79-37-8

Basic information

• Product Name: Oxalyl chloride
• Synonyms: Oxalic dichloride;oxalicdichloride;Oxaloyl chloride;oxaloylchloride;OXALYL CHLORIDE 98%;Oxaloyl dichloride;Oxalyl chloride2.0M solution in dichloromethaneAcroSeal§3;Ethanedioic acid dichloride
• CAS NO: 79-37-8
• Molecular Formula: C₂Cl₂O₂
• Molecular Weight: 126.93
• EINECS: 201-200-2
• Product Categories: Organics;Chlorination;Halogenation;Synthetic Organic Chemistry;Others;Oxidation;Synthetic Reagents;Agrochemicals;Pesticides intermediate
• Mol File: 79-37-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: −10-−8 °C(lit.)
• Boiling Point: 62-65 °C(lit.)
• Flash Point: 176-178°C
• Appearance: APHA: 0-150/Liquid
• Density: 1.5 g/mL at 20 °C(lit.)
• Vapor Density: 4.4 (vs air)
• Vapor Pressure: 150 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.429(lit.)
• Storage Temp.: Store Cold
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• Stability: Stable. Incompatible with bases, alcohols, steel, oxidizing agents, alkali metals. Moisture sensitive. Reacts violently with wat
• Merck: 14,6914
• BRN: 1361988
• CAS DataBase Reference: Oxalyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Oxalyl chloride(79-37-8)
• EPA Substance Registry System: Oxalyl chloride(79-37-8)

Safety Data

• Hazard Codes: C,T
• Statements: 14-20-29-34-40-23/24/25-37-35-23
• Safety Statements: 26-36/37/39-43-45-8-24/25-23-27
• RIDADR: UN 2927 6.1/PG 2
• WGK Germany: 2
• RTECS: KI2950000
• F: 9-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 79-37-8(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid with a pungent odour

Uses

Oxalyl Chloride is used in the preparation of cardiolipin analogs which induce peroxidase activity by Cytochrome C. It is also used in the preparation of fluorescent indicators for cytosolic calcium.

Production Methods

Oxalyl Chloride is produced by the reaction of anhydrous oxalic acid and phosphorus pentachloride.

Preparation

Oxalyl chloride was first prepared in 1892 by the French chemist Adrien Fauconnier, who reacted diethyl oxalate with phosphorus pentachloride. Oxalyl chloride is also produced commercially from ethylene carbonate. Photochlorination gives the tetrachloride, which is subsequently degraded:C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HClC2Cl4O2CO → C2O2Cl2 + COCl2

Application

Oxalyl chloride is used in organic synthesis. It may be used in the following processes:Unncatalyzed reaction of silyl ketene acetals with oxalyl chloride yeilds symmetrical pulvinic acids.Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride.Oxalyl chloride was reportedly used in the first synthesis of dioxane tetraketone.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.

Reactions

Oxalyl Chloride vigorously reacts with water, alcohols, and amines, and is employed for the synthesis of agrochemicals, pharmaceuticals, and fine chemicals.

General Description

Oxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.

Health Hazard

Oxalyl chloride is a corrosive respiratory irritant and lachrymator. The vapors will attack the skin, eyes and especially the mucous membranes of the nose and throat and respiratory system. This material should be used only in a well ventilated area.

Fire Hazard

Extinguish with dry powder or carbon dioxide. Do not use water. Oxalyl chloride decomposes upon contact with water to produce toxic and corrosive fumes. When heated to decomposition, product emits toxic fumes.

Chemical Reactivity

Product is sensitive to temperatures below -10° and above 40°C. It reacts vigorously with water and hydroxyl compounds.

Safety Profile

Poison. Violently decomposed by water and alcohol. Severe irritant to skin, eyes, respiratory tract. Explodeson contact with dimethyl sulfoxide. Forms shock-sensitive explosive mixtures with potassium or with K-Na alloy. Will react with water or steam to

Waste Disposal

Carefully mix acidic compound with dry sodium bicarbonate. Dilute slowly with water and wash down the drain with copious amounts of water.

