Trimethylsilyl cyanide
Trimethylsilyl cyanide
CAS: 7677-24-9
Molecular Formula: C4H9NSi
Trimethylsilyl cyanide - Names and Identifiers
| Name | Trimethylsilyl cyanide |
| Synonyms | TMSCN trimethylsilycyanide TRIMETHYLSILYL CYANIDE Trimethylsilyl cyanide Trimethyl Silane Cyanide trimethylsilylcarbonitrile Cyanotrimethylsilane~TMSCN trimethylsilylformonitrile trimethylsilanecarbonitrile TRIMETHYLSILANECARBONITRILE trimethyl-silanecarbonitril trimethylsilylmethanenitrile TRIMETHYLSILYL CYANIDE FOR SYNTHESIS |
| CAS | 7677-24-9 |
| EINECS | 231-657-3 |
| InChI | InChI=1/C4H9NSi/c1-6(2,3)4-5/h1-3H3 |
| InChIKey | LEIMLDGFXIOXMT-UHFFFAOYSA-N |
Trimethylsilyl cyanide - Physico-chemical Properties
| Molecular Formula | C4H9NSi |
| Molar Mass | 99.21 |
| Density | 0.793g/mLat 20°C(lit.) |
| Melting Point | 8-11°C(lit.) |
| Boling Point | 114-117°C(lit.) |
| Flash Point | 34°F |
| Water Solubility | reacts |
| Solubility | Miscible with organic solvents. |
| Vapor Presure | 16.6mmHg at 25°C |
| Appearance | liquid |
| Specific Gravity | 0.744 |
| Color | Yellow |
| Exposure Limit | NIOSH: IDLH 25 mg/m3 |
| BRN | 1737612 |
| Storage Condition | Inert atmosphere,2-8°C |
| Stability | Moisture Sensitive |
| Sensitive | 8: reacts rapidly with moisture, water, protic solvents |
| Refractive Index | n20/D 1.392(lit.) |
| Physical and Chemical Properties | Appearance: colorless liquid boiling range: 114-117 ℃ Melting Point: 11 ℃ Specific Gravity: 0.744 |
| Use | Used as a raw material for organic polymers |
Trimethylsilyl cyanide - Risk and Safety
| Risk Codes | R11 - Highly Flammable R26/27/28 - Very toxic by inhalation, in contact with skin and if swallowed. R29 - Contact with water liberates toxic gas R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S16 - Keep away from sources of ignition. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A - S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 3384 6.1/PG 1 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-21 |
| TSCA | Yes |
| HS Code | 29310095 |
| Hazard Note | Highly Flammable/Toxic |
| Hazard Class | 6.1 |
| Packing Group | II |
Trimethylsilyl cyanide - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | trimethylcyanosilane (TMSCN) is a volatile liquid at room temperature, this compound is used in organic synthesis as an alternative to highly toxic HCN for the introduction of cyano groups into the molecule. there are few domestic manufacturers of trimethylcyanosilane, the reaction system is heterogeneous sodium cyanide substitution reaction, the conversion rate is very low, only up to about 45%. It can also be replaced by silver cyanide, but the cost is too high and the waste residue is not easy to handle. In addition, cuprous hydride is used as a raw material to participate in the substitution reaction, and the conversion rate of the product is very low, resulting in high price of the product, which makes it difficult for trimethylcyanosilane to be widely used as a cyanidation reagent. |
| Introduction | TMSCN chemical name trimethylsilyl cyanide;Cyanotrimethylsilane, also known as trimethylnitrile silane; Trimethylsilyl cyanide. It is almond flavor colorless liquid, soluble in most organic solvents, such as dichloromethane, chloroform, etc.; And water containing protic solvent reaction. |
| Application | cyanohydrin compounds are an important class of organic synthesis intermediates, which are the synthesis of α-hydroxy acids, α-hydroxy aldehydes, direct starting materials for β-hydroxyamines and the like. Therefore, the preparation of cyanohydrin has attracted wide attention, and the addition reaction of carbonyl compounds with TMSCN (trimethylcyanosilane) is one of the most effective methods for the synthesis of cyanohydrin. |
| preparation | trimethylcyanosilane (TMSCN) can be prepared from lithium cyanide and chlorotrimethylsilane: LiCN (CH3)3SiCl → (CH3)3SiCN LiCl 400kg of N-methyl pyrrolidone was added to the 2000L enamel reactor, then 400kg of sodium cyanide was added, the mixture was stirred for 10 minutes, and 10kg of potassium iodide catalyst was added, trimethylchlorosilane was added dropwise with stirring, and the temperature was controlled below 75 ℃. When trimethylchlorosilane was added dropwise to 950kg, the reaction temperature was controlled at 65 ℃ ~ 70 ℃, refluxed for 24 hours, and filtered, then the filtrate is distilled, and the cut-off component is trimethylcyanosilane (Boiling Point: 112 ℃), the purity is more than 98.5%, and the other components are put into the reaction kettle to continue the secondary reaction, the reaction vessel was heated to 65 ℃ ~ 70 ℃, and the reaction time was 12 hours. After the reaction, the reaction vessel was filtered, and the filtrate was re-rectified, the light component and the reconstituted fraction were sequentially recharged into the reaction vessel as raw materials for the next round of reaction. This process can increase the yield to 89%. |
| safety information | the hydrolysis of trimethylcyanosilane produces highly toxic hydrogen cyanide, so care must be taken to prevent deliquescence: 2 (CH3)3SiCN H2O → (CH3)3SiOSi(CH3)3 2 HCN. |
| analysis of production status | at present, there are few domestic manufacturers of TMSCN, the reaction system is heterogeneous sodium cyanide substitution reaction, and the conversion rate is very low, only about 45%. It can also be replaced by silver cyanide, but the cost is too high and the waste residue is not easy to handle. In addition, when cuprous hydride is used as a raw material to participate in the substitution reaction, the conversion rate of the product is very low, resulting in high price of the product, which makes it difficult for TMSCN to be widely used as a cyanidation reagent. |
| Use | as raw material of organic polymer cyanation reagent |
| production method | 65 grams (1 mole) of dry-boiled potassium in a 1-liter flask, 43.4G and 0.4 mol) trimethylchlorosilane and 1} ML N-methylpyrrolidone. Heat overnight (16 h) with mechanical stirring. At this point the reflux temperature reached approximately 105 °c. Connected to a distillation head and a 15-centimeter-long fractionating column, the pure product was collected to yield 28.0g (71%) after distilling off a small amount of a mixture containing hexamethyldisiloxane and chloromethyltrimethylsilane.. |
Last Update：2024-04-10 22:29:15
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