128-09-6

Basic information

• Product Name: N-Chlorosuccinimide
• Synonyms: 1-Chloro-2,5-piperidinedione;1-chloro-5-pyrrolidinedione;5-Pyrrolidinedione,1-chloro-2;imide,n-chloro-succinicaci;n-chloro-succinimid;Pyrrolidinedione, 1-chloro-;Succinic N-chloroimide;succinicn-chloroimide
• CAS NO: 128-09-6
• Molecular Formula: C₄H₄ClNO₂
• Molecular Weight: 133.53
• EINECS: 204-878-8
• Product Categories: API intermediates;Chlorination;Halogenation;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Synthetic Organic Chemistry;C-X Bond Formation (Halogen);Synthetic Reagents;API Intermediate
• Mol File: 128-09-6.mol

Chemical Properties

• Melting Point: 148-150 °C(lit.)
• Boiling Point: 200.5 °C at 760 mmHg
• Flash Point: 75.1 °C
• Appearance: White/Crystalline Powder
• Density: 1,65 g/cm3
• Vapor Pressure: 0.323mmHg at 25°C
• Refractive Index: 1.4378 (estimate)
• Storage Temp.: Store at +2°C to +8°C.
• Solubility: 14g/l
• PKA: -2.78±0.20(Predicted)
• Water Solubility: Soluble in water, alcohol, benzene, acetone and acetic acid. Slightly soluble in ether, chloroform, carbon tetrachloride and pet
• Sensitive: Moisture Sensitive
• Merck: 14,2164
• BRN: 113915
• CAS DataBase Reference: N-Chlorosuccinimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Chlorosuccinimide(128-09-6)
• EPA Substance Registry System: N-Chlorosuccinimide(128-09-6)

Safety Data

• Hazard Codes: C,Xi
• Statements: 22-34
• Safety Statements: 26-36/37/39-45-37/39
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: UY1013500
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 128-09-6(Hazardous Substances Data)

Usage

Chemical Description

N-chlorosuccinimide is a chlorinating agent used in organic synthesis.

Uses

Used in Chemical Synthesis:
N-Chlorosuccinimide is used as a chlorinating agent for the side-chain halogenation of alkylarenes, particularly for the side-chain chlorination of sensitive hetarenes. It is favored over other chlorinating agents like 1,3-dichloro-5,5-dimethylhydantoin (NDDH) and trichloroisocyanuric acid (TCCA) due to its superior regioselectivity.
Used in Pharmaceutical Industry:
N-Chlorosuccinimide serves as an intermediate in the production of pharmaceuticals, including antibiotic drugs. Its role in this industry is crucial for the synthesis of various medications that contribute to human health.
Used in Rubber Industry:
NCS is employed in the production of rubber additives, enhancing the properties and performance of rubber products.
Used as a Disinfectant:
N-Chlorosuccinimide is utilized as a swimming pool disinfectant, providing a clean and safe environment for swimmers.
Used in Analytical Chemistry:
NCS is used in the microdetermination of hydrazine salts by titrimetry and in the detection of arsenic in the +3 oxidative state, contributing to the accuracy and reliability of chemical analyses.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

Upstream product

• 123-56-8 Succinimide 
• 507-40-4 tert-butylhypochlorite 
• 5775-33-7 N-chlorodiethylamine 
• 5775-34-8 N,N-Dipropyl-chloramine 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 3355-28-0 1-Bromo-2-butyne 
• 205928-50-3 (3-[[(2,2-dimethylpropanoyl)oxy]methyl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)methyl 2,2-dimethylpropanoate 
• 630-19-3 pivalaldehyde 

Downstream Products

• 108-94-1 cyclohexanone 
• 75-07-0 acetaldehyde 
• 141-78-6 ethyl acetate 
• 61044-94-8 5-chloro-2-methylthio-4(1H)-pyrimidinone 
• 6328-59-2 5-chloro-6-methyl-2-(methylthio)pyrimidin-4(3H)-one 
• 40484-36-4 6-(chloromethyl)phenanthridine 
• 18113-22-9 3-chloro-2,6-dimethoxyphenol 
• 2539-26-6 3,4,5-trichlorosyringol 
• 813-77-4 Dimethyl chlorophosphate 
• 612-12-4 o-Xylylene dichloride 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 13101-92-3 1-chloro-2-methoxynaphthalene 
• 2453-46-5 cycloheptyl chloride 
• 104-82-5 4-Methylbenzyl chloride 

Related news

N-Chlorosuccinimide (cas 128-09-6) as a versatile reagent for the sulfenylation of ketones: a facile synthesis of α-ketothioethers09/28/2019

The sulfenylation of ketones having α-hydrogens has been achieved using N-chlorosuccinimide (NCS) under mild reaction conditions to produce α-ketothioethers in excellent yields with high selectivity. The use of NCS makes this method quite simple, convenient and practical.detailed

Synthesis, growth and characterization of donor–acceptor π-conjugated N-Chlorosuccinimide (cas 128-09-6) single crystals for nonlinear optical applications10/01/2019

Single crystals of N-chlorosuccinimide (NCS) were grown by slow evaporation solution growth technique. The grown crystals were confirmed by single crystal X-ray diffraction and FT-IR studies. The theoretical factorial group analysis was carried and the vibrational modes are assigned. The dielect...detailed

N-Chlorosuccinimide (cas 128-09-6) as a novel agent for biofouling control in the polyamide reverse osmosis membrane process09/25/2019

