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105457

Sigma-Aldrich

2,4-Dinitrobenzenesulfenyl chloride

96%

Synonym(s):

2,4-Dinitrophenylsulfenyl chloride, Kharasch reagent

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About This Item

Linear Formula:
(O2N)2C6H3SCl
CAS Number:
528-76-7
Molecular Weight:
234.62
Beilstein:
405600
EC Number:
208-441-2
MDL number:
MFCD00007129
UNSPSC Code:
12352100
PubChem Substance ID:
24846698
NACRES:
NA.22

Assay

96%

mp

94-97 °C (lit.)

solubility

benzene: soluble
diethyl ether: soluble
ethylene chloride: soluble
glacial acetic acid: soluble
methylene chloride: soluble
trichloroethylene: soluble
xylene: soluble

storage temp.

2-8°C

SMILES string

[O-][N+](=O)c1ccc(SCl)c(c1)[N+]([O-])=O

InChI

1S/C6H3ClN2O4S/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H

InChI key

GPXDNWQSQHFKRB-UHFFFAOYSA-N

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General description

2,4-Dinitrobenzenesulfenyl chloride undergoes addition reactions with transannularly substituted cycloalkenes and norbornenes. 2,4-Dinitrobenzenesulfenyl chloride can convert allylic alcohols to dienes by 1,4-elimination.

Application

2,4-Dinitrobenzenesulfenyl chloride was used in preparation of chlorine and bromine biphenyls.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of chlorinated and brominated biphenyl oxides.
Reich LL and Reich HJ.
The Journal of Organic Chemistry, 46(18), 3721-3727 (1981)
Studies on the Effect of Remote Substituents on Reactivity: The Rates of Addition of 2, 4-Dinitrobenzenesulfenyl Chloride to Cyclohexenes and Norbornenes (I) 1a.
Kwart H and Miller LJ.
Journal of the American Chemical Society, 83(22), 4552-4559 (1961)
M J De Wolf et al.
The Journal of biological chemistry, 256(11), 5481-5488 (1981-06-10)
The tryptophan residues on cholera toxin and its A and B protomers have been modified by reaction with 2-nitrophenylsulfenyl chloride and 2,4-dinitrophenylsulfenyl chloride. Modification of the tryptophan residues of cholera toxin results in complete loss of toxicity measured in a
G K Kumar et al.
Biochemistry, 27(16), 5978-5983 (1988-08-09)
Transcarboxylase (TC) from Propionibacterium shermanii consists of a central hexameric 12S subunit to which 6 outer dimeric 5S subunits are attached through 12 biotinyl 1.3S subunits. The enzyme catalyzes the transfer of a carboxyl group from methylmalonyl-CoA to pyruvate, forming

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