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Merck

779903

Sigma-Aldrich

Hexamethylphosphoramide

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

Synonym(s):

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

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About This Item

Linear Formula:
[(CH3)2N]3PO
CAS Number:
Molecular Weight:
179.20
Beilstein:
1099903
EC Number:
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

vapor density

6.18 (vs air)

Quality Level

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.)

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1 of 4

This Item
H11602253189106615
Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

-

mp

7 °C (lit.)

mp

7 °C (lit.)

mp

-

mp

189-191 °C (lit.)

bp

230-232 °C/740 mmHg (lit.)

bp

230-232 °C/740 mmHg (lit.)

bp

80-90 °C/10 mmHg (lit.)

bp

-

form

liquid

form

-

form

liquid

form

solid

density

1.03 g/mL at 25 °C (lit.)

density

1.03 g/mL at 25 °C (lit.)

density

0.903 g/mL at 25 °C (lit.)

density

-

Application

Hexamethylphosphoramide can be used:
  • As an additive to facilitate the enantioselective addition of alkyne to aldehydes to generate propargylic alcohols at room temperature.[1]
  • As a catalyst for the reversible-deactivation radical polymerization of methyl methacrylate with an alkyl iodide initiator to generate poly(methyl methacrylate)(PMMA).[2]
  • To facilitate the conversion of tetra-alkyl methanediphosphonates into (Z)-2-aryl-1-(2-cyanoethyl)ethenylphos-phonates.[3]

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.[4]

Pictograms

Health hazardCorrosion

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


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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)
?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)
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)
Kristopher J Kolonko et al.
The Journal of organic chemistry, 75(18), 6163-6172 (2010-08-26)
A variety of multinuclear NMR techniques, in combination with X-ray diffraction methods, were used to probe the solution structure of α-aryl lithium enolates of bis(4-fluorobenzyl) ketone (1-H), phenyl 4-fluorobenzyl ketone (2-H), and N,N-dimethyl 4-fluorophenylacetamide (3-H) in ethereal solvents and in

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