InChI:InChI=1/C2Cl2O2/c3-1(5)2(4)6

Synthetic route

oxalic acid diethyl ester (95-92-1) → oxalyl dichloride (79-37-8) + chloroethane (75-00-3) + 1,2-diethoxy-tetrachloro-ethane (63938-37-4) + ethoxy-dichloro-acetyl chloride (98019-44-4) + Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With phosphorus pentachloride; manganese(ll) chloride at 90℃; for 5h; Product distribution; other catalysts (CuCl2, ZnCl2, CdCl2, CrCl3, FeCl3, CoCl2, PdCl2) and temperatures (from 70 to 130 deg C);	A n/a B n/a C n/a D n/a E 83.7%

4-fluoroanthranilic acid (446-32-2) → oxalyl dichloride (79-37-8)

Conditions	Yield
In formamide at 150℃; for 6h;	82%

tetrachloro-1,4-dioxin (133349-02-7) → oxalyl dichloride (79-37-8) + 2,3-epoxy-2,3,5,6-tetrachloro-2,3-dihydro-1.4-dioxin (133349-07-2) + phosgene

Conditions	Yield
With oxygen at 28 - 40℃; under 500 - 600 Torr;	A n/a B 32% C n/a
With oxygen at 28 - 40℃; under 500 - 600 Torr;	A n/a B 32% C n/a

pyridine (110-86-1) + bis(trichloromethyl) oxalate (98020-90-7) + chlorobenzene (108-90-7) → phosgene (75-44-5) + oxalyl dichloride (79-37-8)

1,2-diethoxy-tetrachloro-ethane (63938-37-4) → oxalyl dichloride (79-37-8) + chloroethane (75-00-3) + ethoxy-dichloro-acetyl chloride (98019-44-4)

Conditions	Yield
at 165℃;

bis(trichloromethyl) oxalate (98020-90-7) → oxalyl dichloride (79-37-8)

Conditions	Yield
With pyridine; chlorobenzene

oxalic acid (144-62-7) → oxalyl dichloride (79-37-8)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate
With phosphorus pentachloride
With phosphorus pentachloride

oxalic acid diethyl ester (95-92-1) → oxalyl dichloride (79-37-8)

Conditions	Yield
With phosphorus pentachloride beim Erhitzen;

1,1,2,2-tetrachloroethylene (127-18-4) → oxalyl dichloride (79-37-8)

Conditions	Yield
With pyridine; osmium(VIII) oxide 1) n-hexane, r.t., 2) 150 deg C; Yield given. Multistep reaction;

phosphorus pentachloride (10026-13-8, 874483-75-7) + oxalic acid (144-62-7) → oxalyl dichloride (79-37-8)

phosphorus pentachloride (10026-13-8, 874483-75-7) + oxalic acid diethyl ester (95-92-1) → oxalyl dichloride (79-37-8)

CO → oxalyl dichloride (79-37-8)

Conditions	Yield
With pumice stone; chlorine at 200℃; under 147102 Torr;
With metal halide; chlorine at 200℃; under 147102 Torr;
With chlorine; pyrographite at 200℃; under 147102 Torr;

phosgene (75-44-5) + CO → oxalyl dichloride (79-37-8)

Conditions	Yield
With pyrographite at 200℃; under 147102 Torr;
With pumice stone at 200℃; under 147102 Torr;
With metal halide at 200℃; under 147102 Torr;

2,3-dichloro-5,6-difluoro-1,4-dioxin (133349-04-9) → oxalyl dichloride (79-37-8) + Carbonyl fluoride (353-50-4) + oxalyl difluoride (359-40-0) + C3Cl2F2O3 + C3Cl2F2O3 + C4Cl2F2O3 + COCl2, low oligomers

Conditions	Yield
With oxygen

Trichloroethylene (79-01-6) → dichloroacethyl chloride (79-36-7) + oxalyl dichloride (79-37-8) + chloral (75-87-6) + 1,1,2-trichloroethan-2-ol (13287-89-3)

