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779903 Sigma-Aldrich

Hexamethylphosphoramide

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

Synonym: HMPA, Hexamethylphosphoric acid triamide, Tris(dimethylamino)phosphine oxide

  • CAS Number 680-31-9

  • Linear Formula [(CH3)2N]3PO

  • Molecular Weight 179.20

  •  Beilstein/REAXYS Number 1099903

  •  EC Number 211-653-8

  •  MDL number MFCD00008303

  •  PubChem Substance ID 329768110

  •  NACRES NA.22

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Properties

Quality Level   100
vapor density   6.18 (vs air)
vapor pressure   0.07 mmHg ( 25 °C)
assay   ≥98.0% (GC)
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.)
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 & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3082 9 / PGIII
WGK Germany 
WGK 3
RTECS 
TD0875000
Protocols & Articles
Peer-Reviewed Papers
15

References

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