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

• 1、 Zhou, Hui,Zhang, Rui,Lu, Xiao-Bing. "Isolable CO2 Adducts of Polarized Alkenes: High Thermal Stability and Catalytic Activity for CO2 Chemical Transformation". . p. 326 - 334. Retrieved 2019.
• 2、 Guizzardi, Benedetta,Mella, Mariella,Fagnoni, Maurizio,Albini, Angelo. "Phenonium ions from the addition of phenyl cations to alkenes. Photochemical synthesis of (rearranged) aminoalkylanilines from haloanilines in the presence of alkenes and amines". . p. 1067 - 1074. Retrieved 2003.
• 3、 Ren, Qinggang,Chen, Yaju,Qiu, Yongjian,Tao, Leiming,Ji, Hongbing. "Ionization of Porous Hypercrosslinked Polymers for Catalyzing Room-Temperature CO2 Reduction via Formamides Synthesis". . p. 2919 - 2927. Retrieved 2021.
• 4、 Arai, Masahiko,Cheng, Haiyang,Lin, Weiwei,Wu, Qifan,Zhang, Chao,Zhao, Fengyu. "Selective N-Methylation of N-Methylaniline with CO2 and H2 over TiO2-Supported PdZn Catalyst". . p. 3285 - 3296. Retrieved 2020.
• 5、 Christman, William E.,Morrow, Travis J.,Arulsamy, Navamoney,Hulley, Elliott B.. "Absolute Estimates of PdII(n2-Arene) C-H Acidity". . p. 2706 - 2715. Retrieved 2018.
• 6、 Fagnoni, Maurizio,Mella, Mariella,Albini, Angelo. "Smooth synthesis of aryl- and alkylanilines by photoheterolysis of haloanilines in the presence of aromatics and alkenes". . p. 1299 - 1301. Retrieved 1999.
• 7、 Pham,Westaway. "Solvent effects on nucleophilic substitution reactions. III. The effect of adding an inert salt on the structure of the SN2 transition state". . p. 2528 - 2530. Retrieved 1996.
• 8、 Sakata et al.. "". . p. 2945. Retrieved 1975.
• 9、 Zhang, Qi,Fu, Ming-Chen,Yu, Hai-Zhu,Fu, Yao. "Mechanism of Boron-Catalyzed N-Alkylation of Amines with Carboxylic Acids". . p. 6235 - 6243. Retrieved 2016.
• 10、 Zhang, Xiaowei,Wang, Sheng,Xi, Chanjuan. "α-Methylation of 2-Arylacetonitrile by a Trimethylamine-Borane/CO2 System". . p. 9744 - 9749. Retrieved 2019.