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Sigma-Aldrich

Phosphoryl chloride

for synthesis

Synonym(s):

Phosphoryl chloride, Phosphorus oxide trichloride, Phosphorus oxychloride

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About This Item

CAS Number:
10025-87-3
Molecular Weight:
153.33
MDL number:
MFCD00011443
UNSPSC Code:
12352101
EC Index Number:
233-046-7
NACRES:
NA.22

vapor pressure

36 hPa ( 20 °C)

Quality Level

200

assay

≥99.0% (argenometric)

form

liquid

potency

36 mg/kg LD50, oral (Rat)

pH

1.0 (25 °C, 5 g/L in H2O)

bp

105.3 °C/1013 hPa

mp

1-2 °C

density

1.68 g/cm3 at 20 °C (DIN 51757)

storage temp.

2-30°C

InChI

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

InChI key

XHXFXVLFKHQFAL-UHFFFAOYSA-N

General description

for synthesis

Application

Phosphoryl chloride is a strong Lewis acid that can be used as:
  • A phosphorylating agent for the selective phosphorylation of alcohols, amines, and thiols.
  • A dehydrating agent for alcohols, amides, and cyanohydrins.
  • A reagent to synthesize Vilsmeier reagent for Vilsmeier-Haack formylation reactions.
  • A chlorinating agent for the chlorination of heterocyclic compounds.
  • A reagent to prepare dihydroisoquinolines and isoquinolines by cyclization of N-β-phenylethyl amides via Bischler-Napieralski reaction.

Analysis Note

Assay (argentometric)≥ 99.0 %Density (d 20 °C/ 4 °C)1.673 - 1.677Identity (IR)passes test

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Synthesis and chemical transformations of mono-and disubstituted cyanamides
Nekrasov DD
Russ. J. Org. Chem., 40(10) (2004)
Phosphorus Oxychloride
Meier MS, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)

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