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Structure of 75980-60-8 * Storage: {[proInfo.prStorage]}
* 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.
Stage #1: for 6 h; Green chemistry Stage #2: at 8 - 20℃; for 5.5 h; Green chemistry
37.61 g of 2,4,6-trimethylbenzaldehyde and 56.17 g of diphenylphosphine oxide were added to a three-necked flask with 450 mL of methylene chloride and stirred,Reaction for 6 hours,The three bottles into a low-temperature water bath to cool to 8 ~ 10 ,Followed by adding 0.2925g ammonium metavanadate (NH4VO3), 37mL H2O2 (30percent),Low temperature reaction 0.5 hours,After placed at room temperature for mixing,Reaction for 5 hours.After the reaction was completed, 5percent Na2S2O3 aqueous solution was added to the filtrate to neutralize the unreacted H2O2,extraction,The organic layer was collected,Washed three times with saturated salt water,Then add anhydrous sodium sulfate in addition to water,Then recrystallized,Suction filtration, drying,A pale yellow powdery solid was obtained,That is TPO products,Yield 98percent.
Reference：
[1] Patent: CN106905364, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032; 0033; 0034
2
[ 64-17-5 ]
[ 1079-66-9 ]
[ 938-18-1 ]
[ 75980-60-8 ]
Yield
Reaction Conditions
Operation in experiment
92.2%
Stage #1: With sodium In toluene at 65 - 70℃; for 2 h; Stage #2: at 5 - 10℃; for 1 h; Stage #3: at 70 - 75℃; for 5 h;
In 100ml reaction flask was added toluene 32g, 3.45g of sodium metal particles (0.15mol), stirring, dropping 6.9g ethanol (0.15mol) dropwise, the process of maintaining the temperature at 65 ~ 70 ° C.Dropping end, stirring 2h, the reaction system was added dropwise phenylphosphine chloride 33. lg (0.15mol), the control temperature 5 ~ 10 ° C, the dropwise addition is complete,Stirring 1h, continue to the reaction system dropwise 2,4,6-trimethylbenzoyl chloride 30.1g (0.16mol), the dropping temperature was controlled at 70 ~ 75 ° C, and then stirred for 5h. The reaction was completed, the reaction material was added 15g of water, stirred lh, standing stratification, the resulting organic phase was adjusted to a saturated aqueous sodium bicarbonate solution pH 7 ~ 8, points to the aqueous phase, the organic phase was washed with water ,The resulting organic phase was dehydrated, cooled and crystallized, filtered,Dried to give a pale yellow powdery solid 48.2g, melting point 91 ~ 94 ° C, the liquid content of 99.3percent, a yield of 92.2percent
Reference：
[1] Patent: CN107304220, 2017, A, . Location in patent: Paragraph 0006; 0016-0023
3
[ 707-74-4 ]
[ 4559-70-0 ]
[ 75980-60-8 ]
Yield
Reaction Conditions
Operation in experiment
87%
Stage #1: With n-butyllithium In tetrahydrofuran for 0.5 h; Cooling with ice Stage #2: for 0.5 h;
125 g of diphenylphosphine oxide was dissolved in 2 liters of dry tetrahydrofuran, After cooling the ice bath, slowly drop the equivalent amount of butyllithium, The solution was changed from colorless to reddish brown, and the mixture was stirred for half an hour. 150 g of 1,3,5-trimethyl-2-trichloromethyl-benzene in 1 liter of tetrahydrofuran was slowly added, Solution red brown slowly faded, the reaction continued to stir for half an hour, TLC detection reaction was completed, 2 liters of saturated solution of sodium bicarbonate was added, extracted with 5 liters of ethyl acetate, the organic phase was dried and the solvent was removed by steaming to give (diphenylphosphonio) (trimethylphenyl) methanone product yield 87percent.
Stage #1: at 70 - 120℃; Stage #2: at 5 - 10℃; Stage #3: at 5 - 10℃;
70.3 g of benzene (0.90 mol), 48.0 g of aluminum trichloride (0.36 mol),After stirring, 41.2 g of phosphorus trichloride (0.30 mol) was added dropwise thereto.The tail gas is absorbed, the dropping temperature is controlled at about 70° C., and after the drop is completed, the reaction is performed by adding reflux. The maximum reaction temperature is controlled at 120° C. After the reaction is completed,Fall to room temperature. The reaction droplet was slowly added to 240 mL of acid water, and the reaction temperature was controlled to not exceed 20° C. After the dropwise addition, the reaction was continued for 0.5 h. After standing, the aqueous phase and the organic phase were clearly stratified. Both layers were transparent and the organic phase was separated. After washing, 40.0 g of 2,4,6-trimethylbenzaldehyde (0.27 mol) are added dropwise to the organic phase.The dropping temperature and the reaction were controlled at 5-10°C. The reaction was monitored by liquid chromatography or thin layer chromatography. After the reaction was completed, a 20percent NaOH aqueous solution was slowly added dropwise to the reaction system to adjust the pH to 2, and 2.74 g of WO3 was added in sequence. 2.0 g tetrabutylammonium bromide,40.0 g of 30percent hydrogen peroxide water was slowly added dropwise and reacted at this temperature. After the reaction is completed, the mixture is allowed to stand for stratification. The organic phase is washed with saturated saline and 10percent Na2SO3, then the pH is adjusted to neutrality, and finally the solution is desolvated under low pressure. Crystallized from ethyl acetate, filtered, dried and lightened.
