Butamben

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Butamben
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Clinical data
Other namesn-butyl p-aminobenzoate
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Topical
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  • none
Identifiers
  • Butyl 4-aminobenzoate
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Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
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Melting point58 °C (136 °F)
  • O=C(OCCCC)c1ccc(N)cc1
  • InChI=1S/C11H15NO2/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7H,2-3,8,12H2,1H3 checkY
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Butamben is a local anesthetic. Proprietary names includes Alvogil in Spain and Alvogyl in Switzerland. It is one of three components in the topical anesthetic Cetacaine.

Chemistry

It is the ester of 4-aminobenzoic acid and butanol.[1] A white, odourless, crystalline powder. that is mildly soluble in water (1 part in 7000) and soluble in alcohol, ether, chloroform, fixed oils, and dilute acids. It slowly hydrolyses when boiled with water. Synonyms include Butamben, Butilaminobenzoato, and Butoforme.

Synthesis

File:Butamben synthesis.svg
Patents:[2][3] ~97%:[4] ~94%:[5] ~88%:[6] NA:[7][8]

The Fischer esterification of 4-Nitrobenzoic acid [62-23-7] (1) and 1-Butanol [71-36-3] (2) gives n-Butyl 4-Nitrobenzoate [120-48-9] (3). Bechamp reduction then gives Butamben (4).

Alternatively, 4-aminobenzoic acid can be used directly.

References

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  1. ^ drugs.com Butamben
  2. ^ Page Template:Citation/styles.css has no content.GB 148743, "Manufacture of normal butyl paramino benzoate", issued Script error: No such module "auto date formatter"., assigned to Ste Chim Usines Rhone. 
  3. ^ Page Template:Citation/styles.css has no content.US 1440652, Adams R, Volwiler E, issued Script error: No such module "auto date formatter"., assigned to Abbott Labs. 
  4. ^ Page Module:Citation/CS1/styles.css has no content.Morogina OK, Nasibulin AA, Klyuev MV (1998). "Liquid-Phase Hydrogenation of p-Nitrobenzoic Acid Esters on Palladium Catalysts". Petroleum Chemistry. 38 (4): 251–255.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Hosangadi BD, Dave RH (August 1996). "An efficient general method for esterification of aromatic carboxylic acids". Tetrahedron Letters. 37 (35): 6375–6378. doi:10.1016/0040-4039(96)01351-2.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Gök Y, Alici B, Cetinkaya E, Özdemir İ, Özeroğlu Ö (2010). "Ionic liquids as solvent for efficient esterification of carboxylic acids with alkyl halides". Turkish Journal of Chemistry. 34 (2): 187–192. doi:10.3906/kim-0904-39. S2CID 93020800.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Matsunaga Y, Sakamoto S, Togashi A, Tsujimoto M (July 1994). "Smectogenic Salts Formed by Combination of Alkyl p-Aminobenzoates and p-Ethyl-or p-Chlorobenzenesulfonic Acid". Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals. 250 (1): 161–166. Bibcode:1994MCLCA.250..161M. doi:10.1080/10587259408028202.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Brill HC (June 1921). "Esters of Aminobenzoic Acids". Journal of the American Chemical Society. 43 (6): 1320–1323. Bibcode:1921JAChS..43.1320B. doi:10.1021/ja01439a014.

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