CAS 128-09-6|1-Chloropyrrolidine-2,5-dione|chlorosuccinimide|N-Chlorosuccinimide 99%|1-chloropyrrolidine-2,5-dione|N-CHLOROSUCCINIMIDE|Chlorosuccinimide|1-chloropyrrolidine-2,5-dione|NCS|N-氯丁二酰亚...

General Information

Structure

Molecular Formula

C₄H₄ClNO₂

Molecular Mass

133.53306

Exact Mass

132.99305605

Charge

InChI

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

InChIKey

JRNVZBWKYDBUCA-UHFFFAOYSA-N

Canonic Smiles

ClN1C(=O)CCC1=O

Isomeric Smiles

N1(C(=O)CCC1=O)Cl

Calculated Properties

JChem

LogD (pH = 7.4)

-0.23

LogD (pH = 5.5)

-0.23

Log P

-0.23

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

18.08

Polar Surface Area

37.38

Polarizability

10.99

Molar Refractivity

27.62

LOG S

-0.16

Data Source

Names and Identifiers

IUPAC name

1-chloropyrrolidine-2,5-dione

Synonyms

1-Chloropyrrolidine-2,5-dioneN-Chlorosuccinimide 99%N-CHLOROSUCCINIMIDEChlorosuccinimide1-chloropyrrolidine-2,5-dioneN-ChlorosuccinimideNCSN-氯丁二酰亚胺N-氯代丁二酰亚胺1-Chloro-2,5-pyrrolidinedioneSuccinochlorimideSuccinic N-chloroimideN-chlorosuccinimideSuccinchlorimide1-Chloro-2,5-pyrrolidine-dioneN-ChlorosuccinimideChlorosuccinimideNCS

IUPAC Traditional name

chlorosuccinimide

Names and Identifiers

Registration numbers

MDL Number

CAS Number

Beilstein Number

EC Number

PubChem SID

1620392432484693285240350

PubChem CID

31398

Merck Index

142164

Wikipedia Title

N-Chlorosuccinimide

Unique Ingredient Identifier

0FWP306H7X

Chemspider ID

29129

BRENDA Database

5.2.1.11.1.1.1413.4.16.43.4.21.633.2.1.613.2.1.143.4.22.374.2.2.10

SureChEMBL Database

SCHEMBL72

UniProt Database

Q06389P0A3S0Q91614P36608Q3YLA4P62166Q8BNY6Q09711P0A3R9Q16981P62167Q2V8Y7P62168P36609Q5RC90

ACToR Database

Gmelin ID

CHEMBL

CompTox Database

CHEBI ID

NMRShiftDB Database

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150658

Crystalline

05212213

MP Biomedicals Rare Chemical collection

Wikipedia

N-Chlorosuccinimide

Sigma Aldrich

109681

Application
Regioselective chlorination and oxidizing reagent.
Packaging
100, 500 g in poly bottle

26370

Other Notes
Versatile chlorinating and oxidizing agent; antibacterial 2; 1

ChEBI

CHEBI:53203

A five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom.

Molecule Details

References

PubChem Literature

From Data Sources

• In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to alkyl chlorides stereospecifically with inversion: Tetrahedron Lett., 3937 (1973). For a review, see: Org. React., 29, 1 (1983). Amides have been prepared by treatment of a carboxylic acid with NCS/PPh₃ followed by an amine: Synth. Commun., 25,959 (1995).

• With dimethyl sulfide, forms the Corey-Kim reagent, a mild, selective oxidant for alcohols. For a review, see: Synthesis, 857 (1990); for tabulated examples, see: Org. Synth. Coll., 6, 220 (1988).

• Source of positive chlorine in chlorination and oxidation reactions.

• Methyl ketones may be monochlorinated via their Li enolates: J. Org. Chem., 49, 1286 (1984). For the ɑ-chlorination of acid chlorides formed in situ, see: Tetrahedron Lett., 3235 (1974). For chlorination of deactivated anilines, see: Synthesis, 669 (1985).

• NCS in ether is a convenient alternative to hypochlorite for the conversion of amines to N-chloroamines, for use, e.g. in the Hofmann-Loeffler reaction, see: Chem. Ber., 88, 883 (1955).

• Primary alcohols are oxidized cleanly to aldehydes using NCS and a catalytic amount of TEMPO, A12733 under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

1-chloropyrrolidine-2,5-dione

Synonyms

IUPAC Traditional name

chlorosuccinimide

Registration numbers

MDL Number

CAS Number

Beilstein Number

EC Number

PubChem SID

1620392432484693285240350

PubChem CID

31398

Merck Index

142164

Wikipedia Title

N-Chlorosuccinimide

Unique Ingredient Identifier

0FWP306H7X

Chemspider ID

29129

BRENDA Database

5.2.1.11.1.1.1413.4.16.43.4.21.633.2.1.613.2.1.143.4.22.374.2.2.10

SureChEMBL Database

SCHEMBL72

UniProt Database

Q06389P0A3S0Q91614P36608Q3YLA4P62166Q8BNY6Q09711P0A3R9Q16981P62167Q2V8Y7P62168P36609Q5RC90

ACToR Database

Gmelin ID

CHEMBL

CompTox Database

CHEBI ID

NMRShiftDB Database

Molecule Details

Crystalline

MP Biomedicals Rare Chemical collection

Wikipedia

N-Chlorosuccinimide

Sigma Aldrich

109681

Application
Regioselective chlorination and oxidizing reagent.
Packaging
100, 500 g in poly bottle

26370

Other Notes
Versatile chlorinating and oxidizing agent; antibacterial 2; 1

ChEBI

CHEBI:53203

A five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom.

References

PubChem Literature

From Data Sources

• Source of positive chlorine in chlorination and oxidation reactions.

• NCS in ether is a convenient alternative to hypochlorite for the conversion of amines to N-chloroamines, for use, e.g. in the Hofmann-Loeffler reaction, see: Chem. Ber., 88, 883 (1955).

• Primary alcohols are oxidized cleanly to aldehydes using NCS and a catalytic amount of TEMPO, A12733 under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996).

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:74324