4-(Trimethylsilyl)-3-butyn-2-one

Base Information

• Chemical Name: 4-(Trimethylsilyl)-3-butyn-2-one
• CAS No.: 5930-98-3
• Molecular Formula: C7H12OSi
• Molecular Weight: 140.257
• Hs Code.: 29319090
• European Community (EC) Number: 628-294-1
• DSSTox Substance ID: DTXSID20370434
• Nikkaji Number: J911.706G
• Wikidata: Q72514438
• Mol file: 5930-98-3.mol

Synonyms:4-(trimethylsilyl)-3-butyn-2-one;TMSB compound

Chemical Property of 4-(Trimethylsilyl)-3-butyn-2-one

Chemical Property:

• Appearance/Colour: clear slightly yellow liquid
• Vapor Pressure: 2.03E-05mmHg at 25°C
• Melting Point: 99 °C
• Refractive Index: n20/D 1.442(lit.)
• Boiling Point: 144.6 °C at 760 mmHg
• Flash Point: 41.2 °C
• PSA: 17.07000
• Density: 0.875 g/cm³
• LogP: 1.45620
• Storage Temp.: Flammables area
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 140.065741536
• Heavy Atom Count: 9
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

4-(Trimethylsilyl)-3-butyn-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C#C[Si](C)(C)C
• Uses: 4-(Trimethylsilyl)-3-butyn-2-one (TMSB) has been used to investigate its asymmetric bioreduction to (S)-4-(trimethylsilyl)-3-butyn-2-ol {(S)-TMSBOL} by employing biocompatible water-immiscible ionic liquids (ILs). TMSB may be used for the synthesis of entecavir (BMS-200475).

Technology Process of 4-(Trimethylsilyl)-3-butyn-2-one

There total 19 articles about 4-(Trimethylsilyl)-3-butyn-2-one 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: 96.0%

(η5-C5H4Si(CH3)3)2Ti(CCC(CH3)3)2CuCCSi(CH3)3 + acetic anhydride (108-24-7) → (C5H4Si(CH3)3)2Ti(C2C(CH3)3)2CuOCOCH3 + 4-trimethylsilyl-3-butyn-2-one (5930-98-3)

Guidance literature:

In tetrahydrofuran; acetic anhydride was added dropwise to a soln. of complex in THF at -20°C, stirred for 1 h, gradually warmed to 25°C, stirred for 2 h at 25°C; volatiles were removed in vac., the organic products were extd. with cold (-20°C) diethyl ether, the residue was dried in vac.;

DOI:10.1016/S0022-328X(00)00793-2

Reference yield: 92.33%

acetyl chloride (75-36-5) + Bis(trimethylsilyl)ethyne (14630-40-1) → 4-trimethylsilyl-3-butyn-2-one (5930-98-3)

Guidance literature:

With aluminium trichloride; In carbon disulfide;

Reference yield: 90.0%

4-trimethylsilyl-3-butyn-2-ol (103253-60-7,121522-26-7,121522-27-8,6999-19-5) → 4-trimethylsilyl-3-butyn-2-one (5930-98-3)

Guidance literature:

With Iron(III) nitrate nonahydrate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; sodium chloride; In toluene; at 20 - 55 ℃; for 7.4h;

DOI:10.1055/s-0031-1290811

upstream raw materials:

4-trimethylsilyl-3-butyn-2-ol

acetic anhydride

trimethylsilylacetylene

Bis(trimethylsilyl)ethyne

Downstream raw materials:

4-Acetyl-5-(trimethylsilyl)-3-phenyl-pyridazin

(4-Methoxy-phenyl)-[1-methyl-3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-amine

7-methyl-1H-pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

ethyl 2,6-dimethylnicotinate

Refernces

• 1、 -. "INDOLE CARBOXAMIDE COMPOUNDS AND USE THEREOF FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS". Page/Page column 46; 47. . Retrieved 2021/04/02.
• 2、 Li, Zhen,Yu, Hao,Liu, Yang,Zhou, Leijie,Sun, Zhanhu,Guo, Hongchao. "Phosphane-Catalyzed [3+3] Annulation of C,N-Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen-Fused Heterocycles". supporting information. p. 1880 - 1885. Retrieved 2016/07/06.