94-25-7

Basic information

• Product Name: Butyl 4-aminobenzoate
• Synonyms: Benzoicacid, p-amino-, butyl ester (6CI,7CI,8CI);4-(Butoxycarbonyl)aniline;4-Aminobenzoic acid butyl ester;Benzoic acid, 4-amino-,butyl ester;Butambene;Butesin;Butesine;Butoform;Butsein;Butyl Keloform;Butylp-aminobenzoate;Butylcaine;Hemoride;NSC 128464;Planoform;Scuroform;Scuroforme;n-Butyl 4-aminobenzoate;n-Butyl p-aminobenzoate;p-Aminobenzoicacid butyl ester;p-Aminobenzoic acid n-butyl ester
• CAS NO: 94-25-7
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.2423
• EINECS: 202-317-1
• Product Categories: CECLOR;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;Aromatic Esters
• Mol File: 94-25-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 57-58℃
• Boiling Point: 325.7 °C at 760 mmHg
• Flash Point: 184.6 °C
• Appearance: yellow powder
• Density: 1.078 g/cm³
• Vapor Pressure: 0.000227mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: pKa 5.38 (Uncertain)
• Water Solubility: Very slightly soluble in water.
• Merck: 14,1512
• BRN: 1211465
• CAS DataBase Reference: Butyl 4-aminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl 4-aminobenzoate(94-25-7)
• EPA Substance Registry System: Butyl 4-aminobenzoate(94-25-7)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:; R43:
• Safety Statements: S26:; S36/37:
• WGK Germany: 3
• RTECS: DG1530000
• TSCA: Yes
• Hazardous Substances Data: 94-25-7(Hazardous Substances Data)

Usage

Chemical Properties

It is a solid at room temperature, with a melting point of 58°C and a boiling point of 173.4°C (at 8mmHg). Butyl p-aminobenzoate is insoluble in water.

Uses

Different sources of media describe the Uses of 94-25-7 differently. You can refer to the following data:
1. n-Butyl 4-aminobenzoate is used as pharmaceutical intermediate.
2. antibacterial

Definition

ChEBI: An amino acid ester resulting from the formal condensation of the carboxy group of 4-aminobenzoic acid with the hydroxy group of butan-1-ol. Its local anaesthetic properties have been used for surface anaesthesia of the skin and mucous membranes, and for r lief of pain and itching associated with some anorectal disorders.

Production Methods

Butyl p-aminobenzoate is manufactured via esterification of p-nitrobenzoic acid with n-butyl alcohol, followed by the reduction of the nitro group to an amino group.

Brand name

Butesin (Abbott).

General Description

Yellow powder. Insoluble in water.

Air & Water Reactions

May be sensitive to light and air. Insoluble in water. Slowly hydrolyzed when boiled in water. Also will hydrolyze under high and low pH conditions .

Reactivity Profile

Butyl 4-aminobenzoate is an aminophenyl ester derivative. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Fire Hazard

Flash point data for Butyl 4-aminobenzoate are not available. Butyl 4-aminobenzoate is probably combustible.

Purification Methods

Crystallise Butamben from EtOH. [Beilstein 14 IV 1130.]

InChI:InChI=1/C11H15NO2/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7H,2-3,8,12H2,1H3

