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17823-58-4

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17823-58-4 Usage

General Description

3,3-BIS(METHYLTHIO)-2-CYANOACRYLIC ACID ETHYL ESTER is a chemical compound with the molecular formula C9H11NO3S2. It is commonly used as a reagent in organic synthesis and as an intermediate in the production of various chemical compounds. 3,3-BIS(METHYLTHIO)-2-CYANOACRYLIC ACID ETHYL ESTER is a yellow liquid with a strong unpleasant odor. It is reactive and can undergo various chemical reactions such as esterification and polymerization. It is important to handle this compound with caution and follow proper safety protocols as it can be hazardous to health if not handled properly.

Check Digit Verification of cas no

The CAS Registry Mumber 17823-58-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,8,2 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 17823-58:
(7*1)+(6*7)+(5*8)+(4*2)+(3*3)+(2*5)+(1*8)=124
124 % 10 = 4
So 17823-58-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO2S2/c1-4-11-7(10)6(5-9)8(12-2)13-3/h4H2,1-3H3

17823-58-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (B1411)  Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate  >98.0%(N)

  • 17823-58-4

  • 25g

  • 1,190.00CNY

  • Detail
  • TCI America

  • (B1411)  Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate  >98.0%(N)

  • 17823-58-4

  • 500g

  • 7,890.00CNY

  • Detail
  • Aldrich

  • (779687)  Ethyl 2-cyano-3,3-bis(methylthio)acrylate  ≥98.0% (GC)

  • 17823-58-4

  • 779687-10G

  • 1,086.93CNY

  • Detail
  • Aldrich

  • (779687)  Ethyl 2-cyano-3,3-bis(methylthio)acrylate  ≥98.0% (GC)

  • 17823-58-4

  • 779687-100G

  • 3,787.29CNY

  • Detail

17823-58-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate

1.2 Other means of identification

Product number -
Other names ethyl 2-cyano-3,3-dimethylthioacrylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:17823-58-4 SDS

17823-58-4Synthetic route

methyl iodide
74-88-4

methyl iodide

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
With potassium carbonate; tetrabutylammomium bromide In benzene at 60℃; for 3h;100%
Stage #1: ethyl 2-cyanoacetate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: carbon disulfide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
Stage #3: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 4h;
94%
Stage #1: ethyl 2-cyanoacetate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: carbon disulfide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #3: methyl iodide In N,N-dimethyl-formamide for 4h;
85%
carbon disulfide
75-15-0

carbon disulfide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

dimethyl sulfate
77-78-1

dimethyl sulfate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
Stage #1: ethyl 2-cyanoacetate With potassium hydroxide In acetonitrile at 20℃; for 1h; Inert atmosphere;
Stage #2: carbon disulfide In acetonitrile at -5℃; for 1h; Inert atmosphere;
Stage #3: dimethyl sulfate In acetonitrile at 0 - 20℃; for 6h; Inert atmosphere;
93%
Stage #1: carbon disulfide; ethyl 2-cyanoacetate With sodium hydroxide In water; N,N-dimethyl-formamide at 1℃; for 0h;
Stage #2: dimethyl sulfate In water; N,N-dimethyl-formamide at 10 - 15℃; for 4h;
93%
Stage #1: carbon disulfide; ethyl 2-cyanoacetate With potassium hydroxide In water; N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: dimethyl sulfate In water; N,N-dimethyl-formamide at 0 - 20℃; for 24h;
85%
methanol
67-56-1

methanol

carbon disulfide
75-15-0

carbon disulfide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
Stage #1: carbon disulfide; ethyl 2-cyanoacetate With sodium In methanol at 0 - 20℃; for 0.5h;
Stage #2: methanol With dimethyl sulfate for 0.75h;
1,3-dithiapropane
6725-64-0

1,3-dithiapropane

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

methyl iodide
74-88-4

methyl iodide

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;85%
carbon disulfide
75-15-0

carbon disulfide

dimethylsulfide
75-18-3

dimethylsulfide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide
Stage #1: carbon disulfide; ethyl 2-cyanoacetate With potassium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 1h; Cooling;
Stage #2: dimethylsulfide In water; N,N-dimethyl-formamide at 20℃; for 12h;
With potassium hydroxide In N,N-dimethyl-formamide
disodium 2-cyano-3-ethoxy-3-oxoprop-1-ene-1,1-bis(thiolate)

disodium 2-cyano-3-ethoxy-3-oxoprop-1-ene-1,1-bis(thiolate)

methyl iodide
74-88-4

methyl iodide

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
In methanol
In ethanol at 20℃;
ethyl 2-cyano-3,3-dimercaptoacrylate dipotassium salt

ethyl 2-cyano-3,3-dimercaptoacrylate dipotassium salt

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / HCl / H2O; CH2Cl2 / 16 h
2: 1.) methanolic sodium methoxide / 1.) dioxane; 2.) room temperature, 2 h.
View Scheme
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

<2-oxy-styryl>-<4-dimethyl-amino-styryl>-ketone

<2-oxy-styryl>-<4-dimethyl-amino-styryl>-ketone

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / potassium hydroxide / dioxane
2: 28 percent / HCl / H2O; CH2Cl2 / 16 h
3: 1.) methanolic sodium methoxide / 1.) dioxane; 2.) room temperature, 2 h.
View Scheme
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium hydroxide / acetonitrile / 1.5 h / 5 °C
1.2: 5 - 20 °C
2.1: acetonitrile / 0 - 20 °C
View Scheme
2,2-Dimercapto-aethen-1,1-dicarbonsaeure-aethylester-nitril
18771-18-1