Reference：
[1] Patent: CN107556342, 2018, A, . Location in patent: Paragraph 0017-0022
5
[ 938-18-1 ]
[ 2129-89-7 ]
[ 75980-60-8 ]
Reference：
[1] Patent: JP2016/121114, 2016, A, . Location in patent: Paragraph 0169; 0290-0292
[2] Patent: JP2016/121115, 2016, A, . Location in patent: Paragraph 0243-0244
6
[ 707-74-4 ]
[ 1079-66-9 ]
[ 75980-60-8 ]
Yield
Reaction Conditions
Operation in experiment
87 g
Stage #1: With magnesium In tetrahydrofuranReflux Stage #2: With hydrogenchloride; dihydrogen peroxide In water
Step 2: A mixture of 74 g of 1,3,5-trimethyl-2-trichloromethyl-benzene and 500 ml of dry THFmixing,Add 9 grams of acid activated magnesium shoulder,Maintain the reaction temperature at 20 degrees Celsius evenly until the magnesium shoulder almost disappeared,DripA solution of 68 grams of freshly distilled diphenylphosphonium chloride in 200 ml of dry THF,The reaction system was stirred at room temperature for 2 hours and then heated to reflux overnight.After the reaction system was cooled to room temperature,Remove most of the solvent,The residue was poured into 1 liter of water,The pH was adjusted between 3-4 with dilute hydrochloric acid and 90 g of a 30percent hydrogen peroxide solution was added with vigorous stirring. The aqueous phase was extracted three times with 400 ml of methylene chloride. The organic phases were combined, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was crystallized from isopropyl ether87 grams of light yellow target compounds pure.
The reaction flask was evacuated to -0.098 MPa using a vacuum pump.Under this condition will be 23.02gDiphenylethoxyphosphine and 18.26g2,4,6-trimethylbenzoyl chloride was added to the reaction flask, and the reaction was started at a temperature of 40 C.During the reaction, the temperature was raised by 10 C every 20 minutes until the temperature was raised to 90 C.Then react at a constant temperature of 90 C for 8 h.The exhaust gas generated during the reaction is removed by vacuum to the ethyl chloride recovery system and used.After the reaction, 50% ethanol was added to crystallize.33.13 g of the target product TPO were obtained. The purity of the product was 99.2% and the yield was 95.1%.
Example 4 Preparation of 2,4,6-trimethylbenzoyl diphenylphosphine oxide 31.5 g (0.1 mol) of alpha-hydroxy-(2,4,6-trimethylbenzyl)-diphenyl phosphine oxide and 0.9 g (3.4 mmol) of vanadyl(IV) bis-acetylacetonate in 150 g of chlorobenzene were admixed with 15 g (0.12 mol) of 70 wt % strength aqueous tert-butylhydroperoxide over a period of 30 minutes at 5 C. and stirred for 20 h at room temperature. The product was isolated by crystallization. Yield: 82%, mp 92-94 C.
As the monoacylphosphine oxide represented by the above-mentioned general formula (I) preferably used in the present invention, there can be exemplified: 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide, benzoyldi-(2,6-dimethylphenyl)phosphine oxide, 2,4,6-trimethylbenzoyldi-(2,6-dimethylphenyl)phosphine oxide, and 2,6-dimethyl-3-phenylpropionyldiphenylphosphine oxide.
Of particular interest are molecular complex compounds comprising ... bis(2,6-dimethoxybenzoyl)(2,4,4-trimethylpentyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; bis(2,4,6-trimethylbenzoyl)(4-ethoxyphenyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2,4-dihexyloxyphenyl)phosphine oxide and alpha-hydroxy-cyclohexyl phenyl ketone; ...
Example 14 : Preparation of 2,4,6-trimethylbenzoyldiphenylphosphine oxide Under argon and with exclusion of moisture, 2.76 g of lithium (0.40 mol) are suspended at room temperature in 100 ml of THF and this suspension is charged with 0.10 g (0.00078 mol) of naphthalene. This mixture is then stirred for 10 minutes at room temperature. With occasional cooling and vigorous stirring, 45.2 g (0.0 mol) of P-chlorodiphenyl phosphine are added dropwise to the dark brown suspension at 10-25C. After stirring for 4 hours, the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and using argon as protective gas. 38.0 g (0.2 mol) of 2,4,6-trimethylbenzoyl chloride are added dropwise, with stirring and cooling, at 10-20C over 1 hour and the mixture is then stirred for another 30 minutes. The organic phase is concentrated by evaporation in a Rotavap and the residue is taken up in 100 ml of toluene and charged, with vigorous stirring at a temperature from 50-60C, with 23.0 g (0.20 mol) of hydrogen peroxide (30%). The reaction is complete after stirring for 30 minutes. The reaction emulsion is poured on water and washed with an aqueous saturated sodium hydrogencarbonate solution and then dried over magnesium sulfate and filtered. The filtrate is concentrated by evaporation in a Rotavap. The residue is crystallized from petroleum ether/ethyl acetate and dried in a vacuum drying oven at 40C, yielding 55.0 g (79% of theory) of the title compound in the form of a yellow powder having a melting point of 89-90C.
