779903

Hexamethylphosphoramide

absolute, over molecular sieve (H₂O ≤0.03%), ≥98.0% (GC)

• Synonym(s): HMPA, Hexamethylphosphoric acid triamide, Tris(dimethylamino)phosphine oxide
• Linear Formula: [(CH₃)₂N]₃PO
• CAS Number: 680-31-9
• Molecular Weight: 179.20
• Beilstein: 1099903
• EC Number: 211-653-8
• MDL number: MFCD00008303
• UNSPSC Code: 12352111
• PubChem Substance ID: 329768110
• NACRES: NA.22

Properties

• vapor density: 6.18 (vs air)
• Quality Level: 100
• vapor pressure: 0.07 mmHg ( 25 °C)
• Assay: ≥98.0% (GC)
• form: liquid
• quality: absolute, over molecular sieve (H₂O ≤0.03%)
• impurities: ≤0.03% H₂O (coulometric)
• refractive index: n20/D 1.459 (lit.)
• bp: 230-232 °C/740 mmHg (lit.)
• mp: 7 °C (lit.)
• density: 1.03 g/mL at 25 °C (lit.)
• functional group: phosphoramide
• SMILES string: CN(C)P(=O)(N(C)C)N(C)C
• InChI: 1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
• InChI key: GNOIPBMMFNIUFM-UHFFFAOYSA-N

Description

Application

Hexamethylphosphoramide can be used:

• As an additive to facilitate the enantioselective addition of alkyne to aldehydes to generate propargylic alcohols at room temperature.
• As a catalyst for the reversible-deactivation radical polymerization of methyl methacrylate with an alkyl iodide initiator to generate poly(methyl methacrylate)(PMMA).
• To facilitate the conversion of tetra-alkyl methanediphosphonates into (Z)-2-aryl-1-(2-cyanoethyl)ethenylphos-phonates.

Hexamethylphosphoramide is a dipolar co-solvent and an effective additive used in reactions like reduction of halides, deoxygenation of sulfones, halide olefin couplings and cleavage of carbon-sulfur bond.

Safety Information

• Pictograms: GHS08,GHS05
• Signal Word: Danger
• Hazard Statements: H314,H340,H350
• Precautionary Statements: P202 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Carc. 1B - Eye Dam. 1 - Muta. 1B - Skin Corr. 1C
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): 291.2 °F - closed cup
• Flash Point(C): 144 °C - closed cup