29234-88-6

Basic information

• Product Name: 2-methylpropyl 4-chlorobenzoate
• Synonyms: Isobutyl 4-chlorobenzoate
• CAS NO: 29234-88-6
• Molecular Formula: C₁₁H₁₃ClO₂
• Molecular Weight: 212.6727
• Mol File: 29234-88-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 268°C at 760 mmHg
• Flash Point: 121.8°C
• Density: 1.124g/cm³
• Vapor Pressure: 0.00788mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: 2-methylpropyl 4-chlorobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylpropyl 4-chlorobenzoate(29234-88-6)
• EPA Substance Registry System: 2-methylpropyl 4-chlorobenzoate(29234-88-6)

Safety Data

• Hazardous Substances Data: 29234-88-6(Hazardous Substances Data)

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 201230-82-2 carbon monoxide 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 

Downstream Products

• 78-83-1 2-methyl-propan-1-ol 
• 74-11-3 para-chlorobenzoic acid 

Relevant articles and documents

The first general and selective palladium(II)-catalyzed alkoxycarbonylation of arylboronates: Interplay among benzoquinone-ligated palladium(0) complex, organoboron, and alcohol solvent

Methoxycarbonylation of aryl- and alken-ylboron compounds was performed using the palladium (II) acetate/triphenylphosphine [PdACHTUNGTRENNUNG(OAc) 2/PPh3] catalyst with p-benzoquinone as a stoichiometric oxidant in methanol at ambient temperature to obtain the corresponding methyl esters in good yields. A wide variety of functional groups including various carbonyl functionalities, nitrile, nitro, sulfone, and unprotected pyrrole rings were tolerated in the methoxycarbonlation, while the use of higher alcohols except for tert-butanol afforded various pchlorobenzoates in moderate to high yields. The catalytic alkoxycarbonylation proceeded without any acid or base additive, and an oxidative transmetalation step is proposed to explain the exceptional efficacy of this protocol. DFT and MP2 calculations support the proposed mechanism.