Example 5 A melt of 2,4,6-trimethylbenzoyldiphenylphosphine oxide (content of TPO: 95.8 area % HPLC) obtained by reaction of trimethylbenzoyl chloride with ethoxydiphenylphosphine was placed, at 100 C., onto a stainless steel cooling plate (cooled using a coolant at 60 C.) in the form of a melt coating approximately 3.5 mm in thickness and slowly stirred/sheared using a spatula during cooling. After 2 minutes, a hard, crumbly solid was present.
A PSA adhesive composition was prepared by mixing 99 parts DBsBPHA, 1 part EB-9220, a hexa-functional aromatic urethane acrylate, and 1.5 parts of TPO photoinitiator (1.5% of total monomer weight) in an appropriately sized container. The mixture was warmed to 65 C. for 15 minutes and then mixed again. The mixture was coated on a polyester film using a knife coater to a thickness of approximately 25 microns. The coated film construction was passed under a 300 watt/cm UV lamp at a speed of 20 ft/min (6.1 m/min) and then heated in a 100 C. oven for 1 minute. Refractive index, shear, and adhesion results are given in Table II.
11
[ 75980-60-8 ]
[ 1233349-89-7 ]
Yield
Reaction Conditions
Operation in experiment
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 5h;Inert atmosphere; Reflux;
A mixture of 5 g (14.3 mmol) of compound 1, 3.55 g (20.09 mmol) of N-Bromosuccinimide, 0.05 g of AIBN and 30 ml of tetrachloromethane is refluxed for 5 h under Nitrogen atmosphere. The reaction mixture is filtered after cooling. The filtrate evaporated and dried to obtain compound-2 (8.4 g crude), crude TLC shows closure multiple spots. Without further purification the material is taken for next step.
2.8 g
With N-Bromosuccinimide; azobis(2-cyanobutane); In chlorobenzene; at 80℃; for 18h;
10 g (28.7 mmol) <strong>[75980-60-8](2,4,6-trimethylbenzoyl)diphenylphosphine oxide</strong> was dissolved in 100 ml chlorobenzene. 5.11 g (28.7 mmol) N-bromosuccinimid was added and the mixture was heated to 80C. 0.23 g (1.2 mmol) WAKO V59 was added and the reaction was allowed to continue at 80C for 18 hours. The reaction mixture was allowed to cool down to room temperature. 150 ml ethyl acetate was added and the mixture was extracted twice with a mixture of 100 ml water and 50 ml brine. The organic fraction was dried over MgSO4 and evaporated under reduced pressure. (4-bromomethyl-2,6-dimethyl-phenyl)-(diphenyl-phosphinoyl)- methanone was purified using preparative column chromatography on a ProchromTM LC8O column, using KromasilTM Si6OA 10pm as stationary phase and hexane / ethyl acetate 50 I 50 as eluent. 2.8 g of (4- bromomethyl-2,6-dimethyl-phenyl)-(diphenyl-phosphinoyl)-methanone was isolated (TLC analysis on TLC Silica gel 60F254 supplied by Merck, eluent hexane/ethyl acetate 60/40: Rf: 0.27). The molecular mass was confirmed using the TLC-MS methodology described above.
With diphenylphosphane; at 20℃; for 3.5h;Irradiation; Inert atmosphere; Sealed tube;
TMDPO (0.4 mmol),Perfluoroalkyl iodide (nC10 F21 I, 0.1 mmol), and benzotrifluoride (BTF) (0.6 mL) were placed in a sealed Pyrex glass tube under an argon atmosphere. The mixture was stirred for 30 seconds and then irradiated for 24 hours at room temperature (e.g. 15 C. ~ 25 C.) in the mixture a tungsten lamp (450 W, Konanshoji Co., Ltd.). The formation of nC10F21PPh2 was confirmed by 19 F and 31 P NMR analysis. The crude mixture was poured into a 30 mL Schlenk tube and evaporated. MeOH (2 mL) was added to the Schlenk tube and the product was extracted with FC-72 (3 mL × 5).The product obtained (fluorine-containing solvent layer) was sufficiently pure without further purification
41%Spectr.
In chloroform-d1; at 15 - 25℃; for 3.5h;Irradiation; Sealed tube;
General procedure: TMDPO (0.5 mmol), perfluoroalkyl iodide (nC10 F21 I, 0.1 mmol), Ph 2 PH (0.2 mmol) and benzotrifluoride (BTF) (0.6 mL) were placed in a sealed Pyrex glass I put it in a tube. The mixture was stirred for 30 seconds,The mixture was then irradiated with a xenon lamp (500 W) at room temperature (eg 15 C. to 25 C.) for 1.5 hours. The formation of RfPAr 2 was confirmed by 19 F NMR analysis. The crude mixture was poured into a 30 mL Schlenk tube and evaporated.MeOH (2 mL) was added to the Schlenk tube and the product was extracted with FC-72 (3 mL × 5). The product obtained (fluorine-containing solvent layer) was sufficiently pure without further purification.
