*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 1993-03-9 |
Formula : | C6H6BFO2 |
M.W : | 139.92 |
SMILES Code : | FC1=CC=CC=C1B(O)O |
MDL No. : | MFCD00674013 |
InChI Key : | QCSLIRFWJPOENV-UHFFFAOYSA-N |
Pubchem ID : | 2734354 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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 |
---|---|---|
81% | Stage #1: at 60℃; for 4 h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane; water at 60℃; for 4 h; |
To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 ° C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 ° C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81percent and its NMR data was as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.06% | With palladium diacetate; potassium carbonate; tricyclohexylphosphine; In ethanol; water; toluene; at 75 - 78℃; for 4h;Inert atmosphere; | In a 1 L three-necked flask, o-fluorophenylboronic acid (14.0 g, 0.1 mol), <strong>[425379-16-4]2-bromo-3-fluorobenzonitrile</strong> (22.0 g, 0.11 mol) was added under a nitrogen atmosphere.Potassium carbonate (20.7 g, 0.15 mol) and 100 g of water, 200 mL of toluene and 100 mL of ethanol were replaced by nitrogen.Add palladium acetate (450 mg, 0.002 mol) and tricyclohexylphosphine (1.12 g, 0.004 mol), heat to reflux, internal temperature 75-78 C, reflux for 4.0 hrs,The reaction was completed by TLC, the mixture was cooled to room temperature, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate, and then evaporated to silica gel column, and the solvent was evaporated to dryness to give a pale yellow solid, crude intermediate 7-a.After purifying with ethanol, 17.0 g of an off-white solid intermediate 7-a was obtained, the purity of GC was 99.42%, and the yield was 79.06%. |
78% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating; | [134] Step 1. 2',6-DJfIuQrQ-[I, r-biphenyll-2-carbonitrile (27): A mixture of (2- fluorophenyl)boronic acid 26 (6.7 g, 48.0 mmol), <strong>[425379-16-4]2-bromo-3-fluorobenzonitrile</strong> 25 (8 g, 40.0 mmol) and NaHCO3 (8.4 g, 100 mmol) in dioxane (100 mL) and water (20 mL) was purged with N2 for 5 min. Tetrakis(triphenylphosphine)palladium (3.2 g, 2.8 mmol) was added and the mixture heated at 80-85 0C (external) overnight. The reaction showed progress but considerable starting material remained. The reaction was heated at 95 0C (external) for a further 30 hr. The solution was cooled and diluted with EtOAc (500 mL). The mixture was washed with brine (100 mL) and the aqueous layer was back-extracted with EtOAc (2 x 100 mL). The combined organic solution was dried (Na2SO4) and concentrated to a yellow liquid. The crude material was purified by chromatography on an Analogix automated system (115 g column, 0-30% EtO Ac/heptane) to provide 3.5 g (78%) of clean 27 plus 4 g of oil/solid mixture that was approximately 30% starting material by GCMS. |
76% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 48h;Inert atmosphere; | Example 8. 5'-(5-fert-butyl-lH-benzor<ilimidazol-l-yl -2',6-difluorobiphenyl-2- carbonitrile (Compound 112).Scheme 19. Preparation of Compound 112.45 112[173] Step 1. 2',6-Difluorobiphenyl-2-carbonitrile (44): 2-Bromo-3-fluorobenzonitrile (10 g, 50 mmol) was mixed with 2-fluorophenylboronic acid (8.75 g, 62.5 mmol) and K2C03 (22 g, 157 mmol) in dioxane (120 mL) and water (30 mL). The mixture was purged with nitrogen for 10 minutes then tetrakis(triphenylphosphine)palladium (3.5 g, 6 mol%) was added. The reaction was heated at 120 C for two days. The mixture was cooled and diluted with EtOAc (100 mL). The organic layer was washed with water (10 mL), dried (Na2S04), and concentrated. The crude product was purified on an Analogix automatedchromatography system eluting with 0-20% EtO Ac/heptanes to give 8.2 g (76%) of 44 that was contaminated with a small amount of <strong>[425379-16-4]2-bromo-3-fluorobenzonitrile</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; In dichloromethane; at 60℃; for 12h; | A stirred solution of <strong>[1006-33-3]2-bromo-5-fluoroacetophenone</strong> (11.72 g, 54 MMOL) and 2-FLUOROPHENYLBORONIC acid (7.55 g, 54 MMOL) in tetrahydrofuran (600 mL) was treated under nitrogen with [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (ICI) complex with dichloromethane (2.20 g, 2.69 mmol, 5 molepercent) and a 5 N sodium hydroxide solution (21.6 mL, 108 MMOL). The reaction was heated at 60 °C for twelve hours, cooled to room temperature, and the solvent removed in vacuo. The residue was dissolved in diethyl ether, filtered through a short column of silica gel, and the solvent EVAPORATED IN VACUO to a crude brown oil (11.72 g). The crude oil was purified by repetitive, preparative, liquid chromatography on a BIOTAGEE 40 Mi column of pre- packed silica gel (90 g), eluting with a gradient of between 3percent and 10percent methyl TERT- butylether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, the title compound as a