362433

Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

96%

• Synonym(s): N-Methoxy-N-methyl-2-(diethyl phosphono)acetamide, N-Methoxy-N-methyl-phosphonoacetamide diethyl ester, Diethyl N-methoxy-N-methylphosphonoacetamide, Diethylphosphonoacetic acid N-methyl-N-methoxyamide
• Linear Formula: CH₃ON(CH₃)COCH₂P(O)(OC₂H₅)₂
• CAS Number: 124931-12-0
• Molecular Weight: 239.21
• Beilstein/REAXYS Number: 1875865
• MDL number: MFCD00134233
• UNSPSC Code: 12352108
• PubChem Substance ID: 24862312
• NACRES: NA.22

Properties

• assay: 96%
• form: liquid
• reaction suitability: reaction type: C-C Bond Formation
• refractive index: n20/D 1.455 (lit.)
• bp: 90 °C/17 mmHg (lit.)
• density: 1.163 g/mL at 25 °C (lit.)
• functional group: amine; phosphonate
• SMILES string: CCOP(=O)(CC(=O)N(C)OC)OCC
• InChI: 1S/C8H18NO5P/c1-5-13-15(11,14-6-2)7-8(10)9(3)12-4/h5-7H2,1-4H3
• InChI key: WYLRYBDGIILFIR-UHFFFAOYSA-N

Description

Application

Reactant for:

• Preparation of ring-expanded bryostatin analogs as antitumor agents
• Asymmertic synthesis of pinnatoxins A and G via diastereoselective Ireland-Claisen rearrangement, ring closing metathesis, and cyclization
• Rh2(II)-catalyzed nitro-group migration reactions
• Stereoselective synthesis of cyclohexanones via phase transfer catalyzed double addition reactions
• Stereoselective synthesis of (+)-polyrhacitide A via aldol reaction, Horner-Wardsworth-Emmons reaction, Evans acetal intramolecular oxa-Michael reaction and diastereoselective syn reduction reaction as the key steps
• Preparation of substituted furans via olefin cross-metathesis

Wittig carbonylating reagent.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 230.0 °F - closed cup
• flash_point_c: 110 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter