5638-30-2

Basic information

• Product Name: β-Butylbenzenepropanoic acid
• Synonyms: β-Butylbenzenepropanoic acid
• CAS NO: 5638-30-2
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28082
• Mol File: 5638-30-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: β-Butylbenzenepropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: β-Butylbenzenepropanoic acid(5638-30-2)
• EPA Substance Registry System: β-Butylbenzenepropanoic acid(5638-30-2)

Safety Data

• Hazardous Substances Data: 5638-30-2(Hazardous Substances Data)

Upstream product

• 18986-66-8 methyl 5-phenylcyclohexane-1,3-dione 
• 75-35-4 1,1-Dichloroethylene 
• 27059-47-8 1-phenyl-1-chloropentane 
• 6966-37-6 DL-ethyl-3-hydroxy-3-phenyl heptanoate 
• 109-72-8 n-butyllithium 
• 140-10-3 (E)-3-phenylacrylic acid 
• 97023-56-8 (E)-3-phenylhept-2-enoic acid 
• 109-65-9 1-bromo-butane 
• 17377-82-1 (E)-1-methylpropyl cinnamate 
• 220629-77-6 (1-Phenylpentyl)propanedioic acid 
• 63473-85-8 ethyl 3-phenylheptanoate 
• 693-04-9 butyl magnesium bromide 
• 621-82-9 Cinnamic acid 
• 583-03-9 1-Phenyl-1-pentanol 

Downstream Products

• 63473-85-8 ethyl 3-phenylheptanoate 
• 95698-46-7 3-phenyl-heptanoic acid-(4-bromo-phenacyl ester) 
• 30368-28-6 5-Phenylnonansaeuremethylester 
• 63049-32-1 2-Methylthio-3-phenylheptansaeure 
• 220629-78-7 3-Phenylheptanoyl chloride 
• 185674-73-1 2-Diazo-5-phenylnonan-3-one 
• 114376-30-6 3-Phenyl-1-heptanol 
• 63049-43-4 2-Phenylhexanaldimethylacetal 

Relevant articles and documents

Conjugate addition of RMgX-3MeLi to α,β-unsaturated amides and α,β-unsaturated carboxylic acids

In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in good yields. Copyright

Reactions d'addition conjuguee d'organolithiens aux acides carboxyliques α, β-insatures

In THF at -78 deg C, organolithium derivatives and unprotected α,β-unsaturated carboxylic acids give a conjugated addition reaction. Reactions of 1- and 2-napthoic acids with various organolithium derivatives and electrophiles are reported. Two X-ray studies show that the reaction occurs with a good diastereoselectivity: the dilithiated enolate formed as an intermediate adds the electrophile exclusively via the face opposite to that of the organolithium. A study of the 1H NMR spectra of the products obtained shows that these compounds adopt a preffered conformation in solution. The protonolysis of the intermediate enolate by trifluoroacetic acid in an inverted mode gives rise to the formation of 1,2-disubstituted dihydronapthalenes. With acyclic α,β-unsaturated carboxylic acids, the diastereoselectivity of the reaction is marginal. With secondary butyllithium, the protonolysis of the intermediate enolates gives a 1,4-addition and an average diastereoselectivity. Reaction of phenylpropiolic acid with butyllithium gives rise to the formation of a produst resulting from a trans addition to the triple bond; the organolithium derivative adds in α to the carboxylic group. - Key words: 1,4-addition reactions; carboxylic acids; organolithium derivatives.

Directed conjugate addition of organolithium reagents to α,β-unsaturated carboxylic acids

α,β-Unsaturated carboxylic acids undergo predominantly conjugate addition with organolithium reagents at low temperature (-78 °C) in THF and lead to various substituted alkanoic acids after quenching with electrophiles; with (E)-3-phenylpropenoic acid, this tandem alkylation sequence also affords significant amounts of isomeric 1,3-addition products.