2-Methylnaphthalene-1,4-diamine

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2-Methylnaphthalene-1,4-diamine
Vitamin K6.svg
Names
Preferred IUPAC name
2-Methylnaphthalene-1,4-diamine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
  • CC1=C(C2=CC=CC=C2C(=C1)N)N
Properties
C11H12N2
Molar mass 172.231 g·mol−1
Appearanceyellowish crystals [1]
Melting point 110-113 °C [2] [1]
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).

2-Methylnaphthalene-1,4-diamine is a synthetic menadione analog with vitamin K activity. [2] [3]

2-Methylnaphthalene-1,4-diamine was first synthesized 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]

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References

  1. 1 2 3 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.
  2. 1 2 3 4 5 6 7 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.
  3. 1 2 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. S2CID   975055.