Succinyl chloride supplier

Name
SUCCINYL CHLORIDE
EINECS 208-838-0
CAS No. 543-20-4
Article Data58
CAS DataBase
Density 1.389 g/cm³
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
Hazard Symbols C
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;
PSA 34.14000
LogP 1.29740

Synthetic route

: 110-15-6
succinic acid

: 543-20-4
succinoyl dichloride

Conditions

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%

: 108-30-5
succinic acid anhydride

: 543-20-4
succinoyl dichloride

Conditions

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

...Expand

: 108-30-5
succinic acid anhydride

: 4885-02-3
Dichloromethyl methyl ether

: 543-20-4
succinoyl dichloride

Conditions

Conditions	Yield
With zinc(II) chloride

: 4146-43-4
succinic acid dihydrazide

: 543-20-4
succinoyl dichloride

Conditions

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

Conditions	Yield
at 120 - 130℃;

trimer(ic) β-aldehydo-propionic acid: trimer(ic) β-aldehydo-propionic acid

: 543-20-4
succinoyl dichloride

Conditions

Conditions	Yield
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

Conditions	Yield
at 120 - 145℃;

...Expand

: 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

...Expand

: 110-94-1
1,5-pentanedioic acid

: 124-04-9
Adipic acid

: 110-15-6
succinic acid

A: 2873-74-7
gloutaric dichloride

B: 543-20-4
succinoyl dichloride

C: 111-50-2
Adipic acid dichloride

Conditions

Conditions	Yield
With thionyl chloride at 20℃;

...Expand

: 108-98-5
thiophenol

: 543-20-4
succinoyl dichloride

: 29549-28-8
S,S'-diphenyl dithiosuccinate

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;	100%
With silica gel at 20℃; for 4h;	72%

: 543-20-4
succinoyl dichloride

: 124-40-3
dimethyl amine

: 7334-51-2
N,N,N',N'-tetramethylsuccinamide

Conditions

Conditions	Yield
In water at 0℃; for 0.5h;	100%
In diethyl ether at -78 - 20℃;	91%
In dichloromethane; water at 0 - 20℃; for 20h; Inert atmosphere;	81%
With diethyl ether
In water at 0℃; for 0.5h;

: 7677-24-9
trimethylsilyl cyanide

: 543-20-4
succinoyl dichloride

: 63979-84-0
Succinyl Dicyanide

Conditions

Conditions	Yield
With chloro-trimethyl-silane at 20℃; for 72h; Inert atmosphere;	100%
for 168h; Ambient temperature;	63%

: 188290-36-0
thiophene

: 543-20-4
succinoyl dichloride

: 13669-05-1
1,4-bis(thiophen-2-yl)butane-1,4-dione

Conditions

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at 0℃; for 2h; Inert atmosphere;	99%
With aluminum (III) chloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	84%
With aluminum (III) chloride In dichloromethane at 20℃; for 20h; Friedel-Crafts Acylation;	82%

: 67-56-1
methanol

: 563-43-9
ethylaluminum dichloride

: 543-20-4
succinoyl dichloride

: 2955-62-6
methyl 4-oxohexanoate

Conditions

Conditions	Yield
In dichloromethane at -40℃; for 3.5h;	99%
Stage #1: ethylaluminum dichloride; succinoyl dichloride In dichloromethane at -40℃; for 3.5h; Stage #2: methanol In dichloromethane at -40℃;	99%

...Expand

: 89-83-8
thymol

: 543-20-4
succinoyl dichloride

: thymol succinate

Conditions

Conditions	Yield
With sodium hydroxide for 0.05h; microwave irradiation;	99%

: 89-83-8
thymol

: 543-20-4
succinoyl dichloride

Amberlite IRA-400 (chloride form) resin: Amberlite IRA-400 (chloride form) resin

: thymol succinate

Conditions

Conditions	Yield
Stage #1: thymol; Amberlite IRA-400 (chloride form) resin With sodium hydroxide Stage #2: succinoyl dichloride In benzene	98%

