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CAS No. : | 92-88-6 | MDL No. : | MFCD00002348 |
Formula : | C12H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VCCBEIPGXKNHFW-UHFFFAOYSA-N |
M.W : | 186.21 | Pubchem ID : | 7112 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 55.92 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.02 cm/s |
Log Po/w (iLOGP) : | 1.55 |
Log Po/w (XLOGP3) : | 1.99 |
Log Po/w (WLOGP) : | 2.76 |
Log Po/w (MLOGP) : | 2.41 |
Log Po/w (SILICOS-IT) : | 2.56 |
Consensus Log Po/w : | 2.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.82 |
Solubility : | 0.284 mg/ml ; 0.00153 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.47 |
Solubility : | 0.637 mg/ml ; 0.00342 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.77 |
Solubility : | 0.032 mg/ml ; 0.000172 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.07 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P273-P264-P280-P391-P337+P313-P302+P352+P312 | UN#: | 3077 |
Hazard Statements: | H312-H315-H318-H411 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.7 %Chromat. | With hydrogen In isopropyl alcohol at 150℃; for 2 h; Autoclave; Industrial scale | A 300-mL autoclave equipped with a stirring device was charged with 20 g of 4,4'-biphenol, 1 g of Raney nickel, and 80 g of 2-propanol, and a hydrogenation reaction was carried out for 2 hours at a hydrogen pressure of 6 MPa and a reaction temperature of 150°C. 2-Propanol was added to the obtained reaction solution until the crystals had completely dissolved. Then, filtration was carried out to obtain a reaction product solution from which the catalyst had been removed. Then, 21.4 g of crude 4,4'-bicyclohexanol (A) (purity: 96.7percent) was obtained by concentrating and drying this reaction product solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid bei der elektrolytischen Oxydation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 9.2% 2: 32.7% 3: 27.6 % Chromat. | With trifluorormethanesulfonic acid; trifluoroacetic acid at 0℃; for 1h; | |
1: 32.7 % Chromat. 2: 27.6 % Chromat. 3: 9.2 % Chromat. | With trifluorormethanesulfonic acid; trifluoroacetic acid at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-tert-butyl peroxide at 140℃; for 24h; Further byproducts given; | ||
With dihydrogen peroxide In phosphate buffer at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;palladium; In hydrogen; isopropyl alcohol; | EXAMPLE 1 In 1 l of isopropanol was dissolved 100 g (0.54 mol) of biphenyl-4,4'-diol, and 5 g of anhydrous sodium carbonate and 5 g of 5% palladium-on-carbon were added to the solution. The mixture was subjected to reduction reaction in an autoclave at 100 C. and at a hydrogen pressure of 5 kg/cm2 for 25 to 30 hours. After completion of the reaction, the reaction mixture was filtered, and the isopropanol was removed from the filtrate by distillation under reduced pressure to recover a part of dicyclohexyl-4,4'-diol. The crystals obtained as a filter cake were dissolved in 500 ml of tetrahydrofuran while hot and filtered. The tetrahydrofuran was removed from the filtrate by distillation under reduced pressure to obtain dicyclohexyl-4,4'-diol. Both crystals were combined, suspended in 1 l of n-hexane while hot, and allowed to stand at 5 to 6 C. for 1 hour. | |
