3-(Trimethylsilyl)prop-2-ynoyl chloride

Base Information

• Chemical Name: 3-(Trimethylsilyl)prop-2-ynoyl chloride
• CAS No.: 66224-70-2
• Molecular Formula: C6H9ClOSi
• Molecular Weight: 160.675
• European Community (EC) Number: 826-467-8
• Nikkaji Number: J2.125.444D
• Mol file: 66224-70-2.mol

Synonyms:3-(trimethylsilyl)prop-2-ynoyl chloride;66224-70-2;3-(trimethylsilyl)propioloyl chloride;3-trimethylsilylprop-2-ynoyl Chloride;C6H9ClOSi;trimethylsilylpropynoyl chloride;SCHEMBL8331605;3-(trimethylsilyl)propioloylchloride;MFCD25965940;AKOS040766035;AT35549;SY296206;EN300-342084

Chemical Property of 3-(Trimethylsilyl)prop-2-ynoyl chloride

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 160.0111191
• Heavy Atom Count: 9
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC(=O)Cl

Technology Process of 3-(Trimethylsilyl)prop-2-ynoyl chloride

There total 3 articles about 3-(Trimethylsilyl)prop-2-ynoyl chloride 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: 80.0%

3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) → 3-(trimethylsilyl)propynoyl chloride (66224-70-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

DOI:10.1007/s11178-005-0367-8

Reference yield: 55.0%

3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) → (E,Z)-3-chloro-3-trimethylsilyl-2-propenoyl chloride + 3-(trimethylsilyl)propynoyl chloride (66224-70-2)

Guidance literature:

With thionyl chloride; for 0.25h; Heating;

DOI:10.1007/s11178-005-0367-8

Reference yield:

trimethylsilylacetylene (1066-54-2) → 3-(trimethylsilyl)propynoyl chloride (66224-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 20 °C

1.2: 16 h / -20 - 20 °C

2.1: oxalyl dichloride; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 1 h / 20 °C

With oxalyl dichloride; ethylmagnesium bromide; N,N-dimethyl-formamide; In tetrahydrofuran; 2-methyltetrahydrofuran;

DOI:10.1002/adsc.201300055

upstream raw materials:

3-(trimethylsilyl)prop-2-ynoic acid

trimethylsilylacetylene

Downstream raw materials:

1,2-Bis(trimethylsilylpropiolo)toluenesulfonylhydrazide

3-trimethylsilanylpropynoic acid benzylisopropenylamide

N-benzyl-3-(trimethylsilyl)prop-2-ynamide

N-[4-hydroxy-4-(2-prop-2-yn-1-yl-phenyl)but-2-yn-1-yl]-N-methyl-3-(trimethylsilyl)prop-2-ynamide

Refernces

• 1、 Medvedeva,Andreev,Safronova,Afonin. "Synthesis of trimethylsilylpropynoyl chloride". . p. 1463 - 1466. Retrieved 2005.
• 2、 Shiu, Hoi-Yan,Chong, Hiu-Chi,Leung, Yun-Chung,Zou, Taotao,Che, Chi-Ming. "Phosphorescent proteins for bio-imaging and site selective bio-conjugation of peptides and proteins with luminescent cyclometalated iridium(iii) complexes". . p. 4375 - 4378. Retrieved 2014.
• 3、 -. "COMPOUNDS AND METHODS OF USE". Page/Page column 80-83; 90-92; 124; 125. . Retrieved 2021/03/05.
• 4、 -. "COMPOUNDS AND METHOD OF USE". Paragraph 1435. . Retrieved 2019/09/06.