...Expand

: 501668-81-1
1,6-diamino-1,6-dideoxy-3,4-O-isopropylidene-D-mannitol

: 543-20-4
succinoyl dichloride

poly(1,6-dideoxy-3,4-di-O-isopropylidene-D-mannitolsuccinimide); monomer(s): 1,6-diamino-1,6-dideoxy-3,4-di-O-isopropylidene-D-mannitol; succinoyl dichloride: poly(1,6-dideoxy-3,4-di-O-isopropylidene-D-mannitolsuccinimide); monomer(s): 1,6-diamino-1,6-dideoxy-3,4-di-O-isopropylidene-D-mannitol; succinoyl dichloride

Conditions

Conditions	Yield
With sodium carbonate In tetrachloromethane at 20℃; for 3h;	98%

: 741737-80-4
(Z)-2-(3,4-dimethoxy-phenyl)-3-(4-hydroxy-phenyl)-acrylonitrile

: 543-20-4
succinoyl dichloride

: bis-{4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl} succinate

Conditions

Conditions	Yield
With pyridine	98%

: 14243-23-3
(μ-dithio)bis(tricarbonyliron)

: 543-20-4
succinoyl dichloride

: 4294-57-9
para-methylphenylmagnesium bromide

: (CH3C6H4SFe2(CO)6SCO)2C2H4

Conditions

Conditions	Yield
In tetrahydrofuran p-TolMgBr in THF was added under N2 with stirring to a THF soln. of Fe2-complex at -78°C, ClCOCH2CH2COCl (1/2 molar equiv) was added to the resulting anion soln. at -78°C, mixt. was allowed to warm to room temp.; volatiles were removed, residue purified by column chromy.; elem. anal.;	98%

...Expand

: 56777-24-3
benzyl (S)-Lactate

: 543-20-4
succinoyl dichloride

: 314069-31-3
Succinic acid bis-((S)-1-benzyloxycarbonyl-ethyl) ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; under 2585.74 Torr; for 16h;	97%
With pyridine In dichloromethane at 0℃;

: 959397-89-8
C58H68O2Si3

: 543-20-4
succinoyl dichloride

: (C58H67O2Si3)2COCOCH2CH2

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 0.216667h;	97%
With dmap In dichloromethane at 20℃; for 0.133333h; Inert atmosphere;	97%

: 543-20-4
succinoyl dichloride

: 159146-73-3
12-(p-aminophenyl)-9,9-dimethyl-8,9,10,11-tetrahydrobenzacridin-11-one

: N,N'-bis-[4-(9,9-dimethyl-11-oxo-8,9,10,11-tetrahydro-benzo[a]acridin-12-yl)-phenyl]-succinamide

Conditions

Conditions	Yield
In acetone at 5℃; for 0.25h;	96%

: 543-20-4
succinoyl dichloride

: 62-53-3
aniline

: 15510-09-5
Succinanilid

Conditions

Conditions	Yield
In pyridine at 20℃; for 24h;	95%
With benzene

: 3025-88-5
2,5-dimethyl-2,5-dihydroperoxyhexane

: 543-20-4
succinoyl dichloride

: 88-95-9
Phthaloyl dichloride

: 78491-83-5
2-(4-{2-[4-(3-{4-[3-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-propionylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-propionylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	95%

...Expand

: 543-20-4
succinoyl dichloride

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

: 9,9'-Succinylbis<9H-purin-6-amin>

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 3h; Ambient temperature;	95%

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 543-20-4
succinoyl dichloride

: succinic acid bis-(4-methyl-2-oxo-2H-chromen-7-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	95%

: 543-20-4
succinoyl dichloride

: 292140-08-0
Nε-lauroyl-L-lysine ethyl ester

: Nα,Nα'-succinyl-bis(Nε-lauroyl-L-lysine ethyl ester)