96.7%Chromat. | With hydrogen; In isopropyl alcohol; at 150℃; under 45004.5 Torr; for 2h;Autoclave; Industrial scale; | A 300-mL autoclave equipped with a stirring device was charged with 20 g of 4,4'-biphenol, 1 g of Raney nickel, and 80 g of 2-propanol, and a hydrogenation reaction was carried out for 2 hours at a hydrogen pressure of 6 MPa and a reaction temperature of 150C. 2-Propanol was added to the obtained reaction solution until the crystals had completely dissolved. Then, filtration was carried out to obtain a reaction product solution from which the catalyst had been removed. Then, 21.4 g of crude 4,4'-bicyclohexanol (A) (purity: 96.7%) was obtained by concentrating and drying this reaction product solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphate buffer; dihydrogen peroxide; horseradish peroxidase at 20℃; for 2h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 270℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 26.5% 2: 9.35% 3: 9.15% 4: 2.3% | for 240h; Heating; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 7.7% 2: 15% | With potassium carbonate In N,N-dimethyl acetamide; toluene for 8h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
C.2 Preparation 4-(4'-hydroxyphenyl)cyclohexanone The conversion of 4,4'-biphenyldiol as the starting material was 97.7%, and the selectivity of 4-(4'-hydroxyphenyl)cyclohexanone was 62.3%. The coarse crystals of 4-(4'-hydroxyphenyl)cyclohexanone were obtained in amounts of 59.9 g, and the purity of the coarse crystals was 88.5%. The purified crystals were obtained in amounts of 42.6 g, the purity of the purified crystals was 98.0%, and the isolated yield thereof was 40.9%. | ||
C.C.1 Preparation 4-(4'-hydroxyphenyl)cyclohexanone The conversion of 4,4'-biphenyldiol as the starting material was 97.8%, and the selectivity of 4-(4'-hydroxyphenyl)cyclohexanone was 56.8%. The coarse crystals of 4-(4'-hydroxyphenyl)cyclohexanone were obtained in amounts of 56.8 g, and the purity of the coarse crystals was 76.2%. The purified crystals were obtained in amounts of 37.6 g, the purity of the purified crystals was 92.1%, and the isolated yield thereof was 33.9%. | ||
C.C.2 Preparation 4-(4'-hydroxyphenyl)cyclohexanone The conversion of 4,4'-biphenyldiol as the starting material was 99.5%, and the selectivity of 4-(4'-hydroxyphenyl)cyclohexanone was 55.7%. The coarse crystals of 4-(4'-hydroxyphenyl)cyclohexanone were obtained in amounts of 54.9 g, and the purity of the coarse crystals was 75.7%. The purified crystals were obtained in amounts of 37.6 g, the purity of the purified crystals was 89.3%, and the isolated yield thereof was 32.9%. |
Multi-step reaction with 4 steps 1: potassium hydroxide; water; nickel/aluminium alloy / 2 h / 90 - 95 °C 2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 70 - 80 °C 3: sulfuric acid; chromium(VI) oxide / acetone; water / 2.5 h / 10 - 20 °C 4: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 40 - 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.2% | With sodium hydroxide; sodium bromide; In water; | EXAMPLE 17 The reaction was carried out as described in Example 1, introducing: 2 g of 4,4'-dibromobiphenyl: (6.4 mmoles) 20 ml of 5N NaOH in H2 O: (100 mmoles) 10 mg of cuprous oxide: (0.07 mmoles) 1.4 g of NaBr: (14 mmoles) After 3 hours of reaction, a 4,4'-dihydroxybiphenyl yield of 84.7% and a 4-hydroxybiphenyl yield of 1.2% are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.0% | 100 g of 4, 4 -BIPHENOL, 500 g of dimethyl sulfoxide, and 89.5 g of a 48% by weight aqueous sodium hydroxide solution and 50 g of water were charged into a 1 L four- neck flask. equipped with a thermometer, a condenser tube and a stirrer, and the mixture was heated to an inner temperature of about 80C to dissolve it. Thereafter, a solution obtained by dissolving 37.6 G of 1,3- bis (chloromethyl) benzene in 112. 8 g of dimethyl sulfoxide was added dropwise over 1 hour, and an inner temperature was raised to 120C, followed by reaction at the same temperature for 1 hour while stirring. After completion of the reaction, the resulting reaction solution was poured into 1,500 g of water, the resulting crystal was filtered, washed with 300 g of water twice and dried at an inner temperature of 80C for 12 hours to obtain 97.9 g of a crystal of 1, 3-bis [4- (4-HYDROXYPHENYL) phenoxymethyl] benzene. Apparent yield: 96. 