543-20-4

Usage

Uses

Used in Pharmaceutical Industry:
SUCCINYL CHLORIDE is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its ability to react with different functional groups makes it an essential component in the development of new drugs and medications.
Used in Organic Synthesis:
In the field of organic synthesis, SUCCINYL CHLORIDE is used as a versatile reagent for the production of a wide range of organic compounds. Its high reactivity allows for the formation of various chemical bonds, facilitating the creation of complex molecular structures.
Used in Agrochemicals:
SUCCINYL CHLORIDE is used as an important raw material in the agrochemical industry. It plays a crucial role in the synthesis of various agrochemical products, such as pesticides and fertilizers, which are essential for maintaining agricultural productivity.
Used in Dye Stuffs:
In the dye and pigment industry, SUCCINYL CHLORIDE is used as an intermediate for the production of various dyes and pigments. Its ability to form different chemical structures makes it a valuable component in the creation of a wide array of colorants.
Used as a Hydrolytic Reagent:
SUCCINYL CHLORIDE is also applied as a hydrolytic reagent for the determination of water content in various samples. Its reactivity with water allows for accurate measurements and analysis in different applications, such as quality control and research.

InChI:InChI=1/C4H4Cl2O2/c5-3(7)1-2-4(6)8/h1-2H2

Synthetic route

succinic acid (110-15-6) → succinoyl dichloride (543-20-4)

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%

succinic acid anhydride (108-30-5) → succinoyl dichloride (543-20-4)

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℃;

succinic acid anhydride (108-30-5) + Dichloromethyl methyl ether (4885-02-3) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → Methyl formate (107-31-3) + succinoyl dichloride (543-20-4)

succinic acid anhydride (108-30-5) + Dichloromethyl methyl ether (4885-02-3) → succinoyl dichloride (543-20-4)

Conditions	Yield
With zinc(II) chloride

succinic acid dihydrazide (4146-43-4) → succinoyl dichloride (543-20-4)

Conditions	Yield
With hydrogenchloride; nitromethane; chlorine

succinic acid anhydride (108-30-5) + phosphorus pentachloride (10026-13-8, 874483-75-7) → succinoyl dichloride (543-20-4)

Conditions	Yield
at 120 - 130℃;

trimer(ic) β-aldehydo-propionic acid → succinoyl dichloride (543-20-4)

Conditions	Yield
With phosphorus pentachloride

succinic acid (110-15-6) + PCl5 (2 mol) → succinoyl dichloride (543-20-4)

thionyl chloride (7719-09-7) + succinic acid (110-15-6) + ZnCl2 + CuCl → succinoyl dichloride (543-20-4)

Conditions	Yield
at 120 - 145℃;

Succinic semialdehyde (692-29-5) + phosphorus pentachloride (10026-13-8, 874483-75-7) → succinoyl dichloride (543-20-4) + γ-chloro-butyrolactone

1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + succinic acid (110-15-6) → gloutaric dichloride (2873-74-7) + succinoyl dichloride (543-20-4) + Adipic acid dichloride (111-50-2)

Conditions	Yield
With thionyl chloride at 20℃;

thiophenol (108-98-5) + succinoyl dichloride (543-20-4) → S,S'-diphenyl dithiosuccinate (29549-28-8)

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%

succinoyl dichloride (543-20-4) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethylsuccinamide (7334-51-2)

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;

trimethylsilyl cyanide (7677-24-9) + succinoyl dichloride (543-20-4) → Succinyl Dicyanide (63979-84-0)

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

thiophene (188290-36-0) + succinoyl dichloride (543-20-4) → 1,4-bis(thiophen-2-yl)butane-1,4-dione (13669-05-1)

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%

methanol (67-56-1) + ethylaluminum dichloride (563-43-9) + succinoyl dichloride (543-20-4) → methyl 4-oxohexanoate (2955-62-6)

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%

thymol (89-83-8) + succinoyl dichloride (543-20-4) → thymol succinate

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

thymol (89-83-8) + succinoyl dichloride (543-20-4) + Amberlite IRA-400 (chloride form) resin → thymol succinate

