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79-37-8 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 79-37-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 79-37:
(4*7)+(3*9)+(2*3)+(1*7)=68
68 % 10 = 8
So 79-37-8 is a valid CAS Registry Number.
InChI:InChI=1/C2Cl2O2/c3-1(5)2(4)6

79-37-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (O0082)  Oxalyl Chloride  >98.0%(GC)(T)

  • 79-37-8

  • 25g

  • 200.00CNY

  • Detail
  • TCI America

  • (O0082)  Oxalyl Chloride  >98.0%(GC)(T)

  • 79-37-8

  • 100g

  • 450.00CNY

  • Detail
  • TCI America

  • (O0082)  Oxalyl Chloride  >98.0%(GC)(T)

  • 79-37-8

  • 500g

  • 995.00CNY

  • Detail
  • Alfa Aesar

  • (H31617)  Oxalyl chloride, 2M soln. in dichloromethane   

  • 79-37-8

  • 100ml

  • 651.0CNY

  • Detail
  • Alfa Aesar

  • (H31617)  Oxalyl chloride, 2M soln. in dichloromethane   

  • 79-37-8

  • 500ml

  • 1500.0CNY

  • Detail
  • Alfa Aesar

  • (A18012)  Oxalyl chloride, 98%   

  • 79-37-8

  • 50g

  • 314.0CNY

  • Detail
  • Alfa Aesar

  • (A18012)  Oxalyl chloride, 98%   

  • 79-37-8

  • 100g

  • 561.0CNY

  • Detail
  • Alfa Aesar

  • (A18012)  Oxalyl chloride, 98%   

  • 79-37-8

  • 250g

  • 1108.0CNY

  • Detail
  • Alfa Aesar

  • (A18012)  Oxalyl chloride, 98%   

  • 79-37-8

  • 1000g

  • 4100.0CNY

  • Detail
  • Aldrich

  • (221015)  Oxalylchloride  ReagentPlus®, ≥99%

  • 79-37-8

  • 221015-5G

  • 238.68CNY

  • Detail
  • Aldrich

  • (221015)  Oxalylchloride  ReagentPlus®, ≥99%

  • 79-37-8

  • 221015-25G

  • 644.67CNY

  • Detail
  • Aldrich

  • (221015)  Oxalylchloride  ReagentPlus®, ≥99%

  • 79-37-8

  • 221015-100G

  • 1,708.20CNY

  • Detail

79-37-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Oxalyl Chloride

1.2 Other means of identification

Product number -
Other names oxalyl dichloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:79-37-8 SDS

79-37-8Synthetic route

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

A

oxalyl dichloride
79-37-8

oxalyl dichloride

B

chloroethane
75-00-3

chloroethane

C

1,2-diethoxy-tetrachloro-ethane
63938-37-4

1,2-diethoxy-tetrachloro-ethane

D

ethoxy-dichloro-acetyl chloride
98019-44-4

ethoxy-dichloro-acetyl chloride

E

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

Conditions
ConditionsYield
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

4-fluoroanthranilic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
In formamide at 150℃; for 6h;82%
tetrachloro-1,4-dioxin
133349-02-7

tetrachloro-1,4-dioxin

A

oxalyl dichloride
79-37-8

oxalyl dichloride

B

2,3-epoxy-2,3,5,6-tetrachloro-2,3-dihydro-1.4-dioxin
133349-07-2

2,3-epoxy-2,3,5,6-tetrachloro-2,3-dihydro-1.4-dioxin

C

phosgene

phosgene

Conditions
ConditionsYield
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

pyridine

bis(trichloromethyl) oxalate
98020-90-7

bis(trichloromethyl) oxalate

chlorobenzene
108-90-7

chlorobenzene

A

phosgene
75-44-5

phosgene

B

oxalyl dichloride
79-37-8

oxalyl dichloride

1,2-diethoxy-tetrachloro-ethane
63938-37-4

1,2-diethoxy-tetrachloro-ethane

A

oxalyl dichloride
79-37-8

oxalyl dichloride

B

chloroethane
75-00-3

chloroethane

C

ethoxy-dichloro-acetyl chloride
98019-44-4

ethoxy-dichloro-acetyl chloride

Conditions
ConditionsYield
at 165℃;
bis(trichloromethyl) oxalate
98020-90-7

bis(trichloromethyl) oxalate

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With pyridine; chlorobenzene
oxalic acid
144-62-7

oxalic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With phosphorus pentachloride; trichlorophosphate
With phosphorus pentachloride
With phosphorus pentachloride
oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With phosphorus pentachloride beim Erhitzen;
1,1,2,2-tetrachloroethylene
127-18-4

1,1,2,2-tetrachloroethylene

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
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

phosphorus pentachloride

oxalic acid
144-62-7

oxalic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

oxalyl dichloride
79-37-8

oxalyl dichloride

CO

CO

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
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

phosgene

CO

CO

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
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