Step 2: A mixture of 74 g of 1,3,5-trimethyl-2-trichloromethyl-benzene and 500 ml of dry THFmixing,Add 9 grams of acid activated magnesium shoulder,Maintain the reaction temperature at 20 degrees Celsius evenly until the magnesium shoulder almost disappeared,DripA solution of 68 grams of freshly distilled diphenylphosphonium chloride in 200 ml of dry THF,The reaction system was stirred at room temperature for 2 hours and then heated to reflux overnight.After the reaction system was cooled to room temperature,Remove most of the solvent,The residue was poured into 1 liter of water,The pH was adjusted between 3-4 with dilute hydrochloric acid and 90 g of a 30% hydrogen peroxide solution was added with vigorous stirring. The aqueous phase was extracted three times with 400 ml of methylene chloride. The organic phases were combined, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was crystallized from isopropyl ether87 grams of light yellow target compounds pure.
The metal lithium and 31.6 g freshly distilled 2 liters of tetrahydrofuran were mixed under nitrogen, the reaction warmed and maintained at a temperature of 35 degrees Celsius, was slowly added dropwise 416 g diphenyl phosphine chloride, dropwise stirring overnight, the reaction was analyzed NMR complete. The 448 g of 1,3,5-trichloro-2-methyl - of benzene was added slowly diluted with 0.5 l of tetrahydrofuran, and the reaction was stirred at room temperature continues to the end of the reaction by TLC, the resulting solid was filtered off and the insoluble portion after the material, the solvent was recovered under reduced pressure. The residue was mixed and 3 liters of toluene, with mechanical stirring was added 30% hydrogen peroxide solution, until the complete oxidation reaction progress was detected. Saturated sodium bicarbonate solution and an equal volume of the reaction mixture solution, After mechanical stirring for 2 hours, the organic phase was separated and dried, recovering the toluene solvent by rotary evaporation to give (diphenylphosphine group) (mesityl) methanone The crude product can be recrystallized purification, yield 84%.
125 g of diphenylphosphine oxide was dissolved in 2 liters of dry tetrahydrofuran, After cooling the ice bath, slowly drop the equivalent amount of butyllithium, The solution was changed from colorless to reddish brown, and the mixture was stirred for half an hour. 150 g of 1,3,5-trimethyl-2-trichloromethyl-benzene in 1 liter of tetrahydrofuran was slowly added, Solution red brown slowly faded, the reaction continued to stir for half an hour, TLC detection reaction was completed, 2 liters of saturated solution of sodium bicarbonate was added, extracted with 5 liters of ethyl acetate, the organic phase was dried and the solvent was removed by steaming to give (diphenylphosphonio) (trimethylphenyl) methanone product yield 87%.
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
Te-phenyl 2,4,6-trimethyltellurobenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In dichloromethane; at 20℃; for 6.0h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
diphenylphosphinothioic acid S-cyclohexyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
43%Spectr.; 87%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
S-(4-methylphenyl) 2,4,6-trimethylthiobenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%; 94%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
S-(4-chlorophenyl) 2,4,6-trimethylthiobenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%; 64%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
S-(4-methoxyphenyl) 2,4,6-trimethylthiobenzoate[ No CAS ]
[ 99234-85-2 ]
Yield
Reaction Conditions
Operation in experiment
87%; 96%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
S-(3,5-dichlorophenyl) 2,4,6-trimethylthiobenzoate[ No CAS ]
S-(3,5-dichlorophenyl) diphenylthiophosphinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%; 87%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
Se-(4-chlorophenyl) 2,4,6-trimethylselenobenzoate[ No CAS ]
Se-(4-chlorophenyl) diphenylselenophosphinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%; 92%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
P,P-diphenylphosphinoselenoic acid Se-butyl ester[ No CAS ]
Se-(n-butyl) 2,4,6-trimethylselenobenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%; 94%
In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;
General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.
With bis(tri-n-butyltin); In toluene; at 20℃; for 10h;Sealed tube; Inert atmosphere; Irradiation;
General procedure: TMDPO (3) (278.7 mg, 0.8 mmol), alkyl iodide 11 (0.2 mmol),1,1,1,2,2,2-hexabutyldistannane (4ga) (0.2 mmol, only for Scheme 10a), and dry, degassed toluene (0.6 mL, Scheme 10 a) or BTF [(1?,1?,1?-trifluoromethyl)benzene] (0.6 mL, Scheme 10 b] were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. Elemental sulfur (S8) (1 mmol) was added under an inert atmosphere, and the mixture was stirred for 6 h at 40 C. The reaction mixture was concentrated, and product 12 was isolated by gel permeation chromatography.
at 20℃; for 6h;Sealed tube; Inert atmosphere; Irradiation;
General procedure: TMDPO (3) (278.7 mg, 0.8 mmol), alkyl iodide 11 (0.2 mmol),1,1,1,2,2,2-hexabutyldistannane (4ga) (0.2 mmol, only for Scheme 10a), and dry, degassed toluene (0.6 mL, Scheme 10 a) or BTF [(1?,1?,1?-trifluoromethyl)benzene] (0.6 mL, Scheme 10 b] were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. Elemental sulfur (S8) (1 mmol) was added under an inert atmosphere, and the mixture was stirred for 6 h at 40 C. The reaction mixture was concentrated, and product 12 was isolated by gel permeation chromatography.
