2,6-Dinitrobenzaldehyde

Base Information

• Chemical Name: 2,6-Dinitrobenzaldehyde
• CAS No.: 606-31-5
• Molecular Formula: C7H4N2O5
• Molecular Weight: 196.119
• Hs Code.: 2913000090
• European Community (EC) Number: 210-113-9
• DSSTox Substance ID: DTXSID90209404
• Nikkaji Number: J134.824H
• Wikidata: Q72472445
• Mol file: 606-31-5.mol

Synonyms:2,6-dinitrobenzaldehyde;2,6-DNBA

Chemical Property of 2,6-Dinitrobenzaldehyde

Chemical Property:

• Vapor Pressure: 1.83E-05mmHg at 25°C
• Melting Point: 120-122 °C(lit.)
• Refractive Index: 1.66
• Boiling Point: 363.2 °C at 760 mmHg
• Flash Point: 192.1 °C
• PSA: 108.71000
• Density: 1.571 g/cm³
• LogP: 2.36190
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 196.01202123
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

99%, ^*data from raw suppliers

2,6-Dinitrobenzaldehyde 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=C(C(=C1)[N+](=O)[O-])C=O)[N+](=O)[O-]
• Uses: 2,6-Dinitrobenzaldehyde was used in the synthesis of free base tetrakis(2,6-dinitrophenyl) porphyrin.

Technology Process of 2,6-Dinitrobenzaldehyde

There total 10 articles about 2,6-Dinitrobenzaldehyde 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: 97.0%

1,2-bis(2,6-dinitrophenyl)ethylene (859961-12-9) → 2,6-dinitrobenzaldehyde (606-31-5)

Guidance literature:

With ozone; In dichloromethane;

Reference yield:

2,6-dinitrotoluene (606-20-2) → 2,6-dinitrobenzaldehyde (606-31-5) + 2,6-dinitrobenzoic acid (603-12-3) + 2,6-dinitrobenzyl alcohol (96839-34-8)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; rat liver microsomal and cytosol proteins; NAD; In water; acetone; at 37 ℃; Product distribution; phosphate buffer, pH = 7.4; besides of NAD, NADH add of NADP, NADH; add of inhibitor: hydralazine;

DOI:10.1248/cpb.37.1904

Reference yield:

2,6-dinitrotoluene (606-20-2) → 2,6-dinitrobenzaldehyde (606-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: N-bromosuccinimide; benzoyl peroxide / CCl₄ / Heating

2: Hg₂(NO₃)2*2H₂O / 1,2-dimethoxy-ethane / 7.5 h / Heating

3: triethylamine / 1,2-dimethoxy-ethane / 1.5 h / Heating

With N-Bromosuccinimide; mercury(I) nitrate; triethylamine; dibenzoyl peroxide; In tetrachloromethane; 1,2-dimethoxyethane;

DOI:10.1080/00304940309355366

upstream raw materials:

(2,6-dinitro-benzyliden)-aniline

2,6-dinitro-benzaldehyde-[N-(4-dimethylamino-phenyl)-oxime ]

2,6-dinitrotoluene

2-(bromomethyl)-1,3-dinitrobenzene

Downstream raw materials:

4,4'-Dibutyl-3,3'-dimethyl-5-oxo-1,5-dihydro-1'H-[2,2']bipyrrolyl-2,5'-dicarboxylic acid diethyl ester

dinitro-2,6 phenyl-bis(methyl-3', butyl-4', ethoxycarbonyl-5', pyrryl-2') methane

3-Butyl-5-(2,6-dinitroso-benzoyl)-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

3-Butyl-5-(2-hydroxyamino-6-nitroso-benzoyl)-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Refernces

• 1、 -. "Preparation method and application of O-nitrobenzaldehyde". Paragraph 0046-0049. . Retrieved 2020/09/23.
• 2、 Mori,Kawajiri,Sayama,Miyahara,Kozuka. "Metabolism of 2,4-dinitrotoluene and 2,6-dinitrotoluene, and their dinitrobenzyl alcohols and dinitrobenzaldehydes by Wistar and Sprague-Dawley rat liver microsomal and cytosol fractions". . p. 1904 - 1908. Retrieved 2007/10/02.