Conditions	Yield
With BaY-coated optical fibers; oxygen Product distribution; Solid phase reaction; Oxidation; Irradiation;

7-hydroxy-3H-phenoxazin-3-one sodium salt (34994-50-8) + levulinic acid (123-76-2) → oxalyl dichloride (79-37-8)

Conditions	Yield
With triethylamine In dichloromethane; water

3-(tert-butoxycarbonylmethyl)bicyclo[1.1.1]pentane-1-carboxylic acid (1113001-76-5) → oxalyl dichloride (79-37-8)

3-(tert-butyloxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid → oxalyl dichloride (79-37-8)

Conditions	Yield
With triethylamine; trifluoroacetic acid In tetrahydrofuran; [(2)H6]acetone; n-heptane; dichloromethane

indole (120-72-9) + oxalyl dichloride (79-37-8) → indolyl-3-glyoxylyl chloride (22980-09-2)

Conditions	Yield
In diethyl ether for 0.416667h;	100%
In tetrahydrofuran at 0℃;	93%
In diethyl ether at -20℃; for 18h;	93%

4-nitro-phenol (100-02-7) + oxalyl dichloride (79-37-8) → p-Nitrophenyl chloroglyoxylate (78974-67-1)

Conditions	Yield
for 20h; Heating;	100%
for 16h; Heating;

oxalyl dichloride (79-37-8) + 2,3-dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate (1563-66-2) → Chlorooxalyl-methyl-carbamic acid 2,2-dimethyl-2,3-dihydro-benzofuran-7-yl ester (88241-19-4)

Conditions	Yield
In 1,2-dichloro-ethane at 80℃;	100%

oxalyl dichloride (79-37-8) + 4H-1,2,9,10-tetramethoxy-5,6-dihydrodibenzo[de,g]quinoline (39945-38-5) → isatine (78178-94-6)

Conditions	Yield
	100%

oxalyl dichloride (79-37-8) + Ethyl isothiocyanate (542-85-8) → 2,2-Dichloro-3-ethyl-thiazolidine-4,5-dione (91466-84-1)

Conditions	Yield
Ambient temperature;	100%

oxalyl dichloride (79-37-8) + methyl N-propylcarbamate (35601-83-3) → 3-isopropyloxazolidine-2,4,5-trione (91467-24-2)

Conditions	Yield
for 48h; Ambient temperature;	100%

oxalyl dichloride (79-37-8) + (-)-menthol (2216-51-5) → 2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoacetic acid (70894-19-8)

Conditions	Yield
Stage #1: oxalyl dichloride; (-)-menthol In diethyl ether at 0 - 23℃; for 1.5h; Inert atmosphere; Stage #2: With water In diethyl ether at 0 - 23℃; Inert atmosphere;	100%
1) CH2Cl2, room temperature, 2) hydrolysis; Multistep reaction;
In diethyl ether; dichloromethane at 0 - 20℃; for 18h;

oxalyl dichloride (79-37-8) + [2.2]Paracyclophan (1633-22-3) → <2.2>Paracyclophan-4-glyoxylsaeurechlorid (108869-36-9)

Conditions	Yield
With aluminium trichloride In dichloromethane at -10℃; for 0.166667h;	100%
With aluminum (III) chloride at -10 - 5℃; for 0.333333h;	100%
With aluminum (III) chloride In dichloromethane at -20 - -10℃; for 0.333333h;
With aluminum (III) chloride In dichloromethane at -5℃;
With aluminum (III) chloride at -10 - 5℃; for 0.333333h;

oxalyl dichloride (79-37-8) + 4'-methoxy-2,6-dichloro-4-methoxydiphenylamine (127792-36-3) → N-(4-methoxyphenyl)-N-(2',6'-dichloro-4'-methoxyphenyl)oxaniloyl chloride (127792-37-4)

Conditions	Yield
In benzene for 2h; Ambient temperature;	100%

oxalyl dichloride (79-37-8) + 2,3-diamino-1,4-naphthoquinone (13755-95-8) → 1,4-dihydro-benzo[g]quinoxaline-2,3,5,10-tetraone (7029-90-5)

