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p-Toluidine
[CAS# 106-49-0]

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Identification
ClassificationOrganic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
Namep-Toluidine
Synonyms4-Aminotoluene; 4-Methylaniline
Molecular StructureCAS # 106-49-0, p-Toluidine
Molecular FormulaC7H9N
Molecular Weight107.15
CAS Registry Number106-49-0
EC Number203-403-1
SMILESCC1=CC=C(C=C1)N
Properties
Density0.962
Melting point41-46 °C
Boiling point200 °C
Refractive index1.5636
Flash point87 °C
Water solubility1.1 g/100 mL
Safety Data
Hazard Symbolssymbol symbol symbol symbol   GHS06;GHS07;GHS08;GHS09 Danger  Details
Risk StatementsH301+H311+H331-H301-H311-H317-H319-H331-H351-H400-H411  Details
Safety StatementsP203-P261-P262-P264-P264+P265-P270-P271-P272-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P318-P321-P330-P333+P317-P337+P317-P361+P364-P362+P364-P391-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H311
Acute toxicityAcute Tox.3H301
Acute toxicityAcute Tox.3H331
Acute hazardous to the aquatic environmentAquatic Acute1H400
CarcinogenicityCarc.2H351
Eye irritationEye Irrit.2H319
Skin sensitizationSkin Sens.1H317
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
Skin sensitizationSkin Sens.1AH317
Eye irritationEye Irrit.2AH319
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - repeated exposureSTOT RE1H372
Specific target organ toxicity - single exposureSTOT SE1H370
Acute toxicityAcute Tox.4H302
SDSAvailable
up Discovery and Applications
p-Toluidine, also known as para-toluidine, is an organic compound with the molecular formula C7H9N. It is an aromatic amine characterized by a methyl group and an amino group attached to a benzene ring at the para positions. The compound appears as a colorless to yellowish liquid with a distinctive odor reminiscent of amines. p-Toluidine plays a significant role in various industrial applications and chemical syntheses, making it an important substance in organic chemistry.

The discovery of p-toluidine can be traced back to the 19th century, during a period of intense exploration into the properties of aromatic compounds. It was first isolated from coal tar, a byproduct of the coal distillation process. Over the years, the synthesis of p-toluidine has been refined, and it can now be produced through various methods, including the methylation of aniline or through the reduction of p-nitrotoluene. These methods highlight the versatility of p-toluidine in synthetic organic chemistry.

One of the primary applications of p-toluidine is in the production of dyes and pigments. It serves as a key intermediate in the synthesis of various azo dyes, which are widely used in the textile industry for coloring fabrics. p-Toluidine’s ability to react with diazonium salts allows for the creation of a range of vibrant colors, making it essential for achieving the desired hues in textiles, inks, and plastics. The versatility of p-toluidine in dye production underscores its importance in the chemical industry.

In addition to its role in dye manufacturing, p-toluidine is used in the synthesis of pharmaceuticals and agrochemicals. It acts as an intermediate in the production of various drugs, including analgesics and antihistamines. Its ability to form complex structures through chemical reactions enhances its utility in medicinal chemistry. Moreover, p-toluidine is also involved in the synthesis of pesticides and herbicides, contributing to improved agricultural productivity.

Furthermore, p-toluidine is utilized in the formulation of rubber and plastics. It serves as a stabilizer and processing aid in the production of rubber products, enhancing their performance and durability. The incorporation of p-toluidine into polymer formulations can improve thermal stability and mechanical properties, making it an important additive in the materials industry.

Despite its widespread applications, p-toluidine is associated with potential health and environmental risks. It is classified as a hazardous substance, and exposure can lead to adverse health effects, including skin irritation and respiratory problems. Regulatory agencies have established guidelines to limit exposure and ensure safe handling practices in industrial settings. It is crucial for manufacturers and workers to implement safety measures, such as proper ventilation and personal protective equipment, to mitigate the risks associated with p-toluidine.

In summary, p-toluidine is a vital organic compound with significant applications in the dye, pharmaceutical, and materials industries. Its role as a chemical intermediate highlights its importance in the synthesis of various products, contributing to advancements in textile coloration, drug development, and polymer manufacturing. As research continues to explore safer alternatives and more efficient synthesis methods, p-toluidine is expected to remain a relevant substance in organic chemistry and industrial applications.

References

2005. Structural and ionization effects on the adsorption behaviors of some anilinic compounds from aqueous solution onto high-area carbon-cloth. Journal of Hazardous Materials, 119(1-3), 135-143.
DOI: 10.1016/j.jhazmat.2004.12.030

1964. PHOSPHORUS-NITROGEN COMPOUNDS. II. SOME P-TOLUIDINE DERIVATIVES. Journal of Pharmaceutical Sciences, 53(8), 974-976.
DOI: 10.1002/jps.2600530835

1998. [FTIR-PAS of rare earth coordinated compounds of Schiff base derived from vanillin and p-toluidine]. Guang pu xue yu guang pu fen xi = Guang pu, 18(3), 374-376.
https://pubmed.ncbi.nlm.nih.gov/15810270
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