221015
Oxalyl chloride
ReagentPlus®, ≥99%
Synonym(s):
Ethanedioyl dichloride
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About This Item
Linear Formula:
ClCOCOCl
CAS Number:
Molecular Weight:
126.93
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-200-2
Beilstein/REAXYS Number:
1361988
MDL number:
Assay:
≥99%
Form:
liquid
vapor density
4.4 (vs air)
Quality Level
vapor pressure
150 mmHg ( 20 °C)
product line
ReagentPlus®
assay
≥99%
form
liquid
reaction suitability
reagent type: oxidant
impurities
<10 ppb Heavy metals
color
APHA: 0-150
refractive index
n20/D 1.429 (lit.)
bp
62-65 °C (lit.)
mp
−10-−8 °C (lit.)
density
1.5 g/mL at 20 °C (lit.)
functional group
acyl chloride
SMILES string
ClC(=O)C(Cl)=O
InChI
1S/C2Cl2O2/c3-1(5)2(4)6
InChI key
CTSLXHKWHWQRSH-UHFFFAOYSA-N
General description
Oxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.
Application
Oxalyl chloride may be used in the following processes:
- Preparation of Mosher′s acid chloride by reacting with Mosher′s acid in the presence of DMF.
- Activation of dimethyl sulfoxide for use in the oxidation of long-chain alcohols to carbonyls.
- Activation of α-keto carboxylic acids and N-heterocyclic carboxylic acids for alkynylation to form ynediones and N-heterocyclic ynones, respectively.
Reactant involved in:
- Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids
- Chlorination and halogenation
- Three-component [3+2] cycloadditions
- Reactions with organostannanes
- Synthesis of cyclopentenones
- Carbonylations, used as a carbonyl synthon
Suitable for the synthesis of acid chlorides used to produce liquid crystals.
Packaging
The 5g, 25g and 100g units sold in the US are packaged in ampules.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
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signalword
Danger
supp_hazards
Storage Class
4.3 - Hazardous materials which set free flammable gases upon contact with water
ppe
Faceshields, Gloves, Goggles
hcodes
Hazard Classifications
Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1 - Water-react. 1
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
危险化学品
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A simple method for the microscale preparation of Mosher's acid chloride.
Ward DE and Rhee CK.
Tetrahedron Letters, 32(49), 7165-7166 (1991)
Catalytic Syntheses of N-Heterocyclic Ynones and Ynediones by In Situ Activation of Carboxylic Acids with Oxalyl Chloride.
Boersch C, et al.
Angewandte Chemie (International Edition in English), 50(44), 10448-10452 (2011)
Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide" activated" by oxalyl chloride.
Mancuso AJ, et al.
The Journal of Organic Chemistry, 43(12), 2480-2482 (1978)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 221015-5G | 04061838776860 |
| 221015-25G | 04061838776853 |
| 221015-10KG | 04061838161192 |
| 221015-100G | 04061838776846 |