2,3-dichloro-5,6-difluoro-1,4-dioxin

A

oxalyl dichloride
79-37-8

oxalyl dichloride

B

Carbonyl fluoride
353-50-4

Carbonyl fluoride

C

oxalyl difluoride
359-40-0

oxalyl difluoride

D

C3Cl2F2O3

C3Cl2F2O3

E

C3Cl2F2O3

C3Cl2F2O3

F

C4Cl2F2O3

C4Cl2F2O3

G

COCl2, low oligomers

COCl2, low oligomers

Conditions
ConditionsYield
With oxygen
Trichloroethylene
79-01-6

Trichloroethylene

A

dichloroacethyl chloride
79-36-7

dichloroacethyl chloride

B

oxalyl dichloride
79-37-8

oxalyl dichloride

C

chloral
75-87-6

chloral

D

1,1,2-trichloroethan-2-ol
13287-89-3

1,1,2-trichloroethan-2-ol

Conditions
ConditionsYield
With BaY-coated optical fibers; oxygen Product distribution; Solid phase reaction; Oxidation; Irradiation;
7-hydroxy-3H-phenoxazin-3-one sodium salt
34994-50-8

7-hydroxy-3H-phenoxazin-3-one sodium salt

levulinic acid
123-76-2

levulinic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With triethylamine In dichloromethane; water
3-(tert-butoxycarbonylmethyl)bicyclo[1.1.1]pentane-1-carboxylic acid
1113001-76-5

3-(tert-butoxycarbonylmethyl)bicyclo[1.1.1]pentane-1-carboxylic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

3-(tert-butyloxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid

3-(tert-butyloxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With triethylamine; trifluoroacetic acid In tetrahydrofuran; [(2)H6]acetone; n-heptane; dichloromethane
indole
120-72-9

indole

oxalyl dichloride
79-37-8

oxalyl dichloride

indolyl-3-glyoxylyl chloride
22980-09-2

indolyl-3-glyoxylyl chloride

Conditions
ConditionsYield
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

4-nitro-phenol

oxalyl dichloride
79-37-8

oxalyl dichloride

p-Nitrophenyl chloroglyoxylate
78974-67-1

p-Nitrophenyl chloroglyoxylate

Conditions
ConditionsYield
for 20h; Heating;100%
for 16h; Heating;
oxalyl dichloride
79-37-8

oxalyl dichloride

2,3-dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate
1563-66-2

2,3-dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate

Chlorooxalyl-methyl-carbamic acid 2,2-dimethyl-2,3-dihydro-benzofuran-7-yl ester
88241-19-4

Chlorooxalyl-methyl-carbamic acid 2,2-dimethyl-2,3-dihydro-benzofuran-7-yl ester

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 80℃;100%
oxalyl dichloride
79-37-8

oxalyl dichloride

4H-1,2,9,10-tetramethoxy-5,6-dihydrodibenzo[de,g]quinoline
39945-38-5

4H-1,2,9,10-tetramethoxy-5,6-dihydrodibenzo[de,g]quinoline

isatine
78178-94-6

isatine

Conditions
ConditionsYield
100%
oxalyl dichloride
79-37-8

oxalyl dichloride

Ethyl isothiocyanate
542-85-8

Ethyl isothiocyanate

2,2-Dichloro-3-ethyl-thiazolidine-4,5-dione
91466-84-1

2,2-Dichloro-3-ethyl-thiazolidine-4,5-dione

Conditions
ConditionsYield
Ambient temperature;100%
oxalyl dichloride
79-37-8

oxalyl dichloride

methyl N-propylcarbamate
35601-83-3

methyl N-propylcarbamate

3-isopropyloxazolidine-2,4,5-trione
91467-24-2

3-isopropyloxazolidine-2,4,5-trione

Conditions
ConditionsYield
for 48h; Ambient temperature;100%
oxalyl dichloride
79-37-8

oxalyl dichloride

(-)-menthol
2216-51-5

(-)-menthol

2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoacetic acid
70894-19-8

2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoacetic acid

Conditions
ConditionsYield
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

oxalyl dichloride

[2.2]Paracyclophan
1633-22-3

[2.2]Paracyclophan

<2.2>Paracyclophan-4-glyoxylsaeurechlorid
108869-36-9

<2.2>Paracyclophan-4-glyoxylsaeurechlorid

Conditions
ConditionsYield
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

oxalyl dichloride

4'-methoxy-2,6-dichloro-4-methoxydiphenylamine
127792-36-3

4'-methoxy-2,6-dichloro-4-methoxydiphenylamine

N-(4-methoxyphenyl)-N-(2',6'-dichloro-4'-methoxyphenyl)oxaniloyl chloride
127792-37-4

