1118-02-1

Basic information

• Product Name: TRIMETHYLSILYL ISOCYANATE
• Synonyms: trimethylsilanylisocyanate;TRIMETHYLSILYL ISOCYANATE;ISOCYANATOTRIMETHYLSILANE;TRIMETHYLSILYL ISOCYANATE, STAB.;TRIMETHYLSILYLISOCYANATE ,75%;Trimethylsilyl isocyanate,95%;TriMethylsilyl isocyanate, 95% 5GR;Silane,isocyanatotriMethyl-
• CAS NO: 1118-02-1
• Molecular Formula: C4H9NOSi
• Molecular Weight: 115.21
• EINECS: 214-256-8
• Product Categories: Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-N Compounds;Synthetic Organic Chemistry;Trimethylsilylazide, etc.
• Mol File: 1118-02-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: -49°C
• Boiling Point: 90-92 °C(lit.)
• Flash Point: -2 °C
• Appearance: clear colorless liquid
• Density: 0.851 g/mL at 25 °C(lit.)
• Vapor Pressure: 62.1mmHg at 25°C
• Refractive Index: n20/D 1.396(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with ethers and o-dichlorobenzene.
• Sensitive: Moisture Sensitive
• BRN: 1744962
• CAS DataBase Reference: TRIMETHYLSILYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL ISOCYANATE(1118-02-1)
• EPA Substance Registry System: TRIMETHYLSILYL ISOCYANATE(1118-02-1)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23-36/37-42
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2478 3/PG 2
• WGK Germany: 3
• F: 10-19-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 1118-02-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Trimethylsilyl isocyanate is used in the preparation of 1-unsubstituted 4-(dialkylamino) imidazolin-2-ones. It finds application in the carbamoylation of aromatic hydrocarbons and alcohols. It is also used in the preparation of primary amides from Grignard reagents. Further, it is used in the synthesis of cyclic imides. It is also utilized for the synthesis of trifluoroacetyl isocyanate and cyclic imides. In addition to this, it is employed in the conversion of isocyanates to carbodiimides using cyclopentadienyl Mn(CO)3 catalysis.

Purification Methods

Purify it by repeated fractionation as for the isothiocyanate. [Eaborn J Chem Soc 3077 1950, Beilstein 4 III 1861, 4 IV 4011.]

InChI:InChI=1/C4H9NOSi/c1-7(2,3)5-4-6/h1-3H3

Upstream product

• 103-71-9 phenyl isocyanate 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 51649-11-7 Me₃SiNPPh₂CH₃ 
• 4551-15-9 phenylthiotrimethylsilane 
• 55550-17-9 2-isocyanato-1,3,2-benzodioxaphospholane 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 3315-16-0 silver cyanate 
• 2857-97-8 trimethylsilyl bromide 
• 75-77-4 chloro-trimethyl-silane 
• 590-28-3 potassium cyanate 
• 16029-98-4 trimethylsilyl iodide 
• 124-38-9 carbon dioxide 
• 13858-09-8 chlorine isocyanate 
• 917-61-3 sodium isocyanate 

Downstream Products

• 619-55-6 para-methylbenzamide 
• 141579-54-6 N-hydroxy-N-[4-(3-(4-fluorophenoxy)-phenyl)-3-butyn-2-yl]urea 
• 183501-79-3 N,N-diethyl-N'-(chloromethylphenoxyphosphoryl)urea 
• 60561-65-1 α-(o-Anisylamino)-phenylacetamid 

Related news

Interaction of TRIMETHYLSILYL ISOCYANATE (cas 1118-02-1) with xenon difluoride and fluoroxenonium triflate in the presence of alkenes09/24/2019

The title reactions lead to the corresponding β-fluoroisocyanates and β-isocyanatotriflates with the formation of the intermediates FXeNCO and OCNXeOSO2CF3.detailed

Relevant articles and documents

-

-

Photochemical synthesis of a stable terminal uranium(VI) nitride

Terminal uranium nitrides have so far proven impossible to isolate by photolysis of azides. Here we report the second ever example of an isolated terminal uranium(VI) nitride. We show that the terminal nitride [NBu4][U(OSi(OtBu)3)4(N)], 3, can be prepared upon photolysis with UV light of the U(IV) azide analogue. This is achieved by careful tailoring of the azide precursor and of the reaction conditions. Complex 3 is stable under ambient conditions but reacts readily with electrophiles (H+ and CO).

Efficient synthesis of trimethylsilyl pseudohalides catalyzed by PEG400/ZnI2 under ultrasound irradiation

Trimethylsilyl pseudohalides Me3SiX, where X = NCS, NCO, or CN, were readily prepared conveniently in desirable yields by the reaction of Me3SiCl with NaX or KX catalyzed by PEG400 and zinc iodide under ultrasound irradiation. Copyright Taylor & Francis, Inc.

Eine einfache Methode zur Herstellung von Trimethylsilyl-cyanid, -isocyanat und isothiocyanat

-

THE MOLECULAR STRUCTURE OF TRIMETHYLSILYLISOCYANATE IN THE GAS PHASE REDETERMINED BY ELECTRON DIFRACTION

We have redetermined the molecular structure of trimethylsilylisocyanate in the gas phase by electron diffraction.An ra structure is defined with bond distances (pm) SiN 174.0(4), SiC 186.4(2), N=C 120.2(16), C=O 117.6(10) and CH 109.9(5), bond angles (degrees) HCSi 109.0(9), CSiC 108.8(25), SiNC 156.9(30) and NCO 165.8(36), with the N=C bond eclipsing one Si-C bond and the Me3Si group tilted sligthly.The methyl groups are twisted 26.9(35) deg from the position giving the Me3Si group C3v symmetry in an (assumed) concerted fashion.The apparent deviations from linearity of the SiNCO skeleton are shown to be compatible with a pseudolinear structure similar to that of SiH3NCO.

New aspects of isocyanate synthesis with the use of O-silylurethanes

Silyl group at the nitrogen atom in the O-silylurethanes drastically affects the thermolysis processes and allows one to simplify the synthesis of methyl- and trimethylsilyl isocyanates.

-

-

Stoichiometric Reactions of CO2 and Indium-Silylamides and Catalytic Synthesis of Ureas

The indium compounds In(N(SiMe3)2)2Cl?THF (2) and In(N(SiMe3)2)Cl2?(THF)n (3) were shown to react with CO2 to give [(Me3Si)2N)InX(μ-OSiMe3)]2 (X=N(SiMe3)2 4, Cl 5). 0.05–2.0 mol % of the species 3 acts as a pre-catalyst for the conversion of aryl and alkyl silylamines under CO2 (2–3 atm) to give the corresponding ureas in 70–99 % yields. A proposed mechanism is supported by experimental and computational data.