Acetamidine
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
|---|---|
| IUPAC name
Ethanimidamide[1] | |
| Other names | |
| Identifiers | |
3D model (JSmol) |
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| 605302 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| 323199 | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| CH3C(NH)NH2 | |
| Molar mass | 58.084 g·mol−1 |
| Appearance | Colorless crystalline solid[2] |
| Melting point | 66 °C (151 °F; 339 K) |
| Hazards | |
| GHS labelling: | |
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| 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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 [CH3C(NH2)2]+Cl− (acetamidinium chloride).[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, e.g. 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]