α-hydroxy-(2,4,6-trimethylbenzyl)diphenyl phosphine oxide[ No CAS ]
[ 75980-60-8 ]
Yield
Reaction Conditions
Operation in experiment
98%
With manganese(IV) oxide; In dichloromethane; at 20℃;
(1) Compound 30-2 (0.175 g, 0.5 mmol), manganese dioxide (0.870 g, 10 mmol) and dichloromethane (10 mL) were added to the reaction flask,The mixture is stirred at room temperature; (2) TLC tracking reaction until complete; (3) The crude product obtained after the completion of the reaction was separated by column chromatography (n-hexane: ethyl acetate = 5: 1)To give the target product 29-2 (yield 98%).
96%
With vanadium(V) oxide; dihydrogen peroxide; at 8 - 25℃; for 3.5h;Green chemistry;
37.61 g of 2,4,6-trimethylbenzaldehyde and 56.17 g of diphenylphosphine oxide were added to a three-necked flask equipped with 450 mL of methylene chloride and stirred,The reaction was carried out at room temperature (25 C) for 6 hours,Precipitation of white solid TPO intermediates.Then the three bottles into a low temperature water bath cooled to 8 ~ 10 ,Followed by adding 0.2309g vanadium pentoxide (V2O5),37mL H2O2 (mass fraction 30%),Low temperature reaction 0.5 hours,Then placed at room temperature (25 ) were stirred,The reaction for 3 hours.After the reaction to the three-necked flask was added 5% Na2S2O3 aqueous solution of unreacted H2O2,The reaction solution was obtained.Then the reaction solution into the desolventizing kettle,Points to the water layer,The organic layer was collected,Washed three times with saturated salt water,Then add anhydrous sodium sulfate in addition to water,Then recrystallized,Suction filtration, drying,A pale yellow powdery solid was obtained,That is TPO products,Yield 96%.
92.5%
With tert.-butylhydroperoxide; In dichloromethane; at 5 - 20℃; for 6.5h;
Secondly, TBHP (10.28mmol) was added to a stirredsolution of alpha-HDPO (8.57mmol) and catalyst (1mol% Vas alpha-HDPO) in 30mL DCM at 5C. After 30min, the mixturewas then stirred at room temperature for another 6h. Reaction products were analyzed using HPLC (Shimadzu)equipped with UV detector and C-18 column (AnasilAQ-C18, 5mum). The investigated catalysts were V1/M,V2/M, VO(acac)2, NH4VO3and V2O5.Catalytic activity wasdescribed in terms of alpha-HDPO conversion and TPO yield.
With tert.-butylhydroperoxide; at 8 - 20℃; for 4.5h;
Vanadium molecular sieve (V-ZSM-5-N) was obtained by solid-phase grinding 4.17g NH4VO3 and 43.55g ZSM-5 zeolite for 0.5h.37.61 g of 2,4,6-trimethylbenzaldehyde and 56.17 g of diphenylphosphine oxide were charged into a three-necked flask equipped with 450 mL of methylene chloride,The reaction was stirred at room temperature for 6 hours,Then the three bottles into a low temperature water bath cooled to 8 ~ 10 ,3.23g of vanadium molecular sieves (vanadium loading of 4%),37mL t-butanol peroxide,Low temperature reaction 0.5 hours,After placed at room temperature for mixing,Reaction for 4 hours.After the reaction, vanadium molecular sieve was recovered by filtration.To the filtrate was added 5% aqueous solution of Na2S2O3 unreacted tert-butanol peroxide,extraction,The organic layer was collected,Washed three times with saturated salt water,Then add anhydrous sodium sulfate in addition to water,Then recrystallized,Suction filtration, drying,A pale yellow powdery solid was obtained,That is TPO products,Yield 98%.The recovered vanadium molecular sieve washed three times with ethanol,dry,RoastingAccording to the above steps to repeat the experiment was TPO,Yield96%.
With aluminum (III) chloride; In nitrobenzene; at 0 - 40℃; for 2h;
1) The photoinitiator TPO (34.8 g, 0.1 mol) was dissolved in 200 ml of nitrobenzene,The control solution temperature is in the range of 0 to 10 C,Was added aluminum trichloride (82.7g, 0.62mol) After the stir,A solution of alpha-bromoisobutyryl chloride (18.5 g, 0.1 mol) was added dropwise,Slowly heated to 30-40 reaction 2h,Stop the reaction,The reaction solution was poured into 800 g of water and 130 ml of concentrated hydrochloric acid,Stirring 0.5h,Static separation of organic phase,Slowly washed with 200 ml of saturated sodium bicarbonate solution,To the organic phase pH is neutral,dry,The solvent was recovered by distillation under reduced pressure,To give a pale yellow oil,It is also possible not to recover the solvent,Directly to the next step.2) To the organic phase obtained in step 1) was added 150 mL of a 10% sodium hydroxide solution to carry out the reaction,To complete reaction,Standing,The organic phase is separated,Recovery solvent,A yellow oil,Recrystallization from methanol gave 17.4 g of a pale yellow solid.
