2046-17-5

Basic information

• Product Name: METHYL 4-PHENYLBUTYRATE
• Synonyms: TIMTEC-BB SBB007854;Benzenebutanoic acid, methyl ester;benzenebutanoicacid,methylester;Butyric acid, 4-phenyl-, methyl ester;Methyl 4-phenylbutanoate;Methyl ester of benzenebutanoic acid;METHYL 4-PHENYLBUTYRATE;4-Phenylbutanoic acid methyl ester
• CAS NO: 2046-17-5
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 218-067-1
• Mol File: 2046-17-5.mol
• Article Data: 96

Chemical Properties

• Boiling Point: 270.46°C (rough estimate)
• Flash Point: 112.2 °C
• Appearance: /
• Density: 1.0292 (rough estimate)
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 4-PHENYLBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-PHENYLBUTYRATE(2046-17-5)
• EPA Substance Registry System: METHYL 4-PHENYLBUTYRATE(2046-17-5)

Safety Data

• Hazardous Substances Data: 2046-17-5(Hazardous Substances Data)

Usage

Description

Methyl 4-phenylbutyrate has a powerful, sweet, fruity, floral odor. Below 10 ppm, the flavor is extremely sweet and fruity. May be prepared by direct esterification of γγ-butyric acid.

Chemical Properties

Methyl 4-phenylbutyrate has a powerful, sweet, fruity, floral odor. The flavor becomes extremely sweet and fruity at concentrations below 10 ppm

Preparation

By direct esterification of γ-butyric acid.

Synthesis Reference(s)

Synthetic Communications, 20, p. 3131, 1990 DOI: 10.1080/00397919008051536Tetrahedron Letters, 30, p. 219, 1989 DOI: 10.1016/S0040-4039(00)95164-5

InChI:InChI=1/C11H14O2/c1-13-11(12)9-5-8-10-6-3-2-4-7-10/h2-4,6-7H,5,8-9H2,1H3

Upstream product

• 67-56-1 methanol 
• 2046-18-6 4-phenylbutyronitrile 
• 2270-20-4 5-Phenylpentanoic acid 
• 129603-26-5 4-phenyl-2-(phenylseleno)-butan-1-ol 
• 77903-44-7 t-2-Phenyl-c-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 1940-02-9 4-phenylbutyric acid anhydride 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 5861-31-4 methyl trans-2-phenylcyclopropanecarboxylate 
• 5279-78-7 (1R*,2R*)-tert-butyl 2-phenylcyclopropanecarboxylate 
• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 
• 939-88-8 rac-(1R,2R)-2-phenylcyclopropanecarboxamide 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 141543-31-9 (2-Benzyl-cyclopropylmethyl)-dimethyl-phenyl-silane 

Downstream Products

• 39267-35-1 1-Methylsulfinyl-5-phenyl-2-pentanon 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 78508-37-9 methyl 4-acetoxy-4-phenylbutanoate 
• 21895-10-3 4-phenyl<1,1-(2)H2>butanol 
• 1821-12-1 4-Phenylbutyric acid 
• 124211-38-7 2-acetoxy-2-methyl-5-phenylpentane 
• 41882-77-3 4-(3-hydroxycarbonylpropyl)-benzophenone 
• 147862-73-5 4-(diphenylmethylene)-n-butanoic acid 
• 14978-35-9 4-(4-Benzyl-phenyl)-butyric acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 89709-56-8 4-(4-Benzoyl-phenyl)-butyric acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 119-64-2 tetralin 
• 64283-87-0 4-phenyl-1-iodobutane 
• 768-56-9 4-Phenylbut-1-ene 
• 104-51-8 1-butylbenzene 

Relevant articles and documents

C-H Allylic Bond Cleavage to generate an Active Hydridopalladium Species for the Alkoxycarbonylation of Alkenes. X-Ray Crystal Structure of

On the basis of a reactivity study using various alkenes and of the X-ray crystal structure analysis of the title compound isolated from the alkoxycarbonylation reaction, the formation of an active Pd(H)(SnCl3) species, generated from the SnCl2-PPh3 system, is proposed.

Nickel-Mediated Alkoxycarbonylation for Complete Carbon Isotope Replacement

Many commercial drugs, as well as upcoming pharmaceutically active compounds in the pipeline, display aliphatic carboxylic acids or derivatives thereof as key structural entities. Synthetic methods for rapidly accessing isotopologues of such compounds are highly relevant for undertaking critical pharmacological studies. In this paper, we disclose a direct synthetic route allowing for full carbon isotope replacement via a nickel-mediated alkoxycarbonylation. Employing a nickelII pincer complex ([(N2N)Ni-Cl]) in combination with carbon-13 labeled CO, alkyl iodide, sodium methoxide, photocatalyst, and blue LED light, it was possible to generate the corresponding isotopically labeled aliphatic carboxylates in good yields. Furthermore, the developed methodology was applied to the carbon isotope substitution of several pharmaceutically active compounds, whereby complete carbon-13 labeling was successfully accomplished. It was initially proposed that the carboxylation step would proceed via the in situ formation of a nickellacarboxylate, generated by CO insertion into the Ni-alkoxide bond. However, preliminary mechanistic investigations suggest an alternative pathway involving attack of an open shell species generated from the alkyl halide to a metal ligated CO to generate an acyl NiIII species. Subsequent reductive elimination involving the alkoxide eventually leads to carboxylate formation. An excess of the alkoxide was essential for obtaining a high yield of the product. In general, the presented methodology provides a simple and convenient setup for the synthesis and carbon isotope labeling of aliphatic carboxylates, while providing new insights about the reactivity of the N2N nickel pincer complex applied.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.