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779903

Hexamethylphosphoramide

absolute, over molecular sieve (H2O ≤0.03%), ≥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:
329768110
EC Number:
211-653-8
Beilstein/REAXYS Number:
1099903
MDL number:
MFCD00008303
Assay:
≥98.0% (GC)
Form:
liquid
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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.)

functional group

phosphoramide

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

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.

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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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7232
BCCN0120
BCCL8590
BCCK8528
BCCH4397

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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)
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Global Trade Item Number

SKUGTIN
779903-100ML04061832941158