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79625

Sigma-Aldrich

N,N-Dimethylphosphoramic dichloride

≥98.0% (AT)

Synonym(s):

DMPADC, Dimethylamidophosphoric dichloride

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About This Item

Linear Formula:
(CH3)2NP(O)Cl2
CAS Number:
677-43-0
Molecular Weight:
161.95
Beilstein:
969956
EC Number:
211-641-2
MDL number:
MFCD00013896
UNSPSC Code:
12352100
PubChem Substance ID:
57652812
NACRES:
NA.22

Quality Level

100

Assay

≥98.0% (AT)

form

liquid

refractive index

n20/D 1.464

bp

77-79 °C/11 mmHg (lit.)

density

1.362 g/mL at 20 °C (lit.)

functional group

phosphoramide

storage temp.

2-8°C

SMILES string

CN(C)P(Cl)(Cl)=O

InChI

1S/C2H6Cl2NOP/c1-5(2)7(3,4)6/h1-2H3

InChI key

YNHXBEVSSILHPI-UHFFFAOYSA-N

Application

N,N-Dimethylphosphoramic dichloride can be used as a reagent:
  • For the activation of carboxylic acids.
  • To prepare functionalized β-lactams by reacting with acetic acids and imines.
  • To synthesize phosphoramidic esters by reacting with alcohols in the presence of a base catalyst.
  • To prepare [1,2,4]triazolo[4,3-c][1,3,5,2]triazaphosphinine-5-oxide derivatives by reacting with N-alkyl/aryl-N′-(4H-1,2,4-triazol-3-yl) amidines in the presence of triethylamine.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3194
BCCK7701
BCCJ0377
BCCF7207
BCCB2010

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Convenient procedures for esterification of carboxylic acids
Hsing-Jang L, et al.
Tetrahedron Letters, 19, 4461-4464 (1978)
F.P. Cossio et al.
Tetrahedron Letters, 28, 1945-1945 (1987)
A solid supported, rapid and mild synthesis of CWC related phosphoramidates
Shakya P, et al.
Catalysis Communications, 6, 669-673 (2005)
H.J. Liu et al.
Tetrahedron Letters, 4461-4461 (1978)
A new route to [1, 2, 4] triazolo [4, 3-c][1, 3, 5, 2] triazaphosphinine-5-oxides: reactivity of N-alkyl/aryl-n'-(4h-1, 2, 4-triazol-3-yl) amidines with N, N-dimethylphosphoramic dichloride
Hajr A and Marzouki L
Bulletin of the Chemical Society of Ethiopia, 34, 157-161 (2020)

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