2,4-Diaminotoluene

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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)
ChemSpider
ECHA InfoCard 100.002.231 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 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 as a precursor to toluene diisocyanate, a precursor to polyurethane. It is as well a degradation product of polyurethane materials produced using toluene diisocyanate.

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. [4]

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

Related Research Articles

<i>p</i>-Phenylenediamine Chemical compound

p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

<span class="mw-page-title-main">Toluene diisocyanate</span> Chemical compound

Toluene diisocyanate (TDI) is an organic compound with the formula CH3C6H3(NCO)2. Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is often marketed as 80/20 and 65/35 mixtures of the 2,4 and 2,6 isomers respectively. It is produced on a large scale, accounting for 34.1% of the global isocyanate market in 2000, second only to MDI. Approximately 1.4 billion kilograms were produced in 2000. All isomers of TDI are colorless, although commercial samples can appear yellow.

<span class="mw-page-title-main">Methylene diphenyl diisocyanate</span> Aromatic diisocyanate

Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. This isomer is also known as Pure MDI. MDI reacts with polyols in the manufacture of polyurethane. It is the most produced diisocyanate, accounting for 61.3% of the global market in the year 2000.

<span class="mw-page-title-main">2,4-Dinitrotoluene</span> Organic chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–nCln, where n = 1–5 is the number of chlorine atoms.

<span class="mw-page-title-main">Hexamethylene diisocyanate</span> Chemical compound

Hexamethylene diisocyanate (HDI) is the organic compound with the formula (CH2)6(NCO)2. It is classified as an diisocyanate. It is a colorless liquid. It has sometimes been called HMDI but this not usually done to avoid confusion with Hydrogenated MDI.

1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

Mononitrotoluene or nitrotoluene (MNT or NT), is any of three organic compounds with the formula C6H4(CH3)(NO2). They can be viewed as nitro derivatives of toluene or as methylated derivatives of nitrobenzene.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

<span class="mw-page-title-main">3,3'-Dichlorobenzidine</span> Chemical compound

3,3'-Dichlorobenzidine is an organic compound with the formula (C6H3Cl(NH2))2. The pure compound is pale yellow, but commercial samples are often colored. It is barely soluble in water and is often supplied as a wet paste. It is widely used in the production of diarylide yellow pigments used in the production of printing inks. Its use in the production of dyes has been largely discontinued because of concerns about carcinogenicity.

1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum. It is one of the three isomers of trimethylbenzene. It is used in jet fuel, mixed with other hydrocarbons, to prevent the formation of solid particles which might damage the engine.

4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes.

<span class="mw-page-title-main">2,5-Diaminotoluene</span> Chemical compound

2,5-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. 2,5-Diaminotoluene is a colorless crystalline solid, although commercial samples are often colored owing to air oxidation. It is commonly used in hair coloring.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

<span class="mw-page-title-main">1,4-Dichloro-2-nitrobenzene</span> Chemical compound

1,4-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2NO2. One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline. Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.

<span class="mw-page-title-main">2,5-Dichloroaniline</span> Chemical compound

2,5-Dichloroaniline is an organic compound with the formula C6H3Cl2NH2. One of six isomers of dichloroaniline, it is a colorless solid that is insoluble in water. It is produced by hydrogenation of 1,4-dichloro-2-nitrobenzene. It is a precursor to dyes and pigments, e.g., Pigment Yellow 10.

4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.

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. ↑ Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a27_179
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