4,4′-Bis(chloromethyl)-1,1′-biphenyl CAS#: 1667-10-3; 凯望编码 (ChemWhat Code): 31529
Identification
| 英文名 | 4,4′-Bis(chloromethyl)-1,1′-biphenyl |
| IUPAC Name | 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene |
| 分子结构 |  |
| CAS编号 | 1667-10-3 |
| EINECS Number | 216-784-4 |
| MDL Number | MFCD00674019 |
| Beilstein Registry Number | No data available |
| 别名 | 4,4′-bis(chloromethyl)biphenyl, 4,4′-bis-(chloromethyl)-biphenyl, α,α’-dichloro-4,4′-dimethylbiphenylene, 4,4′-bis-(chloromethyl)-1,1′-biphenyl, 4,4’-bis(chloromethyl)-1,1’-biphenyl, 4,4′-bis(chloromethyl)-1,1′-biphenyl, 4,4′-bis(chloromethyl) biphenyl |
| 分子式 | ClCH2C6H4C6H4CH2Cl |
| 分子量 | 251.15 |
| InChI | InChI=1S/C14H12Cl2/c15-9-11-1-5-13(6-2-11)14-7-3-12(10-16)4-8-14/h1-8H,9-10H2 |
| InChI Key | INZDTEICWPZYJM-UHFFFAOYSA-N |
| Canonical SMILES | c1cc(ccc1CCl)c2ccc(cc2)CCl |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| EP1191016 | Diquaternary ammonium compounds | 2002 |
Physical Data
| Appearance | White crystal powder |
| Melting Point, °C | Solvent (Melting Point) |
| 133 – 135 | hexane, dichloromethane |
| 138 – 139 | |
| 136 | ethanol |
| 136 | acetone |
| Boiling Point, °C | Pressure (Boiling Point), Torr |
| 235 | 12 |
| 179 – 184 | 0.2 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 300 |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | |
| Chemical shifts | 1H | CDCl3 | 250 |
| Chemical shifts | 13C | CDCl3 | |
| NMR |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands, Spectrum | ||
| ATR (attenuated total reflectance), Spectrum | ||
| Bands | potassium bromide | |
| Spectrum | potassium bromide | |
| Bands | solid | 1306 – 600 cm**(-1) |
| Description (Mass Spectrometry) |
| spectrum |
| electrospray ionisation (ESI), spectrum |
Route of Synthesis (ROS)
| Conditions | Yield |
| With hydrogenchloride In water; methyl cyclohexane at 70℃; for 10h; | 90% |
| With hydrogenchloride In tetrachloromethane; water at 65℃; for 20h; Temperature; Solvent; Experimental Procedure The 31g (0.2mol) biphenyl, Concentration of 30% hydrochloric acid 122g (1.0mol), 21.9g paraformaldehyde (0.7mol), The 6.2g of Silicon dioxide-supported phosphotungstic acid catalyst prepared in Example 1 and 155ml (248 g) of carbon tetrachloride were added to the reaction flask, Stir the temperature to 65°C, 0.5 ml of HCl gas was introduced, Access time is 18h, And then continue at 65°C for 2 h, The solid catalyst was filtered off, The filtrate separates the acid phase, Organic phase washed 2 times, The solvent was then distilled off, Adding cyclohexane crystals, filter, The crude product was recrystallized from cyclohexane once, To give 45.1 g of 4,4′-dichloromethylbiphenyl, Yield 89.8% Content of 99.4%. | 89.8% |
| With hydrogenchloride; acetic acid at 50℃; for 8h; Temperature; Reagent/catalyst; Experimental Procedure 1-12 Example 10 Add biphenyl (0.5 mol) to the reaction flask,Paraformaldehyde (1.5 mol), acetic acid (300 mL),The mesoporous silica is loaded with a titanium chloride azacrown ether ionic liquid (20.0 g), and a dry hydrogen chloride gas is introduced under stirring.Control the temperature at 50 ° C,The temperature was stabilized and the reaction was stirred for 8 h. The product phase and the catalyst phase can be separated by pouring hot.The product phase is filtered to recover the filtrate, and the filter cake is washed with water.Recrystallization of cyclohexane,Drying gives the pure product 4,4′-dichloromethylbiphenyl.The yield was 88.0%. LC-MS analysis showed thatThe purity of 4,4′-dichloromethylbiphenyl was 99.4%. | 88% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Danger |
| GHS Hazard Statements | H314 (97.67%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Class 8; Packaging Group: II; UN Number: 3261 |
| Under the room temperature and away from light | |
| HS Code | 290399 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Use Pattern |
| 4,4′-Bis(chloromethyl)-1,1′-biphenyl CAS#: 1667-10-3 is an important intermediate of fluorescent whitening agent FP. |
| It is an important intermediate of fluorescent whitening agent CBS. |
| It is a pharmaceutical or resin intermediate. |
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