Ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate

Base Information

• Chemical Name: Ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate
• CAS No.: 17823-58-4
• Molecular Formula: C8H11 N O2 S2
• Molecular Weight: 217.313
• Hs Code.: 29309090
• European Community (EC) Number: 677-988-0
• DSSTox Substance ID: DTXSID90372687
• Nikkaji Number: J254.902F
• Mol file: 17823-58-4.mol

Synonyms:17823-58-4;ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate;Ethyl 2-cyano-3,3-bis(methylthio)acrylate;3,3-Bis(methylthio)-2-cyanoacrylic Acid Ethyl Ester;Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate;2-Propenoic acid, 2-cyano-3,3-bis(methylthio)-, ethyl ester;Ethyl 2-cyano-3,3-bis(methylthio)-2-propenoate;SCHEMBL77082;DTXSID90372687;POABRARINOCORV-UHFFFAOYSA-N;BCP21412;MFCD00143027;STL134948;AKOS004903159;BS-42147;B1411;CS-0074120;ethyl 2-cyano-3,3-bis(methylthio)-acrylate;D73869;EN300-106663;3,3-Bis(methylthio)-2-cyanoacrylicAcidEthylEster;J-011363;2-cyano-3,3-bis-methylsulfanyl-acrylic acid ethyl ester;F2199-0348;Z1269196652;2-cyano-3,3-bis(methylsulfanyl)-acrylic acid ethyl ester;Ethyl 2-cyano-3,3-bis(methylthio)acrylate, >=98.0% (GC)

Chemical Property of Ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate

Chemical Property:

• Vapor Pressure: 0.000432mmHg at 25°C
• Melting Point: 58 °C
• Refractive Index: 1.545
• Boiling Point: 315.6°C at 760 mmHg
• Flash Point: 144.7°C
• PSA: 100.69000
• Density: 1.216g/cm³
• LogP: 2.01068
• Solubility.: soluble in Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 217.02312094
• Heavy Atom Count: 13
• Complexity: 259

Purity/Quality:

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

Ethyl2-Cyano-3,3-bis(methylsulfanyl)prop-2-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 20/21/22-36/37/38-23/24/25
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=C(SC)SC)C#N

Technology Process of Ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate

There total 14 articles about Ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate 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: 100.0%

carbon disulfide (75-15-0,12122-00-8) + ethyl 2-cyanoacetate (105-56-6) + methyl iodide (74-88-4) → ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4)

Guidance literature:

With potassium carbonate; tetrabutylammomium bromide; In benzene; at 60 ℃; for 3h;

Reference yield: 93.0%

carbon disulfide (75-15-0,12122-00-8) + ethyl 2-cyanoacetate (105-56-6) + dimethyl sulfate (77-78-1) → ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4)

Guidance literature:

ethyl 2-cyanoacetate; With potassium hydroxide; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

carbon disulfide; In acetonitrile; at -5 ℃; for 1h; Inert atmosphere;

dimethyl sulfate; In acetonitrile; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c0ob00002g

Reference yield: 85.0%

1,3-dithiapropane (6725-64-0) + ethyl 2-cyanoacetate (105-56-6) + methyl iodide (74-88-4) → ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

DOI:10.1016/j.bmcl.2009.10.074

upstream raw materials:

methyl iodide

(S,S)-dimethyl trithiocarbonate

ethyl 2-cyanoacetate

carbon disulfide

Downstream raw materials:

(E)-2,6,6-Tricyano-3-methylsulfanyl-5-phenyl-hexa-2,5-dienoic acid ethyl ester

(E)-5-(4-Chloro-phenyl)-2,6,6-tricyano-3-methylsulfanyl-hexa-2,5-dienoic acid ethyl ester

(E)-2,6,6-Tricyano-5-(4-methoxy-phenyl)-3-methylsulfanyl-hexa-2,5-dienoic acid ethyl ester

3,4-dihydro-2,6-dimethylmercapto-4-oxopyrimidine-5-carbonitrile

Refernces

• 1、 Dwivedi, Jaya,Kishore, Dharma,Misra, Apoorva,Sharma, Swapnil,Shukla, Shruti. "Bacterial cell leakage potential of newly synthesized quinazoline derivatives of 1,5-benzodiazepines analogue". . . Retrieved 2020.
• 2、 Chhabria, Mahesh T.,Bhatt, Hardik G.,Raval, Hitesh G.,Oza, Pratik M.. "Synthesis and biological evaluation of some 5-ethoxycarbonyl-6-isopropylamino-4-(substitutedphenyl)aminopyrimidines as potent analgesic and anti-inflammatory agents". . p. 1022 - 1024. Retrieved 2007.
• 3、 Wu, Yan-Chao,Li, Hui-Jing,Yang, Hua-Zheng. "A sensitive and highly selective fluorescent sensor for In3+". . p. 3394 - 3397. Retrieved 2010.
• 4、 Shetgaonkar, Samata E.,Singh, Fateh V.. "A Metal-Free Approach for the Synthesis of 2-Tetralones via Carbanion-Induced Ring Transformation of 2 H -Pyran-2-ones". . p. 3540 - 3548. Retrieved 2018.
• 5、 Karelia, Chirag,Parmar, Kailash,Teli, Divya,Chhabria, Mahesh. "Design, synthesis and biological evaluation of novel DPP-IV inhibitors". . p. 1227 - 1235. Retrieved 2020/12/04.