With aluminum (III) chloride; In nitrobenzene; at 0 - 40℃; for 2h;
1) the photoinitiator TPO (34.8g, 0.1mol) was dissolved in 200ml of nitrobenzene,The control solution temperature is in the range of 0 to 10 C,After addition of aluminum trichloride (110.7 g, 0.83 mol)Alpha-bromoisobutyryl chloride (37.0 g, 0.2 mol) was added dropwise,Drop finished,Slowly heated to 30-40 reaction 2h,Stop the reaction,The reaction solution was poured into 800 g of water and 173 ml of concentrated hydrochloric acid,Stirring 0.5h,Static separation of organic phase,Slowly washed with 200 ml of saturated sodium bicarbonate solution,To the organic phase pH is neutral,dry,The solvent was recovered by distillation under reduced pressure,To give a pale yellow oil,It is also possible not to recover the solvent,Directly to the next step.2) To the organic phase obtained in step 1) was added 200 mL of 10% sodium hydroxide solution to carry out the reaction,To complete reaction,Standing,The organic phase is separated,Recovery solvent,A yellow oil,Recrystallization from methanol gave 21.4 g of a pale yellow solid.
In 100ml reaction flask was added toluene 32g, 3.45g of sodium metal particles (0.15mol), stirring, dropping 6.9g ethanol (0.15mol) dropwise, the process of maintaining the temperature at 65 ~ 70 C.Dropping end, stirring 2h, the reaction system was added dropwise phenylphosphine chloride 33. lg (0.15mol), the control temperature 5 ~ 10 C, the dropwise addition is complete,Stirring 1h, continue to the reaction system dropwise 2,4,6-trimethylbenzoyl chloride 30.1g (0.16mol), the dropping temperature was controlled at 70 ~ 75 C, and then stirred for 5h. The reaction was completed, the reaction material was added 15g of water, stirred lh, standing stratification, the resulting organic phase was adjusted to a saturated aqueous sodium bicarbonate solution pH 7 ~ 8, points to the aqueous phase, the organic phase was washed with water ,The resulting organic phase was dehydrated, cooled and crystallized, filtered,Dried to give a pale yellow powdery solid 48.2g, melting point 91 ~ 94 C, the liquid content of 99.3%, a yield of 92.2%
37.61 g of 2,4,6-trimethylbenzaldehyde and 56.17 g of diphenylphosphine oxide were added to a three-necked flask with 450 mL of methylene chloride and stirred,Reaction for 6 hours,The three bottles into a low-temperature water bath to cool to 8 ~ 10 ,Followed by adding 0.2925g ammonium metavanadate (NH4VO3), 37mL H2O2 (30%),Low temperature reaction 0.5 hours,After placed at room temperature for mixing,Reaction for 5 hours.After the reaction was completed, 5% Na2S2O3 aqueous solution was added to the filtrate to neutralize the unreacted H2O2,extraction,The organic layer was collected,Washed three times with saturated salt water,Then add anhydrous sodium sulfate in addition to water,Then recrystallized,Suction filtration, drying,A pale yellow powdery solid was obtained,That is TPO products,Yield 98%.
(3,5-bis(chloromethyl)-2,4,6-trimethylphenyl)(diphenylphosphoryl)methanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
3.43 g
With aluminum (III) chloride; In 1,2-dichloro-ethane; at 45℃; for 0.5h;Inert atmosphere;
Under nitrogen protection and room temperature,1.5 g of paraformaldehyde solids and 5.65 g of aluminum trichloride powder were dispersed in 120 ml of dry dichloroethane.When the system was warmed to 45C, a solution of 3.48 g of photoinitiator TPO in 80 ml of dichloroethane was slowly added dropwise thereto. The reaction was maintained at a temperature lower than the reflux temperature. After half an hour, the reaction liquid was poured on ice water and the liquid was separated. Dry, concentrate, and recrystallize the solid with ethyl acetate to give 3.43 g of the pale yellow target product which can be used directly in the next step.
3.8 g
With aluminum (III) chloride; In chloroform; at 0 - 60℃; for 12h;Inert atmosphere;
A mixture of 5.0 grams (14.3 mmol) of commercially available TPO (1 ) in 100 mL of chloroform was cooled to 0 C under N2 and mechanical stirring. AICI3 (12.0 grams, 85.8 mmol) and paraformaldehyde (2.6 grams, 86 mmol) was added portion-wise. After the completion of the addition, the mixture was heated to 60 C for 12 hours. Then, the reaction mixture was cooled to room temperature and poured into ice-water. The mixture was extracted with dichloromethane (3 x 100 mL). The combined organic layers were washed by water, brine, and then dried over sodium sulfate. Evaporation of solvent gave a residue, which was further purified by flash chromatography using hexanes/ethyl acetate (100% hexanes to 50% hexanes in ethyl acetate) as eluents, giving rise to 3.8 grams (60 wt%) of the desired TPO-dichloride (4).
