Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate
N-(Ethoxycarbonylphenyl)-N'-Methyl-N'-Phenylformamidine
CAS: 57834-33-0
Molecular Formula: C17H18N2O2
Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate - Names and Identifiers
| Name | N-(Ethoxycarbonylphenyl)-N'-Methyl-N'-Phenylformamidine |
| Synonyms | UV-1 UV absorber-1 UvAbsorberUv-1 Ultraviolet absorbent UV-1 4-[[(METHYLPHENYLAMINO)METHYLENE]AMINO]-BENZOIC ACID 4-[[(METHYLPHENYLAMINO)MEHTYLENE]AMINO]-BENZOIC ACID ethyl 4-[[(methylphenylamino)methylene]amino]benzoate N-(Ethoxycabonylphenyl)-N'-methyl-N'-phenyl formamidine N-(ethoxycarbonylphenyl)-N'-methy-N'-phenyl formamidine N-(Ethoxycarbonylphenyl)-N'-Methyl-N'-Phenylformamidine N-(Ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine N-(4-Ethoxycarbonylphenyl)-N'-Methyl-N'-Phenyl Formamidine N-(P-Ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine 4-[[(methylphenylamino)methylene]amino]-benzoicaciethylester ethyl 4-({(E)-[methyl(phenyl)amino]methylidene}amino)benzoate Benzoicacid,4-[[(methylphenylamino)methylene]amino]-,ethylester |
| CAS | 57834-33-0 |
| EINECS | 260-976-0 |
| InChI | InChI=1/C17H18N2O2/c1-3-21-17(20)14-9-11-15(12-10-14)18-13-19(2)16-7-5-4-6-8-16/h4-13H,3H2,1-2H3/b18-13+ |
Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate - Physico-chemical Properties
| Molecular Formula | C17H18N2O2 |
| Molar Mass | 282.34 |
| Density | 1.05±0.1 g/cm3(Predicted) |
| Boling Point | 188 °C(Press: 0.1 Torr) |
| Flash Point | 206°C |
| Water Solubility | 34.7mg/L at 20℃ |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| Vapor Presure | 78Pa at 25℃ |
| Appearance | Light Yellow to Yellow Semi-Solid |
| pKa | 6.94±0.50(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.547 |
| Use | Is a highly effective anti-UV additives, widely used in polyurethane, adhesives, foam and other materials |
Ethyl 4-[[(methylphenylamino)methylene]amino]benzoate - Reference Information
| LogP | 4.46 at 25℃ |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| properties | the chemical name of UV absorber UV-1 is: N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine, whose English name is:[ethyl 4-[(N-methylanilino)methylideneamino]benzoate]. Molecular formula: C17H18N2O2, molecular weight: 282.3,CAS number: 57834-33-0. UV absorber UV-1 is light yellow liquid, water is less than or equal to 1.0%, boiling point is 188~190 ℃/13Pa, relative density: 1.127, viscosity (20 ℃) about 4752mPa · s, the refractive index was 1.64. Solubility:> 50 in ethanol,> 50 in isopropanol,> 50 in butyl acetate, and zero in water. In terms of PU, UV-1 is better than other anti-UV agents, for foam materials, coatings, leather and board, etc. |
| Application | UV-1 excellent UV absorption function, and has good compatibility with epoxy resin, used in adhesives, potting, crystal glue and other materials, especially suitable for outdoor use, high requirements for light resistance products. |
| preparation | with ethyl 4-aminobenzoate, triethyl orthoformate and N-methylaniline as raw materials, the UV absorber N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (UV-1) was synthesized with an overall yield of 82.5%. Synthesis of ethyl (4-ethoxycarbonylphenyl) formamidinate to a four-necked flask were added 82.6g(0.5mol) of ethyl 4-aminobenzoate and 148.2g(1 mol) of triethyl orthoformate, the reaction was heated to 70-145 °c with stirring until the appropriate amount of ethanol was distilled off. Reaction by thin layer chromatography to detect the progress of the reaction, sampling analysis, the content of ethyl 4-aminobenzoate <0.5%, the end of the reaction. Excess triethyl orthoformate was removed by vacuum evaporation and can be applied in the next experiment. The distillation of the residue in the flask was continued under high vacuum to obtain about 93.9g of the desired intermediate, ethyl (4-ethoxycarbonylphenyl) formamidinate in a yield of 85.0% with a content of 99.6%. The obtained intermediate, ethyl (4-ethoxycarbonylphenyl) formamidinate, is a white crystal with a melting point of 41-42 ℃ and a boiling point of 142 ℃ /13Pa, which is consistent with those reported in the literature. This step reaction is more important, improper control of the process point will produce a large number of by-products, affecting the yield and content. The production of by-products during the reaction can be controlled by the amount of ethanol distilled off and the manner in which it is distilled off. This intermediate is unstable and is recommended to be prepared when needed. The recovered triethyl orthoformate can be applied directly. If the reaction is carried out according to the literature at 145 ° C., irrespective of the mode of ethanol distillation, the yield of this step is only 35%. Synthesis of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (4-ethoxycarbonylphenyl) was added to a four-necked flask. Formamidine acid ethyl ester 110G and N-methyl aniline 54g, stirring and heating to 190 ℃ to maintain the reaction, until the appropriate amount of ethanol distilled out, reaction by thin layer chromatography to detect the progress of the reaction, the content of ethyl (4-ethoxycarbonylphenyl) formaminate was analyzed by sampling to be <0.5%. The remaining yellow oil was flash evaporated under a vacuum of 13PA at 188-190 °c to give 136.9G of the target product in 97% yield. The product is light yellow liquid with boiling point of 188~190 ℃ /13Pa, which is consistent with that reported in the literature. The refractive index is 1.64, and the viscosity (20 ℃) is about 4752mPa · s. Through the analysis of Shanghai Haixin company's gas chromatograph GC-950, the content of the product is 99% (area normalization method). The refractive index, viscosity and peak time on the gas chromatograph of the finished product were all in agreement with the N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine standards. |
| application field | UV-1 can also be used in polyurethane materials, such as sponge foam, elastomer, leather, shoe material, adhesive, coatings, etc., can effectively improve the product's yellowing resistance level. |
| Use | UV absorber UV-1 is a highly effective anti-UV additive, widely used in polyurethane, adhesives, foam and other materials. Its excellent absorption properties make it can effectively absorb 240 ~ 340nm of ultraviolet light, in the 300 ~ 330nm band almost all absorption. Its anti-ultraviolet effect is benzophenone or benzotriazole 1.1~1.4 times. UV-1 for the polymer system has good Anti ultraviolet effect, good compatibility with the resin, good resistance to yellowing, with a broad spectrum of UV absorption band. |
Last Update：2024-04-09 20:48:19
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