5-Nitro-2-tetralone

Base Information

• Chemical Name: 5-Nitro-2-tetralone
• CAS No.: 89331-01-1
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 2914700090
• DSSTox Substance ID: DTXSID80519741
• Wikidata: Q72496300
• Mol file: 89331-01-1.mol

Synonyms:5-Nitro-2-tetralone;89331-01-1;5-Nitro-3,4-dihydronaphthalen-2(1H)-one;5-nitro-3,4-dihydro-1H-naphthalen-2-one;2(1H)-Naphthalenone,3,4-dihydro-5-nitro-;3,4-Dihydro-5-nitro-2(1H)-naphthalenone;5-nitrotetralin-2-one;starbld0016998;2(1H)-Naphthalenone, 3,4-dihydro-5-nitro-;3,?4-Dihydro-?5-?nitro-2(1H)?-naphthalenone;DTXSID80519741;AKOS015914889;A843129

Chemical Property of 5-Nitro-2-tetralone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Boiling Point: 357.848 °C at 760 mmHg
• Flash Point: 181.329 °C
• PSA: 62.89000
• Density: 1.322 g/cm³
• LogP: 2.17580
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 259

Purity/Quality:

98%Min ^*data from raw suppliers

3,?4-Dihydro-?5-?nitro-2(1H)?-naphthalenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(CC1=O)C=CC=C2[N+](=O)[O-]
• Uses: 3,?4-Dihydro-?5-?nitro-2(1H)?-naphthalenone is used as a building block to syntehsize Benz[cd]?indoles.

Technology Process of 5-Nitro-2-tetralone

There total 1 articles about 5-Nitro-2-tetralone 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: 70.0%

5-Nitro-1,3,4,5-tetrahydro-benzo[cd]indole → 5-nitro-2-oxo-1,2,3,4-tetrahydronaphthalene (89331-01-1)

Guidance literature:

DOI:10.1016/S0040-4039(00)99863-0

Reference yield:

5-nitro-2-oxo-1,2,3,4-tetrahydronaphthalene (89331-01-1) → methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate (3006-19-7,5143-94-2,35470-53-2,77842-02-5,87247-99-2,96648-31-6,96648-32-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 64 percent / benzene / 40 h / Heating

2: 53 percent / NaBH₃CN, 1N HCl / methanol / 1 h / 5 - 10 °C

3: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

4: tetrahydrofuran / 3 h

5: 88 percent / N-ethyl-N-isopropylisopropylamine, POCl₃ / CH₂Cl₂ / 4 h / Ambient temperature

6: 25 percent / BuLi, diisopropylamine / bis-(2-methoxy-ethyl) ether; hexane / -78 deg C, 20 min; -20 deg C, 45 min

With hydrogenchloride; n-butyllithium; hydrogen; sodium cyanoborohydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; diethylene glycol dimethyl ether; benzene;

DOI:10.1002/hlca.19840670732

Reference yield:

5-nitro-2-oxo-1,2,3,4-tetrahydronaphthalene (89331-01-1) → methyl (6aRS,9SS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate (3006-19-7,5143-94-2,35470-53-2,77842-02-5,87247-99-2,96648-31-6,96648-32-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 64 percent / benzene / 40 h / Heating

2: 53 percent / NaBH₃CN, 1N HCl / methanol / 1 h / 5 - 10 °C

3: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

4: tetrahydrofuran / 3 h

5: 88 percent / N-ethyl-N-isopropylisopropylamine, POCl₃ / CH₂Cl₂ / 4 h / Ambient temperature

6: 28 percent / BuLi, diisopropylamine / bis-(2-methoxy-ethyl) ether; hexane / -78 deg C, 20 min; -20 deg C, 45 min

With hydrogenchloride; n-butyllithium; hydrogen; sodium cyanoborohydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; diethylene glycol dimethyl ether; benzene;

DOI:10.1002/hlca.19840670732

Downstream raw materials:

methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate

methyl (6aRS,9SS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate

Refernces