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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:
Molecular Weight:
153.33
MDL number:
UNSPSC Code:
12352101
EC Index Number:
233-046-7
NACRES:
NA.22
grade:
for synthesis
bp:
105.3 °C/1013 hPa
vapor pressure:
36 hPa ( 20 °C)
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grade

for synthesis

Quality Level

vapor pressure

36 hPa ( 20 °C)

Assay

≥99.0% (argenometric)

form

liquid

potency

36 mg/kg LD50, oral (Rat)

dilution

(for synthesis)

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

SMILES string

[P](=O)(Cl)(Cl)Cl

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.[1]
  • A dehydrating agent for alcohols, amides, and cyanohydrins.[1][2]
  • A reagent to synthesize Vilsmeier reagent for Vilsmeier-Haack formylation reactions.[1]
  • A chlorinating agent for the chlorination of heterocyclic compounds.[1]
  • A reagent to prepare dihydroisoquinolines and isoquinolines by cyclization of N-β-phenylethyl amides via Bischler-Napieralski reaction.[1]

Analysis Note

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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


Certificates of Analysis (COA)

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

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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