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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.)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H.J. Liu et al.
Tetrahedron Letters, 4461-4461 (1978)
A solid supported, rapid and mild synthesis of CWC related phosphoramidates
Shakya P, et al.
Catalysis Communications, 6, 669-673 (2005)
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)
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)

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