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Succinyl chloride

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Name

Succinyl chloride

EINECS 208-838-0
CAS No. 543-20-4 Density 1.389 g/cm3
PSA 34.14000 LogP 1.29740
Solubility Reacts violently with water. Melting Point 16 °C
Formula C4H4Cl2O2 Boiling Point 193.4 °C at 760 mmHg
Molecular Weight 154.981 Flash Point 76.7 °C
Transport Information UN 3265 Appearance clear colourless to slightly brown liquid
Safety 26-36/37/39-45 Risk Codes 14-34
Molecular Structure Molecular Structure of 543-20-4 (SUCCINYL CHLORIDE) Hazard Symbols CorrosiveC
Synonyms

Succinylchloride (6CI,7CI,8CI);1,2-Bis(chlorocarbonyl)ethane;1,2-Ethanediylbis(chloroformate);NSC 87873;Succinic acid chloride;Succinicacid dichloride;Succinic chloride;Succinic dichloride;Succinoyl chloride;Succinoyl dichloride;Succinyl dichloride;

Article Data 58

Succinyl chloride Synthetic route

110-15-6

succinic acid

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
With thionyl chloride for 4h; Inert atmosphere; Schlenk technique; Reflux;99%
With phosgene; N,N-dimethyl-formamide In toluene at 55℃; Product distribution / selectivity;98.2%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h;95%
108-30-5

succinic acid anhydride

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
With thionyl chloride at 80℃; for 4h;93%
With thionyl chloride; zinc(II) chloride at 120 - 145℃;
With thionyl chloride; copper(l) chloride; zinc(II) chloride at 120 - 145℃;
108-30-5

succinic acid anhydride

4885-02-3

Dichloromethyl methyl ether

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

A

107-31-3

Methyl formate

B

543-20-4

succinoyl dichloride

108-30-5

succinic acid anhydride

4885-02-3

Dichloromethyl methyl ether

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
With zinc(II) chloride
4146-43-4

succinic acid dihydrazide

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
With hydrogenchloride; nitromethane; chlorine
108-30-5

succinic acid anhydride

10026-13-8, 874483-75-7

phosphorus pentachloride

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
at 120 - 130℃;
trimer(ic) β-aldehydo-propionic acid

trimer(ic) β-aldehydo-propionic acid

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
With phosphorus pentachloride
110-15-6

succinic acid

PCl5 (2 mol)

PCl5 (2 mol)

543-20-4

succinoyl dichloride

7719-09-7

thionyl chloride

110-15-6

succinic acid

ZnCl2

ZnCl2

CuCl

CuCl

543-20-4

succinoyl dichloride

Conditions
ConditionsYield
at 120 - 145℃;
692-29-5

Succinic semialdehyde

10026-13-8, 874483-75-7

phosphorus pentachloride

A

543-20-4

succinoyl dichloride

B

γ-chloro-butyrolactone

γ-chloro-butyrolactone

Succinyl chloride Consensus Reports

Reported in EPA TSCA Inventory.

Succinyl chloride Specification

The Succinyl chloride with CAS registry number of 543-20-4 is also called 1,2-Ethanediylbis(chloroformate). The IUPAC name is 543-20-4. Its EINECS registry number is 208-838-0. In addition, the formula is C4H4Cl2O2 and the molecular weight is 154.97936. It is a kind of clear colourless to slightly brown liquid. It is sensitive to moisture. What's more, it is the intermediate of synthetic resins, paints and succinylcholine chloride.

Physical properties about this chemical are: (1)ACD/LogP: 1.01; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.01; (4)ACD/LogD (pH 7.4): 1.01; (5)ACD/BCF (pH 5.5): 3.42; (6)ACD/BCF (pH 7.4): 3.42; (7)ACD/KOC (pH 5.5): 84; (8)ACD/KOC (pH 7.4): 84; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.456; (14)Molar Refractivity: 30.33 cm3; (15)Molar Volume: 111.5 cm3; (16)Polarizability: 12.02 ×10-24cm3; (17)Surface Tension: 38.7 dyne/cm; (18)Density: 1.389 g/cm3; (19)Flash Point: 76.7 °C; (20)Enthalpy of Vaporization: 42.96 kJ/mol; (21)Boiling Point: 193.4 °C at 760 mmHg; (22)Vapour Pressure: 0.466 mmHg at 25°C.

Preparation Succinyl chloride: it can be prepared by butanedioic acid and phosphorus pentylchloride. You can put butanedioic acid, phosphorus pentylchloride and chloroform into reactor as sequence. When the reaction turned slow, you should heat the mixture to refluxing. when the reaction products become liquid, steam the low viscosity and  recover chloroform. The yield is about 88%.

Uses of Succinyl chloride: it can react with 4-methyl-aniline to get N,N'-di-p-tolyl-succinamide. This reaction will need reagent pyridine. The reaction time is 24 hours at reaction temperature of 20 °C. The yield is about 91%.

Succinyl chloride can react with 4-methyl-aniline to get N,N'-di-p-tolyl-succinamide

When you are using this chemical, please be cautious about it as the following:
It can react violently with water and cause burns. You should wear suitable protective clothing, gloves and eye/face protection when use it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: ClC(=O)CCC(Cl)=O
(2)InChI: InChI=1/C4H4Cl2O2/c5-3(7)1-2-4(6)8/h1-2H2
(3)InChIKey: IRXBNHGNHKNOJI-UHFFFAOYAK

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 62500ug/kg (62.5mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 4, Pg. 111, 1952.

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