0%. Mass spectrometric value (FD-MS): m/z = 474, melting point: 200C or higher 10 g of the above-obtained crystal of 1, 3-bis [4- (4- hydroxyphenyl) phenoxymethyl] benzene, 61 g of epichlorohydrin, 130 g of dimethyl sulfoxide, and 1.8 g of sodium hydroxide were charged into a 1 L four-neck flask equipped with a thermometer, a condenser tube and a stirrer, and an inner pressure was reduced to about 6 kPa, followed by reaction at an inner temperature about 50C while refluxing for 4 hours. An inner temperature was raised to about 70C, followed by further reaction at the same temperature for 1 hour while refluxing. After completion of the reaction, the resulting reaction solution was poured into 650 g of water, and the precipitated crystal was collected by filtration, washed with 100 g of water twice and recrystallized by using 97 g of tetrahydrofuran to obtain 2.0 g OF L, 3-bis [4- (4-OXIRANYLMETHOXY)- phenyl] phenoxymethyl] benzene. Purity: 92.3% (LC area percentage value), Apparent yield: 16. 2%. Mass spectrometric value (FD-MS): M/Z = 586, melting point : 225C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: PDMS polymer, tosylated; 4,4'-Dihydroxybiphenyl With potassium carbonate In tetrahydrofuran; ethanol at 70℃; for 24h; Heating / reflux; Stage #2: 4-4'-bis(bromomethyl)biphenyl With potassium carbonate In tetrahydrofuran; butanone for 4h; Heating / reflux; | 1.2; 1.3 6.04 g of tosylated PDMS (1.25 mmol) obtained in stage 1), 868 mg of K2C03 and 474 mg of 1,4-dihydroxybiphenyl are mixed in 70 ml of THF and 130 ml of ethanol. The mixture is brought to reflux (70°C) for 24 hours. After cooling, extraction is carried out with water/CH2C12. The excess dihydroxybiphenyl is dissolved in the water, as are the inorganic materials. An additional purification is carried out by precipitating the product, in solution in the CH2C12, from a large excess of methanol. 6 g of a yellow oil are obtained.3) Coupling of bromobiphenyl The 6 g of the product obtained on conclusion of stage 2 are introduced, in the presence of 860 mg of K2C03 and 431 1 of bromobiphenyl, into a mixture of 50 ml of THF and 90 ml of methyl ethyl ketone (MEK). The mixture is brought to reflux for 4 hours. After cooling, extraction is carried out with water/CH2C12. An additional purification is carried out by precipitating the product, in solution in the CH2C12, from a large excess of ice-cold ether. 5 g of the expected rod-coil copolymer are obtained in the form of an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dimethyl sulfoxide; benzene; at 150 - 160℃; for 10h; | This example describes the preparation of a preferred embodiment of a polymer, which contains at least one polymer repeat unit that has at least two side chain sulfonic acid groups. <strong>[383-29-9]4-fluorophenyl sulfone</strong> (about 25.25 g, 0.1 mol) was reacted with 3,3'-bis(sodium-3-propyl sulfonate)-4,4'-biphenol (about 14.23 g, 0.03 mol ) and 4,4'-biphenol (about 13.03 g, 0.07 mol) in the presence of potassium carbonate (about 15.89 g, 0.115 mol) under a dry nitrogen atmosphere in a round bottom flask equipped with nitrogen inlet and a Dean-Stark trap using DMSO (about 300 mL) and benzene. After refluxing/recycling of benzene at about 150 C. for about 4 hours, all the benzene was removed and the heating was continued for about 6 hours at about 160 C. The mixture was cooled and additional DMSO (about 100 mL) was added to the reaction mixture. The viscous solution was