5-Hydroxy-4-methoxy-2-nitrobenzaldehyde

Base Information

• Chemical Name: 5-Hydroxy-4-methoxy-2-nitrobenzaldehyde
• CAS No.: 58749-47-6
• Molecular Formula: C8H7NO5
• Molecular Weight: 197.147
• Hs Code.: 2913000090
• NSC Number: 142136
• DSSTox Substance ID: DTXSID80301264
• Nikkaji Number: J484.058E
• Wikidata: Q82044976
• Mol file: 58749-47-6.mol

Synonyms:5-hydroxy-4-methoxy-2-nitrobenzaldehyde;58749-47-6;5-Hydroxy-4-methoxy-2-nitro-benzaldehyde;6-Nitroisovanillin;NSC142136;benzaldehyde, 5-hydroxy-4-methoxy-2-nitro-;SCHEMBL5898860;DTXSID80301264;PTULGYAZUWPSQM-UHFFFAOYSA-N;MFCD00228444;AKOS000312928;3-hydroxy4-methoxy-6-nitrobenzaldehyde;NSC-142136;3-hydroxy-4-methoxy-6-nitrobenzaldehyde;BS-44337;CS-0187806;E76199;InChI=1/C8H7NO5/c1-14-8-3-6(9(12)13)5(4-10)2-7(8)11/h2-4,11H,1H

Chemical Property of 5-Hydroxy-4-methoxy-2-nitrobenzaldehyde

Chemical Property:

• Vapor Pressure: 1.17E-07mmHg at 25°C
• Boiling Point: 420.2°Cat760mmHg
• Flash Point: 207.9°C
• PSA: 92.35000
• Density: 1.456g/cm³
• LogP: 1.64470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 197.03242232
• Heavy Atom Count: 14
• Complexity: 226

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxy-4-methoxy-2-nitrobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)[N+](=O)[O-])C=O)O

Technology Process of 5-Hydroxy-4-methoxy-2-nitrobenzaldehyde

There total 9 articles about 5-Hydroxy-4-methoxy-2-nitrobenzaldehyde 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: 89.0%

2-aldehyde-4-benzyloxy-5-methoxy nitrobenzene (58662-50-3) → 3-hydroxy-4-methoxy-6-nitrobenzaldehyde (58749-47-6)

Guidance literature:

With trifluoroacetic acid; at 0 - 60 ℃;

DOI:10.1021/acs.jmedchem.1c01272

Reference yield: 67.5%

isovanillin (621-59-0) + lanthanum(III) nitrate hexahydrate → 3-hydroxy-4-methoxy-6-nitrobenzaldehyde (58749-47-6)

Guidance literature:

With hydrogenchloride; sodium nitrate; sodium chloride; sodium hydrogencarbonate; In tetrahydrofuran; water;

Reference yield: 66.1%

6-nitro-1,3-benzodioxole-5-carbaldehyde (712-97-0) → 6-nitrovanillin (2454-72-0) + 3-hydroxy-4-methoxy-6-nitrobenzaldehyde (58749-47-6)

Guidance literature:

With sodium; In methanol; dimethyl sulfoxide; at 150 ℃; for 0.0583333h;

DOI:10.1248/cpb.40.1691

upstream raw materials:

2-aldehyde-4-benzyloxy-5-methoxy nitrobenzene

6-nitro-1,3-benzodioxole-5-carbaldehyde

methanol

isovanillin

Downstream raw materials:

4-methoxy-2-nitro-3-pentyloxybenzaldehyde

5-(tert-butyldimethylsilyloxy)-4-methoxy-2-nitrobenzaldehyde

5-acetoxy-4-methoxy-2-nitrobenzaldehyde

Refernces

• 1、 Greene, Thomas F.,Wang, Shu,Greene, Lisa M.,Nathwani, Seema M.,Pollock, Jade K.,Malebari, Azizah M.,McCabe, Thomas,Twamley, Brendan,OBoyle, Niamh M.,Zisterer, Daniela M.,Meegan, Mary J.. "Synthesis and Biochemical Evaluation of 3-Phenoxy-1,4-diarylazetidin-2-ones as Tubulin-Targeting Antitumor Agents". . p. 90 - 113. Retrieved 2016/01/29.
• 2、 Ty, Nancy,Dupeyre, Gregory,Chabot, Guy G.,Seguin, Johanne,Tillequin, Francois,Scherman, Daniel,Michel, Sylvie,Cachet, Xavier. "Synthesis and biological evaluation of new disubstituted analogues of 6-methoxy-3-(3′,4′,5′-trimethoxybenzoyl)-1H-indole (BPR0L075), as potential antivascular agents". . p. 7494 - 7503. Retrieved 2008/12/23.