3,5-Dimethylaniline

Base Information

• Chemical Name: 3,5-Dimethylaniline
• CAS No.: 108-69-0
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 29214990
• European Community (EC) Number: 203-607-0
• ICSC Number: 1687
• NSC Number: 26880
• UN Number: 0077,1711
• UNII: 1418BR6T2H
• DSSTox Substance ID: DTXSID8026309
• Nikkaji Number: J2.426K
• Wikipedia: 3,5-Xylidine
• Wikidata: Q27251562
• ChEMBL ID: CHEMBL1603782
• Mol file: 108-69-0.mol

Synonyms:3,5-dimethylaniline;3,5-DMA cpd

Chemical Property of 3,5-Dimethylaniline

Chemical Property:

• Appearance/Colour: clear yellow-brown to brown liquid
• Vapor Pressure: 0.105mmHg at 25°C
• Melting Point: 7-9 °C
• Refractive Index: n20/D 1.557(lit.)
• Boiling Point: 218.5 °C at 760 mmHg
• PKA: pK1:4.765(+1) (25°C)
• Flash Point: 93.3 °C
• PSA: 26.02000
• Density: 0.972 g/cm³
• LogP: 2.46680
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 80.6
• Transport DOT Label: Explosive 1.3C Poison

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dimethylaniline >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/24/25-33-51/53
• Safety Statements: 28-36/37-45-61-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CC1=CC(=CC(=C1)N)C
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: Exposure at high levels could cause lowering of consciousness. Exposure at high levels could cause formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in anaemia.
• Uses: 3,5-Dimethylaniline is the reagent commonly useful in the manufacture of dyes. It undergoes polymerization in the presence of cerium(IV) sulfate as an oxidant. 3,5-Dimethylaniline was used in the synthesis of chiral packing materials for high performance liquid chromatography.

Technology Process of 3,5-Dimethylaniline

There total 37 articles about 3,5-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: 99.0%

3,5-dimethylphenyl iodide (22445-41-6) → 3,5-dimethylaminoaniline (108-69-0)

Guidance literature:

With copper(I) oxide; ammonium hydroxide; In 1-methyl-pyrrolidin-2-one; at 80 ℃; for 15h;

DOI:10.1039/b904188e

Reference yield: 99.0%

5-nitro-m-xylene (99-12-7) → 3,5-dimethylaminoaniline (108-69-0)

Guidance literature:

With borane-ammonia complex; In methanol; water; at 49.84 ℃; for 0.166667h; Catalytic behavior;

DOI:10.1039/c9dt03838h

Reference yield: 99.0%

1-chloro-3,5-dimethylbenzene (556-97-8) → 3,5-dimethylaminoaniline (108-69-0)

Guidance literature:

With ammonium hydroxide; potassium phosphate; In dimethyl sulfoxide; at 80 ℃; UV-irradiation;

DOI:10.1007/s11426-020-9859-9

upstream raw materials:

3,5-dimethylbenzoic acid

5-nitro-m-xylene

3,5-dimethylbenzamide

2-amino-4,6-dimethylbenzene-1,3-dicarbonitrile

Downstream raw materials:

6-(3,5-Dimethyl-phenylamino)-1H-pyrimidine-2,4-dione

N-(3,5-Dimethylphenyl)acetimidsaeure-ethylester

3,5-dimethyl-benzenesulfonyl chloride

4-(3,5-Dimethyl-phenylamino)-5-methyl-3-nitro-1H-pyridin-2-one

Refernces

• 1、 Brinkman, Herbert R.,Miles, William H.,Hilborn, Michael D.,Smith, Michael C.. "The reduction of nitrobenzenes by triethylsilane using Wilkinson's catalyst". . p. 973 - 980. Retrieved 1996.
• 2、 Zhao, Tian-Jian,Zhang, Jun-Jun,Zhang, Bing,Liu, Yong-Xing,Lin, Yun-Xiao,Wang, Hong-Hui,Su, Hui,Li, Xin-Hao,Chen, Jie-Sheng. "A New Route to Cyclohexanone using H2CO3 as a Molecular Catalytic Ligand to Boost the Thorough Hydrogenation of Nitroarenes over Pd Nanocatalysts". . p. 2837 - 2842. Retrieved 2019.
• 3、 R?sler, Christoph,Dissegna, Stefano,Rechac, Victor L.,Kauer, Max,Guo, Penghu,Turner, Stuart,Ollegott, Kevin,Kobayashi, Hirokazu,Yamamoto, Tomokazu,Peeters, Daniel,Wang, Yuemin,Matsumura, Syo,van Tendeloo, Gustaaf,Kitagawa, Hiroshi,Muhler, Martin,Llabrés I Xamena, Francesc X.,Fischer, Roland A.. "Encapsulation of bimetallic metal nanoparticles into robust zirconium-based metal–organic frameworks: Evaluation of the catalytic potential for size-selective hydrogenation". . p. 3583 - 3594. Retrieved 2017.
• 4、 Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhao, Yongde,Zhou, Yang. "Sustainable and recyclable palladium nanoparticles–catalyzed reduction of nitroaromatics in water/glycerol at room temperature". . p. 540 - 544. Retrieved 2020/07/14.
• 5、 Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao. "Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation". . p. 17 - 21. Retrieved 2020/11/04.