Methyl phenyldiazoacetate

Methyl phenyldiazoacetate

Names
Preferred IUPAC name Methyl diazo(phenyl)acetate
Identifiers
CAS Number	22979‐35‐7  Y
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. ^[1] Methyl phenyldiazoacetate is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base. ^{[2] [3]}

Solid state structure of tert-butyl diazo(4-nitrophenyl)acetate t-BuO₂CC(N₂)C₆H₄NO₂, a representative of donor-acceptor carbene precursor related to the title compound. Key distances: C-N = 1.329 Å, N-N = 1.121 Å.

References

1. Davies, H. M. L.; Morton, D. (2011). "Guiding Principles for Site Selective and Stereoselective Intermolecular C–H Functionalization by Donor/Acceptor Rhodium Carbenes". Chemical Society Reviews. 40 (4): 1857–1869. doi:10.1039/C0CS00217H. PMID   21359404.
2. Huw M. L. Davies; Wen-hao Hu; Dong Xing (2015). "Methyl Phenyldiazoacetate". EEROS: 1–10. doi:10.1002/047084289X.rn00444.pub2. ISBN   978-0-470-84289-8.
3. Selvaraj, Ramajeyam; Chintala, Srinivasa R.; Taylor, Michael T.; Fox, Joseph M. (2014). "3-Hydroxymethyl-3-phenylcyclopropene". Org. Synth. 91: 322. doi:10.15227/orgsyn.091.0322.
4. Shishkov, I. V.; Rominger, F.; Hofmann, P. (2009). "Remarkably Stable Copper(I) α-Carbonyl Carbenes: Synthesis, Structure, and Mechanistic Studies of Alkene Cyclopropanation Reactions". Organometallics. 28 (4): 1049–1059. doi:10.1021/om8007376.