poured into a large excess of water in order to obtain a transparent white polymer. The resulting product was washed, filtered and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 4.1 Synthesis of P2-P7 General procedure: A suspension of (S)-2,2′-bis(bromomethyl)-1,1′-binaphthyl ((S)-1) (500mg, 1.14mmol), 4,4′-biphenol (209mg, 1.12mmol, 1.0equiv), and potassium carbonate (1.56g, 11.4mmol, 10.0equiv) in DMF (46mL) was stirred for 24h at room temperature. The reaction mixture was poured into the mixed solvent of chloroform and water. The organic layer was separated and washed successively with water (three times) and brine. After dried over sodium sulfate, the solvent was evaporated in vacuo to give a residue. The residue was purified by column chromatography (SiO2; chloroform) and recycling preparative HPLC connected with JAIGEL-1H (20×600mm) and JAIGEL-2H (20×600mm) (Japan Analytical Industry, Co., Ltd.) under the condition of 3.5mL/min of flow rate with eluent (chloroform). Each crude product was subjected to further purification by recycling preparative HPLC connected with COSMOSIL 5SL-II (20×250mm; Nacalai Tesque Inc.) under the condition of 5.0mL/min of flow rate with eluent (chloroform/hexane=7/3) to afford P2-P7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 0.5h; | General procedure: A mixture of halobenzene (1 mmol), K2CO3(2 mmol), phenylboronic acid(1 mmol), and Pd-Schiff-Base(at)Fe3O4 MNPs (5 mg) as catalyst was taken in a 5-mLround-bottomed flask in dimethylformamide (DMF) and heated at 90 °C. After reaction completion (monitored by TLC), the mixture was cooled to room temperatureand the catalyst was separated from the reaction mixture using an external magnet and washed with diethyl ether. The reaction mixture was extracted with water and diethyl ether. The organic layer was dried over Na2SO4.Then, the solvent was evaporated under reduced pressure, and pure biphenyl derivatives were obtained in high yields. Further purification was achieved by column chromatography usingn-hexane:EtOAc (8:2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | The synthesis of 2,2?-bis(5-nitro-2-pyridinoxy)biphenyl (1a) is used as an example to illustrate the detailed synthetic procedures. Under the protection of nitrogen, 2,2?-Dihydroxybiphenyl (5.59g, 30mmol), potassium carbonate (9.12g, 66mmol), and DMF (60mL) were added into a dry round bottom flask with a stir bar. The mixture was allowed to stir at room temperature for 1h. Next, 2-chloro-5-nitropyridine (10.46g, 66mmol) was added into the flask and the mixture was allowed to react at 80C for 7h. Then, the obtained mixture was poured into 500mL of distilled water. The crude product was collected by filtration, washed with water, and dried in vacuo at 80C for 10h. After the crude product was recrystallized from DMF/water, 11.88g of 1a was obtained (92%); Melting point: 141-143C (DSC). FT-IR (KBr): 1602, 1582, 1508, 1464, 1393, 1271, 1198, 1117cm-1; 1H NMR (CDCl3, ppm): 8.91 (d, 1H), 8.34 (dd, 1H), 7.40 (m, 2H), 7.20 (m, 2H), 6.80 (d, 1H); HRLC-MS (ESI): 431.3 (M+H)+, Calcd 430.4 for C22H14N4O6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | The synthesis of 2,2?-bis(5-nitro-2-pyridinoxy)biphenyl (1a) is used as an example to illustrate the detailed synthetic procedures. Under the protection of nitrogen, 2,2?