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h;	95%

: 543-20-4
succinoyl dichloride

: 75-36-5
acetyl chloride

: 621-14-7
diphenyl succinate

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;	95%

: 543-20-4
succinoyl dichloride

: 104-85-8
para-methylbenzonitrile

: 2,2'-(1,2-Ethandiyl)bis<4,6-bis(p-tolyl)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)

Conditions

Conditions	Yield
With antimonypentachloride In tetrachloromethane for 5h; Heating;	94%
With antimonypentachloride In dichloromethane 1) -40 to 25 deg C, 2) 25 deg C, 3 h;	75%

: 543-20-4
succinoyl dichloride

: 117358-75-5
7-(p-Aminophenyl)-10,10-dimethyl-8,9,10,11-tetrahydrobenz[c]acridin-8-one

: N,N'-bis-[4-(10,10-dimethyl-8-oxo-8,9,10,11-tetrahydro-benzo[c]acridin-7-yl)-phenyl]-succinamide

Conditions

Conditions	Yield
In acetone at 5℃; for 0.25h;	94%

: 543-20-4
succinoyl dichloride

: 149-30-4
2-Mercaptobenzothiazole

: dithiosuccinic acid di-S-benzothiazol-2-yl ester

Conditions

Conditions	Yield
With sodium hydroxide; Amberlite IRA-400 chloride form In water; acetone	94%
Stage #1: 2-Mercaptobenzothiazole With aluminum oxide; silica gel; sodium carbonate; fly ash microwave oven; Stage #2: succinoyl dichloride microwave irradiation;

: 524-38-9
N-hydroxyphthalimide

: 543-20-4
succinoyl dichloride

: O,O′-succinyloyl-bis-N,N′-phthalimide ester

Conditions

Conditions	Yield
Stage #1: N-hydroxyphthalimide With sodium hydroxide; Amberlite IRA-400 chloride form Stage #2: succinoyl dichloride In tetrahydrofuran at 20℃;	94%
With pyridine at 20℃; for 24h;	60%

: 543-20-4
succinoyl dichloride

: 95-76-1
m,p-dichloroaniline

: N,N'-bis(3,4-dichlorophenyl)butanediamide

Conditions

Conditions	Yield
In pyridine at 20℃; for 24h;	93%

: 1020108-12-6
(1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-2-hydroxymethyl-8-thiabicyclo[3.2.1]octane

: 543-20-4
succinoyl dichloride

: 1020108-07-9
(3β-(3,4-dichlorophenyl)-8-thiabicyclo[3.2.1]octan-2β-yl)methyl,(3β-(3,4-dichlorophenyl)-8-thiabicyclo[3.2.1]octan-2β-yl)methyl succinate

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	93%

: 25990-96-9
octaethylene glycol monomethyl ether

: 543-20-4
succinoyl dichloride

: C21H39ClO11

Conditions

Conditions	Yield
Stage #1: octaethylene glycol monomethyl ether With sodium hydride In tetrahydrofuran at -20℃; for 0.5h; Stage #2: succinoyl dichloride In tetrahydrofuran at -20 - 20℃;	93%

: 100-41-4
ethylbenzene

: 543-20-4
succinoyl dichloride

: 1,4-bis(4-ethylphenyl)butane-1,4-dione

Conditions

Conditions	Yield
With aluminum (III) chloride In benzene at 0 - 20℃; Friedel-Crafts acylation; Inert atmosphere;	93%

: 543-20-4
succinoyl dichloride

: 108-88-3
toluene

: 13145-56-7
1,4-bis(4-tolyl)butane-1,4-dione

Conditions

Conditions	Yield
With aluminum (III) chloride In benzene at 0 - 20℃; Friedel-Crafts acylation; Inert atmosphere;	92%
Stage #1: succinoyl dichloride; toluene With aluminum (III) chloride In dichloromethane at 0℃; for 0.5h; Stage #2: With hydrogenchloride	73%
With aluminium trichloride
With aluminium trichloride

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.

Product Name

SUCCINYL CHLORIDE

Synthetic route

Succinyl chloride Consensus Reports

Succinyl chloride Specification

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