70.3 g of benzene (0.90 mol), 48.0 g of aluminum trichloride (0.36 mol),After stirring, 41.2 g of phosphorus trichloride (0.30 mol) was added dropwise thereto.The tail gas is absorbed, the dropping temperature is controlled at about 70 C., and after the drop is completed, the reaction is performed by adding reflux. The maximum reaction temperature is controlled at 120 C. After the reaction is completed,Fall to room temperature. The reaction droplet was slowly added to 240 mL of acid water, and the reaction temperature was controlled to not exceed 20 C. After the dropwise addition, the reaction was continued for 0.5 h. After standing, the aqueous phase and the organic phase were clearly stratified. Both layers were transparent and the organic phase was separated. After washing, 40.0 g of 2,4,6-trimethylbenzaldehyde (0.27 mol) are added dropwise to the organic phase.The dropping temperature and the reaction were controlled at 5-10C. The reaction was monitored by liquid chromatography or thin layer chromatography. After the reaction was completed, a 20% NaOH aqueous solution was slowly added dropwise to the reaction system to adjust the pH to 2, and 2.74 g of WO3 was added in sequence. 2.0 g tetrabutylammonium bromide,40.0 g of 30% hydrogen peroxide water was slowly added dropwise and reacted at this temperature. After the reaction is completed, the mixture is allowed to stand for stratification. The organic phase is washed with saturated saline and 10% Na2SO3, then the pH is adjusted to neutrality, and finally the solution is desolvated under low pressure. Crystallized from ethyl acetate, filtered, dried and lightened.
With aluminum (III) chloride; In dichloromethane; for 10h;Reflux;
(a) 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO) (0.1 mol) was dissolved in 100 mL of anhydrous dichloromethane.Anhydrous aluminum trichloride (0.15 mol) and paraformaldehyde (0.12 mol) were added in portions, stirred at room temperature for 10 min, and then heated to reflux for 10 h.The spot plate monitoring reaction has two main products. After the reaction is completed, it is slowly added to an equal volume of ice water with a solvent, and the organic layer is washed with deionized water.Drying with anhydrous sodium sulfate, the product was isolated by column chromatography on ethyl acetate / cyclohexane silica gel to give the intermediate 1a'.This intermediate is a chloromethylated product with a yield of 37%.Light yellow solid.
37%
With aluminum (III) chloride; In dichloromethane; at 20℃; for 10.16h;Reflux;
2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO)(0.1 mol) dissolved in 100 mL of anhydrous dichloromethane,Add anhydrous aluminum trichloride in batches(0.15 mol) and paraformaldehyde (0.12 mol), after stirring at room temperature for 10 min,Warming up to reflux,After reacting for 10 hours, the spot plate monitoring reaction has two main products, and the reaction is completed.Slowly add equal volume of ice water to the solvent, and wash the organic layer with deionized water.Drying with anhydrous sodium sulfate, the product was separated into ethyl acetate/cyclohexane silica gel column chromatography to obtain the intermediate product TPO-Cl.This intermediate was the chloromethylated product in 37% yield as a pale yellow solid.
3.7 g
With aluminum (III) chloride; In chloroform; at 0 - 60℃; for 6h;Inert atmosphere;
A mixture of 5.0 grams (14.3 mmol) of commercially available TPO (1 ) in 100 mL of chloroform was cooled to 0 C under N2 and mechanical stirring. AlC (12.0 grams, 85.8 mmol) and paraformaldehyde (1 .3 grams, 43 mmol) was added portion-wise. After the completion of the addition, the mixture was heated to 60 C for 6 hours. Then, the reaction mixture was cooled to room temperature and poured into ice-water. The mixture was extracted with dichloromethane (3 x 100 mL). The combined organic layers were washed by water and brine and then dried over sodium sulfate. Evaporation of solvent gave a residue, which was further purified by flash chromatography using hexanes/ethyl acetate (100% hexanes to 50% hexanes in ethyl acetate) as eluents, giving rise to 3.7 grams (65 wt%) of the desired TPO chloride (2).
3.7 g
With aluminum (III) chloride; In chloroform; at 0 - 60℃; for 6h;Inert atmosphere;
A mixture of 5.0 grams (14.3 mmol) of commercially available TPO (1) in 100 mL of chloroform was cooled toO C under N2 and, under mechanical stirring, AICI3 (12.0 grams, 85.8 mmol) and paraformaldehyde (1.3 grams, 43 mmol) was added portion-wise. After the addition, the mixture was heated to 60C for 6 hours. Then, the reaction mixture was cooled to room temperature andpoured into ice-water. The mixture was extracted with dichloromethane (3 x 100 mL). The combined organic layers were washed by water, brine, and then dried over sodium sulfate. Evaporation of solvent gave a residue, which was further purified by flash chromatography using hexanes/ethyl acetate (100% hexanes to 50% hexanes in ethyl acetate) as eluents, giving rise to 3.7 grams (65 wt%) ofthe desired TPO chloride (2).
TMDPO (0.4 mmol),Perfluoroalkyl iodide (nC10 F21 I, 0.1 mmol), and benzotrifluoride (BTF) (0.6 mL) were placed in a sealed Pyrex glass tube under an argon atmosphere. The mixture was stirred for 30 seconds and then irradiated for 24 hours at room temperature (e.g. 15 C. ~ 25 C.) in the mixture a tungsten lamp (450 W, Konanshoji Co., Ltd.). The formation of nC10F21PPh2 was confirmed by 19 F and 31 P NMR analysis. The crude mixture was poured into a 30 mL Schlenk tube and evaporated. MeOH (2 mL) was added to the Schlenk tube and the product was extracted with FC-72 (3 mL × 5).The product obtained (fluorine-containing solvent layer) was sufficiently pure without further purification
72%Spectr.; 7%Spectr.
