2094-69-1

Basic information

• Product Name: benzyl pivalate
• Synonyms: benzyl pivalate;Benzyl2,2-dimethylpropanoate;Benzylpivalat;Propanoic acid, 2,2-dimethyl-, phenylmethyl ester;Propanoic acid,2,2-dimethyl-,phenylmethyl ester;2,2-Dimethylpropanoic acid benzyl ester;2,2-Dimethylpropionic acid benzyl ester;Benzyl 2,2-dimethylpropionate
• CAS NO: 2094-69-1
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25424
• EINECS: 218-251-1
• Mol File: 2094-69-1.mol
• Article Data: 60

Chemical Properties

• Boiling Point: 248.3°Cat760mmHg
• Flash Point: 94.9°C
• Appearance: /
• Density: 1.002g/cm³
• Vapor Pressure: 0.0245mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: benzyl pivalate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl pivalate(2094-69-1)
• EPA Substance Registry System: benzyl pivalate(2094-69-1)

Safety Data

• Hazardous Substances Data: 2094-69-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16O2/c1-12(2,3)11(13)14-9-10-7-5-4-6-8-10/h4-8H,9H2,1-3H3

Upstream product

• 3282-30-2 pivaloyl chloride 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 
• 75-98-9 Trimethylacetic acid 
• 598-98-1 Methyl pivalate 
• 156088-51-6 4-isopropyl-3-pivaloyloxazolidin-2-one 
• 183064-96-2 (S)-3-(2',2'-dimethyl-1'-oxopropyl)-4-benzyl-oxazolidin-2-one 
• 3377-92-2 vinyl pivalate 
• 3581-70-2 neopentyl benzoate 
• 100253-83-6 N-benzyl-N-nitrosopivalamide 
• 100-47-0 benzonitrile 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 529-19-1 2-Methylbenzonitrile 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 538-86-3 benzyl methyl ether 
• 60-12-8 2-phenylethanol 
• 1007-26-7 (2,2-dimethyl-1-propyl)benzene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 108-88-3 toluene 
• 95735-85-6 trimethyl-acetic acid 2-nitro-benzyl ester 
• 75-98-9 Trimethylacetic acid 
• 6876-65-9 N-(4-methylphenyl)-2-phenylacetamide 
• 103-81-1 Benzeneacetamide 
• 203247-70-5 1-methoxy-4-(phenethylsulfonyl)benzene 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 81023-75-8 3,3-dimethyl-1-(phenylsulfonyl)butan-2-one 
• 3333-14-0 2,3-diphenylpropionitrile 
• 5350-82-3 2,2,3-triphenylpropanenitrile 

Relevant articles and documents

A study of electronic effects on the kinetics of thermal deamination of N-nitrosoamides

N-4-R-Benzyl-N-nitrosopivalamides (1a-d; R = MeO, Me, H, NO2) were allowed to decompose at 18 °C in C6D12, CDCl3, CD3CN, and d6-DMSO, and the rates of decomposition were followed by 1H NMR spectroscopy. The half-lives of the nitrosoamides were found to vary in a systematic way with the nature of the R group on the aromatic nucleus. Electron-releasing groups were found to decrease the stability of the starting nitrosoamide, whereas electron-withdrawing ones increased the nitrosoamides' thermal stability. A Hammett-type plot of log(rate constants of deamination) vs σp was linear (R2 = 0.986) with a ρ-type value of -0.90 indicating development of significant positive charge at the benzylic position in the transition state of the rate-determining step. The thermal stability of the nitrosoamides was also found to be systematically affected by the polarity of the solvent: as the solvent polarity increased, so did the lability of the nitrosoamides. This observation of intra- and intermolecular electronic perturbations of the kinetics of nitrosoamide decomposition appears to be novel. A closer look at the rate-determining step of nitrosoamide thermolysis is made, and a mechanistic framework is proposed that accounts for both steric and electronic modulation of nitrosoamide stability as well as the greater thermal stabilities of the related N-nitrocarboxamides and N-nitrosotosylamides.

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile

The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.

Sterically congested ester formation from α-substituted malononitrile and alcohol by an oxidative method using molecular oxygen

A metal-free oxidative esterification or thio-esterifica-tion of readily available substituted malononitrile and alcohol or thiol has been developed by simply mixing α-substituted malononitrile and alcohol or thiol in the presence of base under a molecular oxygen atmosphere. Sterically hindered ester or thioester can be prepared efficiently.