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Sigma-Aldrich

4-Amino-6-chloro-1,3-benzenedisulfonamide

98%

Synonym(s):

3-Chloroaniline-4,6-disulfonamide, 4-Amino-6-chlorobenzene-1,3-disulfonamide

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About This Item

Linear Formula:
H2NC6H2(Cl)(SO2NH2)2
CAS Number:
121-30-2
Molecular Weight:
285.73
Beilstein:
1083877
EC Number:
204-463-1
MDL number:
MFCD00007933
UNSPSC Code:
12352100
PubChem Substance ID:
24858677
NACRES:
NA.22

Quality Level

100

Assay

98%

form

powder

mp

257-261 °C (lit.)

SMILES string

Nc1cc(Cl)c(cc1S(N)(=O)=O)S(N)(=O)=O

InChI

1S/C6H8ClN3O4S2/c7-3-1-4(8)6(16(10,13)14)2-5(3)15(9,11)12/h1-2H,8H2,(H2,9,11,12)(H2,10,13,14)

InChI key

IHJCXVZDYSXXFT-UHFFFAOYSA-N

Gene Information

human ... CA1(759) , CA2(760) , CA5A(763) , CA5B(11238) , CA9(768)

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General description

4-Amino-6-chloro-1,3-benzenedisulfonamide is a potent inhibitor of gastric pathogen, Helicobacter pylori (hpCA).

Application

4-Amino-6-chloro-1,3-benzenedisulfonamide was used in the synthesis of deuterated thiazides by undergoing condensation with appropriately labeled aldehydes.

Storage Class Code

11 - Combustible Solids

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)

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Mario Thevis et al.
Analytical chemistry, 74(15), 3802-3808 (2002-08-15)
The mass spectrometric behavior of 21 thiazide-based compounds after electrospray ionization in the negative ion mode and collision-induced dissociation was investigated on a triple-stage quadrupole mass spectrometer. The mass spectra show individual and common fragmentation patterns, the generations of which
B R Thomas et al.
Journal of chromatography. B, Biomedical applications, 657(2), 383-394 (1994-07-15)
A stability-indicating, quality control analysis method was developed and validated for the diuretic drug substances hydrochlorothiazide (HCTZ) and chlorothiazide (CTZ). Micellar electrokinetic capillary chromatography employing the anionic detergent sodium dodecyl sulfate at 30 mM in 20 mM sodium borate buffer
M Yamazaki et al.
Chemical & pharmaceutical bulletin, 38(10), 2882-2883 (1990-10-01)
2-Amino-4-chloro-m-benzenedisulfonamide (ACBS) is a metabolite of hydrochlorothiazide. We reported that the ACBS concentration in erythrocytes was higher than in plasma in a patient. Therefore the binding of ACBS to rabbit erythrocyte was studied. The Scatchard plot showed the nonlinear plot
Biopharmaceutical studies of thiazide diuretics. III. In vivo formation of 2-amino-4-chloro-m-benzenedisulfonamide as a metabolite of hydrochlorothiazide in a patient.
T Okuda et al.
Chemical & pharmaceutical bulletin, 35(8), 3516-3518 (1987-08-01)
K Deventer et al.
Journal of chromatography. A, 1216(12), 2466-2473 (2009-02-04)
In sports, thiazide diuretics are used to flush out previously taken prohibited substances with forced diuresis and in sports where weight classes are involved to achieve acute weight loss. Thiazide diuretics include compounds which are very unstable and hydrolyse in
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