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201170

Sigma-Aldrich

Phosphorus(V) oxychloride

Phosphorus(V) oxychloride
1 of 1 reviewers received a sample product or took part in a promotion

ReagentPlus®, 99%

Synonym(s):

Phosphorus(V) oxide chloride, Phosphoryl chloride

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5 G
$47.30
250 G
$53.90
1 KG
$105.00

About This Item

Linear Formula:
POCl3
CAS Number:
Molecular Weight:
153.33
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
assay:
99%
bp:
105.8 °C (lit.)
vapor pressure:
104 mmHg ( 50 °C)
28 mmHg ( 20 °C)

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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.)

functional group

phosphine oxide

SMILES string

ClP(Cl)(Cl)=O

InChI

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

InChI key

XHXFXVLFKHQFAL-UHFFFAOYSA-N

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Application

Phosphorus(V) oxychloride (POCl3) is a chlorinating agent that reacts with dimethylformamide (DMF) to form Vilsmeier reagent for Vilsmeier-Haack formylation reactions.[1][2][3]
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.[3]
  • Substituted 1-arylseleno-4-halo-2-enes by treating conjugated dienes with arylselenenamides.[4]
  • 3-methylthioimidazo[1,2-a]pyridines and imidazo-fused heterocycles in the presence of DMSO.[5]

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

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

ppe

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


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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)
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)
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)

Questions

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  1. 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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  2. 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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