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79-37-8

Basic Information
CAS No.: 79-37-8
Name: Oxalyl chloride
Article Data: 37
Cas Database
Molecular Structure:
Molecular Structure of 79-37-8 (Oxalyl chloride)
Formula: C2Cl2O2
Molecular Weight: 126.927
Synonyms: Oxalyl chloride (6CI,8CI);Ethanedioylchloride;Oxalic acid chloride;Oxalic acid dichloride;Oxalic dichloride;Oxaloyl chloride;Oxaloyldichloride;Oxalyl dichloride;Ethanedioyl dichloride;
EINECS: 201-200-2
Density: 1.335
Melting Point: -10--8 °C(lit.)
Boiling Point: 63.5 °C at 760 mmHg
Flash Point: 4.5 °C
Solubility: reacts with water
Appearance: colourless liquid with a pungent odour
Hazard Symbols: CorrosiveC, ToxicT
Risk Codes: 14-20-29-34-40-23/24/25-37-35
Safety: 26-36/37/39-43-45-8-24/25-23-27
Transport Information: UN 2927 6.1/PG 2
PSA: 34.14000
LogP: 0.51720
Synthetic route
95-92-1

oxalic acid diethyl ester

A

79-37-8

oxalyl dichloride

B

75-00-3

chloroethane

C

63938-37-4

1,2-diethoxy-tetrachloro-ethane

D

98019-44-4

ethoxy-dichloro-acetyl chloride

E

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%
446-32-2

4-fluoroanthranilic acid

79-37-8

oxalyl dichloride

Conditions
ConditionsYield
In formamide at 150℃; for 6h;82%
133349-02-7

tetrachloro-1,4-dioxin

A

79-37-8

oxalyl dichloride

B

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
110-86-1

pyridine

98020-90-7

bis(trichloromethyl) oxalate

108-90-7

chlorobenzene

A

75-44-5

phosgene

B

79-37-8

oxalyl dichloride

63938-37-4

1,2-diethoxy-tetrachloro-ethane

A

79-37-8

oxalyl dichloride

B

75-00-3

chloroethane

C

98019-44-4

ethoxy-dichloro-acetyl chloride

Conditions
ConditionsYield
at 165℃;
98020-90-7

bis(trichloromethyl) oxalate

79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With pyridine; chlorobenzene
144-62-7

oxalic acid

79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With phosphorus pentachloride; trichlorophosphate
With phosphorus pentachloride
With phosphorus pentachloride
95-92-1

oxalic acid diethyl ester

79-37-8

oxalyl dichloride

Conditions
ConditionsYield
With phosphorus pentachloride beim Erhitzen;
127-18-4

1,1,2,2-tetrachloroethylene

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;
10026-13-8, 874483-75-7

phosphorus pentachloride

144-62-7

oxalic acid

79-37-8

oxalyl dichloride

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  • Oxalyl chlorideCAS NO.: 79-37-8

  • Casno:

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  • Casno:

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  • Casno:

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  • Oxalyl Chloride

  • Casno:

    79-37-8

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Specification

The Oxalyl chloride, with the CAS registry number 79-37-8,is also known as Oxalyl dichloride; Ethanedioyl dichloride. It belongs to the product categories of Synthetic Organic Chemistry;Others;Oxidation;Synthetic Reagents;Agrochemicals. Its EINECS number is 201-200-2. This chemical's molecular formula is C2Cl2O2 and molecular weight is 126.93. What's more,Its systematic name is Oxalyl chloride.It is a colourless liquid with a pungent odour,Stable,incompatible with bases,alcohols,steel,oxidizing agents,alkali metals,moisture sensitive,reacts violently with water,liberating toxic gas.Oxalyl chloride can be prepared by treating oxalic acid with phosphorus pentachloride.

Physical properties about Oxalyl chloride are:
(1)ACD/LogP: 0.257; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.26; (4)ACD/LogD (pH 7.4): 0.26; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 32.89; (8)ACD/KOC (pH 7.4): 32.89; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.449; (13)Molar Refractivity: 21.072 cm3; (14)Molar Volume: 78.558 cm3; (15)Surface Tension: 40.9589996337891 dyne/cm; (16)Density: 1.616 g/cm3; (17)Flash Point: 4.532 °C; (18)Enthalpy of Vaporization: 30.568 kJ/mol; (19)Boiling Point: 63.5 °C at 760 mmHg; (20)Vapour Pressure: 170.671005249023 mmHg at 25°C;

You can still convert the following datas into molecular structure:
(1)SMILES:ClC(=O)C(Cl)=O;
(2)Std. InChI:InChI=1S/C2Cl2O2/c3-1(5)2(4)6;
(3)Std. InChIKey:CTSLXHKWHWQRSH-UHFFFAOYSA-N;

Uses of Oxalyl chloride:
Oxalyl chloride is a useful reagent in organic synthesis. It is mainly used in organic synthesis for the preparation of acid chlorides from the corresponding carboxylic acids. Oxalyl chloride tends to be a milder, more selective reagent. Oxalyl chloride reacts with aromatic compounds in the presence of aluminium chloride to give the corresponding acid chloride in a process known as a Friedel-Crafts acylation. The resulting acid chloride can be hydrolysed in water to form the corresponding carboxylic acid. The combination of DMSO, oxalyl chloride and triethylamine converts alcohols to the corresponding aldehydes and ketones via the process known as the Swern oxidation. Oxalyl chloride was reportedly used in the first syhthesis of dioxane tetraketone (C4O6), a novel oxide  of carbon.

Safety Information of Oxalyl chloride:
(1)Reacts violently with water; (2)Harmful by inhalation; (3)Contact with water liberates toxic gas; (4)Causes burns; (5)Limited evidence of a carcinogenic effect; (6)Toxic by inhalation, in contact with skin and if swallowed; (7)Irritating to respiratory system; (8)Causes severe burns; (9)In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; (10)Wear suitable protective clothing, gloves and eye/face protection; (11)In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.); (12)Keep container dry; (13)Avoid contact with skin and eyes; (14)Do not breathe vapour; (15)Take off immediately all contaminated clothing.

The toxicity data of Oxalyl chloride as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LC50 inhalation 1840ppm/1H (1840ppm) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Industrial Hygiene Association Journal. Vol. 56, Pg. 74, 1995.