(dimethylamino)phosphonoyl dichloride

• ChemBase ID: 127088
• Molecular Formular: C2H6Cl2NOP
• Molecular Mass: 161.954901
• Monoisotopic Mass: 160.95640581
• SMILES: CN(C)P(=O)(Cl)Cl
• Canonical SMILES: CN(P(=O)(Cl)Cl)C
• InChI: InChI=1S/C2H6Cl2NOP/c1-5(2)7(3,4)6/h1-2H3
• InChIKey: YNHXBEVSSILHPI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (dimethylamino)phosphonoyl dichloride
• IUPAC Traditional name: dimethylaminophosphonoyl dichloride
• Synonyms: (Dimethylamido)phosphoryl dichloride; N,N-Dimethylphosphoramidodichloridate; Dimethylamidophosphoric dichloride; Dimethylaminophosphoryl dichloride; N,N-Dimethylphosphoramic dichloride; N,N-Dimethylphosphoramidodichloridate; DMPADC; Dimethylamidophosphoric dichloride; N,N-Dimethylphosphoramic dichloride; 二甲基氨基二氯化磷; N,N-二甲基磷氨基二氯化物

Database IDs

• CAS Number: 677-43-0
• EC Number: 211-641-2
• MDL Number: MFCD00013896
• Beilstein Number: 969956
• PubChem SID: 24887489; 162221411
• PubChem CID: 12673
• Wikipedia Title: Dimethylamidophosphoric_dichloride

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.38316494
• LogD (pH = 7.4): 0.38316497
• Log P: 0.38316497
• Molar Refractivity: 33.1241 cm^3
• Polarizability: 12.833771 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: <0 °C
• Boiling Point: 77-79 °C/11 mmHg(lit.); 89-90°C/20mm
• Flash Point: >110°C(230°F)
• Density: 1.360; 1.362 g/mL at 20 °C(lit.)
• Refractive Index: 1.4630; n20/D 1.464

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: TB4025000
• European Hazard Symbols: Corrosive (C); Nature polluting (N); Toxic (T)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; II
• Risk Statements: 34; 34-37
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• NFPA704:
  

  3

  3

  2

  W
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (AT); 97%
• Linear Formula: (CH3)2NP(O)Cl2

DETAILS

Sigma Aldrich - 79625

Other Notes
Reagent used for the activation of carboxylic acids1,2
Packaging
10 mL in glass bottle

REFERENCES

• In the presence of pyridine, carboxylic acids form active intermediates which react with alcohols in situ to give esters: Tetrahedron Lett., 4461 (1978). Has also been used to convert primary alcohols to alkyl chlorides: Chem. Lett., 923 (1978).
• With 1,2-diols forms cyclic phosphoric amides which can be reduced to alkenes, e.g. with Na in xylene: Synth. Commun., 5, 293 (1975).