2-Propyn-1-ol, 3-(trimethylsilyl)-

Base Information

• Chemical Name: 2-Propyn-1-ol, 3-(trimethylsilyl)-
• CAS No.: 5272-36-6
• Molecular Formula: C6H12OSi
• Molecular Weight: 128.246
• Hs Code.: 29319090
• European Community (EC) Number: 226-094-5
• NSC Number: 617397
• DSSTox Substance ID: DTXSID8063751
• Nikkaji Number: J297.971C
• Wikidata: Q72514559
• Mol file: 5272-36-6.mol

Synonyms:5272-36-6;3-(Trimethylsilyl)propargyl alcohol;3-Trimethylsilyl-2-propyn-1-ol;3-(trimethylsilyl)prop-2-yn-1-ol;2-Propyn-1-ol, 3-(trimethylsilyl)-;3-(Trimethylsilyl)-2-propyn-1-ol;3-trimethylsilylprop-2-yn-1-ol;1-Trimethylsilylpropargyl alcohol;3-Trimethylsilylpropargyl alcohol;3-trimethylsilanyl-prop-2-yn-1-ol;EINECS 226-094-5;MFCD00002913;NSC617397;SCHEMBL140849;3-Trimethylsilylpropargylalcohol;AMY827;DTXSID8063751;3-(Trimethylsilyl)propargylalcohol;BCP21769;AKOS015950997;3-(Trimethylsilyl)-2-propyn-1-ol #;CS-W007721;NSC-617397;s20100;DS-14632;SY020094;3-(Trimethylsilyl)propargyl alcohol, 99%;CS-0173149;FT-0601962;T1500;EN300-129296;A829227;J-802120;J-802302;3-(Trimethylsilyl)prop-2-yn-1-ol

Chemical Property of 2-Propyn-1-ol, 3-(trimethylsilyl)-

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Melting Point: 63.5-65.0 °C
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 176.3 °C at 760 mmHg
• PKA: 13.71±0.10(Predicted)
• Flash Point: 46.4 °C
• PSA: 20.23000
• Density: 0.889 g/cm³
• LogP: 0.85950
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Benzene (Sparingly)
• Water Solubility.: Not miscible with water.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 128.065741536
• Heavy Atom Count: 8
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

TrimethylsilylpropargylAlcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CCO
• Uses: Trimethylsilylpropargyl alcohol is used as a reagent to synthesize Isbogrel, a Thromboxane A 2 (TXA 2) synthase inhibitor and also a TXA 2 receptor antagonist that has potential to treat asthma.

Technology Process of 2-Propyn-1-ol, 3-(trimethylsilyl)-

There total 22 articles about 2-Propyn-1-ol, 3-(trimethylsilyl)- 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%

3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne (36551-06-1) → 3-trimethylsilyl-2-propyn-1-ol (5272-36-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; Ambient temperature;

DOI:10.1016/0040-4020(96)00264-5

Reference yield: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + trimethylsilylacetylene (1066-54-2) → 3-trimethylsilyl-2-propyn-1-ol (5272-36-6)

Guidance literature:

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

formaldehyd; In tetrahydrofuran; hexane; at 20 ℃; for 12h;

DOI:10.1002/chem.200401065

Reference yield: 99.0%

chloro-trimethyl-silane (75-77-4) + propargyl alcohol (107-19-7) → 3-trimethylsilyl-2-propyn-1-ol (5272-36-6)

Guidance literature:

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

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c3ob42191k

upstream raw materials:

chloro-trimethyl-silane

propargyl alcohol

3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne

3-(tetrahydropyran-2'-yloxy)propyne

Downstream raw materials:

trimethyl(phenyl)(1-phenyl-1,2-propadienyl)silane

3-trimethylsilyl-1-propanol

(2E)-3-(trimethylsilyl)prop-2-en-1-ol

3-bromo-1-(trimethylsilyl)-1-propyne

Refernces

• 1、 Magnus, Philip,Exon, Christopher,Albaugh-Robertson, Pamela. "DICOBALTOCTACARBONYL-ALKYNE COMPLEXES AS INTERMEDIATES IN THE SYNTHESIS OF BICYCLOOCTENONES FOR THE SYNTHESIS OF CORIOLIN AND HIRSUTIC ACID". . p. 5861 - 5869. Retrieved 1985.
• 2、 Medvedeva,Novokshonov,Demina,Voronkov. "An unusual rearrangement of 1-trimethylsiloxy-3-bromomagnesium-2-propyne". . p. 481 - 482. Retrieved 1998.
• 3、 Bourkhis, Maroua,Gaspard, Hafida,Rullière, Pauline,de Almeida, Diana K. C.,Listunov, Dymytrii,Joly, Etienne,Abderrahim, Raoudha,de Mattos, Marcos C.,de Oliveira, Maria C. F.,Maraval, Valérie,Chauvin, Remi,Génisson, Yves. "Skeletal Optimization of Cytotoxic Lipidic Dialkynylcarbinols". . p. 1124 - 1130. Retrieved 2018.
• 4、 Yamahira, Tatsuya,Onodera, Gen,Fukuda, Tsutomu,Kimura, Masanari. "Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide". supporting information. p. 853 - 855. Retrieved 2021/05/19.
• 5、 Oka, Kengo,Fuchi, Shunsuke,Komine, Keita,Fukuda, Hayato,Hatakeyama, Susumi,Ishihara, Jun. "Catalytic Asymmetric Total Synthesis of Exiguolide". supporting information. p. 12862 - 12867. Retrieved 2020/09/16.