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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:
680-31-9
Molecular Weight:
179.20
Beilstein/REAXYS Number:
1099903
EC Number:
211-653-8
MDL number:
MFCD00008303
UNSPSC Code:
12352111
PubChem Substance ID:
24895433
NACRES:
NA.22

vapor density

6.18 (vs air)

Quality Level

200

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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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

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

291.2 °F

flash_point_c

144 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hexamethylphosphoramide
Normant H.
Angewandte Chemie (International Edition in English), 6(12), 1046-1067 (1967)
Optical and structural study of thin film of polyazomethine with triphenylamine unit prepared via spin-coating method.
Palewicz M, et al.
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)
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)
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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