Silane, [(6-bromo-2-naphthalenyl)methoxy](1,1-dimethylethyl)dimethyl-

Base Information

• Chemical Name: Silane, [(6-bromo-2-naphthalenyl)methoxy](1,1-dimethylethyl)dimethyl-
• CAS No.: 100751-62-0
• Molecular Formula: C17H23BrOSi
• Molecular Weight: 351.35300
• DSSTox Substance ID: DTXSID50541716
• Wikidata: Q82418149
• Mol file: 100751-62-0.mol

Synonyms:100751-62-0;Silane, [(6-bromo-2-naphthalenyl)methoxy](1,1-dimethylethyl)dimethyl-;6-bromo-2-(tert-butyldimethylsilyloxymethyl)naphthalene;(6-bromonaphthalen-2-yl)methoxy-tert-butyl-dimethylsilane;((6-Bromonaphthalen-2-yl)methoxy)(tert-butyl)dimethylsilane;[(6-Bromonaphthalen-2-yl)methoxy](tert-butyl)dimethylsilane;ZOOFMPPOMQXNLH-UHFFFAOYSA-N;SCHEMBL3825220;DTXSID50541716;AKOS027446393;(6-bromo-naphthalen-2-ylmethoxy)-tert-butyl-dimethyl-silane

Chemical Property of Silane, [(6-bromo-2-naphthalenyl)methoxy](1,1-dimethylethyl)dimethyl-

Chemical Property:

• PSA: 9.23000
• LogP: 6.12410
• Solubility.: Chloroform, DCM, DMF, DMSO, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 350.07015
• Heavy Atom Count: 20
• Complexity: 323

Purity/Quality:

99% ^*data from raw suppliers

6-Bromo-2-(tert-butyldimethylsilyloxymethyl)naphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1=CC2=C(C=C1)C=C(C=C2)Br
• Uses: 6-Bromo-2-(tert-butyldimethylsilyloxymethyl)naphthalene is an intermediate in the synthesis of 2-Naphthylcarbapenem derivatives with broad spectrum antibiotics with enhanced potency against MRSA.

Technology Process of Silane, [(6-bromo-2-naphthalenyl)methoxy](1,1-dimethylethyl)dimethyl-

There total 3 articles about Silane, [(6-bromo-2-naphthalenyl)methoxy](1,1-dimethylethyl)dimethyl- 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: 77.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (6-bromo-2-naphthy)methanol (100751-63-1) → ((6-bromonaphthalen-2-yl)methoxy)(tert-butyl)dimethylsilane (100751-62-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 25 ℃; for 1h;

Reference yield:

methyl 6-bromo-2-naphthoate (33626-98-1) → ((6-bromonaphthalen-2-yl)methoxy)(tert-butyl)dimethylsilane (100751-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene / -78 °C / Inert atmosphere

2: trimethylamine; dmap / dichloromethane / 25 h / 25 °C / Inert atmosphere

With dmap; diisobutylaluminium hydride; trimethylamine; In dichloromethane; toluene;

DOI:10.1016/j.bmc.2017.06.016

Reference yield:

6-bromo-2-naphthoic acid (5773-80-8) → ((6-bromonaphthalen-2-yl)methoxy)(tert-butyl)dimethylsilane (100751-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / tetrahydrofuran / 16 h / 0 - 25 °C

2: 1H-imidazole / dichloromethane / 1 h / 25 °C

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

upstream raw materials:

tert-butyldimethylsilyl chloride

(6-bromo-2-naphthy)methanol

6-bromo-2-naphthoic acid

methyl 6-bromo-2-naphthoate