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H11602

Sigma-Aldrich

Hexamethylphosphoramide

99%

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

vapor density

6.18 (vs air)

Quality Level

vapor pressure

0.07 mmHg ( 25 °C)

Assay

99%

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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This Item
10661577990352730
refractive index

n20/D 1.459 (lit.)

refractive index

-

refractive index

n20/D 1.459 (lit.)

refractive index

n20/D 1.459 (lit.)

bp

230-232 °C/740 mmHg (lit.)

bp

-

bp

230-232 °C/740 mmHg (lit.)

bp

230-232 °C/740 mmHg (lit.)

mp

7 °C (lit.)

mp

189-191 °C (lit.)

mp

7 °C (lit.)

mp

7 °C (lit.)

density

1.03 g/mL at 25 °C (lit.)

density

-

density

1.03 g/mL at 25 °C (lit.)

density

1.03 g/mL at 25 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

General description

Hexamethylphosphoramide is a polar aprotic solvent.

Application

Hexamethylphosphoramide can be used as a solvent:
  • For the conversion of carboxylate salt into esters by reacting with alkyl halides.
  • To synthesize aryl thioethers via nucleophilic displacement of unactivated aryl halides by thiolate ions.
  • To synthesize polyazomethines (PAZs) from dialdehyde and diamine via high-temperature solution polycondensation.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Optical and structural study of thin film of polyazomethine with triphenylamine unit prepared via spin-coating method.
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Polymer Bull., 66(1), 65-76 (2011)
Nucleophilic aromatic substitution reactions of unactivated aryl halides with thiolate ions in hexamethylphosphoramide.
Cogolli P, et al.
The Journal of Organic Chemistry, 44(15), 2642-2646 (1979)
Hexamethylphosphoramide
Normant H.
Angewandte Chemie (International Edition in English), 6(12), 1046-1067 (1967)
Controlled/?Living? Reverse Atom Transfer Radical Polymerization of a Monocyclic Olefin, Methyl 1-Cyclobutenecarboxylate.
Chen X P, et al.
Macromolecules, 35(11), 4277-4281 (2002)
Knud Nairz et al.
Genome biology, 5(10), R83-R83 (2004-10-06)
We report the use of the cross-linking drug hexamethylphosphoramide (HMPA), which introduces small deletions, as a mutagen suitable for reverse genetics in the model organism Drosophila melanogaster. A compatible mutation-detection method based on resolution of PCR fragment-length polymorphisms on standard

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