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779903

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:
680-31-9
Molecular Weight:
179.20
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
329768110
EC Number:
211-653-8
Beilstein/REAXYS Number:
1099903
MDL number:
MFCD00008303
eCl@ss:
32150917
Assay:
≥98.0% (GC)
Form:
liquid
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vapor density

6.18 (vs air)

Quality Segment

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

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.

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Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Codes

H314,H340,H350

Hazard Classifications

Carc. 1B - Eye Dam. 1 - Muta. 1B - Skin Corr. 1C

Storage Class

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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