221015 Aldrich

Oxalyl chloride

ReagentPlus®, ≥99%

Synonym: Ethanedioyl dichloride



Related Categories Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Others, Oxidizing Agents,
grade   ReagentPlus®
vapor density   4.4 (vs air)
vapor pressure   150 mmHg ( 20 °C)
assay   ≥99%
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.)



Suitable for the synthesis of acid chlorides used to produce liquid crystals.

Reactant involved in:
• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids1
• Chlorination and halogenation2
• Three-component [3+2] cycloadditions3
• Reactions with organostannanes4
• Synthesis of cyclopentenones5
• Carbonylations, used as a carbonyl synthon6


10 kg in Nowpak™

5, 25, 100 g in ampule

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Safety & Documentation

Safety Information

Signal word 
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
Contact with water liberates toxic gas., Reacts violently with water.
UN 2922 6.1(8) / PGI
WGK Germany 
Protocols & Articles
Peer-Reviewed Papers


Set your institution to view full text papers.

1. Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride. C. Boersch, et al., Angew. Chem. Int. Ed. Engl. 50, 10448-10452, (2011)


2. Catalysis of phosphorus(V)-mediated transformations: dichlorination reactions of epoxides under Appel conditions. R. M. Denton, et al., Org. Lett. 12, 4678-4681, (2010)


3. Y. L. Zhao, et al., J. Org. Chem. 7, 5622-5625, (2009)

4. Synthesis of 1,2-diketones by the transition metal-catalyst-free reaction of alpha-oxo acid chlorides or oxalyl chloride with organostannanes. T. Kashiwabara and M. Tanaka, J. Org. Chem. 74, 3958-3961, (2009)


5. C. Chen, et al., Tetrahedron Lett. 50, 5434-5436, (2009)

6. M. L. N. Rao, et al., Tetrahedron Lett. 51, 4975-4980, (2010)

Novel capsaicin analogues as potential anticancer agents: synthesis, biological evaluation, and in silico approach. Damião MC, Pasqualoto KF, Ferreira AK, et al. Arch. Pharm. (Weinheim) 347(12), 885-95, (2014)


Astaxanthin diferulate as a bifunctional antioxidant. Papa TB, Pinho VD, do Nascimento ES, et al. Free Radic. Res. 49(1), 102-11, (2014)


Synthesis and characterization of neutral and anionic cellulosic amphiphiles. Liu H, Edgar KJ, et al. Carbohydr. Polym. 113, 480-9, (2014)


Synthesis and in vitro biological evaluation of dihydroartemisinyl-chalcone esters. Smit FJ, van Biljon RA, Birkholtz LM, et al. Eur. J. Med. Chem. 90, 33-44, (2015)


Uncatalyzed reaction of silyl ketene acetals with oxalyl chloride: a straightforward preparation of symmetrical pulvinic acids. Heurtaux B, Lion C, Le Gall T, et al. J. Org. Chem. 70(4), 1474-7, (2005)


A mild method for the formation and in situ reaction of imidoyl chlorides: conversion of pyridine-1-oxides to 2-aminopyridine amides. Manley PJ and Bilodeau MT Org. Lett. 4(18), 3127-9, (2002)


Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride. Sham M Sondhi et al Eur. J. Med. Chem. 43, 2824-30, (2008)


Acute inhalation toxicology of oxalyl chloride. Barbee SJ, Stone JJ, and Hilaski RJ Am. Ind. Hyg. Assoc. J. 56(1), 74-6, (1995)


Enantiomerically pure P-chiral phosphinoselenoic chlorides: inversion of configuration at the P-chirogenic center in the synthesis and reaction of these substances. Kimura T and Murai T Chem. Commun. (Camb.) (32), 4077-9, (2005)


Reactions of oxalyl chloride with 1,2-cycloalkanediols in the presence of triethylamine. Itaya T, Iida T, Natsutani I, et al. Chem. Pharm. Bull. 50(1), 83-6, (2002)


Merck 14,6914

Beil. 2,IV,1853

Fieser 1,767 / Fieser 2,301 / Fieser 3,216 / Fieser 4,361 / Fieser 5,481 / Fieser 6,424 / Fieser 7,257 / Fieser 8,366 / Fieser 11,379 / Fieser 17,241

Aldrich MSDS 1, 1414:C / Corp MSDS 1 (2), 2662:D / FT-IR 2 (1), 1245:A / FT-IR 1 (1), 739:C / IR-Spectra (2), 381:H / IR-Spectra (3), 430:B / RegBook 1 (1), 867:D / Sax 6, 2099 / Sigma FT-IR 1 (2), 814:B / Structure Index 1, 133:B:1

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