(E)-3-Tosylacrylonitrile

Base Information

• Chemical Name: (E)-3-Tosylacrylonitrile
• CAS No.: 19542-67-7
• Molecular Formula: C10H9NO2S
• Molecular Weight: 207.253
• Hs Code.: 2926907090
• European Community (EC) Number: 805-917-7
• UNII: 4Y5G2A4F6O
• DSSTox Substance ID: DTXSID90859645
• Nikkaji Number: J1.602.972F,J646.210C
• Wikidata: Q27074879,Q27164032
• ChEMBL ID: CHEMBL403183
• Mol file: 19542-67-7.mol

Synonyms:3-(4-methylphenylsulfonyl)-2-propenenitrile;BAY 11-7082;BAY-11-7082;BAY-117082;BAY11 compound;BAY11-7082;BAY117082

Chemical Property of (E)-3-Tosylacrylonitrile

Chemical Property:

• Vapor Pressure: 1.57E-06mmHg at 25°C
• Melting Point: 133-135℃
• Boiling Point: 397.6°Cat760mmHg
• Flash Point: 194.3°C
• PSA: 66.31000
• Density: 1.237g/cm³
• LogP: 2.88678
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: 25 mg/mL, soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 207.03539970
• Heavy Atom Count: 14
• Complexity: 347

Purity/Quality:

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

BAY 11-7082 ^*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)C=CC#N
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)/C=C/C#N
• Description: BAY 11-7082 (19542-67-7)?inhibits cytokine-induced IκB-α phosphorylation via inhibition of IκB Kinase which results in inhibition of NFκB .1 Inhibits anchorage-independent growth of mammary epithelial cells induced with 4-hydroxyestradiol via inhibition of NFκB activation.2 Inhibits IFNα production and blocks nuclear translocation of IRF7 in plasmacytoid dendritic cells.3? Facilitates wound healing by inhibiting TNFα-induced MMP expression.4 A useful tool for probing the involvement of NFκB in physiological and pathophysiological processes.5? Cell permeable.
• Uses: Bay 11-7082 has been used as:a nuclear factor-kappa B (NF-kB) inhibitor to verify the action of the NF-kB signaling pathway in the production of interleukin (IL)-8a nuclear factor-kappa B (NF-kB) inhibitor to study the role of NF-kB activation in Mycoplasma hyorhinis -induced epithelial-mesenchymal transition (EMT) and cell migrationa nod-like receptor family pyrin domain containing 3 (NLRP3) selective inhibitor to examine its effects on liver inflammation in mice after hematopoietic stem cell transplantation

Technology Process of (E)-3-Tosylacrylonitrile

There total 16 articles about (E)-3-Tosylacrylonitrile 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: 87.0%

2-iodo-3-(p-tolylsulphonyl)propiononitrile (19520-58-2) → (E)-3-(p-tolylsulfonyl)propenenitrile (19542-67-7)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Ambient temperature;

Reference yield: 77.0%

2-(Phenylseleno)-3-(p-toluenesulfonyl)propionitrile (77825-72-0) → (E)-3-(p-tolylsulfonyl)propenenitrile (19542-67-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.0833333h;

DOI:10.1021/jo00329a021

Reference yield: 73.0%

sodium 4-methylbenzenesulfinate (824-79-3) + acrylonitrile (107-13-1,25014-41-9) → (E)-3-(p-tolylsulfonyl)propenenitrile (19542-67-7)

Guidance literature:

sodium 4-methylbenzenesulfinate; With polystyrene-supported-SeCl; In N,N-dimethyl-formamide; at 20 ℃; for 6h; solid-phase reaction;

acrylonitrile; 2,2'-azobis(isobutyronitrile); In benzene; for 20h; Heating;

With dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1055/s-2001-18779

upstream raw materials:

2,3-dibromopropionitrile

sodium 4-methylbenzenesulfinate

2-iodo-3-(p-tolylsulphonyl)propiononitrile

trans-β-chloroacrylonitrile

Downstream raw materials:

toluene-p-sulfonyl bromide

α,β-Dibrom-β-(p-tolylsulfonyl)-propionitril

(E)-3-(p-toluenesulfonyl)-acrylic acid

3-morpholin-4-yl-3-(toluene-4-sulfonyl)-propionitrile

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF ARYLSULFONYLPROPENENITRILES BY PHOTOCATALYTIC REACTIONS". Page/Page column 11. . Retrieved 2019/03/17.
• 2、 Li, Xianwei,Xu, Yanli,Wu, Wanqing,Jiang, Chang,Qi, Chaorong,Jiang, Huanfeng. "Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers". supporting information. p. 7911 - 7915. Retrieved 2014/07/07.