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779903

Sigma-Aldrich

Hexamethylphosphoramide

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

Synonym(s):
Tris(dimethylamino)phosphine oxide, HMPA, Hexamethylphosphoric acid triamide
Linear Formula:
[(CH3)2N]3PO
CAS Number:
Molecular Weight:
179.20
Beilstein:
1099903
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

6.18 (vs air)

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.)

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

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Application

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.
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.

Pictograms

CorrosionHealth hazard

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

?One-pot? synthesis of (Z)-2-aryl-1-(2-cyanoethyl) ethenylphosphonates via hexamethylphosphoramide-promoted sequential transformation
Wang G and Shen Y
Heteroatom Chem., 13(2), 116-119 (2002)
Hexamethylphosphoramide as a highly reactive catalyst for the reversible-deactivation radical polymerization of MMA with an in situ formed alkyl iodide initiator
Wang Y, et al.
Polym. Chem., 8(39), 6073-6085 (2017)
Phenyl- Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide
Shiue J, et al.
The Journal of Organic Chemistry, 62(14), 4643-4649 (1997)
Samarium diiodide-induced reductive cross-coupling of nitrones with aldehydes and ketones.
Géraldine Masson et al.
Angewandte Chemie (International ed. in English), 41(10), 1772-1775 (2002-05-17)
Ge Gao et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(15), 5417-5420 (2004-03-18)
It is found that the addition of hexamethylphosphoramide to the solution of an alkyne, Et(2)Zn, and (S)-1,1'-bi-2-naphthol in methylene chloride allows the generation of an alkynylzinc at room temperature and shows highly enantioselective additions to aldehydes. The mild condition for

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