Conditions	Yield
	100%

oxalyl dichloride (79-37-8) + (difluoroamino)difluoroacetamidoxime (115983-87-4) → O-oxalylbis<(difluoroamino)difluoroacetamidoxime> (129177-46-4)

Conditions	Yield
In diethyl ether 1. -20 deg C, 0.5 h 2. 25 deg C, 0.5 h;	100%

oxalyl dichloride (79-37-8) + 2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohept-1-enecarboxylic acid ethyl ester (130655-37-7) → 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2,3-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclohepta[b]pyrrole-3a-carboxylic acid ethyl ester (130655-38-8)

Conditions	Yield
In benzene at 0℃; for 0.666667h;	100%
In benzene for 1h;

oxalyl dichloride (79-37-8) + 8-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-1,4-dioxa-spiro[4.5]dec-7-ene-7-carboxylic acid ethyl ester (130655-26-4) → C23H27NO8 (77793-25-0)

Conditions	Yield
In benzene at 0℃; for 0.5h;	100%

Upstream product

• 10026-13-8 Phosphorus pentachloride 

Downstream Products

• 106560-14-9 Faropenem sodium hemipentahydrate 
• 113808-86-9 3,5-DIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID 
• 41339-61-1 2-(5-BENZYLOXY-1H-INDOL-3-YL)-ETHANOL 
• 66728-98-1 4-Bromo-1-chloroisoquinoline 
• 119169-78-7 Epristeride 
• 3001-72-7 1,5-Diazabicyclo[4.3.0]non-5-ene 
• 41340-25-4 Etodolac 
• 117500-61-5 3-DIMETHYLAMINOBENZOYL CHLORIDE HYDROCHLORIDE 
• 22204-89-3 4-HO-DET 
• 60731-73-9 2,6-Difluorobenzoyl isocyanate 
• 116252-53-0 4-Thiazolemethanamine, 2-amino-N,N-dimethyl- 
• 101601-00-7 2-[5-(Benzyloxy)-1H-indol-3-yl]-2-oxoacetic acid ,97% 
• 10166-09-3 O-TOLYL-ACETYL CHLORIDE 
• 102-92-1 Cinnamoyl chloride 
• 1125-29-7 1,3,5-TRIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID 
• 113293-70-2 2,6-Dichloropyridine-4-carboxaldehyde 
• 14002-51-8 4-Biphenylcarbonyl chloride 
• 159178-03-7 2,6-DICHLORO-4-ISOCYANATOPYRIDINE 
• 20776-45-8 2-(5-BENZYLOXY-1H-INDOL-3-YL)-ETHYLAMINE 
• 21615-34-9 o-Anisoyl chloride 
• 22424-62-0 5-BENZYLOXYINDOLE-3-GLYOXYLAMIDE 
• 4461-30-7 CHLOROACETYL ISOCYANATE 
• 4461-34-1 2-Chlorobenzoyl isocyanate 
• 6068-72-0 4-Cyanobenzoyl chloride 
• 610-14-0 2-Nitrobenzoyl chloride 
• 6329-74-4 5-BROMOSALICYLAMIDE 
• 67748-61-2 1,3-BENZOTHIAZOLE-2-CARBONYL CHLORIDE 
• 71463-16-6 2-(2-NITROPHENYL)ACRYLALDEHYDE 
• 7250-84-2 4-(chloromethyl)-2-thiazolamine 
• 782-45-6 4-AMINOBENZANILIDE 
• 82626-01-5 ALPIDEM 
• 82626-48-0 Zolpidem 
• 98298-63-6 1H-Pyrazole-4-carbonyl chloride, 1,3,5-trimethyl- (9CI) 
• 2438-05-3 4-Propylbenzoic acid 
• 4461-33-0 BENZOYL ISOCYANATE 
• 4755-50-4 4-DIMETHYLAMINOBENZOYL CHLORIDE 

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