-Dihydroxybiphenyl (5.59g, 30mmol), potassium carbonate (9.12g, 66mmol), and DMF (60mL) were added into a dry round bottom flask with a stir bar. The mixture was allowed to stir at room temperature for 1h. Next, 2-chloro-5-nitropyridine (10.46g, 66mmol) was added into the flask and the mixture was allowed to react at 80°C for 7h. Then, the obtained mixture was poured into 500mL of distilled water. The crude product was collected by filtration, washed with water, and dried in vacuo at 80°C for 10h. After the crude product was recrystallized from DMF/water, 11.88g of 1a was obtained (92percent); Melting point: 141?143°C (DSC). FT-IR (KBr): 1602, 1582, 1508, 1464, 1393, 1271, 1198, 1117cm?1; 1H NMR (CDCl3, ppm): 8.91 (d, 1H), 8.34 (dd, 1H), 7.40 (m, 2H), 7.20 (m, 2H), 6.80 (d, 1H); HRLC-MS (ESI): 431.3 (M+H)+, Calcd 430.4 for C22H14N4O6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | General procedure: p-Benzenediol (Hydroquinone, defined as BP1 here) (2.2 g,20 mmol) and sodium hydroxide (2.4 g, 60 mmol) were dissolved in 120 mL DMF in a 250-mL round bottomed Schlenk flask, then themixture was stirred for 30 min, and a solution of <strong>[7766-50-9]11-bromo-1-undecene</strong> (12 g, 51.5 mmol) in DMF (120 mL) was added dropwise over 10 min. The resulting reaction mixture was heated at 70 C and left stirring for more than 8 h. Subsequently, the reaction was cooled to RT and quenched with addition of diethyl ether (100 mL) and water (100 mL). The aqueous phase was extracted with diethyl ether (300 mL 2), and the combined organic fractions were washed with brine and dried over MgSO4 and concentrated. The residue was recrystallized from EtOH twice to obtain 6.1 g BP1-M1. Yield: 74%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.4% | With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 24.0h; | Ten millimole compound (1) and 32 mmol 4, 4-biphenyl were dissolved in 40 mL dry THF,10 mmol DCC, and 2 mmol DMAP were added with stirring at room temperature for 24 hr. The dicyclohexylurea formed as precipitation was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatographyon silica gel (200-300 mesh) using a mixture of petroleum ether (60-90 C)and ethyl acetate (4/1, v/v) as eluent, white solid powder was obtained. Yield: 51.4%. mp.135.5-137 C. FR-IR (KBr, cm-1): 3475, 2956, 1751, 1731, 1611, 1530, 1408, 1368, 1267, 1207,1153, 969, 891, 824. 1HNMR (CDCl3, ppm): 7.74-7.49 (d, 2H), 7.37-7.40 (d, 2H),7.09-7.12 (d, 2H), 6.82-6.95 (d, 2H), 5.29 (s, 1H), 4.70-4.79 (m, 1H), 2.89-2.93 (t,4H), 2.73-2.77 (t, 4H), 0.74-2.02 (broad, 18H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71 %Chromat. | With 3.6mol% Au4-Pd alloy nanoparticles supported on Mg-Al-layered double hydroxide (LDH); air In N,N-dimethyl acetamide at 130℃; for 2h; | |
87 %Chromat. | With Pd(OH)x/Ni1Mg2Al1-layered triple hydroxide In N,N-dimethyl acetamide at 150℃; for 5h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 g | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 2h; | To a solution of biphenyl-4,4?-diol (7.02 g, 37.7 mmol), 2-hydroxylpropane-1,3-diol (4.00 g, 37.7 mmol) and triphenylphosphine (11.22 g, 42.8 mmol) in THF (100 ml) is added diisopropylazodicarboxylate (8.72 ml, 44.4 mmol) dropwise at room temperature. The resulted suspension is stirred at room temperature for 2 hs. The solvent is then removed in vacuo. The oily residue is purified by silica gel chromatography with dichloromethane/methyl-t-butylether as eluent. The obtained crude product is recrystallized with acetonitrile to provide 2-(4?-hydroxy-biphenyl-4-yloxymethyl)-propane-1,3-diol as white solid (1.0 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | General procedure: To a stirred solution of 1.86 g (10 mmol) of 4,4-dihydroxybiphenyl (biphenol) in 10 ml THF, 50 mg (0.4 mmol) of DMAP and 10 mmol of carboxylic acid were added. After the mixture was stirred for 5 min, 1.26 g (10 mmol) of DIC was added into the mixture, and then, the final reaction mixture was stirred under nitrogen purge for 3 h at room temperature through Steglich esterification. Insoluble solids, primarily