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| CAS No.: | 543-20-4 |
|---|---|
| Name: | SUCCINYL CHLORIDE |
| Article Data: | 58 |
| Molecular Structure: | |
|
|
|
| Formula: | C4H4Cl2O2 |
| Molecular Weight: | 154.981 |
| 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; |
| EINECS: | 208-838-0 |
| Density: | 1.389 g/cm3 |
| Melting Point: | 16 °C |
| Boiling Point: | 193.4 °C at 760 mmHg |
| Flash Point: | 76.7 °C |
| Solubility: | Reacts violently with water. |
| Appearance: | clear colourless to slightly brown liquid |
| Hazard Symbols: |
 C
|
| Risk Codes: | 14-34 |
| Safety: | 26-36/37/39-45 |
| Transport Information: | UN 3265 |
| PSA: | 34.14000 |
| LogP: | 1.29740 |
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| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| With zinc(II) chloride |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; nitromethane; chlorine |
- 108-30-5
succinic acid anhydride
- 10026-13-8, 874483-75-7
phosphorus pentachloride
- 543-20-4
succinoyl dichloride
| Conditions | Yield |
|---|---|
| at 120 - 130℃; |
- 543-20-4
succinoyl dichloride
| Conditions | Yield |
|---|---|
| With phosphorus pentachloride |
| Conditions | Yield |
|---|---|
| at 120 - 145℃; |
- 692-29-5
Succinic semialdehyde
- 10026-13-8, 874483-75-7
phosphorus pentachloride
A
- 543-20-4
succinoyl dichloride
- Total:16 Page 1 of 1 1
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Consensus Reports
Reported in EPA TSCA Inventory.
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%.
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. |