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201170

Phosphorus(V) oxychloride

ReagentPlus®, 99%

Synonym(s):

Phosphorus(V) oxide chloride, Phosphoryl chloride

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About This Item

Linear Formula:
POCl3
CAS Number:
10025-87-3
Molecular Weight:
153.33
NACRES:
NA.22
PubChem Substance ID:
57647818
UNSPSC Code:
12352101
EC Number:
233-046-7
MDL number:
MFCD00011443
Assay:
99%
Bp:
105.8 °C (lit.)
Vapor pressure:
104 mmHg ( 50 °C), 28 mmHg ( 20 °C)
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Quality Level

200

vapor density

5.3 (vs air)

vapor pressure

104 mmHg ( 50 °C), 28 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

form

liquid

dilution

(for general lab use)

pH

1 (20 °C)

bp

105.8 °C (lit.)

mp

1.25 °C (lit.)

density

1.645 g/mL at 25 °C (lit.)

functional group

phosphine oxide

SMILES string

ClP(Cl)(Cl)=O

InChI

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

InChI key

XHXFXVLFKHQFAL-UHFFFAOYSA-N

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

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Legal Information

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

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Danger

Hazard Classifications

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

target_organs

Respiratory Tract

supp_hazards

EUH014,EUH029

Storage Class

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT4431
SHBT4430
BCCN6758
SHBT0091
SHBS9286

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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)
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