precipitated urea, were then filtered off, and the filtrate was concentrated by a rotary evaporator until complete solvent removal. The residue was dissolved in a small amount of CHCl3 and purified by a silicagel column, using CHCl3 as an eluent to remove residual reactants and side reaction compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | General procedure: To a stirred solution of 1.86 g (10 mmol) of 4,4-dihydroxybiphenyl (biphenol) in 10 ml THF, 50 mg (0.4 mmol) of DMAP and 10 mmol of carboxylic acid were added. After the mixture was stirred for 5 min, 1.26 g (10 mmol) of DIC was added into the mixture, and then, the final reaction mixture was stirred under nitrogen purge for 3 h at room temperature through Steglich esterification. Insoluble solids, primarily precipitated urea, were then filtered off, and the filtrate was concentrated by a rotary evaporator until complete solvent removal. The residue was dissolved in a small amount of CHCl3 and purified by a silicagel column, using CHCl3 as an eluent to remove residual reactants and side reaction compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With hexamethylenetetramine; at 110℃; for 3.0h; | First,In a 500 mL eggplant flask,27 g of 4,4'-dihydroxybiphenyl represented by the formula (1-1-1)(150 mmol),46 g of hexamethylenetetramine(330 mmol)Is dissolved in 320 ml of trifluoroacetic acid,The reaction was carried out at 110 C. for 3 hours.After the reaction,Under an ice bath, 3 L of 4 N hydrochloric acid was added and stirred overnight.After completion of stirringThe precipitate was filtered off.Add water (1 L) to the obtained crude product,The suspension was purified by stirring for 1 hour.Filter the precipitate,By drying the obtained crystals,7.5 g (21 mmol, 21% yield) of an intermediate 1 represented by the formula (1-1-2)Obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | 4,4?-Dihydroxybiphenyl (60 g, 0.32 mol) was dissolved in a mixed solvent of dry DMF (0.6 L) and pyridine (80 mL, 0.97 mol). Trimellitic anhydride chloride (139 g, 0.64 mol) was dissolved in anhydrous DMF (0.4 L) and added dropwise to the 4,4?-dihydroxybiphenyl solution at 0 C with continuous stirring over 1 h, then subsequently reacted at 80 C for 20 h. The reaction mixture was filtered off to collect the yellow precipitate consisting of crude product and pyridine/hydrochloride salt as by-product. The precipitate was repeatedly washed with water and dry THF to remove the salt. Since the product undergoes partial hydrolysis toward anhydride ring opening on the procedure, it was heated at 160 C for 24 h in vacuum to ensure ring closure dehydration to yield the product as a yellow solid (138 g, 80 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 90℃; for 12h; | 1 is a synthesis of host reactive mesogen (H-6BPBA) of Chemical Formula 5It shows the process. As shown in Figure 1, the formula 5A host reactive mesogen compound containing was synthesized.First, 4,4'-Biphenol (7 g, 37.6 mmol) was mixed with purified dimethylformamide (DMF) (50 ml), and then 6-Bromohexyloxy-tert-butyldimethylsilane (2 g, 6.8 mmol) was slowly added. . After refluxing at 90 C. for about 12 hours, the temperature was lowered to room temperature.The compound was put in water and precipitated, and the precipitate was filtered out. Chloroform and meth4'-((6-((tertbutyldimethylsilyl))oxy)hexyl)oxy)-[1,1'-biphenyl]-4-ol (Compound 1) was synthesized. |
Tags: 92-88-6 synthesis path| 92-88-6 SDS| 92-88-6 COA| 92-88-6 purity| 92-88-6 application| 92-88-6 NMR| 92-88-6 COA| 92-88-6 structure
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P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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