O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol

Base Information

• Chemical Name: O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol
• CAS No.: 152893-54-4
• Molecular Formula: C10H21IOSi
• Molecular Weight: 312.266
• DSSTox Substance ID: DTXSID00451457
• Nikkaji Number: J2.279.610K
• Wikidata: Q82271496
• Mol file: 152893-54-4.mol

Synonyms:O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol;152893-54-4;tert-butyl-[(E)-3-iodobut-2-enoxy]-dimethylsilane;1-(tert-Butyldimethylsiloxy)-3-iodo-2-butene;DTXSID00451457;tert-Butyl{[(2E)-3-iodobut-2-en-1-yl]oxy}dimethylsilane

Chemical Property of O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol

Chemical Property:

• PSA: 9.23000
• LogP: 4.34700
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 312.04064
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

97% ^*data from raw suppliers

O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCO[Si](C)(C)C(C)(C)C)I
• Isomeric SMILES: C/C(=C\CO[Si](C)(C)C(C)(C)C)/I
• Uses: O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol is a reagent used in the synthesis of Retinoids.

Technology Process of O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol

There total 5 articles about O-tert-Butyldimethylsilyl-3-iodo-(2E)-buten-1-ol 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%

t-butyldimethylsiyl triflate (69739-34-0) + (E)-β-iodocrotyl alcohol (37428-58-3) → (E)-tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane (152893-54-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1055/s-0037-1610387

Reference yield: 88.0%

(but-2-yn-1-yloxy)(tert-butyl)dimethylsilane (83591-03-1) → (E)-tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane (152893-54-4)

Guidance literature:

(but-2-yn-1-yloxy)(tert-butyl)dimethylsilane; With zirconocene dichloride; diisobutylaluminium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

With iodine; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2017.03.089

Reference yield: 68.0%

(E)-β-iodocrotyl alcohol (37428-58-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (E)-tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane (152893-54-4)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201812096

upstream raw materials:

(E)-β-iodocrotyl alcohol

tert-butyldimethylsilyl chloride

(but-2-yn-1-yloxy)(tert-butyl)dimethylsilane

methyl propargyl alcohol

Downstream raw materials:

3-{(1E,3E,7E)-9-[(tert-butyl)dimethylsilyloxy]-3,7-dimethylnona-1,3,7-trien-5-ynyl}-2,4,4-trimethylcyclohex-2-en-1-ol

((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane

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