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201170

Sigma-Aldrich

Phosphorus(V) oxychloride

ReagentPlus®, 99%

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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

vapor density

5.3 (vs air)

Quality Level

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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1 of 4

This Item
2620998.223398.45113
Phosphoryl chloride for synthesis

Sigma-Aldrich

8.22339

Phosphoryl chloride

Phosphoryl chloride Msynth™plus

Sigma-Aldrich

8.45113

Phosphoryl chloride

vapor pressure

104 mmHg ( 50 °C), 28 mmHg ( 20 °C)

vapor pressure

104 mmHg ( 50 °C), 28 mmHg ( 20 °C)

vapor pressure

36 hPa ( 20 °C)

vapor pressure

36 hPa ( 20 °C)

assay

99%

assay

99.999%

assay

≥99.0% (argenometric)

assay

≥99.0% (argenometric)

form

liquid

form

liquid

form

liquid

form

liquid

pH

1 (20 °C)

pH

1 (20 °C)

pH

1.0 (25 °C, 5 g/L in H2O)

pH

1.0 (25 °C, 5 g/L in H2O)

bp

105.8 °C (lit.)

bp

105.8 °C (lit.)

bp

105.3 °C/1013 hPa

bp

105.3 °C/1013 hPa

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1A - STOT RE 1 Inhalation

Target Organs

Respiratory Tract

Supplementary Hazards

Storage Class Code

6.1B - Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

Slide 1 of 2

1 of 2

Arylselenenation of conjugated dienes by arylselenenamides in the presence of phosphorus (V) oxyhalides
Antipin RL, et al.
Tetrahedron Letters, 48(4), 729-731 (2007)
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)
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)
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)

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