N-Benzyl-p-toluenesulfonamide

Base Information

• Chemical Name: N-Benzyl-p-toluenesulfonamide
• CAS No.: 1576-37-0
• Molecular Formula: C14H15NO2S
• Molecular Weight: 261.345
• Hs Code.: 2935009090
• European Community (EC) Number: 622-364-5
• NSC Number: 37123
• DSSTox Substance ID: DTXSID40166290
• Nikkaji Number: J426.785K
• Wikidata: Q27195409
• Pharos Ligand ID: P39WWP9CDBPW
• ChEMBL ID: CHEMBL1332361
• Mol file: 1576-37-0.mol

Synonyms:N-Benzyl-p-toluenesulfonamide;1576-37-0;N-Tosylbenzylamine;N-Benzyl-4-methylbenzenesulfonamide;N-Benzyl-4-methyl-benzenesulfonamide;N-Benzyl-p-toluenesulphonamide;p-Toluenesulfonamide, N-benzyl-;N-benzyl-4-methylbenzene-1-sulfonamide;Benzenesulfonamide, 4-methyl-N-(phenylmethyl)-;BRN 2217277;4-Methyl-N-(phenylmethyl)benzenesulfonamide;AI3-30867;N-Benzyl-p-toluene sulphonamide;CHEMBL1332361;MFCD00159328;3-12-00-02328 (Beilstein Handbook Reference);4-Methyl-N-(Phenylmethyl)-Benzenesulfonamid;NSC37123;NSC 37123;Tocris-1870;Probes1_000098;Probes2_000056;Cambridge id 5116373;TimTec1_000144;Oprea1_691087;Oprea1_824524;CBDivE_002319;MLS001209249;n-benzyl-p-toluenesulfonarnide;SCHEMBL198318;DTXSID40166290;CHEBI:114205;HMS1534G12;HMS2833D03;HMS3268M08;HMS3412L18;HMS3676L18;BDBM50046167;NSC-37123;AKOS000506046;N-Benzyl-4-methylbenzenesulfonamide #;ANGC-1576-37-0;CS-3222;NCGC00025316-01;NCGC00025316-02;NCGC00025316-03;AS-15817;HY-16690;SMR000504783;SY053403;LS-154104;B3082;FT-0663056;EN300-15765;D70200;A883488;SR-01000597548;J-009430;SR-01000597548-1;BRD-K64178227-001-01-7;BRD-K64178227-001-04-1;Q27195409;Z45508789

Chemical Property of N-Benzyl-p-toluenesulfonamide

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 3.12E-07mmHg at 25°C
• Melting Point: 115 °C
• Refractive Index: 1.589
• Boiling Point: 419.1 °C at 760 mmHg
• PKA: 11.54±0.30(Predicted)
• Flash Point: 207.3 °C
• PSA: 54.55000
• Density: 1.204 g/cm³
• LogP: 3.94520
• Storage Temp.: Desiccate at RT
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Slightly), Dichloromethane, Ethyl Acetate (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 261.08234989
• Heavy Atom Count: 18
• Complexity: 333

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Benzyl-p-Toluenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NCC2=CC=CC=C2
• Description: BTS is an inhibitor of skeletal muscle myosin II ATPase activity that reduces the affinity of ADP-myosin for actin. It inhibits calcium-stimulated ATPase activity of rabbit muscle myosin subfragment 1 (S1) in an actin-independent manner with an IC50 value of approximately 5 μM. It is selective for calcium-stimulated myosin II over human platelet myosin II, kinesin, pyruvate kinase, and lactate dehydrogenase at 100 μM. BTS (2 μM) inhibits the activity of skeletal muscle myosin, reversibly reducing the sliding velocity of heavy meromyosin in a gliding-filament assay. It inhibits isometric calcium-activated tension in isolated fast-twitch rabbit psoas muscle fibers (IC50 = ~3 μM) but not in isolated slow-twitch rat trabeculae and papillary cardiac muscle. BTS is also an intermediate in the synthesis of sulfonamides.
• Uses: A potent inhibitor of skeletal muscle Ca2+-stimulated myosin S1 ATPase (IC50 approx. 5uM) activity. Reversible blocks the gliding motility. Also weakens myosin interaction with F-actin. Does not affect platelet myosin II A potent inhibitor of calcium-stimulated myosin S1 ATPase

