4593-90-2

Basic information

• Product Name: 3-PHENYLBUTYRIC ACID
• Synonyms: RARECHEM AL BE 0683;BETA-PHENYL-N-BUTYRIC ACID;(+/-)-BETA-METHYLHYDROCINNAMIC ACID;(+/-)-3-PHENYLBUTYRIC ACID;3-PHENYLBUTYRIC ACID;3-Phenylbutanoic acid;Benzenepropanoic acid, beta-methyl-;3-PHENYLBUTYRIC ACID 99%
• CAS NO: 4593-90-2
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 224-987-4
• Product Categories: C10;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Building Blocks
• Mol File: 4593-90-2.mol
• Article Data: 113

Chemical Properties

• Melting Point: 35-38 °C(lit.)
• Boiling Point: 170-172 °C20 mm Hg(lit.)
• Flash Point: 77 °F
• Appearance: /
• Density: 1.515 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: 1.5160 (estimate)
• PKA: 4.67±0.10(Predicted)
• Water Solubility: 9.254g/L(30 oC)
• BRN: 2044322
• CAS DataBase Reference: 3-PHENYLBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLBUTYRIC ACID(4593-90-2)
• EPA Substance Registry System: 3-PHENYLBUTYRIC ACID(4593-90-2)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-10
• Safety Statements: 22-24/25-36-26-16
• RIDADR: 1325
• WGK Germany: 3
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 4593-90-2(Hazardous Substances Data)

Usage

Description

3-Phenylbutyric acid, a metabolite derived from the oxidation of sec-octylbenzene, is an organic compound with potential applications in various industries due to its unique chemical properties.

Uses

Used in Microbial Isolation:
3-Phenylbutyric acid is used as a selective agent for the isolation of Rhodococcus rhodochrous PB1 from compost soil. This application is particularly relevant in the field of microbiology and environmental science, where the isolation of specific bacterial strains can provide insights into their ecological roles and potential for biotechnological applications.

InChI:InChI=1/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)

Upstream product

• 3724-65-0 2-butenoic acid 
• 71-43-2 benzene 
• 3068-88-0 4-methyloxetan-2-one 
• 7446-70-0 aluminium trichloride 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 2722-36-3 3-phenyl-1-butanol 
• 704-79-0 (Z)-3-phenylbut-2-enoic acid 
• 5155-87-3 3-phenylbut-3-enoic acid 
• 70532-73-9 (Z)-4-Phenyl-2-(trimethylsilyloxy)-2-butennitril 
• 14371-10-9 (E)-3-phenylpropenal 
• 34713-70-7 2-Phenylpropanal 
• 29621-69-0 2-(1-phenylethyl)propanedinitrile 
• 64-17-5 ethanol 
• 1134-71-0 ethyl 3-phenylbutanoate 

Downstream Products

• 4593-90-2 (S)-2-phenylbutanoic acid 
• 1533-20-6 1,3-diphenylbutane-1-one 
• 36318-77-1 [1-(dichloromethyl)-1-methylpropyl]benzene 
• 17913-10-9 1-methyl-3-phenyl-butanal 
• 772-14-5 (R)-3-phenylbutyric acid 
• 3461-39-0 3-phenyl-butyric acid methyl ester 
• 1134-71-0 ethyl (3R)-3-phenylbutanoate 
• 1134-71-0 ethyl (3S)-3-phenylbutanoate 
• 5801-17-2 1-bromo-3-phenylbutane 
• 4681-28-1 3-(4-amino-phenyl)-butyric acid 
• 861596-21-6 3-(2,4-dinitro-phenyl)-butyric acid 
• 767-58-8 (-)-(S)-1-methylindane 
• 26524-38-9 α-chloro-β,β-dimethylstyrene 
• 1119832-32-4 N-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-3-phenylbutanamide 

Relevant articles and documents

Asymmetric conjugate addition reaction using pyrazole derivatives as a chiral catalyst

The conjugate addition of Grignard reagent (2) onto 1-(α,β -unsaturated)acyl 3,5-dimethylpyrazole (1) was enantioselectively catalyzed by the copper complex from cuprous compounds and 3-phenyl-l-menthopyrazole (3).

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Asymmetric conjugate addition reactions with chiral oxadiazinones: Unusual conformational properties of the oxadiazinones

A series of Ephedra based oxadiazinones have been prepared, acylated, and examined in the asymmetric conjugate addition reaction with Grignard reagents in the presence of copper(I) bromide-dimethyl sulfide complex. The highest diastereoselectivity that was obtained in the conjugate addition reaction was observed with the (1R,2S)-ephedrine based N4-methyloxadiazinone (5:1 d.r.) favoring the formation of the (S)-configuration of the conjugate addition product. Efforts to enhance the level of diastereoselection via increasing the steric volume of the stereo-directing N4-substituent of the oxadiazinone (N4- = p-methoxyphenyl or -isopropyl) led to an observed decrease in the level of diastereoselection. A computational study was conducted to examine the conformations adopted by the N4-methyloxadiazinone vs. the N4-isopropyl-oxadiazinone that yielded the lower diastereoselectivity. An argument is made for the stereoelectronic properties of the N4-substituent being the cause of both the moderate diastereoselectivity and the unexpected facial preference for the conjugate addition.

Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes

Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can leverage commercially available formate carbon isotologues to enable the direct synthesis of isotopically labeled carboxylic acids. Mechanistic studies support the working model involving a thiol-catalyzed radical chain process wherein the atoms from formate are delivered across the alkene substrate via CO2?- as a key reactive intermediate.