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

1,6-diamino-1,6-dideoxy-3,4-O-isopropylidene-D-mannitol (501668-81-1) + succinoyl dichloride (543-20-4) → 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	Yield
With sodium carbonate In tetrachloromethane at 20℃; for 3h;	98%

(Z)-2-(3,4-dimethoxy-phenyl)-3-(4-hydroxy-phenyl)-acrylonitrile (741737-80-4) + succinoyl dichloride (543-20-4) → bis-{4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl} succinate

Conditions	Yield
With pyridine	98%

(μ-dithio)bis(tricarbonyliron) (14243-23-3) + succinoyl dichloride (543-20-4) + para-methylphenylmagnesium bromide (4294-57-9) → (CH3C6H4SFe2(CO)6SCO)2C2H4

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%

benzyl (S)-Lactate (56777-24-3) + succinoyl dichloride (543-20-4) → Succinic acid bis-((S)-1-benzyloxycarbonyl-ethyl) ester (314069-31-3)

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

C58H68O2Si3 (959397-89-8) + succinoyl dichloride (543-20-4) → (C58H67O2Si3)2COCOCH2CH2

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

succinoyl dichloride (543-20-4) + 12-(p-aminophenyl)-9,9-dimethyl-8,9,10,11-tetrahydrobenzacridin-11-one (159146-73-3) → N,N'-bis-[4-(9,9-dimethyl-11-oxo-8,9,10,11-tetrahydro-benzo[a]acridin-12-yl)-phenyl]-succinamide

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

succinoyl dichloride (543-20-4) + aniline (62-53-3) → Succinanilid (15510-09-5)

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

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + succinoyl dichloride (543-20-4) + Phthaloyl dichloride (88-95-9) → 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 (78491-83-5)

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

succinoyl dichloride (543-20-4) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → 9,9'-Succinylbis<9H-purin-6-amin>

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

7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + succinoyl dichloride (543-20-4) → succinic acid bis-(4-methyl-2-oxo-2H-chromen-7-yl) ester

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

succinoyl dichloride (543-20-4) + Nε-lauroyl-L-lysine ethyl ester (292140-08-0) → Nα,Nα'-succinyl-bis(Nε-lauroyl-L-lysine ethyl ester)

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

succinoyl dichloride (543-20-4) + acetyl chloride (75-36-5) → diphenyl succinate (621-14-7)

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

succinoyl dichloride (543-20-4) + para-methylbenzonitrile (104-85-8) → 2,2'-(1,2-Ethandiyl)bis<4,6-bis(p-tolyl)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)

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%

succinoyl dichloride (543-20-4) + 7-(p-Aminophenyl)-10,10-dimethyl-8,9,10,11-tetrahydrobenz[c]acridin-8-one (117358-75-5) → N,N'-bis-[4-(10,10-dimethyl-8-oxo-8,9,10,11-tetrahydro-benzo[c]acridin-7-yl)-phenyl]-succinamide

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

succinoyl dichloride (543-20-4) + 2-Mercaptobenzothiazole (149-30-4) → dithiosuccinic acid di-S-benzothiazol-2-yl ester

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;

N-hydroxyphthalimide (524-38-9) + succinoyl dichloride (543-20-4) → O,O′-succinyloyl-bis-N,N′-phthalimide ester

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%

succinoyl dichloride (543-20-4) + m,p-dichloroaniline (95-76-1) → N,N'-bis(3,4-dichlorophenyl)butanediamide

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

(1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-2-hydroxymethyl-8-thiabicyclo[3.2.1]octane (1020108-12-6) + succinoyl dichloride (543-20-4) → (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 (1020108-07-9)

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

octaethylene glycol monomethyl ether (25990-96-9) + succinoyl dichloride (543-20-4) → C21H39ClO11

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%

ethylbenzene (100-41-4) + succinoyl dichloride (543-20-4) → 1,4-bis(4-ethylphenyl)butane-1,4-dione

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

succinoyl dichloride (543-20-4) + toluene (108-88-3) → 1,4-bis(4-tolyl)butane-1,4-dione (13145-56-7)

