3-(Trimethylsilyl)propiolic acid

Base Information

• Chemical Name: 3-(Trimethylsilyl)propiolic acid
• CAS No.: 5683-31-8
• Molecular Formula: C6H10O2Si
• Molecular Weight: 142.23
• Hs Code.: 29319090
• European Community (EC) Number: 628-042-0
• DSSTox Substance ID: DTXSID40375385
• Nikkaji Number: J988.424F
• Wikidata: Q72514556
• Mol file: 5683-31-8.mol

Synonyms:3-(Trimethylsilyl)propiolic acid;5683-31-8;3-(Trimethylsilyl)propynoic acid;3-trimethylsilylprop-2-ynoic Acid;3-trimethylsilylpropynoic acid;Trimethylsilylpropiolic acid;2-Propynoic acid, 3-(trimethylsilyl)-;3-(trimethylsilyl)prop-2-ynoic acid;MFCD00190216;3-(TRIMETHYLSILYL)PROPIOLICACID;C6H10O2Si;TMS-propynoic acid;SCHEMBL1285864;DTXSID40375385;IPEATTYBFBRNEB-UHFFFAOYSA-N;3-(Trimethylsilyl)propargylic Acid;AKOS006220775;CS-W018277;DS-4941;3-(Trimethylsilyl)propynoic acid, 98%;?3-(TRIMETHYLSILYL)PROPIOLIC ACID;SY040249;FT-0651711;T3040;C75665;EN300-203654;A831194;3-trimethylsilylprop-2-ynoic acid

Chemical Property of 3-(Trimethylsilyl)propiolic acid

Chemical Property:

• Vapor Pressure: 0.046mmHg at 25°C
• Melting Point: 47-49 °C(lit.)
• Refractive Index: 1.452
• Boiling Point: 219.1 °C at 760 mmHg
• PKA: 1.88±0.10(Predicted)
• Flash Point: 86.3 °C
• PSA: 37.30000
• Density: 1.006 g/cm³
• LogP: 0.95180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 142.045006092
• Heavy Atom Count: 9
• Complexity: 176

Purity/Quality:

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

3-(Trimethylsilyl)propiolic Acid >97.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC(=O)O
• Uses: 3-(Trimethylsilyl)propiolic acid may be used in the regioselective preparation of 1,5-trisubstituted 1H-1,2,3-triazoles. It is also used as pharmaceutical intermediate.

Technology Process of 3-(Trimethylsilyl)propiolic acid

There total 7 articles about 3-(Trimethylsilyl)propiolic acid 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: 100.0%

carbon dioxide (124-38-9,18923-20-1) + trimethylsilylacetylene (1066-54-2) → 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 78 ℃; for 0.5h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

DOI:10.1039/c3cc48486f

Reference yield: 90.0%

3-trimethylsilyl-2-propyn-1-ol (5272-36-6) → 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8)

Guidance literature:

With jones reagent; In acetone; at 0 ℃;

DOI:10.1039/c39850000421

Reference yield: 70.0%

chloro-trimethyl-silane (75-77-4) + propiolic acid dianion (54620-69-8) → 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8)

Guidance literature:

upstream raw materials:

chloro-trimethyl-silane

propiolic acid dianion

3-trimethylsilyl-2-propyn-1-ol

carbon dioxide

Downstream raw materials:

ethyl 3-(trimethylsilyl)propynoate

4,5-Dimethyl-2-(trimethylsilyl)-1,4-cyclohexadien-1-carbonsaeure

3-(trimethylsilyl)propynoyl chloride

3-(4-carboxy-benzyl)-3H-[1,2,3]triazole-4-carboxylic acid

Refernces

• 1、 Song, Fengbin,Chen, Lu,Lin, Ronghui,Salter, Rhys. "Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) and [1-14C]-CA (PEG)n via oxa-Michael addition of amino-polyethylene glycols to propiolates vs to acrylates". . p. 15 - 24. Retrieved 2019/12/30.
• 2、 Trivedi, Manoj,Smreker, Jacob R.,Singh, Gurmeet,Kumar, Abhinav,Rath, Nigam P.. "Cis -1,2-Bis(diphenylphosphino)ethylene copper(i) catalyzed C-H activation and carboxylation of terminal alkynes". . p. 14145 - 14151. Retrieved 2017/11/28.