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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/REAXYS Number:
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

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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