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

Upstream product

• 108-30-5 succinic acid anhydride 
• 4885-02-3 Dichloromethyl methyl ether 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 110-15-6 succinic acid 
• 4146-43-4 succinic acid dihydrazide 
• 10026-13-8 phosphorus pentachloride 
• 7719-09-7 thionyl chloride 
• 692-29-5 Succinic semialdehyde 
• 110-94-1 1,5-pentanedioic acid 
• 124-04-9 Adipic acid 

Downstream Products

• 1037306-25-4 succinic acid di-all-trans-retinyl ester 
• 108-30-5 succinic acid anhydride 
• 63979-84-0 Succinyl Dicyanide 
• 83329-71-9 Bernsteinsaeure-diimidazolid 
• 90085-84-0 succinic acid bis-(2-bromo-ethyl ester) 
• 854007-00-4 4-oxo-4-(5-phenyl-2-thienyl)butanoic acid 
• 5343-01-1 Perhydro-1,4,6,9-tetraketo-pyridazo<1,2-a>pyridazin 
• 114212-43-0 (E)-4,5-Dihydro-5-(2'-oxocylohexyliden)furan-2(3H)-on 
• 711-91-1 4-Oxo-4-(2'-oxocyclohexyl)butansaeure 
• 103159-65-5 succinic acid bis-(1-phenyl-2-pyrrolidino-ethyl ester) 
• 6343-27-7 1-benzoylpyrrolidine-2,5-dione 
• 98-87-3 benzylidene dichloride 
• 6876-55-7 N,N'-di-p-tolyl-succinamide 
• 32368-44-8 1-tosylpyrrolidine-2,5-dione 

Relevant academic research and scientific papers

Modulation of charge transport through single-molecule bilactam junctions by tuning hydrogen bonds

Bilactam derivatives with different side groups were synthesized and the twisting angle tuning effect induced by the intramolecular hydrogen bond on the charge transport through their single-molecule junctions was investigated. Molecules with strong intramolecular hydrogen bonds exhibited twice higher conductance because of the reduced dihedral twisting, which was reversible with the addition of hydrogen bond destroying solvent. Our findings reveal that the presence of intramolecular hydrogen bonds promotes the planarization of the molecular structure without additional transmission channels, offering a new strategy for controlling molecular switchesviatuning the molecular twisting.

A distorted lactam unit with intramolecular hydrogen bonds as the electron donor of polymer solar cells

A novel distorted lactam motif, namely 4,4′-dialkyl-[6,6′-bithieno[3,2-b]pyridine]-5,5′(4H,4′H)-dione (BTP), could lock itself by intramolecular hydrogen bonds. In view of the potential of the motif, two D-A conjugated polymers, PBDT-BTP-HD and PBDT-BTP-OD, with two different long side chains consisting of 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene (BDT) as a donor unit and BTP as an acceptor unit were designed and synthesized. Furthermore, the photophysical, electrochemical and photovoltaic properties of both polymers were investigated. The morphologies and molecular ordering of the neat polymers and blend films were also probed to relate the side chain structures with aggregation states and device parameters. The device based on PBDT-BTP-OD with IT-M exhibited a power conversion efficiency of up to 9.54% thanks to the synergistic effect of the building blocks and side-chain engineering. As a result, it is successfully demonstrated that the novel distorted lactam BTP is a promising building block in organic solar cells.

Dimeric 3,5-bis(benzylidene)-4-piperidones: A novel cluster of tumour-selective cytotoxins possessing multidrug-resistant properties

A series of bis[3,5-bis(benzylidene)-4-oxo-1-piperidinyl]amides 1 display potent cytotoxic properties towards a wide range of tumours. A number of the CC50 and IC50 values are in the range of 10-8 M. Specifically, these compounds have the following important properties. First, greater toxicity was demonstrated towards certain tumours than various non-malignant cells. Second, various compounds in series 1 are toxic to a number of human colon cancer and leukaemic cells. Third, these compounds reverse P-gp mediated multidrug resistance. Various prototypic molecules such as 1a,b and 1i were identified as lead molecules for further studies. A representative lead molecule 1b induces apoptosis via internucleosomal DNA fragmentation and PARP cleavage in HSC-2 and HL-60 cells while flow cytometry revealed that this compound blocked the G2/M and S-phases in the cell cycle of human colon cancer HCT-116 cells.

