Chemistry:2-Methylnaphthalene-1,4-diamine
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| Preferred IUPAC name
2-Methylnaphthalene-1,4-diamine | |
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| Properties | |
| C11H12N2 | |
| Molar mass | 172.231 g·mol−1 |
| Appearance | yellowish crystals[1] |
| Melting point | 110-113 °C [3][1] |
| dihydrochloride is freely soluble[2] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
2-Methylnaphthalene-1,4-diamine is a synthetic menadione analog with vitamin K activity.[3][2]
2-Methylnaphthalene-1,4-diamine was first synthesized in 1925.[1][3] In 1942 two different research groups noted the vitamin K activity of the compound.[3][4][5] It forms a dihydrochloride salt (C11H14Cl2N2) with hydrochloric acid and one of the aforementioned research groups suggested the name vitamin K6 for the salt.[3]
2-Methylnaphthalene-1,4-diamine and its dihydrochloride can be made from 2-methylnaphthalene or its close analogs. Dihydrochloride blackens without melting at about 300 °C.[3]
4-Amino-3-methyl-1-naphthol or its dihydrochloride have not been used as commercial medicinal forms of vitamin K unlike phylloquinone and menadione for example.[6]
Oral toxicity of dihydrochloride for rats is approximately the same as for 4-amino-2-methyl-1-naphthol hydrochloride.[3]
References
- ↑ 1.0 1.1 1.2 "Sur les dérivés nitres du méthyl-2-naphtalène". Recueil des Travaux Chimiques des Pays-Bas 44 (4): 360–375. 1925. doi:10.1002/recl.19250440409. ISSN 0165-0513.
- ↑ 2.0 2.1 The Merck index (12th ed.). Chapman & Hall Electronic Pub. Division. 2000. pp. 1581. ISBN 9781584881292.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "Water soluble antihemorrhagic substances I: synthesis of 2-methyl-4-aminonaphthol-1 hydrochloride and of 2-methyl-1,4-diaminonaphthalene dihydrochloride, the water soluble synthetic vitamins K5 and K6". Recueil des Travaux Chimiques des Pays-Bas 62 (2): 75–84. 1943. doi:10.1002/recl.19430620203. ISSN 0165-0513.
- ↑ "Water-soluble compounds with antihemorrhagic activity". Journal of the American Chemical Society 64 (11): 2657–2664. 1942. doi:10.1021/ja01263a038. ISSN 0002-7863.
- ↑ "Preparation of water-soluble derivatives of 2-methylnaphthalene". Journal of the Chemical Society 2: 182–186. 1948. doi:10.1039/JR9480000182. ISSN 0368-1769. PMID 18906382.
- ↑ "Anaphylactoid reactions to vitamin K". Journal of Thrombosis and Thrombolysis 11 (2): 175–183. 2001. doi:10.1023/A:1011237019082. ISSN 1573-742X. PMID 11406734.
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