4-(2-Aminoethyl)benzenesulfonamide

Base Information

• Chemical Name: 4-(2-Aminoethyl)benzenesulfonamide
• CAS No.: 35303-76-5
• Molecular Formula: C8H12N2O2S
• Molecular Weight: 200.261
• Hs Code.: DERIVATION
• European Community (EC) Number: 252-501-0
• UNII: WIA59Y34CJ
• DSSTox Substance ID: DTXSID20188814
• Nikkaji Number: J236.453K
• Wikidata: Q27097962
• Pharos Ligand ID: HCF68PFJ52A7
• Metabolomics Workbench ID: 151897
• ChEMBL ID: CHEMBL7087
• Mol file: 35303-76-5.mol

Synonyms:4-(2-aminoethyl)benzenesulfonamide;AEBSNH2

Chemical Property of 4-(2-Aminoethyl)benzenesulfonamide

Chemical Property:

• Appearance/Colour: white to yellowish crystalline powder powder
• Vapor Pressure: 3.31E-06mmHg at 25°C
• Melting Point: 150-152 °C(lit.)
• Refractive Index: 1.587
• Boiling Point: 387.4 °C at 760 mmHg
• PKA: 10.16±0.10(Predicted)
• Flash Point: 188.1 °C
• PSA: 94.56000
• Density: 1.293 g/cm³
• LogP: 2.31660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 15.5g/L at 20℃
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 200.06194880
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

≥98.0% ^*data from raw suppliers

4-(2-Aminoethyl)benzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xi,Xn
• Statements: 34-22-36/37/38-20/21/22
• Safety Statements: 45-36/37/39-26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCN)S(=O)(=O)N
• General Description: 4-(2-Aminoethyl)benzenesulfonamide, also known as p-aminoethyl-benzenesulfonamide, serves as a key precursor in the synthesis of Schiff base derivatives that exhibit selective inhibitory activity against carbonic anhydrase (CA) isozymes, particularly the membrane-bound CA IV. These derivatives demonstrate a modest two-fold selectivity for CA IV over cytosolic isozymes (CA I and II), attributed to reduced potency against hCA II. This selectivity suggests potential for developing targeted CA IV inhibitors with improved therapeutic profiles and minimized side effects.

Technology Process of 4-(2-Aminoethyl)benzenesulfonamide

There total 13 articles about 4-(2-Aminoethyl)benzenesulfonamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

4-cyanomethyl-benzenesulfonic acid amide (3665-08-5) → 4-(2-aminoethyl)benzenesulfonamide (35303-76-5)

Guidance literature:

With sodium methylate; nickel; In methanol; at 45 ℃; Electrochemical reaction;

DOI:10.1002/hlca.200690123

Reference yield: 78.0%

4-(β-acetylaminoethyl)phenylsulfonamide (41472-49-5) → 4-(2-aminoethyl)benzenesulfonamide (35303-76-5)

Guidance literature:

With sodium hydroxide; water; for 3h; Reflux;

DOI:10.1016/j.bmcl.2009.01.082

Reference yield:

4-[2-(2,2,2-trifluoroacetamido)ethyl]benzenesulfonyl chloride (223253-87-0) → 4-(2-aminoethyl)benzenesulfonamide (35303-76-5)

Guidance literature:

With ammonium hydroxide; In acetone; at 20 ℃;

upstream raw materials:

4-(β-acetylaminoethyl)phenylsulfonamide

4-(2-carboxyethyl)-benzenesulfonamide

4-cyanomethyl-benzenesulfonic acid amide

4-sulfamoyl-trans-cinnamic acid

Downstream raw materials:

2-Methylamino-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzamide

2-Ethylamino-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzamide

5-Chloro-2-ethylamino-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzamide

5-Chloro-2-methylamino-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzamide

Refernces

Carbonic anhydrase inhibitors. Part 43. Schiff bases derived from aromatic sulfonamides: Towards more specific inhibitors for membrane-bound versus cytosolic isozymes

10.1016/S0223-5234(97)81681-9

The study investigates the development of more specific carbonic anhydrase (CA) inhibitors, focusing on Schiff bases derived from aromatic sulfonamides. The researchers synthesized 21 new Schiff bases using sulfanilamide, homosulfanilamide, and p-aminoethyl-benzenesulfonamide as starting materials, reacting them with various substituted benzene- and heterocyclic aldehydes. These compounds were characterized and tested for their inhibitory effects on three CA isozymes: CA I, CA II, and CA IV. The results showed that several of these new Schiff bases exhibited a modest two-fold selectivity for the membrane-bound CA IV compared to the cytosolic human isozymes CA I and II. This selectivity is attributed to a decreased potency against hCA II relative to classical inhibitors. The study suggests that these compounds could potentially lead to the development of low molecular weight, isozyme-specific CA IV inhibitors, which may have improved therapeutic profiles and fewer side effects.