2-Benzyloxyphenylisocyanide

Base Information

• Chemical Name: 2-Benzyloxyphenylisocyanide
• CAS No.: 86652-64-4
• Molecular Formula: C14H11NO
• Molecular Weight: 209.247
• European Community (EC) Number: 689-210-7
• DSSTox Substance ID: DTXSID40408566
• Nikkaji Number: J3.010.161H
• Wikidata: Q82214080
• Mol file: 86652-64-4.mol

Synonyms:86652-64-4;1-Benzyloxy-2-isocyano-benzene;2-benzyloxyphenylisocyanide;1-(BENZYLOXY)-2-ISOCYANOBENZENE;Benzene, 1-isocyano-2-(phenylmethoxy)-;1-isocyano-2-phenylmethoxybenzene;2-benzyloxyphenylisonitrile;SCHEMBL1598565;DTXSID40408566;FZJCCDZQKLSBHT-UHFFFAOYSA-N;GS3833;MFCD02664595;2-[(phenylmethyl)oxy]phenyl isocyanide;SB39171;AS-81829;CS-0133092;E81639;EN300-1865616

Chemical Property of 2-Benzyloxyphenylisocyanide

Chemical Property:

• PSA: 9.23000
• LogP: 3.04710
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 209.084063974
• Heavy Atom Count: 16
• Complexity: 249

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: [C-]#[N+]C1=CC=CC=C1OCC2=CC=CC=C2

Technology Process of 2-Benzyloxyphenylisocyanide

There total 6 articles about 2-Benzyloxyphenylisocyanide 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: 93.0%

N-(2-benzyloxyphenyl)formamide (82725-38-0) → 1-benzyloxy-2-isocyanobenzene (86652-64-4)

Guidance literature:

With ethyl phosphodichloridite; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-0030-1260211

Reference yield:

formic acid (64-18-6) + o-(benzyloxy)aniline (20012-63-9) → 1-benzyloxy-2-isocyanobenzene (86652-64-4)

Guidance literature:

formic acid; With acetic anhydride; at 20 - 60 ℃; for 2h; Inert atmosphere;

o-(benzyloxy)aniline; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;

With diisopropylamine; trichlorophosphate; In dichloromethane; at 0 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol2005616

Reference yield:

2-benzyloxynitrobenzene (4560-41-2) → 1-benzyloxy-2-isocyanobenzene (86652-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C

2.1: acetic anhydride / 2 h / 20 - 60 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

2.3: 12 h / 0 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; acetic anhydride; In methanol;

DOI:10.1021/ol2005616

upstream raw materials:

N-(2-benzyloxyphenyl)formamide

formic acid

o-(benzyloxy)aniline

2-benzyloxynitrobenzene

Downstream raw materials:

Retosiban

2-{(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl}-2-(4,6-dimethyl-3-pyridinyl)-N-{2-[(phenylmethyl)oxy]phenyl}acetamide