2,2-Dimercapto-aethen-1,1-dicarbonsaeure-aethylester-nitril

dimethyl sulfate
77-78-1

dimethyl sulfate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
In acetonitrile at 0 - 20℃;
carbon disulfide
75-15-0

carbon disulfide

cyanoacetic acid ethyl ester, sodium-compound

cyanoacetic acid ethyl ester, sodium-compound

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
With diethyl ether Mehrtaegiges Erwaermen des Reaktionsgemisches mit Methyljodid.;
6-Amino-2-[1-cyano-1-ethoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester
74598-55-3

6-Amino-2-[1-cyano-1-ethoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester

methyl iodide
74-88-4

methyl iodide

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

Conditions
ConditionsYield
With sodium methylate 1.) dioxane; 2.) room temperature, 2 h.; Yield given;
(S,S)-dimethyl trithiocarbonate
2314-48-9

(S,S)-dimethyl trithiocarbonate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

N-trimethylsilylmethylamine
18166-02-4

N-trimethylsilylmethylamine

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
17823-58-4

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate

(E)-2-Cyano-3-methylsulfanyl-3-(trimethylsilanylmethyl-amino)-acrylic acid ethyl ester
129757-47-7

(E)-2-Cyano-3-methylsulfanyl-3-(trimethylsilanylmethyl-amino)-acrylic acid ethyl ester

Conditions
ConditionsYield
In methanol for 0.166667h; Heating;99%

17823-58-4Relevant articles and documents

Design and synthesis of potent N-phenylpyrimidine derivatives for the treatment of skin cancer

Chaube, Udit J.,Vyas, Vivek K.,Bhatt, Hardik G.

, p. 10285 - 10297 (2016)

The development of novel synthetic compounds for the treatment of skin cancer is much needed, as there is a sudden rise in the incidence of skin cancer throughout the world and the available chemotherapy is facing problems of resistance. Hence, present re

Synthesis and bioactivity of 2-cyanoacrylates containing a trifluoromethylphenyl moiety

Song, Baoan,Yang, Song,Zhong, Huimin,Jin, Linhong,Hu, Deyu,Liu, Gang

, p. 87 - 92 (2005)

A series of 2-cyanoacrylates containing a trifluoromethylphenyl moiety were synthesized in three steps: ethyl 2-cyano-3,3-dimethylthioacrylate was prepared from ethyl cyanoacetate with carbon disulfide and dimethyl sulfate, then its reaction with 4-trifluoromethylaniline yielded ethyl 2-cyano-3-(4- trifluoromethylphenylamino)-3-methylthioacrylate, and then reacted with an alkylamine. The new structures were verified by elemental analysis, IR, 1H NMR and mass spectra. In the MTT test, these new compounds were found to possess high antitumor activities against PC3 and A431 cells.

Ketene aminal-based lactam derivatives as a novel class of orally active FXa inhibitors

Shi, Yan,Zhang, Jing,Stein, Philip D.,Shi, Mengxiao,O'Connor, Stephen P.,Bisaha, Sharon N.,Li, Chi,Atwal, Karnail S.,Bisacchi, Gregory S.,Sitkoff, Doree,Pudzianowski, Andrew T.,Liu, Eddie C.,Hartl, Karen S.,Seiler, Steven M.,Youssef, Sonia,Steinbacher, Thomas E.,Schumacher, William A.,Rendina, Alan R.,Bozarth, Jeffrey M.,Peterson, Tara L.,Zhang, Ge,Zahler, Robert

, p. 5453 - 5458 (2005)

N,N′-Disubstituted ketene aminals are good bioisosteres of thiourea functional groups. We report the design and synthesis of a novel class of ketene aminal-based lactam derivatives as potent and orally active FXa inhibitors.

Synthesis, antiviral and antifungal bioactivity of 2-cyano-acrylate derivatives containing phosphonyl moieties

Lv, Yin-Pu,Wang, Xian-You,Song, Bao-An,Yang, Song,Yan, Kai,Xu, Guang-Fang,Bhadury, Pinaki S.,Liu, Fang,Jin, Lin-Hong,Hu, De-Yu

, p. 965 - 978 (2007)

Alkyl 2-cyano-3-methylthio-3-phosphonylacrylates were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1H-, 13

Synthesis, spectral characterization and photophysical studies of tetrahydroquinolines

Kennedy, L. John,Singh, Fateh V.,Subashini, C.

, (2020/10/18)

A metal-free, ultrasound-assisted, fast synthesis of fluorescent N-Boc-protected 1,2,3,4–tetrahydroquinolines 9a-p is described through carbanion-induced ring transformation of 6-aryl-2H-pyran-2-ones 7 with tert?butyl 3-oxopiperidine-1-carboxylate 8 under

Tailored-design Synthesis of Sulfapyrimidine Derivatives

Azzam, Rasha A.

, p. 619 - 627 (2019/01/04)

In this paper, we report an efficient and convenient approach for the synthesis of tailored-design target sulfapyrimidine derivatives expected to show remarkable antimicrobial activities. The approach is based on reacting arylsulfonyl guanidine with α,β-unsaturated carbonyl compounds to afford N-(4,6-diarylpyrimidin-2-yl)arylsulfonamide or with ylidene derivatives to afford N-(6-aryl-5-cyanopyrimidin-2-yl)arylsulfonamide, N-(4-amino-5-cyano-6-(methylthio)-pyrimidin-2-yl)-arylsulfonamide, and N-(5-cyanopyrimidin-2-yl)arylsulfonamide compounds through Michael addition reaction. The structure of the newly synthesized compounds was confirmed from spectral data and elemental analysis.

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