Введение
Группа химических соединений: ариламины
Существует три изомера толуидина, которые являются органическими соединениями. Эти изомеры – о-толуидин, м-толуидин и р-толуидин, причем приставка указывает соответственно ortho, meta и para. Все три – ариламины, химическая структура которых схожа с анилином, за исключением того, что к бензольному кольцу присоединена метильная группа. Различие между этими тремя изомерами заключается в положении, в котором метильная группа (–CH3) связана с кольцом относительно аминогруппы (–NH2); см. иллюстрацию химических структур ниже.
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 amino functional group (–NH2); see illustration of the chemical structures below. Toluidine isomers Methyl position ortho meta para Common name o toluidine m toluidine p toluidine Other names o methylaniline m methylaniline p methylaniline Chemical name 2 methylaniline 3 methylaniline 4 methylaniline Chemical formula C7H9N Molecular mass 107.17 g/mol Glass transition temperature 189 K 187 K Glass not formed Melting point −23 °C −30 °C 43 °C Boiling point 199–200 °C 203–204 °C 200 °C Density 1.00 g/cm3 0.98 g/cm3 1.05 g/cm3 Magnetic susceptibility 76.0 × 10−6 cm3/mol 74.6 × 10−6 cm3/mol 72.1 × 10−6 cm3/mol CAS number [95 53 4] [108 44 1] [106 49 0] SMILES Cc1ccccc1N Cc1cccc(N)c1 Cc1ccc(N)cc1 Disclaimer and references
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.
Изомеры толуидина
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 amino functional group (–NH2); see illustration of the chemical structures below. Toluidine isomers Methyl position ortho meta para Common name o toluidine m toluidine p toluidine Other names o methylaniline m methylaniline p methylaniline Chemical name 2 methylaniline 3 methylaniline 4 methylaniline Chemical formula C7H9N Molecular mass 107.17 g/mol Glass transition temperature 189 K 187 K Glass not formed Melting point −23 °C −30 °C 43 °C Boiling point 199–200 °C 203–204 °C 200 °C Density 1.00 g/cm3 0.98 g/cm3 1.05 g/cm3 Magnetic susceptibility 76.0 × 10−6 cm3/mol 74.6 × 10−6 cm3/mol 72.1 × 10−6 cm3/mol CAS number [95 53 4] [108 44 1] [106 49 0] SMILES Cc1ccccc1N Cc1cccc(N)c1 Cc1ccc(N)cc1 Disclaimer and references
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.
| Метильное положение | орто | мета | пара |
|---|---|---|---|
| Обычное название | о-толуидин | м-толуидин | р-толуидин |
| Другие названия | о-метиланилин | м-метиланилин | р-метиланилин |
| Химическое название | 2-метиланилин | 3-метиланилин | 4-метиланилин |
| Химическая формула | C7H9N | | |
| Молекулярная масса | 107,17 г/моль | | |
| Температура стеклования | 189 K | 187 K | Стекло не образуется |
| Температура плавления | −23 °C | −30 °C | 43 °C |
| Температура кипения | 199–200 °C | 203–204 °C | 200 °C |
| Плотность | 1,00 г/см3 | 0,98 г/см3 | 1,05 г/см3 |
| Магнитная восприимчивость | 76,0 × 10−6 см3/моль | 74,6 × 10−6 см3/моль | 72,1 × 10−6 см3/моль |
| CAS-номер | [95-53-4] | [108-44-1] | [106-49-0] |
| SMILES | Cc1ccccc1N | Cc1cccc(N)c1 | Cc1ccc(N)cc1 |
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 amino functional group (–NH2); see illustration of the chemical structures below. Toluidine isomers Methyl position ortho meta para Common name o toluidine m toluidine p toluidine Other names o methylaniline m methylaniline p methylaniline Chemical name 2 methylaniline 3 methylaniline 4 methylaniline Chemical formula C7H9N Molecular mass 107.17 g/mol Glass transition temperature 189 K 187 K Glass not formed Melting point −23 °C −30 °C 43 °C Boiling point 199–200 °C 203–204 °C 200 °C Density 1.00 g/cm3 0.98 g/cm3 1.05 g/cm3 Magnetic susceptibility 76.0 × 10−6 cm3/mol 74.6 × 10−6 cm3/mol 72.1 × 10−6 cm3/mol CAS number [95 53 4] [108 44 1] [106 49 0] SMILES Cc1ccccc1N Cc1cccc(N)c1 Cc1ccc(N)cc1 Disclaimer and references
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.
В связи с наличием аминогруппы, связанной с ароматическим кольцом, толуидины являются слабыми основаниями. Толуидины плохо растворимы в чистой воде, но хорошо растворяются в кислой воде из-за образования солей аммония, что характерно для органических аминов. Орто- и мета-толуидины – вязкие жидкости, а пара-толуидин – чешуйчатое твердое вещество. Это различие связано с тем, что молекулы р-толуидина более симметричны. р-Толуидин можно получить путем восстановления р-нитротолуола. р-Толуидин реагирует с формальдегидом с образованием основания Трёгера.
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 amino functional group (–NH2); see illustration of the chemical structures below. Toluidine isomers Methyl position ortho meta para Common name o toluidine m toluidine p toluidine Other names o methylaniline m methylaniline p methylaniline Chemical name 2 methylaniline 3 methylaniline 4 methylaniline Chemical formula C7H9N Molecular mass 107.17 g/mol Glass transition temperature 189 K 187 K Glass not formed Melting point −23 °C −30 °C 43 °C Boiling point 199–200 °C 203–204 °C 200 °C Density 1.00 g/cm3 0.98 g/cm3 1.05 g/cm3 Magnetic susceptibility 76.0 × 10−6 cm3/mol 74.6 × 10−6 cm3/mol 72.1 × 10−6 cm3/mol CAS number [95 53 4] [108 44 1] [106 49 0] SMILES Cc1ccccc1N Cc1cccc(N)c1 Cc1ccc(N)cc1 Disclaimer and references
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.
Использование и распространение
Изомер орто производится в наибольших масштабах. Его основное применение – в качестве предшественника пестицидов металахлор и ацетоклор. Другие изомеры толуидина используются в производстве красителей. Они входят в состав ускорителей для цианоакрилатных клеев. У некоторых пациентов о-толуидин является метаболитом прилокаина, что может вызывать метгемоглобинемию. Это состояние лечат метиленовым синим.