav (2011). "Synthesis and properties of acetamidinium salts". Chemistry Central Journal. 5 84. doi:10.1186/1752-153X-5-84. PMC 3275501. PMID 22152129.
  4. ^ Kaur, Navjeet; Yadav, Neerja; Verma, Yamini (2023). "Acetamidine in heterocycle synthesis". Synthetic Communications. 53 (9): 577–614. doi:10.1080/00397911.2023.2191204.

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