5-(t-Butyldimethylsilyloxy)pent-1-yne

Base Information

• Chemical Name: 5-(t-Butyldimethylsilyloxy)pent-1-yne
• CAS No.: 61362-77-4
• Molecular Formula: C11H22OSi
• Molecular Weight: 198.381
• DSSTox Substance ID: DTXSID70446416
• Nikkaji Number: J757.675G
• Wikidata: Q82265048
• Mol file: 61362-77-4.mol

Synonyms:61362-77-4;5-(t-Butyldimethylsilyloxy)pent-1-yne;TERT-BUTYLDIMETHYL(PENT-4-YN-1-YLOXY)SILANE;Silane, (1,1-dimethylethyl)dimethyl(4-pentynyloxy)-;(1,1-DIMETHYLETHYL)DIMETHYL(4-PENTYN-1-YLOXY)SILANE;tert-butyl-dimethyl-pent-4-ynoxysilane;tert-butyl-dimethyl-pent-4-ynoxy-silane;SCHEMBL1578618;DTXSID70446416;FZRCJGZEADULEQ-UHFFFAOYSA-N;1-t-butyldimethylsilyloxy-4-pentyne;1-t-butyldimethylsilyloxypent-4-yne;tert-Butyldimethyl(4-pentynyloxy)silane;5-(tert-Butyldimethylsiloxy)-1-pentyne;5-(tert-butyldimethylsiloxy)pent-1-yne;BS-52667;tert-Butyl-dimethyl-pent-4-ynyloxy-silane;CS-0309758;E73595;5-(tert-Butyldimethylsilyloxy)-1-pentyne, 97%

Chemical Property of 5-(t-Butyldimethylsilyloxy)pent-1-yne

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 198.143991855
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCCC#C

Technology Process of 5-(t-Butyldimethylsilyloxy)pent-1-yne

There total 6 articles about 5-(t-Butyldimethylsilyloxy)pent-1-yne 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%

pent-1-yn-5-ol (5390-04-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-[tert-butyldimethylsilyloxy]pent-1-yne (61362-77-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃;

DOI:10.1016/j.tetlet.2011.01.093

Reference yield: 95.0%

pent-1-yn-5-ol (5390-04-5) + t-butyldimethylsiyl triflate (69739-34-0) → 5-[tert-butyldimethylsilyloxy]pent-1-yne (61362-77-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1016/S0040-4020(02)00656-7

Reference yield: 91.0%

5-hexyl-1-ol (928-90-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-[tert-butyldimethylsilyloxy]pent-1-yne (61362-77-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.201905539

upstream raw materials:

pent-1-yn-5-ol

tert-butyldimethylsilyl chloride

3-(tert-butyldimethylsilyloxy)propyl bromide

dilithium acetylide

Downstream raw materials:

6-(tert-butyldimethylsilanyloxy)-1-cyclohexylhex-2-yn-1-ol

8-((tertbutyldimethylsilyl)oxy)-1-phenyloct-4-yn-3-ol

tert-butyl-(5-cyclohexylpent-4-yn-1-yloxy)dimethylsilane

3-<2-(5-((tert-butyldimethylsilyl)oxy)-1-pentynyl)phenyl>-2-propyn-1-ol

Refernces

• 1、 Codesido, Eva M.,Rodriguez, J. Ramon,Castedo, Luis,Granja, Juan R.. "Toward an analogue of the transition state of preD3-D3 isomerization: Stereoselective synthesis of linearly fused 6-8-6 carbocyclic systems". . p. 1651 - 1654. Retrieved 2002.
• 2、 Kimbrough, Jennifer R.,Austin, Zachary,Milne, Ginger L.,Sulikowski, Gary A.. "Synthesis of a Human Urinary Metabolite of Prostaglandin D2". . p. 10048 - 10051. Retrieved 2019.
• 3、 Fan, Shilu,Zheng, Chenggong,Zheng, Kaiting,Li, Junlan,Liu, Yaomei,Yan, Fangpei,Xiao, Hua,Feng, Yi-Si,Zhu, Yuan-Yuan. "Copper-Catalyzed Perfluoroalkylation of Alkynyl Bromides and Terminal Alkynes". supporting information. p. 3190 - 3194. Retrieved 2021/05/05.
• 4、 Lu, Benjamin L.,Williams, Geoffrey M.,Verdon, Daniel J.,Dunbar, P. Rod,Brimble, Margaret A.. "Synthesis and Evaluation of Novel TLR2 Agonists as Potential Adjuvants for Cancer Vaccines". supporting information. p. 2282 - 2291. Retrieved 2019/10/02.