tert-butyl 2-(diethoxyphosphoryl)acetate

• ChemBase ID: 74908
• Molecular Formular: C10H21O5P
• Molecular Mass: 252.244501
• Monoisotopic Mass: 252.1126604
• SMILES: P(=O)(OCC)(OCC)CC(=O)OC(C)(C)C
• Canonical SMILES: CCOP(=O)(CC(=O)OC(C)(C)C)OCC
• InChI: InChI=1S/C10H21O5P/c1-6-13-16(12,14-7-2)8-9(11)15-10(3,4)5/h6-8H2,1-5H3
• InChIKey: NFEGNISFSSLEGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-(diethoxyphosphoryl)acetate
• IUPAC Traditional name: tert-butyl 2-(diethoxyphosphoryl)acetate
• Synonyms: Diethyl(2-tert-butoxycarbonylmethyl)phosphonate; (Diethoxyphosphinyl)acetic acid 1,1-dimethylethyl ester; tert-Butyl (diethoxyphosphinyl)acetate; Diethyl tert-butoxycarbonylmethanephosphonate; tert-Butyl diethylphosphonoacetate; tert-Butyl 2-(diethoxyphosphoryl)acetate; Diethylphosphonoacetic acid tert butyl ester; 二乙基膦酰基乙酸叔丁酯

Database IDs

• CAS Number: 27784-76-5
• EC Number: 000-000-0
• MDL Number: MFCD00075414
• Beilstein Number: 2050126
• PubChem SID: 24861567; 162039826
• PubChem CID: 2773685

CALCULATED PROPERTIES

• Acid pKa: 17.379942
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1920279
• LogD (pH = 7.4): 1.1920279
• Log P: 1.1920279
• Molar Refractivity: 60.6705 cm^3
• Polarizability: 24.684145 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 100-103 °C/1.5 mmHg(lit.); 100-103°C/1.5mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.074; 1.074 g/mL at 25 °C(lit.)
• Refractive Index: 1.4310; n20/D 1.431(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%
• Linear Formula: (C2H5O)2P(O)CH2CO2C(CH3)3

DETAILS

Sigma Aldrich - 348333

Packaging
5 g in glass bottle
Application
Reactant for:
• Preparation of ydroxymethylated dihydroxyvitamin D3 analogs via Wittig-Horner approach, as potential antitumor agents1
• Synthesis of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat 3)2
• One-pot synthesis of the DPP4-selective inhibitor ABT-341 by a four-component coupling mediated by a diphenylprolinol silyl ether3
• Bicyclic triaminophosphine-promoted stereoselective synthesis of a,β-unsaturated esters, fluorides, and nitriles from aldehydes and ketones using Wadsworth-Emmons phosphonates4
• Preparation of amidopropenyl hydroxamates as human histone deacetylase (HDAC) inhibitors5