Ice-like encapsulated water by two cholic acid moieties

Starting from the structure of ice (in which each water molecule is surrounded by other four water molecules forming a tetrahedron with a value of 4.51 A for the edge O-O distance), and the knowledge that this value also corresponds to the O7-O12 distance of the skeleton of cholic acid, it is hypothesized that two steroid cholic acid moieties, with an appropriate steroid-steroid distance and a belly-to-belly orientation, could encapsulate a single water molecule between them. To check this hypothesis two succinyl derivatives of cholic acid (a monomer and the related head-head dimer in which the succinyl group is the linking bridge) were designed. The expected "ice-like" structure is found in the crystal of the dimer. There is a hydrogen bond synergy between those participating in the "ice-like" structure, and those in which the bridge is involved with the O7-H hydroxy group and the side chain of the steroid.

Ruthenium-catalyzed cascade metathetical cyclopolymerization of bisnorbornenes with flexible linkers

Treatments of bisnorbornenes tethered by a flexible linker (triethylene glycol, tetramethylene moiety, or crown ether) with the first generation of Grubbs catalyst give the corresponding single-stranded polybisnorbornenes via cascade metathetical cyclopolymerization (CMCP). The structures of these polymers were proved by spectroscopic means, MALDI-TOF mass spectrometry, gel permeation chromatography, and dynamic light scatterings as well as by chemical degradation via hydrolysis followed by esterification. The presence of N-aryl pendants to connect the norbornene moiety and the flexible linker is crucial for the success of such CMCP process. Presumably, intramolecular π-π interactions between the pending aryl groups may take place to direct the ring closure process. Substrates without such N-aryl pendants give a mixture of single- and double-stranded polynorbornenes in addition to cross-linking polymers.

Citrate plasticizer

The invention discloses a citrate plasticizer and a preparation method thereof, and the preparation method of citrate comprises the following steps: firstly, citric acid and alcohol react to prepare citric acid triester, and then dianhydride acylation is carried out to prepare carboxyl-containing citric acid triester. After chlorination, the carboxyl-containing citric acid triester and the tris(2-ethoxyl) isocyanurate are subjected to esterification reaction to prepare triester citrate containing the isocyanurate. According to the present invention, the preparation method has characteristics of simple operation, wide raw material source and mild reaction condition, and meets the 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.

Citrate plasticizer and preparation method thereof

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.

Succinylcholine chloride preparation method

The invention relates to a succinylcholine chloride preparation method, and specifically discloses a synthetic method for preparing succinylcholine chloride by using succinic acid as a starting raw material through a chlorination reaction and an esterification reaction. According to the invention, the method has advantages of safe production, low production cost, high reaction efficiency and simple product purification, and is suitable for mass production of bulk drugs.

Refining method of succinylcholine chloride

The invention discloses a refining method of succinylcholine chloride. A crude product of succinylcholine chloride is added into a polar aprotic solvent and recrystallized to obtain a refined productof succinylcholine chloride, and related substances of the product meet USP pharmacopoeia standards. The invention provides a refining method of succinylcholine chloride with simple process, convenient operation, low production cost, high product purity, stable process and suitability for industrial production, and also provides a raw material or bulk drug of high-purity succinylcholine chloride.

ALK-targeted PROTAC and application thereof

The invention relates to ALK-targeted PROTAC and application thereof, and belongs to the technical field of anti-tumor drugs. The invention aims to provide an ALK-targeted PROTAC molecule. The PROTACmolecule has the structural formula which is shown in a formula I. A ligand pomalidomide of CRBN and a derivative of pomalidomide are adopted as a ligand of an E3 ligase, and coupling of an ALK inhibitor LDK378 with the E3 ligase is achieved through linkers of different types and different chain lengths so as to prepare the ALK-targeted PROTAC molecule successfully; through the ALK-targeted PROTACmolecule, target proteins can be targeted effectively, the content of ALK in cells is reduced, and meanwhile, the ALK-targeted PROTAC is characteristics of good anti-tumor activity in vitro and in vivo, low toxicity to normal cells and high efficiency and low toxicity.