1-(Dibutoxymethyl)-2-nitrobenzene

Base Information

• Chemical Name: 1-(Dibutoxymethyl)-2-nitrobenzene
• CAS No.: 53951-34-1
• Molecular Formula: C15H23NO4
• Molecular Weight: 281.352
• DSSTox Substance ID: DTXSID90567253
• Wikidata: Q82453075
• Mol file: 53951-34-1.mol

Synonyms:1-(DIBUTOXYMETHYL)-2-NITROBENZENE;53951-34-1;2-nitrobenzaldehyde dibutyl acetal;SCHEMBL1803434;DTXSID90567253;o-nitrobenzaldehyde dibutyl acetal;QHWNJUDUNHLQCI-UHFFFAOYSA-N

Chemical Property of 1-(Dibutoxymethyl)-2-nitrobenzene

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 281.16270821
• Heavy Atom Count: 20
• Complexity: 257

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCOC(C1=CC=CC=C1[N+](=O)[O-])OCCCC

Technology Process of 1-(Dibutoxymethyl)-2-nitrobenzene

There total 2 articles about 1-(Dibutoxymethyl)-2-nitrobenzene 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: 100.0%

2-nitro-benzaldehyde (552-89-6) + butan-1-ol (71-36-3) → o-nitrobenzaldehyde dibutyl acetal (53951-34-1)

Guidance literature:

toluene-4-sulfonic acid; In toluene; for 48h; Molecular sieve; Heating / reflux;

Reference yield:

→ o-nitrobenzaldehyde dibutyl acetal (53951-34-1)

Guidance literature:

o-Nitrobenzaldehyd, 1-Butanol;

DOI:10.1021/jo00895a037

Reference yield:

o-nitrobenzaldehyde dibutyl acetal (53951-34-1) → (7S,7aS,11aR)-10-methyl-7-phenyl-4-(2,2,2-trifluoroacetyl)-7,7a-dihydropyrano[3,4-c]pyrrolo[3,2,1-ij]quinolin-8(11aH)-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 0.75 h / -45 °C / Sealed tube; Inert atmosphere

1.2: 0.75 h / 25 °C / Sealed tube; Inert atmosphere

2.1: N,N-dimethyl-formamide / 16 h / Reflux; Sealed tube; Inert atmosphere

3.1: acetonitrile / 12 h / Inert atmosphere; Sealed tube; Reflux

4.1: C₂₂H₂₃N₂O⁽¹⁺⁾*Cl^(1-); 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; 1,4-diaza-bicyclo[2.2.2]octane / dimethyl sulfoxide / 12 h / 25 °C / Inert atmosphere; Sealed tube

With 1,4-diaza-bicyclo[2.2.2]octane; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C₂₂H₂₃N₂O⁽¹⁺⁾*Cl^(1-); In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.8b02820

upstream raw materials:

2-nitro-benzaldehyde

butan-1-ol

Downstream raw materials:

2-methyl-1H-indole-7-carbaldehyde

1H-indole-7-carbaldehyde

(1-methyl-1H-indol-7-yl)-methanol

2,3-dimethyl-indole-7-carbaldehyde

Refernces

• 1、 Jadhav, Pankaj P.,Kahar, Nilesh M.,Dawande, Sudam G.. "Ruthenium(II)-Catalyzed Highly Chemo- And Regioselective Oxidative C6 Alkenylation of Indole-7-carboxamides". supporting information. p. 8673 - 8677. Retrieved 2021/11/20.
• 2、 Mukherjee, Subrata,Shee, Sayan,Poisson, Thomas,Besset, Tatiana,Biju, Akkattu T.. "Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles". supporting information. p. 6998 - 7002. Retrieved 2018/11/24.