30698-30-7

Basic information

• Product Name: Benzeneacetic acid, a-cyano-, methyl ester
• Synonyms: isocyanoacetate;methyl α-cyanophenylacetate;methyl (2-cyano-2-phenyl)acetate;Methyl 2-cyano-2-phenylacetate;Methyl Phenylcyanoacetate;methyl (2RS)-2-phenylcyanoacetate
• CAS NO: 30698-30-7
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Mol File: 30698-30-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 148-151 °C(Press: 13 Torr)
• Density: 1.145±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzeneacetic acid, a-cyano-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-cyano-, methyl ester(30698-30-7)
• EPA Substance Registry System: Benzeneacetic acid, a-cyano-, methyl ester(30698-30-7)

Safety Data

• Hazardous Substances Data: 30698-30-7(Hazardous Substances Data)

Upstream product

• 140-29-4 phenylacetonitrile 
• 616-38-6 carbonic acid dimethyl ester 
• 14025-79-7 α-phenylcyanoacetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 7677-24-9 trimethylsilyl cyanide 
• 22979-35-7 Methyl phenyldiazoacetate 
• 86298-22-8 1H-benzotriazole-1-carboxylic acid methyl ester 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 79-22-1 methyl chloroformate 
• 613-90-1 benzoyl cyanide 
• 75436-12-3 Bromo-cyano-phenyl-acetic acid methyl ester 
• 186581-53-3 diazomethane 
• 31413-60-2 2-phenyl-3,3-dichloroacrylonitrile 
• 124-41-4 sodium methylate 

Downstream Products

• 1039756-15-4 methyl 2-cyano-2-phenyl-4-(mesitylsulfonamido)butanoate 
• 1107634-45-6 2,4-dimethylpentan-3-yl 2-cyano-2-phenylacetate 
• 1107634-96-7 methyl 2-cyano-5-oxo-2-phenylhexanoate 
• 1190830-34-2 methyl 3-amino-3-oxo-2-phenylpropanoate 
• 1316673-23-0 (R)-methyl 2-cyano-2-((S)-2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-phenylacetate 

Relevant articles and documents

Carbonylative coupling of: N -chloroamines with alcohols: Synthesis of esterification reagents

Herein we report a new method for the carbonylative synthesis of carbamates. Starting from N-chloroamines and alcohols, with copper or Pd/C as the catalyst, the corresponding carbamates were produced in moderate to good yields. No additional oxidant or base is needed in this system. Notably, the produced benzotriazole-carboxylates can be used as esterification reagents.

An asymmetric hydrocyanation/Michael reaction of α-diazoacetates: Via Cu(i)/chiral guanidine catalysis

An asymmetric one-pot hydrocyanation/Michael reaction of α-aryl diazoacetates with trimethylsilyl cyanide, tert-butanol, and N-phenylmaleimides has been realized. Using a chiral guanidinium salt/CuBr catalyst, a series of cyanide-containing pyrrolidine-2,5-diones could be obtained in good yields with excellent diastereo- and enantioselectivities.

Regioselective Asymmetric Allylic Alkylation Reaction of α -Cyanoacetates Catalyzed by a Heterobimetallic Platina-/Palladacycle

Allylic substitution reactions provide a valuable tool for the functionalization of CH acidic pronucleophiles. Often, control over the stereocenter generated at the nucleophilic reactant is still a challenge. The majority of studies that address this issue employ metal complexes with a low metal oxidation state (e.g. Pd0) to form allyl complexes through oxidative addition. In this article we describe the use of heterobimetallic PtII/PdII complexes, which probably activate the olefinic substrates through an SN2′ pathway. The reaction of α-cyanoacetates delivers linear allylation products with exclusive regioselectivity and high E/Z-selectivity for the new C=C double bond. Although the enantioselectivities attained are moderate, they are significantly higher than with related mono-PdII or -PtII catalysts or the corresponding bis-PdII complex, which indicates cooperation of the different metals. Control experiments suggest simultaneous activation of both reaction partners.