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52730

Sigma-Aldrich

Hexamethylphosphoramide

purum, ≥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
Beilstein:
1099903
EC Number:
211-653-8
MDL number:
MFCD00008303
UNSPSC Code:
12352111
PubChem Substance ID:
57651380
NACRES:
NA.22

vapor density

6.18 (vs air)

Quality Level

100

vapor pressure

0.07 mmHg ( 25 °C)

grade

purum

Assay

≥98.0% (GC)

impurities

≤2.0% water (Karl Fischer)

refractive index

n20/D 1.459 (lit.)
n20/D 1.459

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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Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H314,H340,H350

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

291.2 °F

Flash Point(C)

144 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Kristopher J Kolonko et al.
The Journal of organic chemistry, 75(18), 6163-6172 (2010-08-26)
A variety of multinuclear NMR techniques, in combination with X-ray diffraction methods, were used to probe the solution structure of α-aryl lithium enolates of bis(4-fluorobenzyl) ketone (1-H), phenyl 4-fluorobenzyl ketone (2-H), and N,N-dimethyl 4-fluorophenylacetamide (3-H) in ethereal solvents and in
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
Wojciech Bartkowiak et al.
Journal of molecular modeling, 11(4-5), 317-322 (2005-07-12)
In this work, for the first time, a theoretical approach to describing the influence of hydrogen-bond formation on the electronic absorption spectrum and nonlinear optical properties of an aminobenzodifuranone derivative (ABF) that exhibits the largest positive solvatochromic shift compared to
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
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
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