Name | α-phenyl-2-p-tolylethylamine |
Synonyms | α-phenyl-2-p-tolylethylamine (R)-1-phenyl-(2-p-tolyl)ethylamine Benzeneethanamine, 4-methyl-α-phenyl-, (αR)- |
CAS | 30339-32-3 |
Molecular Formula | C15H17N |
Molar Mass | 211.3 |
Density | 1.037±0.06 g/cm3(Predicted) |
Boling Point | 317.8±11.0 °C(Predicted) |
Physical and Chemical Properties | Chemical quality This product is white needle-like crystal, m.p.169.5 ~ 170 ℃,[α]21D = 69~69.4 (95% ethanol, C≈ 0.5), insoluble in water, soluble in benzene, toluene, ethanol and other organic solvents. |
Use | Uses ()-1-phenyl -2-(p-methylphenyl) ethylamine (PTE), is an important separation agent of pyrethroid, can be used to split (±) CIS, anti-Chrysanthemum acid,(±) trans-Chrysanthemum acid,(±) CIS, trans-dichloro-Chrysanthemum acid,(±)3-methyl -2-(4-chlorophenyl) butyric acid, is an important resolving agent. |
Raw Materials | Nickel Benzaldehyde 4-Chlorobenzaldehyde Benzeneacetonitrile Biphenyl Ethylbenzene Diphenylmethane Sodium ethylate solution,in ethyl alcohol 2-Phenylacetophenone 4-Methylbenzyl chloride |
There are several preparation methods.
Nitrobenzyl method
Nitrobenzyl was added to the ethanol solution of sodium ethoxide, then p-methyl benzyl chloride was added under stirring, and the reaction mixture was refluxed for 10h to obtain 1-nitro-2-(4-methylphenyl) phenylethane, which was reduced by Raney nickel in ethanol at 45~50 ℃ for 6h to obtain the product.
Ammonolysis
The product is obtained by heating 1-chloro -2-(methylphenyl) phenylethane and ammonia in methanol at 110 ℃ for 8h at a pressure of 2.5 MPa. This is an industrial method.
Benzaldehyde method
Benzaldehyde and p-methyl chlorobenzyl are placed in a reaction kettle, condensed to form p-methyl phenylacetophenone, and then reacted with hydroxylamine to form the corresponding oxime compound, and then hydrogenated with 10% palladium/carbon to react at room temperature for 6h to obtain the product.
Benzylacetonitrile method
2-(4-methylbenzyl) phenylacetonitrile was obtained with phenylacetonitrile and p-methylbenzyl chloride, which was further hydrolyzed in an aqueous solution of sodium hydroxide containing H2O2 and Bu4NOH to obtain the corresponding amide, which was refluxed with bromine at 0 ℃ under the condition of adding a small amount of Bu4NOH in a methanol solution containing NaOH to obtain the product.
No matter which of the above methods is used to obtain 1-phenyl-2-(p-methylphenyl) ethylamine is a racemic compound. To be resolved, cinnamic acid can be used to separate ()-1-Phenyl -2-(p-methylphenyl) ethylamine; it can also be resolved with other resolution agents.