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Merck
CN

52730

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

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Product Name

Hexamethylphosphoramide, purum, ≥98.0% (GC)

InChI key

GNOIPBMMFNIUFM-UHFFFAOYSA-N

InChI

1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3

SMILES string

CN(C)P(=O)(N(C)C)N(C)C

vapor density

6.18 (vs air)

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.)

functional group

phosphoramide

Quality Level

100

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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

WGK 3

flash_point_f

291.2 °F - closed cup

flash_point_c

144 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6402
BCCK7486
BCCH3647
BCCD4456
BCCB5292

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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
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
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
Samarium diiodide-induced reductive cross-coupling of nitrones with aldehydes and ketones.
Géraldine Masson et al.
Angewandte Chemie (International ed. in English), 41(10), 1772-1775 (2002-05-17)
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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