583-04-0

Basic information

• Product Name: ALLYL BENZOATE
• Synonyms: Allylbenzoate,97%;prop-2-enyl benzoate;BENZOIC ACID ALLYL ESTER;ALLYL BENZOATE;2-Propenyl benzoate;benzoicacid,2-propenylester
• CAS NO: 583-04-0
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 209-494-4
• Product Categories: monomer
• Mol File: 583-04-0.mol
• Article Data: 102

Chemical Properties

• Boiling Point: 83-84°C 5mm
• Flash Point: 98.4°C
• Appearance: /
• Density: 1.05
• Vapor Pressure: 0.0335mmHg at 25°C
• Refractive Index: 1.5160-1.5190
• Solubility: soluble in Methanol
• CAS DataBase Reference: ALLYL BENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL BENZOATE(583-04-0)
• EPA Substance Registry System: ALLYL BENZOATE(583-04-0)

Safety Data

• Hazardous Substances Data: 583-04-0(Hazardous Substances Data)

Usage

Uses

Allyl Benzoate is a versatile reactant used in the preparation of stable potassium alkyltrifluoroborates for Suzuki-Miyaura cross-coupling reactions with aryltriflates and arylhalides.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2166, 1992 DOI: 10.1021/jo00033a048Tetrahedron Letters, 29, p. 4513, 1988 DOI: 10.1016/S0040-4039(00)80534-1Synthetic Communications, 5, p. 213, 1975 DOI: 10.1080/00397917508064112

InChI:InChI=1/C10H10O2/c1-2-8-12-10(11)9-6-4-3-5-7-9/h2-7H,1,8H2

Upstream product

• 532-32-1 sodium benzoate 
• 107-05-1 3-chloroprop-1-ene 
• 107-18-6 allyl alcohol 
• 65-85-0 benzoic acid 
• 591-87-7 Allyl acetate 
• 765-30-0 Cyclopropylamine 
• 24850-33-7 allyltributylstanane 
• 94-36-0 dibenzoyl peroxide 
• 36847-76-4 1,3-dichloropropan-2-ol benzoate 
• 6750-04-5 propargyl benzoate 
• 346425-59-0 (3-oxo-cyclobutyl)methyl benzoate 
• 93-58-3 benzoic acid methyl ester 
• 618-32-6 Benzoyl bromide 
• 14593-43-2 benzyl allyl ether 

Downstream Products

• 6266-56-4 bis(4-methylphenyl)phenylmethanol 
• 4810-05-3 2,4,6-trimethylallylbenzene 
• 18052-94-3 1-(trimethylsilyl)-1-(benzoyloxy)-2-propene 
• 40815-73-4 1-phenyl-1-(2-propenyloxy)ethene 
• 103-71-9 phenyl isocyanate 
• 118017-13-3 trans-benzoic acid 4-oxo-but-2-enyl ester 
• 91813-32-0 N-(2-chloro-3-pyridinyl)phenylamide 
• 3743-28-0 N-(3-hydroxyphenyl)benzamide 
• 94088-74-1 N-(3,5-dimethoxyphenyl)benzamide 
• 1239910-88-3 C₁₂H₁₂O₄ 
• 1485-70-7 N-benzylbenzamide 
• 31410-01-2 1-allylimidazole 
• 1366504-03-1 (2E,4E)-5-phenylpenta-2,4-dien-1-yl benzoate 
• 34414-53-4 (E)-1-methoxy-4-(3-(4-methoxyphenyl)allyl)benzene 

Relevant articles and documents

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Electrochemical esterification via oxidative coupling of aldehydes and alcohols

An electrolytic method for the direct oxidative coupling of aldehydes with alcohols to produce esters is described. Our method involves anodic oxidation in presence of TBAF as supporting electrolyte in an undivided electrochemical cell equipped with graphite electrodes. This method successfully couples a wide range of alcohols to benzaldehydes with yields ranging from 70 to 90%. The protocol is easy to perform at a constant voltage conditions and offers a sustainable alternative over conventional methods.

An Atom-Economic and Stereospecific Access to Trisubstituted Olefins through Enyne Cross Metathesis Followed by 1,4-Hydrogenation

The combination of intermolecular enyne cross metathesis and subsequent 1,4-hydrogenation opens a stereocontrolled and atom-economic access to trisubstituted olefins. By investigating different combinations of functionalized alkyne and alkene substrates, we found that the outcome (yield, E / Z ratio) of the Grubbs II-catalyzed enyne cross-metathesis step depends on the substrate's structure, the amount of the alkene (used in excess), and the (optional) presence of ethylene. In any case, the 1,4-hydrogenation, catalyzed by 1,2-dimethoxybenzene-Cr(CO) 3, proceeds stereospecifically to yield exclusively the E -products from both the E- and Z- 1,3-diene intermediates obtained by metathesis. A rather broad scope and functional group compatibility of the method is demonstrated by means of 15 examples.