Basic information
- Standard SMILES
C[Si](C)(C)C#N- InChIKey
LEIMLDGFXIOXMT-UHFFFAOYSA-N- Molecular formula
- C4H9NSi
- Average molar mass
- 99.21 g/mol
- Monoisotopic mass
- 99.05042582
Overview
Trimethylsilyl cyanide is a chemical compound of cyanide. It is used in organic synthesis. (L106)
Names & identifiers
- Preferred name
- Trimethylsilyl cyanide
- IUPAC
- trimethylsilylformonitrile
- English name
- Trimethylsilyl cyanide
- Molecular formula
- C4H9NSi
- Molecular weight
- 99.21
Names & synonyms
Show more names
Database identifiers
- CAS
7677-24-9- PubChem CID
- 82115
- DTXSID
DTXSID9064766- UNII
- X7M2DZS7WZ
- EC Number
- 231-657-3
- Nikkaji
- J81.438E
Properties
Computed structural properties
- Topological polar surface area
- 23.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 81.5
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 8 · 8-11 °C(lit.)
- Boiling point
- 114 · 114-117 °C(lit.)
- Density
- 0.793 g/mL · 0.793 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.392(lit.)
- Flash point
- 34 °F · 34 °F
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Miscible with organic solvents.
- form
- liquid
- Specific Gravity
- 0.744 · 0.744
- color
- Yellow
- Water Solubility
- reacts
- Sensitive
- Moisture Sensitive
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- BRN
- 1737612 · 1737612
- Exposure limits
- 25 mg/m3 · NIOSH: IDLH 25 mg/m3
- Stability
- Moisture Sensitive
- InChIKey
- LEIMLDGFXIOXMT-UHFFFAOYSA-N
- CAS DataBase Reference
- 7677 · 7677-24-9(CAS DataBase Reference)
- EPA Substance Registry System
- Silanecarbonitrile, trimethyl- (7677-24-9)
- Symbol(GHS)
- 2 · GHS02,GHS06,GHS09
- Signal word
- Danger
- Hazard statements
- 225 · H225-H300+H310+H330-H410
- Precautionary statements
- 210 · P210-P233-P273-P280-P303+P361+P353-P304+P340+P310
- Hazard Codes
- F,T+,T,N
- Risk Statements
- 11 · 11-26/27/28-29-50/53
- Safety Statements
- 16 · 16-36/37/39-45-61-28A-26
- RIDADR
- 3384 · UN 3384 6.1/PG 1
- WGK Germany
- 3 · 3
- F
- 10 · 10-21
- Hazard Note
- Highly Flammable/Toxic
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29310095 · 29310095
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P320, P321, P330, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 82 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Silanecarbonitrile, trimethyl-
Status: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34122
Trimethylsilyl cyanide: HSNO Approval: HSR004750 Approved with controls
Toxicology
Treatment
Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Toxicity Summary
Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Safety data
- F
- 10-21
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3384 6.1/PG 1
- hs_code
- 29310095
- risk_code
- 11-26/27/28-29-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS09
- hazard_code
- F,T+,T,N
- hazard_note
- Highly Flammable/Toxic
- safety_code
- 16-36/37/39-45-61-28A-26
- hazard_class
- 6.1
- packing_group
- II
- Hazard statements
- H225-H300+H310+H330-H410
- REACH Registrations
- Active
- Precautionary statements
- P210-P233-P273-P280-P303+P361+P353-P304+P340+P310
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
Uses & manufacturing
Applications
UsesReacts with aldehydes and ketones to give cyanohydrin-TMS ethers which can be reduced to β-aminoethyl alcohols.Trimethylsilyl cyanide (TMSCN) participates in carbonyl aminomethylation via α-silyloxy nitriles.TMSCN can be used as a reagent in the:Trimethylsilyl cyanide was used in the second step of an oxidative Michael addition of cyanide anion to Baylis–Hillman adducts. The importance of the addition of cyanide to α,β-unsaturated carbonyl derivatives is that the products can be converted into a variety of compounds including γ-aminobutyric acids. The reaction took place in a liquid ionic medium ([bmim]Br), which was reused several times without losing its activity. The β-cyano carbonyl compounds were obtained with high regioselectivity and yields (>79%).Cyanosilylation of carbonyl compounds using various catalysts.Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.Cyanation of aryl halides using palladium-complex as a catalyst.
UsesCyanotrimethylsilane is a highly versatile reagent that reacts with a multitude of functional groups to yield an array of products and/or highly valuable synthetic intermediates. Aldehydes and ketones are readily transformed into the corresponding cyanohydrin trimethylsilyl ethers when treated with cyanotrimethylsilane in the presence of Lewis acids (eq 1), triethylamine,or solid bases such as CaF2 or hydroxyapatite. The products can be readily hydrolyzed to the corresponding cyanohydrins. The cyanosilylation of aromatic aldehydes can be achieved with high enantioselectivity in the presence of catalytic amounts of a modified Sharpless catalyst consisting of titanium tetraisopropoxide and L-(+)-diisopropyl tartrate (eq 2).Catalysis with chiral titanium reagents yields aliphatic and aromatic cyanohydrins in high chemical and optical yields (eq 3). Cyanohydrins can be subsequently transformed into a variety of useful synthetic intermediates (eq 4).
UsesTrimethylsilyl Cyanide is used as a reagent in the synthesis of optically active cyanohydrins. Used in the preparation of Reissert compounds, which represent reactive polyamides. Toxic to humans.
Preparation methods
PreparationTrimethylsilyl cyanide, (CH3)3 Si-CN, is obtained by reacting trimethylsilyl chloride with an approximately equimolar amount of an alkali metal cyanide in the absence of water and in the presence of catalytic, sub-stoichiometric amounts of both an alkali metal iodide and N-methylpyrrolidone, at a temperature of from 15°-25° C. Trimethylsilyl cyanide is very toxic. All reactions in this sequence should be carried out in a hood. Preparation of trimethylsilyl cyanide TRIMETHYLSILYL CYANIDE: CYANOSILATION OF p-BENZOQUINONE
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
Loading…