22134-75-4

Basic information

• Product Name: 3,5-DICHLOROSULFANILAMIDE
• Synonyms: 4-amino-3,5-dichloro-benzenesulfonamid;4-Amino-3,5-dichlorobenzenesulfonamide;Benzenesulfonamide, 4-amino-3,5-dichloro-;Sulfanilamide, 3,5-dichloro-;3,5-DICHLOROSULFANILAMIDE;3,5-DICHLOROSULPHANILAMIDE;AKOS BBS-00007978;4-AMINO-3,5-DICHLOROBENZENESULFAMIDE
• CAS NO: 22134-75-4
• Molecular Formula: C₆H₆Cl₂N₂O₂S
• Molecular Weight: 241.1
• EINECS: 244-799-6
• Mol File: 22134-75-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 206-208°C
• Boiling Point: 427.5 °C at 760 mmHg
• Flash Point: 212.4 °C
• Appearance: /
• Density: 1.667 g/cm³
• Vapor Pressure: 1.63E-07mmHg at 25°C
• Refractive Index: 1.645
• PKA: 9.57±0.60(Predicted)
• BRN: 2727109
• CAS DataBase Reference: 3,5-DICHLOROSULFANILAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DICHLOROSULFANILAMIDE(22134-75-4)
• EPA Substance Registry System: 3,5-DICHLOROSULFANILAMIDE(22134-75-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• TSCA: Yes
• Hazardous Substances Data: 22134-75-4(Hazardous Substances Data)

Usage

General Description

3,5-Dichlorosulfanilamide is a chemical compound mostly known for its role in the synthesis of certain drugs. It is an organosulfur compound characterized by two chlorine atoms attached to the phenyl group and a sulfanilamide group in the molecule. It is used extensively in the field of medicine and chemistry due to its capacity as an intermediate in the manufacturing of various drugs. Notably, it's a starting material in the production of sulfa drugs and diuretics, which are employed in the treatment of bacterial infections and hypertension respectively. As with all chemicals, appropriate safety and handling measures should be used to limit exposure and potential health risks.

InChI:InChI=1/C6H6Cl2N2O2S/c7-4-1-3(13(10,11)12)2-5(8)6(4)9/h1-2H,9H2,(H2,10,11,12)

Upstream product

• 53297-68-0 4-amino-3-chlorobenzenesulfonamide 
• 7647-01-0 hydrogenchloride 
• 7722-84-1 dihydrogen peroxide 
• 63-74-1 sulfanilamide 
• 95-51-2 o-chloroaniline 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 16761-18-5 4-acetamido-3-chlorobenzenesulphonyl chloride 
• 68252-72-2 4-acetamido-3-chlorobenzenesulfonamide 

Downstream Products

• 176639-33-1 4-thioureido-3,5-dichlorobenzenesulfonamide 
• 150729-70-7 3,4,5-trichlorobenzenesulfonamide 
• 697-88-1 4-bromo-2,6-dichloroaniline 
• 100249-14-7 N,N-diethyl-glycine-(2,6-dichloro-4-sulfamoyl-anilide) 
• 858474-33-6 4-acetylamino-3,5-dichloro-benzenesulfonic acid acetylamide 
• 99-30-9 4-nitro-2,6-dichloroaniline 
• 667909-71-9 N-((2,6-dichloro-4-sulfamoylphenyl)carbamothioyl)benzamide 
• 19797-72-9 2,6-Dichlor-4-sulfamoyl-benzolsulfonsaeurechlorid 
• 608-31-1 2,6-Dichloroaniline 
• 86045-24-1 3,5-Dichlor-4-(1,3,4-triazol-1-yl)benzolsulfonsaeureamid 
• 99310-45-9 3,5-dichloro-4-(2-chloro-acetylamino)-benzenesulfonic acid amide 
• 857943-80-7 acetyl-(4-amino-3,5-dichloro-benzenesulfonyl)-amine 

Relevant articles and documents

PROCESS FOR PREPARATION OF 5-BROMO-1, 2, 3-TRICHLOROBENZENE

The present invention relates to a process for preparation of 5-bromo-1,2,3-trichlorobenzene of formula (I) in simple, economical manner with high yield. The 5-bromo-1,2,3-trichlorobenzene of formula (I) is used in preparation of 1-(3,4,5-trichloro-phenyl)-2,2,2-trifluoro-ethanone which is a key intermediate of isoxazoline derivatives. (I)

Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives

Two series of halogenated sulfonamides have been prepared. The first consists of mono/ dihalogenated sulfanilamides, whereas the second one consists of the mono/dihalogenated aminobenzolamides, incorporating equal or different halogens (F, Cl, Br, and I). These sulfonamides have been synthesized from the corresponding anilines by acetylation (protection of the amino group), chlorosulfonylation, followed either by amidation, or reaction with 5-amino1,3,4-thiadiazole-2-sulfonamide (and eventually deacetylation). All these compounds, together with the six clinically used sulfonamide inhibitors (acetazolamide, methazolamide, ethoxzolamide, dichlorophenamide, dorzolamide, and brinzolamide) were investigated as inhibitors of the transmembrane, tumor-associated isozyme carbonic anhydrase (CA) IX. Inhibition data against the classical, physiologically relevant isozymes I, II, and IV were also obtained. CA IX shows an inhibition profile which is generally completely different from those of isozymes I, II, and IV, with potent inhibitors (inhibition constants in the range of 12-40 nM) among both simple aromatic (such as 3-fluoro-5-chloro-4-aminobenzenesulfonamide) as well as heterocyclic compounds (such as acetazolamide, methazolamide, 5-amino-1,3,4-thiadiazole-2-sulfonamide, aminobenzolamide, and dihalogenated aminobenzolamides). This first detailed CA IX inhibition study revealed many interesting leads, suggesting the possibility to design even more potent and eventually CA IX-selective inhibitors, with putative applications as antitumor agents.

Magnetic susceptibilities of organic compounds: Part V - Influence of substituents on diamagnetic susceptibilities of disubstituted and trisubstituted benzenes

The magnetic susceptibilities of a number of triads of isomeric disubstituted benzenes have been determined, choosing the compounds in such a way that the substituents are present in the following combinations: (i) two electron-releasing substituents, (ii) a halogeno and an electron-releasing substituent, (iii) a halogeno and an electron-attracting substituent, and (iv) two halogeno substituents.The data show that for types (i), (ii) and (iv), the ortho isomers have the highest magnetic susceptibilities, the susceptibilities decreasing in the order: ortho > meta > para; for type (iii), the meta-isomers have the highest susceptibilities, the susceptibilities decreasing in the order: meta > para > ortho.The diamagnetic susceptibilities of some isomeric trisubstituted benzenes have also been determined and the data reveal that the susceptibility is the highest where the crowding of substituents is the highest (1,2,3-isomer) and lowest where the substituents are staggered and least crowded (1,3,5-isomer).Another observation made in the case of trisubstituted benzene is the applicability of a principle of additivity of their diamagnetic susceptibilities.