Technology Process of N-Benzyl-p-toluenesulfonamide

There total 197 articles about N-Benzyl-p-toluenesulfonamide 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: 95.0%

toluene-4-sulfonamide (70-55-3) + benzyl alcohol (100-51-6,185532-71-2) → N-benzyl-p-toluenesulfonamide (1576-37-0) + benzaldehyde (100-52-7)

Guidance literature:

With potassium hydroxide; at 130 ℃; for 10h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02685

Reference yield: 50.0%

N-benzyl p-toluenesulfonamido-2 cyclohexanone (75682-59-6) → N-benzyl-p-toluenesulfonamide (1576-37-0) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4)

Guidance literature:

In diethyl ether; for 4h; Product distribution; Irradiation;

DOI:10.1016/S0040-4020(01)83126-4

Reference yield: 47.0%

N-benzyl-N-tosylacetamide (121618-47-1) → N-benzyl-p-toluenesulfonamide (1576-37-0) + benzylamine (100-46-9)

Guidance literature:

With magnesium; In methanol; at 20 ℃; for 0.333333h;

DOI:10.1081/SCC-100104475

upstream raw materials:

benzyl chloride

toluene-4-sulfonamide

p-toluenesulfonyl chloride

benzylamine

Downstream raw materials:

N-benzyl-N-ethyl-4-methylbenzenesulfonamide

2-(N-benzyl-4-methylphenylsulfonamido)acetic acid

N-(phenylmethyl)-di(p-toluenesulfonyl)amine

N-(benzylidene)-p-methylbenzenesulfonamide

Refernces

• 1、 Zhou, Zhongshi,He, Xuehan. "Synthesis of sulfonamides promoted by alkyl iodide via a hypervalent iodine intermediate". . p. 280 - 284. Retrieved 2020.
• 2、 Huang, Ruohe,Peng, Guo,Wang, Weixiang,Xu, Pengyu,Yu, Hui. "PhI(OAc)2-mediated synthesis of propargylic N, O-acetals by 1, 2-addition of alcohols to allenamides". . . Retrieved 2020.
• 3、 Andersen,Kociolek. "Acidity of cyclic sulfamates: Study of substituted 1,2,3-benzoxathiazole 2,2,-dioxides and theoretical investigation of the effect of conformation on acidity". . p. 2003 - 2007. Retrieved 1995.
• 4、 Bellos, Konstantinos,Stamm, Helmut. "Two-step 1,2-shifts by β-cleavage of carbenium ions and recombination in friedel-crafts reactions of 2-ferf-butyl-l-tosylaziridines". . p. 7749 - 7752. Retrieved 1998.
• 5、 Kumar, Anil,Ye, Guofeng,Ahmadibeni, Yousef,Parang, Keykavous. "Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: Applications in solid-phase organic synthesis". . p. 7915 - 7918. Retrieved 2006.
• 6、 Diaz-Requejo, M. Mar,Belderrain, Tomas R.,Nicasio, M. Carmen,Trofimenko, Swiatoslaw,Perez, Pedro J.. "Cyclohexane and benzene amination by catalytic nitrene insertion into C-H bonds with the copper-homoscorpionate catalyst TpBr3Cu(NCMe)". . p. 12078 - 12079. Retrieved 2003.
• 7、 Yamada, Ken-Ichi,Yamamoto, Yasutomo,Maekawa, Masaru,Chen, Jingbo,Tomioka, Kiyoshi. "Direct aminoalkylation of cycloalkanes through dimethylzinc-initiated radical process". . p. 6595 - 6597. Retrieved 2004.
• 8、 Hajiloo Shayegan, Mojtaba,Li, Zhong-Yuan,Cui, Xin. "Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides". supporting information. . Retrieved 2021/12/02.
• 9、 Li, Zhenya,Xu, Ronghua,Guo, Huichuang,Yang, He,Xu, Guangqing,Shi, Enxue,Xiao, Junhua,Tang, Wenjun. "Enantioselective Rhodium-Catalyzed Hydrogenation of (Z)-N-Sulfonyl-α-dehydroamido Boronic Esters". supporting information. p. 714 - 719. Retrieved 2022/01/20.