2-Methylnaphthalene-1,4-diamine

2-Methylnaphthalene-1,4-diamine
Names
	IUPAC name 2-Methylnaphthalene-1,4-diamine
Identifiers
CAS Number	83-68-1;
3D model (JSmol)	Interactive image;
ChemSpider	8012912;
PubChem CID	9837191;
CompTox Dashboard (EPA)	DTXSID30431565;
	InChI InChI=1S/C11H12N2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,12-13H2,1H3 Key: BCKLPBBBFNWJHH-UHFFFAOYSA-N;
	SMILES CC1=C(C2=CC=CC=C2C(=C1)N)N;
Properties
Chemical formula	C11H12N2
Molar mass	172.231 g·mol−1
Appearance	yellowish crystals[1]
Melting point	110-113 °C [2][1]
Solubility in water	dihydrochloride is freely soluble[3]
	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.[2][3]

2-Methylnaphthalene-1,4-diamine was first synthetized in 1925.[1][2] In 1942 two different research groups noted the vitamin K activity of the compound.[2][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.[2]

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.[2]

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.[2]

References

Veselý V, Kapp J (1925). "Sur les dérivés nitres du méthyl-2-naphtalène". Recueil des Travaux Chimiques des Pays-Bas. 44 (4): 360–375. doi:10.1002/recl.19250440409. ISSN 0165-0513.
Veldstra H, Wiardi PW (1943). "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. doi:10.1002/recl.19430620203. ISSN 0165-0513.
Budavari S, et al. (2000). The Merck index (12th ed.). Chapman & Hall Electronic Pub. Division. p. 1581. ISBN 9781584881292.
Baker BR, Carlson GH (1942). "Water-soluble compounds with antihemorrhagic activity". Journal of the American Chemical Society. 64 (11): 2657–2664. doi:10.1021/ja01263a038. ISSN 0002-7863.
Robinson FA, Holland DO (1948). "Preparation of water-soluble derivatives of 2-methylnaphthalene". Journal of the Chemical Society. 2: 182–186. doi:10.1039/JR9480000182. ISSN 0368-1769. PMID 18906382.
Fiore LD, et al. (2001). "Anaphylactoid reactions to vitamin K". Journal of Thrombosis and Thrombolysis. 11 (2): 175–183. doi:10.1023/A:1011237019082. ISSN 1573-742X. PMID 11406734.

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[:v-1] Veselý V, Kapp J (1925). "Sur les dérivés nitres du méthyl-2-naphtalène". Recueil des Travaux Chimiques des Pays-Bas. 44 (4): 360–375. doi:10.1002/recl.19250440409. ISSN 0165-0513.

[:a-2] Veldstra H, Wiardi PW (1943). "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. doi:10.1002/recl.19430620203. ISSN 0165-0513.

[:m-3] Budavari S, et al. (2000). The Merck index (12th ed.). Chapman & Hall Electronic Pub. Division. p. 1581. ISBN 9781584881292.

[4] Baker BR, Carlson GH (1942). "Water-soluble compounds with antihemorrhagic activity". Journal of the American Chemical Society. 64 (11): 2657–2664. doi:10.1021/ja01263a038. ISSN 0002-7863.

[5] Robinson FA, Holland DO (1948). "Preparation of water-soluble derivatives of 2-methylnaphthalene". Journal of the Chemical Society. 2: 182–186. doi:10.1039/JR9480000182. ISSN 0368-1769. PMID 18906382.

[6] Fiore LD, et al. (2001). "Anaphylactoid reactions to vitamin K". Journal of Thrombosis and Thrombolysis. 11 (2): 175–183. doi:10.1023/A:1011237019082. ISSN 1573-742X. PMID 11406734.