2-Methylbenzene-1-sulfonamide

Base Information

• Chemical Name: 2-Methylbenzene-1-sulfonamide
• CAS No.: 88-19-7
• Molecular Formula: C7H9NO2S
• Molecular Weight: 171.22
• Hs Code.: 2935.00.
• European Community (EC) Number: 215-578-1,201-808-8,232-394-7
• ICSC Number: 1581
• NSC Number: 2185
• UNII: R81Z6V889P
• DSSTox Substance ID: DTXSID7021362
• Nikkaji Number: J3.544K
• Wikidata: Q27287945
• ChEMBL ID: CHEMBL176892
• Mol file: 88-19-7.mol

Synonyms:o-Toluenesulfonamide(7CI,8CI);2-Methylbenzenesulfonamide;2-Methylphenyl sulfonamide;2-Tolylsulfonamide;NSC 2185;Toluene-2-sulfonamide;o-Methylbenzenesulfonamide;o-Toluenesulfamide;p-Toluene-2-sulfonamide;Benzenesulfonamide,2-methyl-;

Chemical Property of 2-Methylbenzene-1-sulfonamide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0-0.008Pa at 25℃
• Melting Point: 155 °C
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 330.2 °C at 760 mmHg
• PKA: 10.17±0.60(Predicted)
• Flash Point: 153.5 °C
• PSA: 68.54000
• Density: 1.271 g/cm³
• LogP: 2.42350
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• Water Solubility.: Soluble in water (1.6 g/L at 25°C).
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 171.03539970
• Heavy Atom Count: 11
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

2-Methylbenzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36-40
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Sulfonamides
• Canonical SMILES: CC1=CC=CC=C1S(=O)(=O)N
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: May cause mechanical irritation to the eyes.
• Uses: 2-Methylbenzene-1-sulfonamide is a methylated sulfonamide and a major Impurity if Saccharin (S080800). Studies suggest that o-Toluenesulfonamide has potential mutagenic activity. Plasticizer of thermosetting resin, as a raw material used in organic synthesis, preparation of nail polish, dyes, fluorescent pigments and coatings. o-Toluenesulfonamide is a methylated sulfonamide and a major impurity if Saccharin (S080800). Studies suggest that o-Toluenesulfonamide has potential mutagenic activity.

Technology Process of 2-Methylbenzene-1-sulfonamide

There total 28 articles about 2-Methylbenzene-1-sulfonamide 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: 93.0%

2-methyl-2-(toluene-2-ylsulfonylamino)propionic acid → methyl 2-(aminosulfonyl)benzoate (88-19-7)

Guidance literature:

With oxygen; copper(II) oxide; In dimethyl sulfoxide; at 100 ℃; for 8h;

DOI:10.1080/00397911.2016.1202981

Reference yield: 72.0%

hexylidenetriphenylphosphoran (16666-79-8,19493-12-0) + N-benzylidene-2-methylbenzenesulfonamide (14674-28-3) → methyl 2-(aminosulfonyl)benzoate (88-19-7) + (18)O-triphenylphosphine oxide (98511-61-6)

Guidance literature:

hexylidenetriphenylphosphoran; N-benzylidene-2-methylbenzenesulfonamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; Inert atmosphere;

With ¹⁸O-labeled water; In tetrahydrofuran; hexane; at 20 ℃; for 4h; stereoselective reaction;

DOI:10.1039/c0cc04739b

Reference yield: 70.0%

2-methylphenyl diazonium tetrafluoroborate (2093-46-1) → methyl 2-(aminosulfonyl)benzoate (88-19-7)

Guidance literature:

With sodium metabisulfite; sodium azide; tetrabutylammomium bromide; triphenylphosphine; In water; acetonitrile; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c8gc03014f

upstream raw materials:

toluenesulfinic acid

toluene

Toluene-2-sulfonyl chloride

2-methylbenzenesulfonyl isocyanate

Downstream raw materials:

N-(2-hydroxy-ethyl)-toluene-2-sulfonamide

1,3,5-tris-(toluene-2-sulfonyl)-[1,3,5]triazinane

N-xanthen-9-yl-toluene-2-sulfonamide

N-chloro-toluene-2-sulfonamide; sodium-salt

Refernces

Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives

10.1002/chem.200800210

The study explores the use of gold catalysis to synthesize various heterocycles, including chromans, dihydrobenzofurans, dihydroindoles, and tetrahydroquinolines. The researchers prepared furans containing ynamide or alkynyl ether moieties in the side chain and used gold-catalyzed transformations to achieve these syntheses at room temperature through fast reactions. The heteroatom directly attached to the intermediate arene oxides stabilized the intermediates, leading to highly selective reactions, even with mono-substituted furans. The study involved various chemicals, including lithiated furans for the introduction of side chains, oxiranes and enones for synthesis of alcohols, and dichlorovinyl ethers and toluenesulfonamides as starting points for ynamide syntheses. The gold-catalyzed reactions resulted in the formation of the desired heterocycles with good yields and selectivity, highlighting the efficiency and versatility of gold catalysis in organic synthesis.