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779903

Sigma-Aldrich

Hexamethylphosphoramide

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

Sinónimos:

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

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About This Item

Fórmula lineal:
[(CH3)2N]3PO
Número de CAS:
680-31-9
Peso molecular:
179.20
Beilstein/REAXYS Number:
1099903
EC Number:
211-653-8
MDL number:
MFCD00008303
UNSPSC Code:
12352111
PubChem Substance ID:
329768110
NACRES:
NA.22

vapor density

6.18 (vs air)

Quality Level

100

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 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.

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.

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

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_germany

WGK 3

flash_point_f

291.2 °F - closed cup

flash_point_c

144 °C - closed cup

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
Anthony J Pearson et al.
Organic letters, 6(13), 2121-2124 (2004-06-18)
[reaction: see text] Vicinal stereocontrol during nucleophilic addition of tert-butyl lithiopropionate to eta(6)-anisole chromium tricarbonyl complexes with differing para substituents has been studied. Excellent vicinal double stereoinduction (>99:1) was observed when the para substituent was Si(CH(3))(3), and this has been
Drug-HPMA-HuIg conjugates effective against human solid cancer.
Blanka Ríhová et al.
Advances in experimental medicine and biology, 519, 125-143 (2003-04-05)
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