52267-51-3

Basic information

• Product Name: Acetic acid, diazo-, phenylmethyl ester
• Synonyms: benzyl diazoacetate
• CAS NO: 52267-51-3
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Mol File: 52267-51-3.mol
• Article Data: 37

Chemical Properties

• Flash Point: 7℃
• Density: 0.894 g/mL at 25 °C
• Refractive Index: n20/D1.504
• CAS DataBase Reference: Acetic acid, diazo-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, diazo-, phenylmethyl ester(52267-51-3)
• EPA Substance Registry System: Acetic acid, diazo-, phenylmethyl ester(52267-51-3)

Safety Data

• Hazardous Substances Data: 52267-51-3(Hazardous Substances Data)

Upstream product

• 14661-69-9 p-toluenesulfonylhydrazone glyoxylic acid chloride 
• 100-51-6 benzyl alcohol 
• 5437-45-6 Benzyl bromoacetate 
• 2462-31-9 benzyl 2-aminoacetate hydrochloride 
• 1738-68-7 Gly-OBz 
• 100-39-0 benzyl bromide 
• 941-55-9 4-toluenesulfonyl azide 
• 5396-89-4 benzyl acetoacetate 
• 52267-50-2 benzyl-α-diazo-acetoacetate 
• 79844-27-2 Malonic acid benzyl ester 4-oxo-azetidin-2-yl ester 
• 186581-53-3 diazomethane 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 108985-35-9 Boc-Gly-Glc-OBn 
• 102013-00-3 N-Benzyloxycarbonyl-L-alanyl-glykolsaeure-benzylester 
• 30450-80-7 N-Benzyloxycarbonyl-glycyl-glykolsaeure-benzylester 
• 32786-24-6 benzyl 2-methoxyacetate 
• 142504-42-5 benzyl <2-<2-(2-hydroxyethoxy)ethoxy>ethoxy>acetate 
• 195071-47-7 14-hydroxy-3,6,9,12-tetraoxatetradecanoic acid phenylmethyl ester 
• 573968-14-6 (R,R)-trans-2-phenyl-cyclopropane-1-carboxylic acid benzyl ester 

Relevant articles and documents

Comparative study on post-polymerization modification of C1 poly(benzyl 2-ylidene-acetate) and its C2 analog poly(benzyl acrylate)

The present study investigates the challenging approach of post-polymerization modification on polymers with a sterically demanding reaction center. Therefore, the general possibility to functionalize polymethylene moieties was investigated. Poly(benzyl 2-ylidene-acetate) was synthesized by polymerization of benzyl 2-diazoacetate utilizing [(L-prolinate)RhI(1,5-dimethyl-1,5-cyclooctadiene)] as a catalyst. Subsequently, the modification of C1 polymerized poly(benzyl 2-ylidene-acetate) with amines was analyzed and the obtained data set was compared with experimental data derived for the C2 analog poly(benzyl acrylate). This is the first study on post-polymerization modification utilizing densely functionalized polymethylenes as starting materials.

Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization

Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.

NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).