N,N-Dimethylaniline

Base Information

• Chemical Name: N,N-Dimethylaniline
• CAS No.: 121-69-7
• Deprecated CAS: 162744-63-0,168153-21-7,171745-67-8,171745-67-8
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 2921.42
• European Community (EC) Number: 204-493-5
• ICSC Number: 0877
• NSC Number: 7195
• UN Number: 2253
• UNII: 7426719369
• DSSTox Substance ID: DTXSID2020507
• Nikkaji Number: J2.488K
• Wikipedia: Dimethylaniline
• Wikidata: Q310473
• Metabolomics Workbench ID: 37554
• ChEMBL ID: CHEMBL371654
• Mol file: 121-69-7.mol

Synonyms:N,N-dimethylaniline;N,N-dimethylaniline hydrochloride;N,N-dimethylaniline hydroiodide;N,N-dimethylaniline sulfate (1:1)

Chemical Property of N,N-Dimethylaniline

Chemical Property:

• Appearance/Colour: A yellow to brown colored oily liquid with a fishlike odor
• Vapor Pressure: 2 mm Hg ( 25 °C)
• Melting Point: 1100 °C(lit.)
• Refractive Index: 1.5580
• Boiling Point: 193.539 °C at 760 mmHg
• PKA: 5.15(at 25℃)
• Flash Point: 62.778 °C
• PSA: 3.24000
• Density: 1.038 g/mL at 25 °C
• LogP: 1.75260
• Storage Temp.: 0-6°C
• Solubility.: 1.2g/l
• Water Solubility.: 1 g/L (20 ºC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 72.6
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

N,N-Dimethylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 61-20/21-51/53-40-23/24/25
• Safety Statements: 53-45-61-36/37-28A-28

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CN(C)C1=CC=CC=C1
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure far above the OEL could cause lowering of consciousness. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Physical properties: Straw to brown-colored oily liquid with a characteristic amine-like odor. Odor threshold concentration is 13 ppb (quoted, Amoore and Hautala, 1983).
• Uses: N,N-Dimethylaniline is used in production of dyestuffs, as a solvent, a reagent in methylation reactions, and a hardener in fiberglass reinforced resins. N,N-dimethylaniline is an important dye intermediate. It can be used to prepare alkaline yellow, Crystal Violet 5BN, basic magenta green, basic lake blue BB, basic brilliant blue R, cationic red 2BL, brilliant red 5GN, violet 3BL, brilliant blue, etc. In the pharmaceutical industry, the product can be used to manufacture cefazolin V, sulfamonomethoxine, Sulfadoxine, fluorocytosine, etc. moreover, It can be used as an intermediate to vanillin, a stabilizer for colorimetric peroxidase determination or as a reagent in chemical synthesis.

Technology Process of N,N-Dimethylaniline

There total 702 articles about N,N-Dimethylaniline 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: 94.0%

lithium iodide monohydrate + 4-(dimethylamino)phenylthallium bis(trifluroacetate) * 2CF3COOH → thallium(III) iodide (13453-37-7) + lithium trifluoroacetate (2923-17-3) + N,N-dimethyl-aniline (121-69-7,77733-26-7)

Guidance literature:

In acetone; -70°C, several hours, warming to room temp.; redn. of vol. (distn., vac., room temp.), pptn. on addn. of water, crystn. (overnight), dissolving (acetone), pptn. on pentane addn., crystn. (several days);

Reference yield: 88.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + phenyltrimethylammonium chloride (138-24-9) → para-methoxynitrobenzene (100-17-4) + N,N-dimethyl-aniline (121-69-7,77733-26-7)

Guidance literature:

With caesium carbonate; In toluene; for 48h; Heating;

DOI:10.3891/acta.chem.scand.51-0343

Reference yield: 66.0%

bis(chloromethyl)mercury (5293-94-7) + N-methylaniline (100-61-8) → 4,4'-methylenebis(N-methylaniline) (1807-55-2) + N,N-dimethyl-aniline (121-69-7,77733-26-7)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 36h;

upstream raw materials:

methanol

sodium methylate

phenyltrimethylammonium iodide

aniline hydrochloride

Downstream raw materials:

(N-methyl-anilinomethyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

2-Benzoxazolinone

N'-(2-hydroxy-phenyl)-N-methyl-N-phenyl-urea

N-methyl-N-nitrosoaniline

Refernces

Characterisation of the first authenticated organomercury hydroxide, 4-Me₂NC₆H₄HgOH

10.1016/j.jorganchem.2003.10.040

The study presents the synthesis and comprehensive characterization of 4-Me2NC6H4HgOH, the first verified organomercury hydroxide that crystallizes as discrete molecules in the solid state. The researchers detail its preparation from 4-Me2NC6H4HgOAc and discuss the structures of related compounds, including 4-Me2NC6H4HgOAc and (4-Me2NC6H4)2Hg. The study delves into the complex history of organomercury hydroxides, resolving previous conflicting reports and misconceptions about their existence and properties. It also explores the behavior of these compounds in aqueous solution, pointing to pH-dependent equilibria involving various species. The researchers used techniques such as electrospray mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, and X-ray crystallography to characterize the compounds. The results provide a clear structural and spectral signature of 4-Me2NC6H4HgOH, confirming its status as a true organomercury hydroxide and contributing to a better understanding of arylmercury chemistry.

Photocyclization and photooxidation of 3-styrylthiophene

10.1016/S0040-4039(00)00097-6

The study focuses on the photocyclization and photooxidation processes of 3-styrylthiophene, a compound with two isomers: trans-3-styrylthiophene (1) and cis-3-styrylthiophene (2). The research investigates how these isomers react under different photochemical conditions, including in nonpolar and polar solvents, with and without sensitizers. The key findings include that cis-3-styrylthiophene (2) undergoes photochemical cis–trans isomerization and cyclization to form dihydronaphtho-[1,2-b]thiophene (3), with a higher quantum efficiency in nonpolar solvents. Dye-sensitized photooxidation of 3-styrylthiophene results in the production of benzaldehyde and 3-thiophenecarboxaldehyde, and the process is suggested to occur via a superoxide radical anion pathway rather than through singlet oxygen. Additionally, auto-photooxidation in the presence of oxygen leads to photocyclization, oxidation, and dimerization products. The study proposes that these reactions may involve the formation of a charge transfer complex between oxygen and the substrate. The research is significant for understanding the behavior of polythiophenes, which are important for the production of conductive polymers, and could contribute to improving the photostability of these materials.