2,4-Diaminotoluene

Last updated
2,4-Diaminotoluene
2,4-diaminotoluene.png
Names
Preferred IUPAC name
4-Methylbenzene-1,3-diamine
Other names
2,4-Toluenediamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.231 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-453-1
KEGG
PubChem CID
RTECS number
  • XS9445000
UNII
UN number 1709
  • InChI=1S/C7H10N2/c1-5-2-3-6(8)4-7(5)9/h2-4H,8-9H2,1H3
    Key: VOZKAJLKRJDJLL-UHFFFAOYSA-N
  • CC1=C(C=C(C=C1)N)N
Properties
C7H10N2
Molar mass 122.171 g·mol−1
AppearanceWhite solid
Density 1.521 g/cm3
Melting point 97 to 99 °C (207 to 210 °F; 370 to 372 K)
Boiling point 283 to 285 °C (541 to 545 °F; 556 to 558 K)
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
Ca [1]
IDLH (Immediate danger)
Ca [N.D.] [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4-Diaminotoluene is an aromatic organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid, although commercial samples are often yellow-tan. [2]

Contents

Preparation

It is prepared by hydrogenation of 2,4-dinitrotoluene using a nickel catalyst. Commercial samples often contain up to 20% of the 2,6-isomer. [2]

A laboratory method involves reduction of 2,4-dinitrotoluene with iron powder. [3]

Use

It is mainly used to manufacture toluene diisocyanate, which is a key raw material in polyurethane chemistry. [4] It is still the starting material used when non-phosgene methods of production of toluene diisocyanate are used. [5] [6]

It is also a degradation product of polyurethane materials produced using toluene diisocyanate.

Synthesis of C.I. Basic Yellow 9, an acridine dye. SynthesisBasicYellow9.png
Synthesis of C.I. Basic Yellow 9, an acridine dye.

Its reaction with benzenediazonium chloride gives the cationic azo dye Basic Orange 1. Condensation of 2,4-diaminotoluene with acetaldehyde gives the acridine dye called Basic Yellow 9. [7]

Toxicity

Aromatic amines in general often are classed as toxic and so the toxicity profile of this species has been studied. [8] [9] [10] It has received more in depth study in the 21st century. [11] [12]

References

  1. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a19_405
  3. ↑ Mahood, S. A.; Schaffner, P. V. L. (1931). "2,4-Diaminotoluene" . Organic Syntheses. 11: 32. doi:10.15227/orgsyn.011.0032.
  4. ↑ Ji, Lu; Li, Fang; Che, Conghui; Xue, Wei; Yang, Qiusheng; Ding, Xiaoshu; Zhang, Dongsheng; Zhao, Xinqiang; Wang, Yanji (October 2023). "Single-atom Au-modified CeO2 catalyst: Structure and its catalytic performance in 2,4-diaminotoluene methoxycarbonylation reaction" . Applied Catalysis A: General. 667 119459. Bibcode:2023AppCA.667k9459J. doi:10.1016/j.apcata.2023.119459. ISSN   0926-860X.
  5. ↑ Sun, Shuai; Liang, Ning; An, Hualiang; Zhao, Xinqiang; Wang, Guirong; Wang, Yanji (2013-06-12). "Kinetics for Dimethyl Toluene-2,4-dicarbamate Synthesis from 2,4-Diaminotoluene, Urea, and Methanol" . Industrial & Engineering Chemistry Research. 52 (23): 7684–7689. doi:10.1021/ie4005095. ISSN   0888-5885.
  6. ↑ Juárez, Raquel; Padilla, Ana; Corma, Avelino; García, Hermenegildo (2008-11-05). "Organocatalysts for the Reaction of Dimethyl Carbonate with 2,4-Diaminotoluene" . Industrial & Engineering Chemistry Research. 47 (21): 8043–8047. doi:10.1021/ie800126t. ISSN   0888-5885.
  7. ↑ Gessner, Thomas; Mayer, Udo (2000). "Triarylmethane and Diarylmethane Dyes". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_179. ISBN   978-3-527-30385-4.
  8. ↑ National Toxicology Program (1979). "Bioassay of 2,4-diaminotoluene for possible carcinogenicity". National Cancer Institute Carcinogenesis Technical Report Series. 162: 1–139. ISSN   0163-7185. PMID   12799700.
  9. ↑ George, E.; Westmoreland, C. (1991). "Evaluation of the in vivo genotoxicity of the structural analogues 2,6-diaminotoluene and 2,4-diaminotoluene using the rat micronucleus test and rat liver UDS assay" . Carcinogenesis. 12 (12): 2233–2237. doi:10.1093/carcin/12.12.2233. ISSN   0143-3334. PMID   1747922.
  10. ↑ Bermudez, Edilberto; Tillery, Deborah; Butterworth, Byron E. (January 1979). "The effect of 2,4-diaminotoluene and isomers of dinitrotoluene on unscheduled dna synthesis in primary rat hepatocytes" . Environmental Mutagenesis. 1 (4): 391–398. doi:10.1002/em.2860010412. ISSN   0192-2521. PMID   553809.
  11. ↑ Femina Carolin, C.; Senthil Kumar, P.; Janet Joshiba, G.; Ramamurthy, Racchana; Varjani, Sunita J. (July 2020). "Bioremediation of 2,4-Diaminotoluene in Aqueous Solution Enhanced by Lipopeptide Biosurfactant Production from Bacterial Strains" . Journal of Environmental Engineering. 146 (7) 04020069. doi:10.1061/(ASCE)EE.1943-7870.0001740. ISSN   0733-9372.
  12. ↑ Séverin, Isabelle; Jondeau, Adeline; Dahbi, Laurence; Chagnon, Marie-Christine (2005-09-15). "2,4-Diaminotoluene (2,4-DAT)-induced DNA damage, DNA repair and micronucleus formation in the human hepatoma cell line HepG2" . Toxicology. 213 (1): 138–146. Bibcode:2005Toxgy.213..138S. doi:10.1016/j.tox.2005.05.021. ISSN   0300-483X. PMID   15996806.
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