3-Hydroxymethyl-2-methylbiphenyl
2-methyl-3-biphenylmethyanol
CAS: 76350-90-8
Molecular Formula: C14H14O
3-Hydroxymethyl-2-methylbiphenyl - Names and Identifiers
| Name | 2-methyl-3-biphenylmethyanol |
| Synonyms | Bifenthrin alcohol 2-methyl-3-biphenylmethanol 2-methyl-3-biphenylmethyanol (2-methylbiphenyl-3-yl)methanol 3-Hydroxymethyl-2-methylbiphenyl |
| CAS | 76350-90-8 |
| InChI | InChI=1/C14H14O/c1-11-13(10-15)8-5-9-14(11)12-6-3-2-4-7-12/h2-9,15H,10H2,1H3 |
3-Hydroxymethyl-2-methylbiphenyl - Physico-chemical Properties
| Molecular Formula | C14H14O |
| Molar Mass | 198.26 |
| Density | 1.072g/cm3 |
| Melting Point | 73-76℃ |
| Boling Point | 330.9°C at 760 mmHg |
| Flash Point | 143°C |
| Vapor Presure | 6.44E-05mmHg at 25°C |
| Storage Condition | Room Temprature |
| Refractive Index | 1.587 |
| MDL | MFCD00134200 |
| Physical and Chemical Properties | Chemical quality This product is white crystal, m.p.73 ~ 76 ℃, soluble in ethanol, benzene, toluene and other organic solvents, insoluble in water. |
| Use | Use 2-methyl-(1,1 '-biphenyl)-3-methanol is an intermediate of the insecticide Bifenthrin. |
3-Hydroxymethyl-2-methylbiphenyl - Upstream Downstream Industry
3-Hydroxymethyl-2-methylbiphenyl - Nature
| storage conditions | Sealed in dry,Room Temperature |
| acidity coefficient (pKa) | 14.28±0.10(Predicted) |
| InChIKey | BGTLHJPGBIVQLJ-UHFFFAOYSA-N |
| EPA chemical information | [1,1'-Biphenyl]-3-methanol, 2-methyl- (76350-90-8) |
Last Update：2024-04-10 22:29:15
3-Hydroxymethyl-2-methylbiphenyl - Uses and synthesis methods
application
3-hydroxymethyl-2-methylbiphenyl is a product obtained by reacting 3-chloro-2-methylbiphenyl with magnesium to form Grignard reagent, which is then reacted with polyoxymethylene diacetate. It is an intermediate of insecticide bifenthrin.
Preparation
PdCl2(dppf) was added to the stirred solution of (3-bromo-2-methylphenyl) methanol (4,1g,5mmol) and phenylboronic acid (5,1.4g,10mmol) in toluene (12mL) and EtOH(4mL). DCM(0.04g,0.05mmol) and 2 MNaHCO3 aqueous solution (4mL), the reaction mixture was degassing with nitrogen for 10 minutes. The reaction mixture was then heated in a sealed tube at 80°C for 12 hours. The reaction mixture was filtered by diatomite, the filtrate was diluted with water and extracted with ethyl acetate (2x 100mL). The organic layer was then dried and evaporated with sodium sulfate, and the crude product was purified on a Combiflash MPLC using an ethyl acetate-20% hexane solution as an eluent to obtain an off-white solid 3-hydroxymethyl-2-methylbiphenyl (6, yield: 0.81g,73%).
production method
2-methyl-(1,1 & prime;-biphenyl)-3-methanol is produced by the reaction of 3-chloro-2-methylbiphenyl with magnesium metal Grignard reagent, and then with polyoxymethylene diacetate Reaction to obtain the product.
3-chloro-2-methylbiphenyl and tetrahydrofuran are added to the reactor, then fresh metal magnesium and recovered metal magnesium are added for reflux for 5 hours, then polyoxymethylene diacetate is added, reflux is continued for several hours, cooling is carried out for post-treatment, and the product is distilled to obtain a yield of 70.8%.
In addition, 3-chloro-2-methylbiphenyl can also be used as raw material to react with cuprous cyanide in the presence of pyridine to form 3-cyano-2-methylbiphenyl, which is first reduced to obtain 2-Methyl-biphenyl -3-formaldehyde, and further reduced to 2-methyl-(1,1 & prime;-biphenyl)-3-methanol.
2-methyl -3-nitrobenzyl alcohol can also be used as raw material, first hydrogenated and reduced to 2-methyl -3-amino benzyl alcohol, and Sander Mayer reaction can be carried out in the presence of sodium nitrite, potassium iodide and copper powder to generate 3-iodo-2-methylbenzyl alcohol, and then reacted with benzene under ultraviolet lamp irradiation in a photoreactor to generate 2-methyl (1,1;-Biphenyl)-3-Methanol.
Last Update：2024-04-10 22:29:15
3-Hydroxymethyl-2-methylbiphenyl - Security information
| WGK Germany | 3 |
Last Update：2024-04-10 22:29:15
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Raw Materials for 3-Hydroxymethyl-2-methylbiphenyl
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