One of the biggest challenges in reverse osmosis membrane process is formation of biofilms on membrane surface (biofouling) which significantly lowers membrane performance and shortens life cycle of the membrane. In an effort to find a more effective biocide to control biofouling, we investigate...detailed

N-Chlorosuccinimide (cas 128-09-6) promoted direct C(sp2)–H bond thiolation of the methoxybenzenes with thiophenols09/24/2019

A simple and an efficient procedure for the formation of diaryl sulfides via direct sp2 C–H functionalization have been developed from simple and readily available thiophenols and substituted methoxy benzenes. In this process thiophenols were used as the sulfur source. In this transformation br...detailed

Visible-light photocatalytic activation of N-Chlorosuccinimide (cas 128-09-6) by organic dyes for the chlorination of arenes and heteroarenes09/09/2019

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use w...detailed

Relevant articles and documents

Electrophilic Substitution of Hydrogen in Betulin and Diacetylbetulin

Betulin and diacetylbetulin, which can be regarded as sterically hindered alkenes, reacted with N-chloro-, N-bromo-, and N-iodosuccinimides to give products of allylic and vinylic substitution in quantitative overall yield. The contribution of allylic substitution increases in the series Cl Br I. Quantum chemical simulation of the reactions of diacetylbetulin with N-halosuccinimides showed that, regardless of the electrophile power, all reactions involve open-chain carbocationic intermediates. The direction of deprotonation of the latter with formation of allylic or vinylic substitution products is determined by preferential orientation of the vacant orbital and C–Hlg bond.

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

The kinetics of N-chlorination reaction of pyrrolidine, pyrrolidone, succinimide, 5,5,-dimethyloxazolidine-2,4-dione, 5,5-dimethylhydantoin and 1-hydroximethyl-5,5-dimethylhydantoin with HOCl in aqueous solution were studied at 25 °C, constant ionic strength and under isolation conditions in a wide pH range. The set of compounds studied in this paper is characterized by having different functional groups and the same cyclic structure, consisting of a five-member ring with a nitrogen atom in the ring, which is susceptible to be chlorinated. This series of compounds covers nine pKa units, and the kinetic studies allow us to know, like, the presence of an amino, amide or imide group modify the reactivity of nitrogenous compound. Experimental data were fitted to the first-order kinetic equation. All reactions were found to be of first order in both HOCl and nitrogenous compound concentration. Kinetics studies demonstrate that some of these compounds are hydrolyzed in alkaline medium. In each case, reaction mechanism in agreement with the experimental results is proposed. The results were compared with other compounds with similar cyclic structure (2-oxazolidinone and proline). Copyright

CYCLOBUTYL AMIDE MONOACYLGLYCEROL LIPASE MODULATORS

Compounds of Formula (I), and pharmaceutically acceptable salts, isotopes, N-oxides, solvates, and stereoisomers thereof, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with MGL modulation, such as those associated with pain, psychiatric disorders, neurological disorders (including, but not limited to depression, major depressive disorder, treatment resistant depression, anxious depression, autism spectrum disorders, Asperger syndrome, and bipolar disorder), cancers and eye conditions: wherein R1, , R3, and L are as defined herein.

4-(IMIDAZO[1,2-A]PYRIDIN-3-YL) -PYRIMIDINE DERIVATIVES

Compounds of the formula (I) in which R1, R2, V, X, Y and Z have the meanings indicated in Claim 1, are inhibitors of c-Kit kinase, and can be employed for the treatment of cancer.

Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation

A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.

Preparation of several active N-chloro compounds from trichloroisocyanuric acid

A very simple method for the preparation of several activeN-chloro compounds that have extensive applications in organic synthesis, industry, and medicine has been developed.Tetrachloroglycolurils, chloramine-T, N-chlorosaccharin, N-chlorosuccinimide, N-chlorophthalimide, N,N￠-dichlorophenobarbital,and N,N￠-dichlorobarbital were synthesized by chlorination with trichloroisocyanuric acid under mild reaction conditions at roomtemperature. This method is clean, fast, and efficient; the yields are also good to excellent. Georg Thieme Verlag Stuttgart.

Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate

AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.

Xanthine derivatives as DPP-IV inhibitors

The present invention provides novel compounds exhibiting an excellent DPPIV inhibition effect. The compounds are represented by the formula: wherein, m is 0 or 1; n is 0; R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, and R42 each represent a hydrogen atom; X represents an alkynyl group, an aryl group, and such, which group may be substituted; and, R1 and R2 each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, or such, or salts or hydrates thereof.

Metal salt catalyzed process to oxazolines and subsequent formation of chloroketones

This invention relates to a process for the preparation of an α-chloroketone compound comprising the steps of (i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline STR1 (ii) chlorinating the 5-methyleneoxazoline using trichlorolsocyanuric acid to produce a chlorinated oxazoline intermediate STR2 and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone STR3 wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene, R is a hydrogen atom or alkyl, and R1 and R2 are each independently an alkyl or substituted alkyl group, or R1 and R2 together with the carbon atom to which they are attached form a cyclic structure. Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.

Synthesis and solid state and solution characterization of mono- and di-(η1-C) carbamoyl-palladium complexes. New efficient palladium-catalyzed routes to carbamoyl chlorides: Key intermediates to isocyanates, carbamic esters, and ureas

The catalytic conversion of primary and secondary amines into isocyanates or carbamoyl chlorides is performed using palladium complexes. The palladium-based catalytic systems is very active and avoids the synthesis of phosgene. The palladium (II) complex