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Basic Information
| CAS No.: | 17823-58-4 | ||||
|---|---|---|---|---|---|
| Name: | 3,3-BIS(METHYLTHIO)-2-CYANOACRYLIC ACID ETHYL ESTER | ||||
| Article Data: | 37 | ||||
| Molecular Structure: | |||||
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| Formula: | C8H11 N O2 S2 | ||||
| Molecular Weight: | 217.313 | ||||
| Synonyms: | Acrylicacid, 2-cyano-3-oxo-, ethyl ester, 3-(dimethyl mercaptole) (8CI);2-Cyano-3,3-bis(methylsulfanyl)acrylic acid ethyl ester;2-Cyano-3,3-bis(methylthio)-2-propenoic acid ethyl ester;3,3-(Bismethylthio)-2-cyanoacrylic acid ethyl ester; Ethyl2-cyano-3,3-bis(methylthio)-2-propenoate; Ethyl2-cyano-3,3-bis(methylthio)acrylate; Ethyl 2-cyano-3,3-bis(methylthio)propenoate;Ethyl 3,3-bis(methylthio)-2-cyanoacrylate | ||||
| Density: | 1.216g/cm3 | ||||
| Melting Point: | 58 °C | ||||
| Boiling Point: | 315.6°C at 760 mmHg | ||||
| Flash Point: | 144.7°C | ||||
| Hazard Symbols: | T | ||||
| Risk Codes: | 20/21/22-36/37/38-23/24/25 | ||||
| Safety: |
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| PSA: | 100.69000 | ||||
| LogP: | 2.01068 | ||||
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| 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% |
...Expand
- 75-15-0
carbon disulfide
- 105-56-6
ethyl 2-cyanoacetate
- 77-78-1
dimethyl sulfate
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| 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% |
...Expand
- 67-56-1
methanol
- 75-15-0
carbon disulfide
- 105-56-6
ethyl 2-cyanoacetate
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| 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; |
...Expand
- 6725-64-0
1,3-dithiapropane
- 105-56-6
ethyl 2-cyanoacetate
- 74-88-4
methyl iodide
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; | 85% |
...Expand
- 75-15-0
carbon disulfide
- 75-18-3
dimethylsulfide
- 105-56-6
ethyl 2-cyanoacetate
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| 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 |
...Expand
- 74-88-4
methyl iodide
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| In methanol | |
| In ethanol at 20℃; |
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| 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 |
- 105-56-6
ethyl 2-cyanoacetate
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| 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 |
- 105-56-6
ethyl 2-cyanoacetate
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| 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 |
- 18771-18-1
2,2-Dimercapto-aethen-1,1-dicarbonsaeure-aethylester-nitril
- 77-78-1
dimethyl sulfate
- 17823-58-4
ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate
Conditions
| Conditions | Yield |
|---|---|
| In acetonitrile at 0 - 20℃; |
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3,3-BIS(METHYLTHIO)-2-CYANOACRYLIC ACID ETHYL ESTER
