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779903

Sigma-Aldrich

Hexamethylphosphoramide

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

Sinonimo/i:

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

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About This Item

Formula condensata:
[(CH3)2N]3PO
Numero CAS:
680-31-9
Peso molecolare:
179.20
Beilstein:
1099903
Numero CE:
211-653-8
Numero MDL:
MFCD00008303
Codice UNSPSC:
12352111
ID PubChem:
329768110
NACRES:
NA.22

Densità del vapore

6.18 (vs air)

Livello qualitativo

100

Tensione di vapore

0.07 mmHg ( 25 °C)

Saggio

≥98.0% (GC)

Forma fisica

liquid

Qualità

absolute, over molecular sieve (H2O ≤0.03%)

Impurezze

≤0.03% H2O (coulometric)

Indice di rifrazione

n20/D 1.459 (lit.)

P. eboll.

230-232 °C/740 mmHg (lit.)

Punto di fusione

7 °C (lit.)

Densità

1.03 g/mL at 25 °C (lit.)

Stringa SMILE

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
GNOIPBMMFNIUFM-UHFFFAOYSA-N

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Applicazioni

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.

Pittogrammi

Health hazardCorrosion
GHS08,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314,H340,H350

Classi di pericolo

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

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

291.2 °F - closed cup

Punto d’infiammabilità (°C)

144 °C - closed cup

Certificati d'analisi (COA)

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?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)
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)
Robert B Grossman et al.
The Journal of organic chemistry, 68(3), 871-874 (2003-02-01)
Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, alpha-cyano esters, beta-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the
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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