Butamben

Butamben
Clinical data
Other names	n-butyl p-aminobenzoate
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Topical
ATC code	none;
Identifiers
	IUPAC name Butyl 4-aminobenzoate;
CAS Number	94-25-7 ;
PubChem CID	2482;
ChemSpider	2388 ;
UNII	EFW857872Q;
KEGG	D00730;
ChEBI	CHEBI:3231;
ChEMBL	ChEMBL127516 ;
CompTox Dashboard (EPA)	DTXSID7022417 ;
ECHA InfoCard	100.002.107
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	58 °C (136 °F)
	SMILES O=C(OCCCC)c1ccc(N)cc1;
	InChI 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 ; Key:IUWVALYLNVXWKX-UHFFFAOYSA-N ;
	(verify)

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

Patents:^[2]^[3] ~97%:^[4] ~94%:^[5] ~88%:^[6] NA:^[7]^[8]

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

Alternatively, 4-aminobenzoic acid can be used directly.

References

^ drugs.com Butamben
^ GB 148743, "Manufacture of normal butyl paramino benzoate", issued 1920, assigned to Ste Chim Usines Rhone.
^ US 1440652, Adams R, Volwiler E, issued 1923, assigned to Abbott Labs.
^ Morogina OK, Nasibulin AA, Klyuev MV (1998). "Liquid-Phase Hydrogenation of p-Nitrobenzoic Acid Esters on Palladium Catalysts". Petroleum Chemistry. 38 (4): 251–255.
^ 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.
^ 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.
^ 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.
^ Brill HC (June 1921). "Esters of Aminobenzoic Acids". Journal of the American Chemical Society. 43 (6): 1320–1323. doi:10.1021/ja01439a014.

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[1] rugs.com Butamben

[2] GB 148743, "Manufacture of normal butyl paramino benzoate", issued 1920, assigned to Ste Chim Usines Rhone.

[3] US 1440652, Adams R, Volwiler E, issued 1923, assigned to Abbott Labs.

[4] 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] 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] 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] 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] Brill HC (June 1921). "Esters of Aminobenzoic Acids". Journal of the American Chemical Society. 43 (6): 1320–1323. doi:10.1021/ja01439a014.

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