Benzaldehyde, 2,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-nitro-

Base Information

• Chemical Name: Benzaldehyde, 2,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-nitro-
• CAS No.: 860613-38-3
• Molecular Formula: C19H33NO5Si2
• Molecular Weight: 411.646
• DSSTox Substance ID: DTXSID90458571
• Nikkaji Number: J2.190.050H
• Wikidata: Q82281976

Synonyms:860613-38-3;Benzaldehyde, 2,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-nitro-;DTXSID90458571;2,5-Bis(tert-butyldimethylsiloxy)-3-nitrobenzaldehyde

Chemical Property of Benzaldehyde, 2,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-nitro-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 411.18972622
• Heavy Atom Count: 27
• Complexity: 546

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1=CC(=C(C(=C1)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C)C=O

Technology Process of Benzaldehyde, 2,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-nitro-

There total 2 articles about Benzaldehyde, 2,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-nitro- 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: 94.0%

5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-nitro-benzaldehyde + tert-butyldimethylsilyl chloride (18162-48-6) → 2,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-nitro-benzaldehyde (860613-38-3)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/anie.200500247

Reference yield:

5-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzaldehyde (860613-37-2) → 2,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-nitro-benzaldehyde (860613-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / Cu(NO₃)2*3H₂O; Ac₂O / 0 - 25 °C

2: 94 percent / Et₃N / dimethylformamide / 20 °C

With acetic anhydride; copper(II) nitrate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200500247

Reference yield: 99.0%

2,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-nitro-benzaldehyde (860613-38-3) + (R,R)-diisopropyl tartrate (Z)-crotylboronate (106357-20-4) → (1S,2R)-1-[2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-nitro-phenyl]-2-methyl-but-3-en-1-ol (860613-39-4)

Guidance literature:

In dichloromethane; at -78 - 25 ℃;

DOI:10.1002/anie.200500247

upstream raw materials:

tert-butyldimethylsilyl chloride

5-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzaldehyde

Downstream raw materials:

(1S,2R)-1-[2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-nitro-phenyl]-2-methyl-but-3-en-1-ol

(E)-(2R,3R)-4-Ethyl-3-methoxymethoxy-2,6-dimethyl-hepta-4,6-dienoic acid 4-(tert-butyl-dimethyl-silanyloxy)-2-[(1S,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-enyl]-6-nitro-phenyl ester

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