599-87-1

Basic information

• Product Name: 4-CHLORO-N-(4-CHLOROPHENYL)BENZENESULFONAMIDE
• Synonyms: 4-CHLORO-N-(4-CHLOROPHENYL)BENZENESULFONAMIDE;N-(4-CHLOROPHENYL)-4-CHLOROBENZENSULFONAMIDE
• CAS NO: 599-87-1
• Molecular Formula: C₁₂H₉Cl₂NO₂S
• Molecular Weight: 302.18
• Mol File: 599-87-1.mol

Chemical Properties

• Melting Point: 145.4-146 °C
• Boiling Point: 430.3 °C at 760 mmHg
• Flash Point: 214 °C
• Appearance: /
• Density: 1.492 g/cm³
• Vapor Pressure: 1.31E-07mmHg at 25°C
• Refractive Index: 1.647
• PKA: 7.33±0.10(Predicted)
• CAS DataBase Reference: 4-CHLORO-N-(4-CHLOROPHENYL)BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-N-(4-CHLOROPHENYL)BENZENESULFONAMIDE(599-87-1)
• EPA Substance Registry System: 4-CHLORO-N-(4-CHLOROPHENYL)BENZENESULFONAMIDE(599-87-1)

Safety Data

• Hazardous Substances Data: 599-87-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H9Cl2NO2S/c13-9-1-5-11(6-2-9)15-18(16,17)12-7-3-10(14)4-8-12/h1-8,15H

Upstream product

• 106-47-8 4-chloro-aniline 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 64-17-5 ethanol 
• 129957-30-8 N¹-(p-chlorobenzenesulfonyl)-N¹,N²-di(p-chlorophenyl)acetamidine 
• 183440-84-8 4-Chloro-benzenesulfonic acid cyano-dimethyl-methyl ester 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 4547-68-6 p-chlorobenzenesulfonyl azide 
• 30066-82-1 N-chloro-p-chlorobenzenesulfonamide sodium salt 
• 134899-48-2 4-Chloro-N-(4-chloro-phenyl)-N-{1-[(E)-3-nitro-phenylimino]-ethyl}-benzenesulfonamide 

Downstream Products

• 601-72-9 4-chloro-benzenesulfonic acid-(N-ethyl-4-chloro-anilide) 
• 104094-54-4 4-chloro-benzenesulfonic acid-(4,N-dichloro-anilide) 
• 631-93-6 4-chloro-benzenesulfonic acid-(4-chloro-N-methyl-anilide) 
• 920011-89-8 N-{1-[2-(3-bromo-propoxy)-phenyl]-ethyl}-4-chloro-N-(4-chloro-phenyl)-benzenesulfonamide 
• 10589-67-0 4,4'-dichloro-2'-nitrobenzenesulfonanilide 

Relevant articles and documents

Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature

A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides

A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling reaction of sulfonyl azides with arylboronic acids leading to: N -arylsulfonamides

A heterogeneous Chan-Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily available and inexpensive reagents, and recovered by simple filtration of the reaction solution and recycled at least 8 times without any decreases in activity.

Cu(OAc)2-catalyzed N-arylation of sulfonamides with arylboronic acids or trimethoxy(phenyl)silane

Cu(OAc)2-catalyzed C-N bond-formation reaction of sulfonamides with organoboronic acids or trimethoxy(phenyl)silane was achieved in the presence of 20mol% of Cu(OAc)2, providing N-arylation products with yields ranging from moderate to good.

Synthesis of biotinylated photoaffinity probes based on arylsulfonamide γ-secretase inhibitors

Synthesis and biological evaluation of an arylsulfonamide class of γ-secretase inhibitors are described. Design, synthesis, and biological evaluation of multifunctional molecular probes harboring a benzophenone photophore as a cross-linking group and a biotin tag are also reported.

Effect of para substitution on dissociation of N-phenylbenzenesulfonamides

The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C6H4SO2NHC6H4-Y- 4′. Their purity was checked by elemental analysis. The substituents X and Y include H, CH3, CH3O, Cl, Br, CN, and NO2. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pKHA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σp constants and the Yukawa-Tsuno equation with σp- and σp constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO2 group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.

Sulfonamide derivatives

The present invention relates to microbicides for agricultural or horticultural use containing a sulfonamide derivative.

SULFONAMIDE DERIVATIVES

The present invention relates to microbicides for agricultural or horticultural use containing sulfonamide derivative of, for example, a formula (I):or a salt thereof,[wherein A1is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X1is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B1is a five-membered heterocyclic group comprising nitrogen or sulfur atoms as the ring-constructing atoms except for carbon atoms and may be substituted or a condensed heterocyclic group which may be substituted, Z1is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by -N=CR1R2(wherein each of R1and R2is a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by -OR3(wherein R3is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted) or (8) -S(O)nR4(wherein n stands for an integer from 0 to 2, R4stands for a hydrogen atom or a hydrocarbon group which may be substituted). The said compounds or the salts thereof are sulfonamide derivatives with microbicidal action, areuseful as excellent microbicides for agricultural or horticultural use, because they are safe, and they have little influence on human beings, farm animals, natural enemies, or the environment, and exert excellent control effects even on resistant microbes.

Bimolecular nucleophilic displacement at tertiary carbon centers: Aminolyses of 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates

Kinetic studies were carried out on the reactions of anilines with 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates in acetonitrile at 50·0°C. The second-order rate constants for the former are in general greater than those for the latter but the rates of the two become comparable for a strong nucleofuge. The cross-interaction constants, ρXZ (and βXZ), are considerably smaller (ca -0·04) than those for the primary (ca 0·33) and secondary (ca 0·12) compounds. The negative sign and small magnitude are consistent with a dissociative SN2 mechanism with a loose transition state structure. The ab initio MO theoretical results for Cl- + RCl?ClR + Cl- at the MP2 level (MP2/6-31 + G*//MP2/6-31 + G*) confirm the looseness of the transition state for the tertiary (R) alkyl compounds. The average r*(Cl...Cl) value is 4·88 ± 0·03 A, which is larger than those for the reactions at primary (4·68± 0·02 A) and secondary (4·80 ± 0·02 A) carbon centers. Thus a looser transition state with a smaller magnitude of ρXZ for the tertiary carbon centers has a larger theoretical r*(Cl-Cl) value.