Upstream product

• 120-48-9 butyl p-nitrobenzoate 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 15226-74-1 dicobalt octacarbonyl 
• 106-40-1 4-bromo-aniline 
• 71-36-3 butan-1-ol 
• 201230-82-2 carbon monoxide 
• 540-37-4 p-aminoiodobenzene 
• 13939-06-5 molybdenum hexacarbonyl 
• 109-65-9 1-bromo-butane 
• 150-13-0 4-amino-benzoic acid 
• 122-04-3 4-nitro-benzoyl chloride 
• 556-08-1 p-(acetylamino)benzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 110272-11-2 4-[8]quinolylmethylenamino-benzoic acid butyl ester 
• 28318-85-6 4-β-D-glucopyranosylamino-benzoic acid butyl ester 
• 122063-90-5 4-amino-3,5-dibromo-benzoic acid butyl ester 
• 698992-36-8 4-isothiocyanato-benzoic acid butyl ester 
• 36969-65-0 4-(3-p-tolyl-thioureido)-benzoic acid butyl ester 
• 118058-63-2 n-butyl 4-acetylaminobenzoate 
• 122446-70-2 4-(2,2-diphenyl-acetylamino)-benzoic acid butyl ester 
• 60011-35-0 4-{[furan-2-yl-(8-hydroxy-quinolin-7-yl)-methyl]-amino}-benzoic acid butyl ester 
• 65234-64-2 4-{[2-thioxo-5-(2,4,5-trichloro-phenoxymethyl)-[1,3,4]oxadiazol-3-ylmethyl]-amino}-benzoic acid butyl ester 
• 49569-71-3 4-[(2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoic acid butyl ester 
• 70070-85-8 3-(4-butoxycarbonyl-anilinomethyl)-2-oxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 131293-74-8 C₂₅H₂₂ClNO₄ 
• 141397-60-6 n-butyl-4-amino-4-deoxy-5-deazapteroate 

Relevant articles and documents

Biorenewable carbon-supported Ru catalyst for: N -alkylation of amines with alcohols and selective hydrogenation of nitroarenes

Herein, we developed a renewable carbon-supported Ru catalyst (Ru/PNC-700), which was facilely prepared via simple impregnation followed by the pyrolysis process. The prepared Ru/PNC-700 catalyst demonstrated remarkable catalytic activity in terms of conversion and selectivity towards N-alkylation of anilines with benzyl alcohol and chemoselective hydrogenation of aromatic nitro compounds. In addition, local anesthetic pharmaceutical agents (e.g., butamben and benzocaine), including key drug intermediates, were synthesized in excellent yields under mild conditions and in the presence of water as a green solvent. Moreover, the prepared Ru/PNC-700 catalyst could be easily recovered and reused up to five times without any apparent loss in activity and selectivity.

Pd/C-catalyzed transfer hydrogenation of aromatic nitro compounds using methanol as a hydrogen source

We describe the selective transfer hydrogenation of aromatic nitro compounds to anilines using Pd/C as a heterogeneous catalyst with methanol as a green reductant. Nitroarenes bearing both electron-releasing and electron-deficient groups are amenable to this method and enable the synthesis of corresponding arylamines in moderate to good selectivities including the synthesis of butamben, a local anesthictic drug molecule. This new concise protocol is simple, ligand-free and does not require the supply of external molecular hydrogen.

Method for preparing p-aminobenzoic acid alkyl ester

The invention discloses a method for preparing p-aminobenzoic acid alkyl ester. The method comprises the following steps: performing an esterification reaction on p-nitrobenzoic acid and a corresponding alkyl alcohol so as to obtain p-nitrobenzoic acid alkyl ester, and further performing catalytic hydrogenation, so as to obtain the p-aminobenzoic acid alkyl ester, wherein the solvent used in the esterification reaction is p-nitrobenzoic acid alkyl ester; the mole ratio of p-nitrobenzoic acid to the p-nitrobenzoic acid alkyl ester is (1:0.5)-(1:1); the alkyl alcohol is a C4-C8 alcohol; the moleratio of the p-nitrobenzoic acid to the alkyl alcohol is (1:0.98)-(1:1.1); the esterification reaction is implemented in the presence of the catalyst; and the catalyst is sulfuric acid or p-toluenesulfonic acid. The invention unexpectedly shows that an esterification reaction product, namely the p-aminobenzoic acid alkyl ester, can be used as a solvent of the esterification reaction, with the esterification reaction solvent, the process that an alcohol or benzene solvent needs to be recycled in a conventional method is avoided, not only is aftertreatment simple, but also solvent consumption is avoided, and the method is environment-friendly.