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2-Methylnaphthalene-1,4-diamine

From Wikipedia, the free encyclopedia
2-Methylnaphthalene-1,4-diamine
Names
Preferred IUPAC name
2-Methylnaphthalene-1,4-diamine
Identifiers
3D model (JSmol)
ChemSpider
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 mass172.231 g·mol−1
Appearanceyellowish crystals[1]
Melting point110-113 °C[3][1]
dihydrochloride is freely soluble[2]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

2-Methylnaphthalene-1,4-diamine is a syntheticmenadioneanalog withvitamin 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 adihydrochloride salt (C11H14Cl2N2) withhydrochloric acid and one of the aforementioned research groups suggested the namevitamin K6 for the salt.[3]

2-Methylnaphthalene-1,4-diamine and its dihydrochloride can be made from2-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 unlikephylloquinone and menadione for example.[6]

Oral toxicity of dihydrochloride for rats is approximately the same as for4-amino-2-methyl-1-naphthol hydrochloride.[3]

References

[edit]
  1. ^abcVeselý 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. ^abBudavari S, et al. (2000).The Merck index (12th ed.). Chapman & Hall Electronic Pub. Division. p. 1581.ISBN 9781584881292.
  3. ^abcdefgVeldstra 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.
  4. ^Baker BR, Carlson GH (1942). "Water-soluble compounds with antihemorrhagic activity".Journal of the American Chemical Society.64 (11):2657–2664.Bibcode:1942JAChS..64.2657B.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.
Fat
soluble
A
D
E
K (B02B)
Water
soluble
B
C
Combinations
Antihemorrhagics
(coagulation)
Systemic
Vitamin K
Coagulation
factors
Other
systemic
Local
Antifibrinolytics


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