tert-butyl 2-(dimethoxyphosphoryl)acetate

• ChemBase ID: 152135
• Molecular Formular: C8H17O5P
• Molecular Mass: 224.191341
• Monoisotopic Mass: 224.08136027
• SMILES: CC(C)(C)OC(=O)CP(=O)(OC)OC
• Canonical SMILES: COP(=O)(CC(=O)OC(C)(C)C)OC
• InChI: InChI=1S/C8H17O5P/c1-8(2,3)13-7(9)6-14(10,11-4)12-5/h6H2,1-5H3
• InChIKey: SAZYDWOWLRDDRQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-(dimethoxyphosphoryl)acetate
• IUPAC Traditional name: tert-butyl 2-(dimethoxyphosphoryl)acetate
• Synonyms: tert-Butyl ((oxo)dimethoxyphosphino)acetate; tert-Butyl (dimethoxyphosphinyl)acetate; Dimethyl (tert-butoxycarbonyl)methylphosphonate; tert-Butyl P,P-dimethylphosphonoacetate; (叔丁氧羰基)甲基膦酸二甲酯; P,P-二甲基膦酰乙酸叔丁酯

Database IDs

• CAS Number: 62327-21-3
• MDL Number: MFCD00042939
• Beilstein Number: 4861886
• PubChem SID: 162246280; 24887464
• PubChem CID: 4564495

CALCULATED PROPERTIES

• Acid pKa: 17.777706
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.4924598
• LogD (pH = 7.4): 0.4924598
• Log P: 0.4924598
• Molar Refractivity: 51.1733 cm^3
• Polarizability: 21.043863 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 86-87 °C/0.02 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.131 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.434

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (GC)
• Linear Formula: (CH3O)2P(O)CH2COOC(CH3)3

DETAILS

Sigma Aldrich - 79522

Other Notes
Horner-Wittig reagent giving preferentially (E)-α,β-unsat. esters which are mildly saponified with acid6,7,8. Synthesis of derivatives by reductive alkylation9
Packaging
25, 100 mL in glass bottle
Application
Reactant for:
• Preparation of phosphonate terminated PPH dendrimers as anti-HIV-1 agents1
• Preparation of monodehydro diketopiperazines from ketoacyl amino acid amides via acid-catalyzed cyclization2
• Preparation of α,β-unsaturated esters for use in the guanidine-catalyzed oxa-Michael addition3
• Preparation of myxopyronin B and desmethyl myxopyronin B analogs, with antibacterial activity and inhibitory activity against bacterial RNA polymerase4
• Allylation and subsequent ring-closing metathesis in presence of Grubbs′ catalyst or intramolecular rhodium-catalyzed cyclopropanation reactions5