Isocyanatotrimethylsilane

Base Information

• Chemical Name: Isocyanatotrimethylsilane
• CAS No.: 1118-02-1
• Molecular Formula: C4H9NOSi
• Molecular Weight: 115.207
• Hs Code.: 29319090
• European Community (EC) Number: 214-256-8
• DSSTox Substance ID: DTXSID3061504
• Nikkaji Number: J203.339I
• Wikidata: Q15632694
• Mol file: 1118-02-1.mol

Synonyms:Isocyanatotrimethylsilane;Trimethylsilyl isocyanate;1118-02-1;Silane, isocyanatotrimethyl-;isocyanato(trimethyl)silane;(Trimethylsilyl)isocyanate;EINECS 214-256-8;trimethylsilylisocyanate;Trimethylisocyanatosilane;TMSisocyanate;TMS isocyanate;TMS-isocyanate;TMS isocynate;Me3SiNCO;MFCD00001993;TMSNCO;trimethylsilylisocynate;Trimethylsilyliscyanate;trimethyisiiyiisocyanate;Iscyanatotrimethylsilane;trimethylsilyl isocynate;TMS-NCO;Trimethylsilyl Iscyanate;C4H9NOSi;trimethylsilyl-isocyanate;(trimethylsily)isocyanate;trimethyl silyl isocyanate;(trimethyl)silyl isocyanate;SCHEMBL5463;C4-H9-N-O-Si;Trimethylsilyl Iscyanate, 95%;DTXSID3061504;(Trimethylsilyl)Iscyanate, 95%;ISOCYANATE, TRIMETHYLSILYL;(Trimethylsilyl)isocyanate, 85%;Isocyanic acid, trimethylsilyl ester;GEO-02424;AKOS015840060;BS-44115;T1106;D92451;EN300-100825;J-802299;Q15632694

Chemical Property of Isocyanatotrimethylsilane

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 62.1mmHg at 25°C
• Melting Point: -49 °C
• Refractive Index: n20/D 1.396(lit.)
• Boiling Point: 91 °C at 760 mmHg
• Flash Point: 5.7 °C
• PSA: 29.43000
• Density: 0.85 g/cm³
• LogP: 1.15710
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with ethers and o-dichlorobenzene.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 115.045340445
• Heavy Atom Count: 7
• Complexity: 98.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

Trimethylsilyl Isocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, T
• Hazard Codes: F,T
• Statements: 11-23-36/37-42
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)N=C=O
• 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.

Technology Process of Isocyanatotrimethylsilane

There total 57 articles about Isocyanatotrimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

trimethylsilyl ester of N-trimethylsilyl-N-trimethylsiloxycarbamic acid (70726-27-1) → chloro-trimethyl-silane (75-77-4) + trimethylsilyl isocyanate (1118-02-1)

Guidance literature:

With Phenyltrichlorosilane; at 70 ℃;

DOI:10.1016/j.mencom.2017.01.033

Reference yield: 94.0%

chloro-trimethyl-silane (75-77-4) + carbon dioxide (124-38-9,18923-20-1) + (η5-C5Me5)*Mo{N(iPr)C(Me)N(iPr)}(NSiMe3) → Hexamethyldisiloxane (107-46-0) + trimethylsilyl isocyanate (1118-02-1) + (η5-C5Me5)*Mo{N(iPr)C(Me)N(iPr)}Cl2

Guidance literature:

With 1,2,4,5-tetramethylbenzene; In benzene-d6; at 75 ℃; for 72h; under 3620.13 Torr; Sealed tube;

DOI:10.1002/anie.201502293

Reference yield: 94.0%

chloro-trimethyl-silane (75-77-4) + sodium isocyanate (917-61-3) → trimethylsilyl isocyanate (1118-02-1)

Guidance literature:

With 15-crown-5; at -20 - 120 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejic.202100237

upstream raw materials:

potassium cyanate

chloro-trimethyl-silane

silver cyanate

trimethylsilyl bromide

Downstream raw materials:

methoxycarbonyl isocyanate

5,6,7,8-tetrahydro-[2]naphthamide

(4-Trimethylsilanyloxy-phenyl)-urea

2-ureidobenzoic acid

Refernces

• 1、 Chechik, Victor,Conte, Marco,Dransfield, Trevor,North, Michael,Omedes-Pujol, Marta. "Cyanogen formation during asymmetric cyanohydrin synthesis". . p. 3372 - 3374. Retrieved 2010.
• 2、 Churakov,Ioffe,Voronin,Tartakovsky. "Synthesis of N-nitro-N′-(trimethylsilyl)carbodiimide". . . Retrieved 2017.
• 3、 Yonke, Brendan L.,Reeds, Jonathan P.,Fontaine, Philip P.,Zavalij, Peter Y.,Sita, Lawrence R.. "Catalytic production of isocyanates via orthogonal atom and group transfers employing a shared formal group 6 M(II)/M(IV) redox cycle". . p. 3239 - 3242. Retrieved 2014.
• 4、 Neville,McGee. "". . p. 27,29, 30. Retrieved 1966.
• 5、 Leimeister,Dehnicke. "". . p. C3,C4. Retrieved 1971.
• 6、 Demuth, Joshua C.,Liang, Qiuming,Lin, Jack H.,Neidig, Michael L.,Song, Datong. "Syntheses and characterizations of iron complexes of bulky: O -phenylenediamide ligand". . p. 12287 - 12297. Retrieved 2020.
• 7、 Bl?sing, Kevin,Bresien, Jonas,Maurer, Steffen,Schulz, Axel,Villinger, Alexander. "Trimethylsilyl Pseudohalide Adducts of GaCl3 and B(C6F5)3". supporting information. p. 1913 - 1920. Retrieved 2021/05/10.