p-Toluidine

Base Information

• Chemical Name: p-Toluidine
• CAS No.: 106-49-0
• Deprecated CAS: 12221-03-3
• Molecular Formula: C7H9N
• Molecular Weight: 107.155
• Hs Code.: 38220000
• European Community (EC) Number: 203-403-1,248-105-2
• ICSC Number: 0343
• NSC Number: 15350
• UN Number: 3451,1708
• UNII: I1D0KL7I4U
• DSSTox Substance ID: DTXSID6021872
• Nikkaji Number: J3.612I
• Wikidata: Q2043499
• Pharos Ligand ID: 8Q6LXYWT3Q5Q
• Metabolomics Workbench ID: 55695
• ChEMBL ID: CHEMBL58521
• Mol file: 106-49-0.mol

Synonyms:4-aminotoluene;4-toluidine;4-toluidine dihydrofluoride;4-toluidine hydrobromide;4-toluidine hydrochloride;4-toluidine ion(1+);4-toluidine nitrate;4-toluidine perchlorate;4-toluidine tosylate;4-toluidine, monolithium salt;4-toluidine, sodium salt;p-toluidine;para-toluidine

Chemical Property of p-Toluidine

Chemical Property:

• Appearance/Colour: white lustrous plates or leaflets with an amine odour
• Vapor Pressure: 0.379mmHg at 25°C
• Melting Point: 43 ºC
• Refractive Index: 1.5636
• Boiling Point: 197.4 ºC at 760 mmHg
• PKA: 5.08(at 25℃)
• Flash Point: 84.5 ºC
• PSA: 26.02000
• Density: 0.992 g/cm³
• LogP: 2.15840
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol, pyridine, diethyl ether, acetone, carbon tetrachloride, methanol, carbon disulfide, oils and dilute acids.
• Water Solubility.: 1.1 g/100 mL
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 107.073499291
• Heavy Atom Count: 8
• Complexity: 62.8
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Toluidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T:Toxic;;
• Statements: R23/24/25:; R36:; R40:; R43:; R50:
• Safety Statements: S28A:; S36/37:; S45:; S61:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CC1=CC=C(C=C1)N
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Tumours have been detected in experimental animals but may not be relevant to humans.
• Uses: p-Toluidine is used as an intermediate in themanufacture of various dyes. It is also usedas a reagent for lignin and nitrites. Manufacture of various dyes and other organic chemicals. o-Isomer also in printing textiles blue black; making colors fast to acids. p-Isomer also as a reagent for lignin, nitrite, phloroglucinol. p-Toluidine is an intermediate in the production of dyes, organic chemicals and aromatic azo compounds. It serves as a component of accelerators for cyanoacrylate glues. Furthermore, it acts as a bidentate Schiff base ligand through condensation with salicylaldehyde. It reacts with catecholamine to form a dye which is useful for spectrophotometric determination of catecholamine drugs.

Technology Process of p-Toluidine

There total 819 articles about p-Toluidine 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: 17.0%

1-methyl-4-nitrobenzene (99-99-0) → N-(4-methylphenyl)hydroxylamine (623-10-9) + p-toluidine (106-49-0,12221-03-3)

Guidance literature:

With [Pd₂(2,7-bis(2-pyridinyl)-1,8-naphthyridine)(μ-OH)(CF₃CO₂)₂](CF₃CO₂); hydrogen; In methanol; at 25 ℃; for 6h; under 760.051 Torr;

DOI:10.1021/acs.organomet.7b00460

Reference yield:

N-((1H-pyrrol-2-yl)methylene)-4-methylbenzenamine (14479-37-9) → 2-pyrrole aldehyde (1003-29-8,254729-95-8) + p-toluidine (106-49-0,12221-03-3)

Guidance literature:

With hydrogenchloride; In methanol; water; at 25 ℃; Rate constant; Mechanism; pH=0.65-13.5, buffers, aq.NaOH;

Reference yield:

N-(2,4-Dinitro-phenyl)-N'-p-tolyl-acetamidine (128915-25-3) → 2,4-dinitroacetanilide (610-53-7) + p-toluidine (106-49-0,12221-03-3)

Guidance literature:

With acetic acid; In water; at 25 ℃; Rate constant;

DOI:10.1248/cpb.38.1158

upstream raw materials:

p-aminophenylacetonitrile

p-cresol

diethyl ether

methane

Downstream raw materials:

2-[(4-methylphenyl)amino]-ethanol

N,N-bis-(2-hydroxyethyl)-P-toluidine

1,4-bis(4-methylphenyl)piperazine

2-p-toluidino-ethanethiol

Refernces

• 1、 Jacobson. "". . p. 13. Retrieved 1909.
• 2、 Van Der Waals, Dominic,Pettman, Alan,Williams, Jonathan M. J.. "Copper-catalysed reductive amination of nitriles and organic-group reductions using dimethylamine borane". . p. 51845 - 51849. Retrieved 2014.
• 3、 Adamson, Marquix A. S.,Chen, Yunhua,Daniels, Carena L.,Dorn, Rick W.,Fan, Huajun,Knobeloch, Megan,Rossini, Aaron J.,Vela, Javier,Wu, Hao,Yox, Philip,Zhou, Guoquan. "Intermetallic Nanocatalysts from Heterobimetallic Group 10-14 Pyridine-2-thiolate Precursors". . . Retrieved 2020.
• 4、 Carlin,Wich. "". . p. 4023,4025. Retrieved 1958.
• 5、 Hashimoto, Hideo,Ikemoto, Tomomi,Itoh, Tatsuya,Maruyama, Hideaki,Hanaoka, Tadashi,Wakimasu, Mitsuhiro,Mitsudera, Hiroyuki,Tomimatsu, Kiminori. "Process development of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline dihydrochloride: A key intermediate for TAK-779, a small-molecule nonpeptide CCR5 antagonist". . p. 70 - 73. Retrieved 2002.
• 6、 Mehdizadeh, Soofia,Ahmadi, Seyed Javad,Sadjadi, Sodeh,Outokesh, Mohammad. "Rapid, efficient and selective reduction of aromatic nitro compounds with hydrazine hydrate in the presence of the plain and supported platinum nanoparticles as catalysts". . p. 1587 - 1592. Retrieved 2014.
• 7、 Park, Kwanghee Koh,Oh, Chang Hun,Joung, Won Kyou. "Sodium dithionite reduction of nitroarenes using viologen as an electron phase-transfer catalyst". . p. 7445 - 7446. Retrieved 1993.
• 8、 Han, Byung Hee,Shin, Dae Hyun,Cho, Sung Yun. "GRAPHITE CATAlYZED REDUCTION OF AROMATIC AND ALIPHATIC NITRO COMPOUNDS WITH HYDRAZINE HYDRATE". . p. 6233 - 6234. Retrieved 1985.
• 9、 Kovacic,Bennett. "-". . p. 221,224. Retrieved 1961.
• 10、 Ogata et al.. "-". . p. 2399. Retrieved 1979.