N-(4-methoxyphenyl)-N-(2',6'-dichloro-4'-methoxyphenyl)oxaniloyl chloride

Conditions
ConditionsYield
In benzene for 2h; Ambient temperature;100%
oxalyl dichloride
79-37-8

oxalyl dichloride

2,3-diamino-1,4-naphthoquinone
13755-95-8

2,3-diamino-1,4-naphthoquinone

1,4-dihydro-benzo[g]quinoxaline-2,3,5,10-tetraone
7029-90-5

1,4-dihydro-benzo[g]quinoxaline-2,3,5,10-tetraone

Conditions
ConditionsYield
100%
oxalyl dichloride
79-37-8

oxalyl dichloride

(difluoroamino)difluoroacetamidoxime
115983-87-4

(difluoroamino)difluoroacetamidoxime

O-oxalylbis<(difluoroamino)difluoroacetamidoxime>
129177-46-4

O-oxalylbis<(difluoroamino)difluoroacetamidoxime>

Conditions
ConditionsYield
In diethyl ether 1. -20 deg C, 0.5 h 2. 25 deg C, 0.5 h;100%
oxalyl dichloride
79-37-8

oxalyl dichloride

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohept-1-enecarboxylic acid ethyl ester
130655-37-7

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohept-1-enecarboxylic acid ethyl ester

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

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

Conditions
ConditionsYield
In benzene at 0℃; for 0.666667h;100%
In benzene for 1h;
oxalyl dichloride
79-37-8

oxalyl dichloride

8-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-1,4-dioxa-spiro[4.5]dec-7-ene-7-carboxylic acid ethyl ester
130655-26-4

8-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-1,4-dioxa-spiro[4.5]dec-7-ene-7-carboxylic acid ethyl ester

C23H27NO8
77793-25-0

C23H27NO8

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

79-37-8Relevant articles and documents

In silico design and pharmacological evaluation of conjugates of atenolol with modified saccharide for cardiovascular targeting

Kumbhar, Smita Tukaram,Patil, Shitalkumar Shivgonda,Bhatia, Manish Sudesh

, p. 261 - 271 (2021)

Amongst a wide range of biological macromolecules, saccharides exhibit the potential to be specifically recognized by cell-surface receptors and hence can be utilized as ligands in targeted drug delivery. The current study aims to use saccharides viz. Galactose, Pectin and Chitosan to improve targeting of Atenolol by oxalyl chloride mediated grafting. Conjugates were engineered by grafting Atenolol, a cardiovascular agent with the modified saccharide units. The conjugates were characterized by FTIR, DSC and 1H NMR study. Drug release analysis and cellular uptake study was carried out using H9c2 cell lines which represent that concentration of drug in cells treated with all atenolol-saccharide conjugates is enhanced by almost two-folds in comparison with cells treated with atenolol solution. Thus cell line study confers the evidence of selective cardiac delivery. No significant cytotoxicity was observed in case of all synthesized conjugates in the Brine shrimp lethality bioassay. Possible binding of the developed conjugates with the GLUT-4 receptors was assessed by in silico analysis using homology model developed by Swiss Model server. Hence it was concluded that the application of these conjugates with saccharides in selective cardiovascular drug delivery can be a promising approach to increase bioavailability, minimize drug loss by degradation and prevent harmful side effects by increasing specific cell targeting. Graphical abstract: [Figure not available: see fulltext.]

Citrate plasticizer and preparation method thereof

-

Paragraph 0054; 0057, (2021/05/29)

The invention discloses a citrate plasticizer and a preparation method thereof. The preparation method comprises the following steps: firstly, carrying out reaction on citric acid and alcohol to prepare citric acid triester; acylating dianhydride to prepare carboxyl-containing triester citrate; carrying out acylating chlorination on the carboxyl-containing triester citrate, and then carrying out esterification reaction on the carboxyl-containing triester citrate and tri(2-hydroxyethyl) isocyanurate to prepare triester citrate containing isocyanurate; and finally, esterifying with fatty acyl chloride to obtain the modified citrate plasticizer. The preparation method is simple to operate, wide in raw material source and mild in reaction condition, and meets industrial production. The prepared triester citrate containing isocyanurate has a good plasticizing effect and excellent thermal stability, low-temperature flexibility, solvent extraction resistance, migration resistance and flame retardance, and can be widely applied to plastic rubber plasticizers.

Sensor Comprising Resrufin Levulinate Having Sulfite Ion Selectivity and Method for Monitoring Sulfite Ion Using the Same

-

, (2012/06/16)

The present invention relates to a sensor comprising a resorufin compound having sulfite ion selectivity and a method for detecting sulfite ions using the same. More specifically, the resorufin compound may have outstandingly increased fluorescence intensity by a deprotection reaction that a levulinyl group is cleaved with a sulfite ion to be used as a selective fluorescence sensor of turn-on type, and also represent a chromogenic change to detect sulfite ions by naked eye.

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