201170

Sigma-Aldrich

Phosphorus(V) oxychloride

ReagentPlus®, 99%

Synonym(s):
Phosphorus(V) oxide chloride, Phosphoryl chloride
Linear Formula:
POCl3
CAS Number:
Molecular Weight:
153.33
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

vapor density

5.3 (vs air)

vapor pressure

104 mmHg ( 50 °C)
28 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

form

liquid

pH

1 (20 °C)

bp

105.8 °C (lit.)

mp

1.25 °C (lit.)

density

1.645 g/mL at 25 °C (lit.)

SMILES string

ClP(Cl)(Cl)=O

InChI

1S/Cl3OP/c1-5(2,3)4

InChI key

XHXFXVLFKHQFAL-UHFFFAOYSA-N

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Related Categories

Application

Phosphorus(V) oxychloride (POCl3) is a chlorinating agent that reacts with dimethylformamide (DMF) to form Vilsmeier reagent for Vilsmeier-Haack formylation reactions.
It can also be used as a reagent in the synthesis of:
  • Quinazolin-4(3H)-one derivatives from 2-aminobenzamides via in situ preparation of Vilsmeier reagent.
  • Substituted 1-arylseleno-4-halo-2-enes by treating conjugated dienes with arylselenenamides.
  • 3-methylthioimidazo[1,2-a]pyridines and imidazo-fused heterocycles in the presence of DMSO.

Packaging

1 kg in glass bottle
5, 250 g in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1810 8

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

DMSO-POCl3: a reagent for methylthiolation of imidazo [1, 2-a] pyridines and other imidazo-fused heterocycles
Patil SM, et al.
Tetrahedron, 69(38), 8255-8262 (2013)
Arylselenenation of conjugated dienes by arylselenenamides in the presence of phosphorus (V) oxyhalides
Antipin RL, et al.
Tetrahedron Letters, 48(4), 729-731 (2007)
Vilsmeier Reagent: An Efficient Reagent for the Transformation of 2-Aminobenzamides into Quinazolin-4 (3 H)-one Derivatives.
Farzipour S, et al.
Synthetic Communications, 44(4), 481-487 (2014)
Vilsmeier-Haack formylation of 2-(1H-pyrazol-1-yl) ethanol and its methyl derivatives.
Rstakyan VI, et al.
Russ. J. Gen. Chem., 85(5), 1191-1193 (2015)
Regioselective formylation of pyrazolo [3, 4-b] pyridine and pyrazolo [1, 5-a] pyrimidine systems using Vilsmeier?Haack conditions.
Quiroga J
Tetrahedron Letters, 49(17), 2689-2691 (2008)

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