Dimethyl (diazomethyl)phosphonate

HCID 5115033CAS 27491-70-9

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Basic information

Standard SMILES: COP(=O)(C=[N+]=[N-])OC
InChIKey: QUZMIAJIRIZFQN-UHFFFAOYSA-N
Molecular formula: C3H7N2O3P
Average molar mass: 150.07 g/mol
Monoisotopic mass: 150.01942871

Names & identifiers

Preferred name: Dimethyl (diazomethyl)phosphonate
IUPAC: diazo(dimethoxyphosphoryl)methane
English name: Nsc294729
Molecular formula: C3H7N2O3P
Molecular weight: 150.073041

Names & synonyms

27491-70-9Dimethyl (diazomethyl)phosphonate(Dimethoxyphosphoryl)diazomethaneDimethylphosphonodiazomethanePhosphonic acid, P-(diazomethyl)-, dimethyl esterSeyferth-gilbert reagentSeyferth-gilbert reagent [MI]NSC-294729UNII-WK47F6C50TWK47F6C50TDTXSID60408487RefChem:134200

Show more names

Nsc294729P-(DiazoMethyl)phosphonic Acid DiMethyl Ester

DTXCID10359339dimethyl diazomethylphosphonatediazo(dimethoxyphosphoryl)methaneMFCD16876592Phosphonic acid,P-(diazomethyl)-, dimethyl esterC3H7N2O3PSCHEMBL669123QUZMIAJIRIZFQN-UHFFFAOYSA-N

Database identifiers

CAS: 27491-70-9
PubChem CID: 5115033
DTXSID: DTXSID60408487
UNII: WK47F6C50T
Nikkaji: J730.814K

Properties

Computed structural properties

XLogP: -0.4
Topological polar surface area: 37.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 166

Physicochemical properties

Boiling point: 0.42 · bp0.42 59°
refractive index: 25 · nD25 1.4585
storage temp.: -20 °C · -20°C Freezer, Under Inert Atmosphere
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Oil
color: Light Yellow to Very Dark Yellow
Stability: Moisture Sensitive
FDA UNII: 47 F6C50T · WK47F6C50T

Chemistry & industry

Applications

UsesReagent for one-carbon homologation of aldehydes and ketones to alkynes.

UsesSeyferth-Gilbert Reagent

Preparation methods

PreparationNsc294729 has been prepared by the method of Seyferth, a convenient three-step sequence beginning with commercially available N-(bromomethyl)phthalimide.