7467-12-1

Basic information

• Product Name: Benzenesulfonamide, 2,4-dimethyl- (9CI)
• Synonyms: Benzenesulfonamide, 2,4-dimethyl- (9CI);Benzenesulfonamide,2,4-dimethyl-
• CAS NO: 7467-12-1
• Molecular Formula: C₈H₁₁NO₂S
• Molecular Weight: 185.24344
• EINECS: 231-261-0
• Product Categories: SULFONAMIDE
• Mol File: 7467-12-1.mol

Chemical Properties

• Melting Point: 139～141℃
• Boiling Point: 336.9 °C at 760 mmHg
• Flash Point: 157.5 °C
• Appearance: /
• Density: 1.227 g/cm³
• Vapor Pressure: 0.000109mmHg at 25°C
• Refractive Index: 1.554
• PKA: 10.30±0.60(Predicted)
• CAS DataBase Reference: Benzenesulfonamide, 2,4-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 2,4-dimethyl- (9CI)(7467-12-1)
• EPA Substance Registry System: Benzenesulfonamide, 2,4-dimethyl- (9CI)(7467-12-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 7467-12-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, 2,4-dimethyl(9CI) is used as an intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be incorporated into the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
Benzenesulfonamide, 2,4-dimethyl(9CI) is also used in the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to inhibit the growth of certain microorganisms makes it a valuable component in the development of effective agricultural products.
Used in Dye and Pigment Industry:
Benzenesulfonamide, 2,4-dimethyl(9CI) is used as a key building block in the production of various dyes and pigments. Its chemical properties enable the creation of a wide range of colors and shades, making it an essential component in the dye and pigment industry.
Used in Polymer Industry:
Benzenesulfonamide, 2,4-dimethyl(9CI) is also utilized in the synthesis of polymers, which are long chains of repeating units. Its presence in the polymer structure can enhance the properties of the final product, such as strength, flexibility, and durability.
Used in Medical Research:
Benzenesulfonamide, 2,4-dimethyl(9CI) has been studied for its potential use in the treatment of various medical conditions, including cancer and infectious diseases. Its unique chemical structure allows it to interact with specific biological targets, making it a promising candidate for the development of new therapeutic agents.

InChI:InChI=1/C8H11NO2S/c1-6-3-4-8(7(2)5-6)12(9,10)11/h3-5H,1-2H3,(H2,9,10,11)

Upstream product

• 609-60-9 2,4-dimethylbenzenesulfonyl chloride 
• 2905-29-5 2,6-dimethyl-benzene-sulfonyl chloride 
• 257953-14-3 N-ethyl-2,4-dimethylbenzenesulfonamide 
• 13616-82-5 2,4-dimethyl-thiophenol 

Downstream Products

• 6325-82-2 N-xanthen-9-yl-m-xylene-4-sulfonamide 
• 885440-93-7 1-[(2,4-dimethylphenyl)sulfonyl]-1H-pyrrole 
• 1009604-24-3 (palladium)2Cl₂(2,4-dimethylphenylsulfonamide)2 
• 670255-96-6 N-(2,4-dimethyl-benzenesulfonyl)-glycine 

Relevant articles and documents

Mechanism of Action of an EPAC1-Selective Competitive Partial Agonist

The exchange protein activated by cAMP (EPAC) is a promising drug target for a wide disease range, from neurodegeneration and infections to cancer and cardiovascular conditions. A novel partial agonist of the EPAC isoform 1 (EPAC1), I942, was recently discovered, but its mechanism of action remains poorly understood. Here, we utilize NMR spectroscopy to map the I942-EPAC1 interactions at atomic resolution and propose a mechanism for I942 partial agonism. We found that I942 interacts with the phosphate binding cassette (PBC) and base binding region (BBR) of EPAC1, similar to cyclic adenosine monophosphate (cAMP). These results not only reveal the molecular basis for the I942 vs cAMP mimicry and competition, but also suggest that the partial agonism of I942 arises from its ability to stabilize an inhibition-incompetent activation intermediate distinct from both active and inactive EPAC1 states. The mechanism of action of I942 may facilitate drug design for EPAC-related diseases.

Preparation method and medical application of benzisothiazole and benzothiophene

The invention discloses a preparation method and medical application of benzisothiazole and benzothiophene, and telates to the field of pharmaceutical chemistry. According to the invention, benzisothiazole and benzothiophene are the first type of HIF-2 agonists; compared with a compound M1001 found by the applicant in the earlier stage, the invention has better HIF-2 agonist activity, and has remarkable enhancement activity on expression of mRNA and protein of EPO, VGEF, Glut1, NDRG1 and the like at the downstream of HIF-2, so that the invention can be used for preparing drugs for treating and/or preventing chronic kidney diseases/chronic renal anemia, dyslipidemia and high cholesterol caused by abnormal expression of HIF-2; and the method has a good industrialization prospect.

SELECTIVE NON-CYCLIC NUCLEOTIDE ACTIVATORS FOR THE CAMP SENSOR EPAC1

The invention relates generally to novel EPAC1 activators, such as Formula (I) and (II) and the preparation thereof as well as the use of EPAC1 activators disclosed herein as to selectively activate EPAC1 in cells.

Synthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators

Exchange proteins directly activated by cAMP (EPAC) play a central role in various biological functions, and activation of the EPAC1 protein has shown potential benefits for the treatment of various human diseases. Herein, we report the synthesis and biochemical evaluation of a series of noncyclic nucleotide EPAC1 activators. Several potent EPAC1 binders were identified including 25g, 25q, 25n, 25u, 25e, and 25f, which promote EPAC1 guanine nucleotide exchange factor activity in vitro. These agonists can also activate EPAC1 protein in cells, where they exhibit excellent selectivity toward EPAC over protein kinase A and G protein-coupled receptors. Moreover, 25e, 25f, 25n, and 25u exhibited improved selectivity toward activation of EPAC1 over EPAC2 in cells. Of these, 25u was found to robustly inhibit IL-6-activated signal transducer and activator of transcription 3 (STAT3) and subsequent induction of the pro-inflammatory vascular cell adhesion molecule 1 (VCAM1) cell-adhesion protein. These novel EPAC1 activators may therefore act as useful pharmacological tools for elucidation of EPAC function and promising drug leads for the treatment of relevant human diseases.

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).

Multiprotein Dynamic Combinatorial Chemistry: A Strategy for the Simultaneous Discovery of Subfamily-Selective Inhibitors for Nucleic Acid Demethylases FTO and ALKBH3

Dynamic combinatorial chemistry (DCC) is a powerful supramolecular approach for discovering ligands for biomolecules. To date, most, if not all, biologically templated DCC systems employ only a single biomolecule to direct the self-assembly process. To expand the scope of DCC, herein, a novel multiprotein DCC strategy has been developed that combines the discriminatory power of a zwitterionic “thermal tag” with the sensitivity of differential scanning fluorimetry. This strategy is highly sensitive and could differentiate the binding of ligands to structurally similar subfamily members. Through this strategy, it was possible to simultaneously identify subfamily-selective probes against two clinically important epigenetic enzymes: FTO (7; IC50=2.6 μm) and ALKBH3 (8; IC50=3.7 μm). To date, this is the first report of a subfamily-selective ALKBH3 inhibitor. The developed strategy could, in principle, be adapted to a broad range of proteins; thus it is of broad scientific interest.

A general iodine-mediated synthesis of primary sulfonamides from thiols and aqueous ammonia

A general and efficient methodology for preparing primary sulfonamides has been developed. In the presence of iodine as the catalyst and TBHP (70% in water) as the oxidant, a wide range of primary sulfonamides were prepared from the corresponding thiols and aqueous ammonia in moderate to good yields.

Kinetics and mechanism of oxidation of D-fructose and D-glucose by sodium salts of N-(chloro)-mono/di-substituted benzenesulfonamides in aqueous alkaline medium

In an effort to introduce N-chloroarylsulfonamides of different oxidizing strengths, nine sodium salts of mono- and di-substituted N- chloroarylsulfonamides are employed as oxidants for studying the kinetics of oxidation of D-fructose and D-glucose in aqueous alkaline medium. The results are analyzed along with those by the sodium salts of N-chlorobenzenesulfonamide and N-chloro-4-methylbenzenesulfonamide. The reactions show first-order kinetics each in [oxidant], [Fru/Glu], and [OH-]. The rates slightly increase with increase in ionic strength of the medium. Further, the rate of oxidation of fructose is higher by 4 to 5 times than that of the glucose oxidation, by the same oxidant. Similarly, Ea values for glucose oxidations are higher by about 1.5 times the Ea values for fructose oxidations. The results have been explained by a plausible mechanism, and the related rate law deduced. The significant changes in the kinetics and thermodynamic data are observed with change of substituent in the benzene ring. It is because Cl + is the effective oxidizing species in the reactions of N-chloroarylsulfonamides. The oxidative strengths of the latter therefore depend on the ease with which Cl+ is released from them. The ease with which Cl+ is released from N-chloroarylsulfonamides depends on the electron density of the nitrogen atom of the sulfonamide group, which in turn depends on the nature of the substituent in the benzene ring. The following Hammett equations are valid for the oxidation of fructose and glucose, log kobs = -3.13 + 0.54 σ ρ and log kobs = -3.81 + 0.28 σ ρ, respectively. The enthalpies and entropies of activations for oxidations by all the N-chloroarylsulfonamides correlate well with isokinetic temperatures of 301 K and 299 K, for fructose and glucose oxidations, respectively. The effect of substitution in the oxidants on the Ea and log A for the oxidations is also considered.

Oxidatively sonochemical dealkylation of various N-alkylsulfonamides to free sulfonamides and aldehydes

Various N-alkylsulfonamides were easily dealkylated to give the corresponding free sulfonamides in moderate to good yields in the presence of (diacetoxyiodo)benzene and iodine under ultrasonic irradiation. Application of this methodology to various N-prot

Novel sonochemical dealkylation of N-alkylsulfonamides in the presence of (diacetoxyiodo)benzene and iodine

Various N-alkylsulfonamides were easily dealkylated in moderate to good yields by the ultrasonic irradiation in the presence of (diacetoxyiodo)benzene and iodine.