at 15 - 25℃; for 1.5h;Irradiation; Sealed tube;
General procedure: TMDPO (0.5 mmol), perfluoroalkyl iodide (nC10 F21 I, 0.1 mmol), Ph 2 PH (0.2 mmol) and benzotrifluoride (BTF) (0.6 mL) were placed in a sealed Pyrex glass I put it in a tube. The mixture was stirred for 30 seconds,The mixture was then irradiated with a xenon lamp (500 W) at room temperature (eg 15 C. to 25 C.) for 1.5 hours. The formation of RfPAr 2 was confirmed by 19 F NMR analysis. The crude mixture was poured into a 30 mL Schlenk tube and evaporated.MeOH (2 mL) was added to the Schlenk tube and the product was extracted with FC-72 (3 mL × 5). The product obtained (fluorine-containing solvent layer) was sufficiently pure without further purification.
In chloroform-d1; at 15 - 25℃; for 1.5h;Irradiation; Sealed tube;
General procedure: TMDPO (0.5 mmol), perfluoroalkyl iodide (nC10 F21 I, 0.1 mmol), Ph 2 PH (0.2 mmol) and benzotrifluoride (BTF) (0.6 mL) were placed in a sealed Pyrex glass I put it in a tube. The mixture was stirred for 30 seconds,The mixture was then irradiated with a xenon lamp (500 W) at room temperature (eg 15 C. to 25 C.) for 1.5 hours. The formation of RfPAr 2 was confirmed by 19 F NMR analysis. The crude mixture was poured into a 30 mL Schlenk tube and evaporated.MeOH (2 mL) was added to the Schlenk tube and the product was extracted with FC-72 (3 mL × 5). The product obtained (fluorine-containing solvent layer) was sufficiently pure without further purification.
In chloroform-d1; at 15 - 25℃; for 1.5h;Irradiation;
General procedure: TMDPO (0.5 mmol), perfluoroalkyl iodide (nC10 F21 I, 0.1 mmol), Ph 2 PH (0.2 mmol) and benzotrifluoride (BTF) (0.6 mL) were placed in a sealed Pyrex glass I put it in a tube. The mixture was stirred for 30 seconds,The mixture was then irradiated with a xenon lamp (500 W) at room temperature (eg 15 C. to 25 C.) for 1.5 hours. The formation of RfPAr 2 was confirmed by 19 F NMR analysis. The crude mixture was poured into a 30 mL Schlenk tube and evaporated.MeOH (2 mL) was added to the Schlenk tube and the product was extracted with FC-72 (3 mL × 5). The product obtained (fluorine-containing solvent layer) was sufficiently pure without further purification.
Under an inert gas atmosphere,Toluene (10 mL) was added at 0 C.,Ph2 POMe (5 mmol),2,4,6-trimethylbenzoyl chloride (5 mmol) was added to a 30 mL two-necked flask and stirred,The temperature was gradually returned to room temperature.Followed by heating at 80 C. for 3 hours.TMDPO was obtained by distilling off the solvent.
In toluene; at 0 - 80℃; for 3h;Inert atmosphere;
Toluene (10 mL), Ph 2 POMe (5 mmol), 2,4,6-trimethylbenzoyl chloride (5 mmol) were added to a 30 mL two-necked flask under an inert gas atmosphere at 0 C. and the mixture was stirred and gradually returned to room temperature. Followed by heating at 80 C. for 3 hours. TMDPO was obtained by distilling off the solvent.
With aluminum (III) chloride; In dichloromethane; at 10 - 35℃; for 7h;
After 133 parts of dichloromethane (CH2Cl2) was dissolved in 2,4,6-trimethylbenzoyldiphenylphosphine oxide (30.0 parts, 86.1 molar equivalents, IRGACURE TPO manufactured by BASF), anhydrous aluminum(III) chloride (AlCl3, 45.9 parts, 344.5 molar equivalents) was added thereto in portions and dissolved by performing stirring. Then, chloroacetyl chloride (57.9 parts, 516.7 molar equivalents) was added dropwise and stirred at room temperature (rt, 10 C. to 35 C., the same applies hereafter) for 7 hours. The reaction solution was gradually added dropwise to ice water to stop the reaction, then extracted with ethyl acetate, washed with water, and dried with magnesium sulfate. The resulting filtrate was concentrated, purified using a silica gel column (hexane/ethyl acetate=50/50 (volume ratio)), concentrated, and then washed with hexane to obtain a white compound A-1a (33.65 parts, yield 92%).
With aluminum (III) chloride; In dichloromethane; at 10 - 35℃; for 7h;
After 133 parts of dichloromethane (CH2Cl2) was dissolved in 2,4,6-trimethylbenzoyldiphenylphosphine oxide (30.0 parts, 86.1 molar equivalents, IRGACURE TPO manufactured by BASF), anhydrous aluminum(III) chloride (AlCl3, 45.9 parts, 344.5 molar equivalents) was added thereto in portions and dissolved by performing stirring. Then, 3-chloropropionyl chloride (65.6 parts, 516.7 molar equivalents) was added dropwise and stirred at room temperature (rt, 10 C. to 35 C., the same applies hereafter) for 7 hours. Purification was performed in the same manner as in the case of the compound A1-a to obtain a compound A-4a (42.0 parts, yield 99%).
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