5-methoxy-3-nitro-2H-1-benzopyran

Base Information

• Chemical Name: 5-methoxy-3-nitro-2H-1-benzopyran
• CAS No.: 92210-62-3
• Molecular Formula: C10H9NO4
• Molecular Weight: 207.18300
• Hs Code.: 2909199090
• DSSTox Substance ID: DTXSID70533178
• Wikidata: Q82406317
• Mol file: 92210-62-3.mol

Synonyms:5-methoxy-3-nitro-2H-chromene;5-methoxy-3-nitro-2H-1-benzopyran;92210-62-3;SCHEMBL5763685;DTXSID70533178;WMCOCZRHXSXZBH-UHFFFAOYSA-N

Chemical Property of 5-methoxy-3-nitro-2H-1-benzopyran

Chemical Property:

• PSA: 64.28000
• 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:

2H-1-BENZOPYRAN,5-METHOXY-3-NITRO- 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1C=C(CO2)[N+](=O)[O-]

Technology Process of 5-methoxy-3-nitro-2H-1-benzopyran

There total 2 articles about 5-methoxy-3-nitro-2H-1-benzopyran 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: 63.0%

6-methoxysalicylaldehyde (700-44-7) + 2-nitro-1-ethanol (625-48-9) → 5-methoxy-3-nitro-2H-1-benzopyran (92210-62-3)

Guidance literature:

With dibutylamine hydrochloride; In various solvent(s); for 8h; Heating;

DOI:10.1055/s-1984-30841

Reference yield: 49.0%

6-methoxysalicylaldehyde (700-44-7) + 1-nitroethylene (3638-64-0,26618-70-2) → 5-methoxy-3-nitro-2H-1-benzopyran (92210-62-3)

Guidance literature:

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

Reference yield:

5-methoxy-3-nitro-2H-1-benzopyran (92210-62-3) → NDO 008 (109140-25-2)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄, SiO₂ / CHCl₃; propan-2-ol / 0.25 h

2: 40percent hydrazine hydrate / Raney Ni / ethanol / 0.5 h / 45 °C

3: K₂CO₃ aq. / toluene / 48 h / 80 - 90 °C

4: 85 percent / H₂, Et₃N / 10percent Pd/C / ethyl acetate / 0.75 h / Ambient temperature

5: 95 percent / HBr / acetic acid / 4 h / 130 - 140 °C

With sodium tetrahydroborate; hydrogen bromide; hydrogen; silica gel; potassium carbonate; hydrazine hydrate; triethylamine; palladium on activated charcoal; nickel; In ethanol; chloroform; acetic acid; ethyl acetate; isopropyl alcohol; toluene;

DOI:10.1016/0223-5234(91)90145-D

upstream raw materials:

6-methoxysalicylaldehyde

1-nitroethylene

2-nitro-1-ethanol

Downstream raw materials:

(R)-3-amino-5-methoxy-3,4dihydro-2H-1-benzopyran

3-(Di-n-propylamino)-5-methoxychroman

NDO 008

Refernces

• 1、 Hatzenbuhler, Nicole T.,Baudy, Reinhardt,Evrard, Deborah A.,Failli, Amedeo,Harrison, Boyd L.,Lenicek, Steven,Mewshaw, Richard E.,Saab, Annmarie,Shah, Uresh,Sze, Jean,Zhang, Minsheng,Zhou, Dahui,Chlenov, Michael,Kagan, Michael,Golembieski, Jeannette,Hornby, Geoffrey,Lai, Margaret,Smith, Deborah L.,Sullivan, Kelly M.,Schechter, Lee E.,Andree, Terrance H.. "Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2". scheme or table. p. 6980 - 7004. Retrieved 2009/11/30.
• 2、 Neirabeyeh, Mamdouh Al,Koussini, Rafik. "New Direct Synthesis of 3-Nitro-2H-chromenes Using Nitroethylene". . p. 783 - 788. Retrieved 2007/10/02.