2,4-Diaminotoluene

2,4-Diaminotoluene
Names
	Preferred IUPAC name 4-Methylbenzene-1,3-diamine
	Other names 2,4-Toluenediamine
Identifiers
CAS Number	95-80-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	6991;
ECHA InfoCard	100.002.231
PubChem CID	7261;
UNII	IS1AKN4HYB ;
CompTox Dashboard (EPA)	DTXSID4020402 ;
	SMILES CC1=C(C=C(C=C1)N)N;
Properties
Chemical formula	C7H10N2
Molar mass	122.171 g·mol−1
Appearance	White 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
REL (Recommended)	Ca
IDLH (Immediate danger)	Ca [N.D.]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

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.

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

^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405
^ Mahood, S. A.; Schaffner, P. V. L. (1931). "2,4-Diaminotoluene". Organic Syntheses. 11: 32. doi:10.15227/orgsyn.011.0032.
^ 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. doi:10.1016/j.apcata.2023.119459. ISSN 0926-860X.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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). doi:10.1061/(ASCE)EE.1943-7870.0001740. ISSN 0733-9372.
^ 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. doi:10.1016/j.tox.2005.05.021. ISSN 0300-483X. PMID 15996806.

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-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. 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). 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. doi:10.1016/j.tox.2005.05.021. ISSN 0300-483X. PMID 15996806.

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