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Merck

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)

Key Documents

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Quality Level

200

InChI key

XHXFXVLFKHQFAL-UHFFFAOYSA-N

InChI

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

SMILES string

ClP(Cl)(Cl)=O

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

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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.
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Poisonous substance

pdsc

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

201170-430KG-DW: + 201170-1L: + 201170-BULK: + 201170-250ML:4548173250441 + 201170-5G:4548173113586 + 201170-2.5L: + 201170-5ML:4548173250458 + 201170-VAR: + 201170-4X2.5KG: + 201170-10L: + 201170-1KG:4548173113562 + QR-027-1KG: + 201170-10KG: + 201170-5L: + 201170-250G:4548173113579

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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)
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)
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