105310-97-2

Basic information

• Product Name: Acetamide, 2-diazo-N-(phenylmethyl)-
• CAS NO: 105310-97-2
• Molecular Formula: C9H9N3O
• Molecular Weight: 175.19
• Mol File: 105310-97-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Acetamide, 2-diazo-N-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, 2-diazo-N-(phenylmethyl)-(105310-97-2)
• EPA Substance Registry System: Acetamide, 2-diazo-N-(phenylmethyl)-(105310-97-2)

Safety Data

• Hazardous Substances Data: 105310-97-2(Hazardous Substances Data)

Upstream product

• 14661-69-9 p-toluenesulfonylhydrazone glyoxylic acid chloride 
• 100-46-9 benzylamine 
• 20432-97-7 N-benzylglycinamide hydrochloride 
• 116433-53-5 2-azido-N-(phenylmethyl)acetamide 
• 2945-03-1 N-benzyl-2-bromoacetamide 
• 1227099-19-5 C₂₈H₂₅N₄O₃P 
• 19811-52-0 Boc-glycine-benzylamide 
• 147666-20-4 succinimidyl diazoacetate 

Downstream Products

• 1155946-48-7 C₂₄H₂₄N₃O₃P 
• 2586-35-8 N-benzyl-2-fluoroacetamide 
• 10229-22-8 N-benzyl-3-oxo-3-phenylpropionamide 
• 884816-30-2 benzylacetamidethioacetate 
• 19340-77-3 N-Phenylmethyl hydroxyacetamide 

Relevant articles and documents

Transition metal mediated surface modification of porous silicon

Porous silicon has received considerable attention lately due to its unique optical properties and use in sensor applications. The utility of this material can be further advanced with the aid of new surface chemical modification methods. Here we describe two transition metal mediated reactions that allow for the mild and chemoselective functionalization of porous silicon. The first method utilizes rhodium carbene chemistry to modify porous silicon surfaces with esters and amides. The second technique exploits a pt-based Karstedt's catalyst to affect the hydrosilylation of porous silicon with alkenes. The mildness and selectivity of the hydrosilylation is highlighted by modification of n-type porous silicon matrix with an 8-residue cyclic peptide.

1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain

Like azides, diazoacetamides undergo 1,3-dipolar cycloadditions with oxanorbornadienes (OND) in a reaction that is accelerated by the relief of strain in the transition state. The cycloaddition of a diazoacetamide with unstrained ethyl 4,4,4-trifluoro-2-butynoate is, however, 35-fold faster than with the analogous OND because of favorable interactions with the fluoro groups. Its rate constant (k = 0.53 M-1 s-1 in methanol) is comparable to those of strain-promoted azide-cyclooctyne cycloadditions.

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%).

Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts

A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.