N,N-Dimethyl-3-nitroaniline

Base Information

• Chemical Name: N,N-Dimethyl-3-nitroaniline
• CAS No.: 619-31-8
• Molecular Formula: C8H10N2O2
• Molecular Weight: 166.18
• Hs Code.: 29214990
• European Community (EC) Number: 210-590-3
• NSC Number: 9814
• UNII: 9QFQ32CUQ5
• DSSTox Substance ID: DTXSID5060699
• Nikkaji Number: J95.675I
• Wikidata: Q81989160
• ChEMBL ID: CHEMBL2023697
• Mol file: 619-31-8.mol

Synonyms:N,N-Dimethyl-3-nitroaniline;619-31-8;3-Nitro-N,N-dimethylaniline;Benzenamine, N,N-dimethyl-3-nitro-;1-(Dimethylamino)-3-nitrobenzene;m-Nitro-N,N-dimethylaniline;N,N-Dimethyl-m-nitroaniline;Aniline, N,N-dimethyl-m-nitro-;Benzene, 1-(dimethylamino)-3-nitro-;NSC 9814;N,N-dimethyl-3-nitro-aniline;AI3-08873;Dimethyl-(3-nitro-phenyl)-amine;NSC-9814;EINECS 210-590-3;NSC9814;MFCD00007236;m-nitrodimethylaniline;3-Nitro-dimethylanilin;9QFQ32CUQ5;Aniline,N-dimethyl-m-nitro-;dimethyl-(3-nitrophenyl)-amine;SCHEMBL1413129;CHEMBL2023697;DTXSID5060699;Benzenamine,N-dimethyl-3-nitro-;N,N-dimethyl-N-(3-nitrophenyl)amine;AKOS003616734;AS-20019;D0759;FT-0629506;F16660;A833492;F0020-1799

Chemical Property of N,N-Dimethyl-3-nitroaniline

Chemical Property:

• Appearance/Colour: red cyrstalline solid
• Vapor Pressure: 0.00334mmHg at 25°C
• Melting Point: 57-61 °C
• Refractive Index: 1.591
• Boiling Point: 282.5 °C at 760 mmHg
• PKA: 2.62(at 25℃)
• Flash Point: 117 °C
• PSA: 49.06000
• Density: 1.193 g/cm³
• LogP: 2.18400
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 166.074227566
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

N,N-Dimethyl-3-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 36/37/38-23/24/25
• Safety Statements: 45-36/37/39-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC(=CC=C1)[N+](=O)[O-]

Technology Process of N,N-Dimethyl-3-nitroaniline

There total 74 articles about N,N-Dimethyl-3-nitroaniline 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: 99.0%

3-chloro-N,N-dimethylaniline (6848-13-1) → N,N-dimethyl-3-nitroaniline (619-31-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite; In tert-butyl alcohol; at 130 ℃; for 24h; regioselective reaction;

DOI:10.1021/ja905768k

Reference yield: 97.0%

N,N-dimethyl-3-nitroaniline N-oxide (109384-41-0) → N,N-dimethyl-3-nitroaniline (619-31-8)

Guidance literature:

With phenylboronic acid; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2017.01.051

Reference yield: 90.0%

4-fluoro-2-nitrobenzonitrile (80517-21-1) → N,N-dimethyl-3-nitroaniline (619-31-8)

Guidance literature:

With sulfuric acid; In water; at 160 - 170 ℃; for 6h;

upstream raw materials:

4-dimethylamino-2-nitro-benzoic acid

N,N-dimethyl-3-nitroaniline N-oxide

N,N,N-trimethyl-3-nitroanilinium iodide

N,N-dimethyl-aniline

Downstream raw materials:

3,3'-bis(dimethylamino)azoxybenzene

N,N-dimethyl-3,4-dinitroaniline

bis-(3-dimethylamino-phenyl)-diazene

N-methyl-N-nitroso-3-nitrobenzenamine

Refernces

• 1、 -. "PYRIMIDINE COMPOUND, PREPARATION METHOD THEREOF AND MEDICAL USE THEREOF". Paragraph 0823; 0824. . Retrieved 2021/04/10.
• 2、 Toyooka, Genki,Tuji, Akiko,Fujita, Ken-Ichi. "Efficient and versatile catalytic systems for the n-methylation of primary amines with methanol catalyzed by n-heterocyclic carbene complexes of iridium". . p. 4617 - 4626. Retrieved 2019/02/01.