P toluidine

P toluidine DEFAULT
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p-toluidine, 4-toluidine, p-tolylamine, 4-aminotoluene, benzenamine, 4-methyl, 4-methylbenzenamine, p-methylaniline, p-methylbenzenamine, p-toluidin, p-aminotoluene
p-toluidine, 4-toluidine, p-tolylamine, 4-aminotoluene, benzenamine, 4-methyl, 4-methylbenzenamine, p-methylaniline, p-methylbenzenamine, p-toluidin, p-aminotoluene


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.

Soluble in ethanol, pyridine, diethyl ether, acetone, carbon tetrachloride, methanol, carbon disulfide, oils and dilute acids.

Incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.


SensitivityAir and light sensitive
Boiling Point199°C to 202°C
Flash Point88°C (190°F)
Melting Point42°C to 46°C
UN NumberUN3451
Merck Index14,9536
Solubility InformationSoluble in ethanol,pyridine,diethyl ether,acetone,carbon tetrachloride,methanol,carbon disulfide,oils and dilute acids.
Formula Weight107.16
Percent Purity≥99%
Chemical Name or Materialp-Toluidine
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Safety and Handling

GHS H Statement
Toxic if swallowed.
Toxic in contact with skin.
Toxic if inhaled.
Suspected of causing cancer.
Causes serious eye irritation.
May cause an allergic skin reaction.



DOTInformation : Transport Hazard Class: 6.1; Packing Group: II; Proper Shipping Name: TOLUIDINES, SOLID

EINECSNumber : 203-403-1

RTECSNumber : XU3150000

TSCA : Yes

Recommended Storage : Ambient temperatures


Sours: https://www.fishersci.com/shop/products/p-toluidine-99-thermo-scientific/AAA1369830


Data at NIST subscription sites:

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  • Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
  • The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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Sours: https://webbook.nist.gov/cgi/cbook.cgi?ID=106-49-0
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Group of chemical compounds: aryl amines

There are three isomers of toluidine, which are organic compounds. These isomers are o-toluidine, m-toluidine, and p-toluidine, with the prefixed letter abbreviating, respectively, ortho; meta; and para. All three are aryl amines whose chemical structures are similar to aniline except that a methyl group is substituted onto the benzene ring. The difference between these three isomers is the position where the methyl group (–CH3) is bonded to the ring relative to the aminofunctional group (–NH2); see illustration of the chemical structures below.[1]

The chemical properties of the toluidines are quite similar to those of aniline, and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic. The toluidines are poorly soluble in pure water but dissolve well in acidic water due to formation of ammonium salts, as usual for organic amines. ortho- and meta-toluidines are viscous liquids, but para-toluidine is a flaky solid. This difference is related to the fact that the p-toluidine molecules are more symmetrical. p-Toluidine can be obtained from reduction of p-nitrotoluene. p-Toluidine reacts with formaldehyde to form Tröger's base.

Uses and occurrence[edit]

The ortho isomer is produced on the largest scale. Its primary application is as a precursor to the pesticides metolachlor and acetochlor.[1] The other toluidine isomers are used in the production of dyes. They are a component of accelerators for cyanoacrylate glues (for example sold as the brand name Zip Kicker).

In some patients o-toluidine is a metabolite of prilocaine, which may cause methemoglobinemia. This is then treated with methylene blue.


  1. ^ abBowers, Joseph S. "Toluidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_159.
  2. ^ abPratesi, G.; Bartolini, P.; Senatra, D.; Ricci, M.; Righini, R.; Barocchi, F.; Torre, R. (2003). "Experimental studies of the ortho-toluidine glass transition". Physical Review E. 67 (2). doi:10.1103/PhysRevE.67.021505.
  3. ^Alba-Simionesco, C.; Fan, J.; Angell, C. A. (1999). "Thermodynamic aspects of the glass transition phenomenon. II. Molecular liquids with variable interactions". The Journal of Chemical Physics. 110 (11): 5262. doi:10.1063/1.478800.

External links[edit]

Sours: https://en.wikipedia.org/wiki/Toluidine

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Toluidine p

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Benzocaine synthesis step1: Synthesis of p-acetotoluidide and p-acetamidobenzoic acid

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