6-Methoxy-3-nitro-2H-chromene

Base Information

• Chemical Name: 6-Methoxy-3-nitro-2H-chromene
• CAS No.: 92210-61-2
• Molecular Formula: C10H9 N O4
• Molecular Weight: 207.18
• Hs Code.: 2909199090
• DSSTox Substance ID: DTXSID10533177
• Nikkaji Number: J2.859.178K
• Wikidata: Q82406315
• Mol file: 92210-61-2.mol

Synonyms:92210-61-2;6-METHOXY-3-NITRO-2H-CHROMENE;2H-BENZOPYRAN,6-METHOXY-3-NITRO-;6-methoxy-3-nitro-2H-1-benzopyran;DTXSID10533177

Chemical Property of 6-Methoxy-3-nitro-2H-chromene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 90 °C(Solv: hexane (110-54-3))
• Refractive Index: 1.595
• Boiling Point: 347.759°C at 760 mmHg
• Flash Point: 168.07°C
• PSA: 64.28000
• Density: 1.344g/cm³
• LogP: 2.22840
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 207.05315777
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

99% ^*data from raw suppliers

6-methoxy-3-nitro-2H-chromene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)OCC(=C2)[N+](=O)[O-]

Technology Process of 6-Methoxy-3-nitro-2H-chromene

There total 2 articles about 6-Methoxy-3-nitro-2H-chromene 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: 85.0%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + 2-nitro-1-ethanol (625-48-9) → 6-methoxy-3-nitro-2H-1-benzopyran (92210-61-2)

Guidance literature:

With phthalic anhydride; dibutylamine; In toluene; Heating;

Reference yield: 72.0%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + 1-nitroethylene (3638-64-0,26618-70-2) → 6-methoxy-3-nitro-2H-1-benzopyran (92210-61-2)

Guidance literature:

With dibutylamine; In chloroform; at 80 ℃; for 24h;

Reference yield: 93.0%

6-methoxy-3-nitro-2H-1-benzopyran (92210-61-2) + 1-benzyl-2-vinyl-1H-indole (81787-95-3) → (6aS,13cR)-9-benzyl-2-methoxy-6a-nitro-6,6a,7,8,9,13c-hexahydrochromeno[3,4-c]carbazole (1370549-72-6)

Guidance literature:

With C₄₂H₃₃N₃O₂; zinc trifluoromethanesulfonate; In toluene; at 20 ℃; for 17h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/asia.201100820

upstream raw materials:

2-hydroxy-5-methoxybenzaldehyde

1-nitroethylene

2-nitro-1-ethanol

Downstream raw materials:

6-methoxy-3-amino-3,4-dihydro-2H-1-benzopyran

(6aS,13cR)-9-benzyl-2-methoxy-6a-nitro-6,6a,7,8,9,13c-hexahydrochromeno[3,4-c]carbazole

Refernces

• 1、 Wu, Na,Wahl, Benoit,Woodward, Simon,Lewis, William. "1,4-addition of TMSCCl3 to nitroalkenes: Efficient reaction conditions and mechanistic understanding". supporting information. p. 7718 - 7724. Retrieved 2014/07/07.
• 2、 Viaud,Mamai,Guerin,Bennejean,Renard,Delagrange,Guardiola-Lemaitre,Howell,Guillaumet. "Substituted 3-amido and 3-amidoalkylbenzopyran derivatives: Synthesis and pharmacological activity as melatonin ligands". . p. 47 - 56. Retrieved 2007/10/03.