Methyl phenyldiazoacetate

Methyl phenyldiazoacetate
Names
	Preferred IUPAC name Methyl diazo(phenyl)acetate
Identifiers
CAS Number	22979-35-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	10708515;
PubChem CID	53436974;
UNII	GV2N699A75;
CompTox Dashboard (EPA)	DTXSID50700982 ;
	InChI InChI=1S/C9H8N2O2/c1-13-9(12)8(11-10)7-5-3-2-4-6-7/h2-6H,1H3 Key: HYAAEBUKCXOFDT-UHFFFAOYSA-N;
	SMILES COC(=O)C(=[N+]=[N-])C1=CC=CC=C1;
Properties
Chemical formula	C9H8N2O2
Molar mass	176.175 g·mol−1
Appearance	Yellow oil
Solubility in alkanes	Soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methyl phenyldiazoacetate is the organic compound with the formula C₆H₅C(N₂)CO₂Me. It is a diazo derivative of methyl phenylacetate. Colloquially referred to as "phenyldiazoacetate", it is generated and used in situ after isolation as a yellow oil.

Methyl phenyldiazoacetate and many related derivatives are precursors to donor-acceptor carbenes, which can be used for cyclopropanation or to insert into C-H bonds of organic substrates. These reactions are catalyzed by dirhodium tetraacetate or related chiral complexes. Methyl phenyldiazoacetate is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base.