purified, colorless oil (10.2 g, 43.9 mmol, 81percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 20 - 95℃; | (1) 4-(2-fluorophenyl)-2-piperazin-1-ylpyrimidine Dihydrochloride To a solution of <strong>[479691-42-4]tert-butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate</strong> (10 g, 33.5 mmol), 2-fluorophenyl boronic acid (7.02 g, 50.2 mmol), and 2 N aqueous sodium carbonate solution (45 ml) in 1,2-dimethoxyethane (300 ml) was added tetrakistriphenylphosphine palladium (4.64 g, 40.2 mmol) under nitrogen atmosphere at room temperature, and the mixture was stirred at 95 C. overnight. The reaction was poured into the saturated saline, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain tert-butyl 4-[4-(2-fluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 130℃;Microwave irradiation; Sealed tube; | General procedure: To a solution of a 3- or 4-bromobenzaldehyde in a mixture DMF/water (3:1; 14.8mL/mmol) were added boronic acid derivative (1.5 equiv.), Pd(PPh3)4 (5mol%), and K2CO3 (2 equiv.). The reaction mixture was heated under microwave irradiation (130C) until TLC showed complete conversion of the starting material (0.5-1h). After cooling, the mixture was extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered off, and concentrated under reduced pressure to afford the corresponding crude product 2. (0027) Compounds 2a-2p were synthesized following the procedure described above from the corresponding boronic acids. | |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 18.0h;Reflux; | General procedure: 4-Bromobenzaldehyde and boronic acid were subjected to Suzuki cross coupling reaction using a palladiumcatalyst as shown in [Scheme 1a]. Specifically, 4-bromobenzaldehyde (3 g, 16.21 mmol), boronic acid (1.28 equivalents),tetrakis(triphenylphosphine)palladium(0) (4-8 mol%) and sodium carbonate (4.86 equivalents) were refluxed in degassedtoluene/distilled water (150 mL/21.6 mL) for 18 hours while heating. The reaction mixture was filtered through celite andthe filtrate was washed twice with ethyl acetate (200 mL) and water (200 mL). The organic layer was combined anddried with sodium sulfate, concentrated in vacuo and then separated and purified by silica gel column chromatography | |
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; N,N-dimethyl-formamide; at 90℃; for 16.0h;Inert atmosphere; | 2'-Fluorobiphenyl-4-carbaldehvde Into a 100 mL pressure flask equipped with a magnetic stirbar and under nitrogen was added 2-fluoroboronic acid (4.76 g, 34.1 mmol), 4-bromobenzaldehyde (5.25 g, 28.4 mmol), PdCl2(dppf) (1.16 g, 1.42 mmol) and DMF (40 mL). The solution was treated with 2 M aqueous sodium carbonate solution (28 mL, 56.8 mmol) and the vial was sealed and heated to 90 0C for 16 h. The cooled mixture was poured into a 250 mL separatory funnel containing water (125 mL) and the mixture extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with 0% EtOAc in hexanes to 20% EtOAc in hexanes as a gradient, gave the title compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 95℃;Inert atmosphere; | Specific Example of Step 1 Synthesis of methyl 1-(2-fluorophenyl)isoquinoline-3-carboxylate: Methyl 4-chloroisoquinoline-2-carboxylate (0.221g, 1mmole) was dissolved in toluene (10mIs) and 2-fluorophenylboronic acid (0.280mgs, 2mmoles), anhydrous potassium carbonate (0.276g, 2mmoles) and tetrakis (0.060mgs) was added and the vessel flushed with nitrogen. The reaction was heated (950C) overnight and after cooling the reaction was filtered through silica the filtrate was then washed with saturated sodium bicarbonate solution (10mIs), water (10mIs) and then brine (10mIs). After drying over magnesium sulphate and evaporating an off white solid (140mgs, 50% yield, 95% pure was left. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; toluene; for 24.0h;Inert atmosphere; Reflux; | (A-3) Synthesis of 2,4-bis(2-fluorophenyl)-1,3-dimethoxybenzene In the atmosphere of argon, 23.2g of 1,3-dibromo-2,6-dimethoxybenzene, 32.9g of 2-fluorophenylboronic acid, 5.43g of tetrakis(triphenylphosphine)palladium(0), 150 mL of toluene, 150 mL of 1,2-dimethoxyethane and 150 mL of a 2M aqueous sodium carbonate solution were placed in a flask. The resulting mixture was stirred with heating under reflux for 24 hours. After being cooled to room temperature, an aqueous phase was removed, and an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography. The resulting crystals were recrystallized from hexane, whereby 11.6g (yield: 45%) of white crystals of 2,4-bis(2-fluorophenyl)-1,3-dimethoxybenzene were obtained. |
45% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 24.0h;Reflux; Inert atmosphere; | Under argon atmosphere Intermediate 15 (23.2g), 2-fluorophenylboronic acid (32.9 g), tetrakis triphenylphosphine palladium (0) (5.43g), toluene (150 mL), 1,2-dimethoxyethane ( 150 mL), 2M aqueous sodium carbonate (150 mL) were charged to a flask and stirred heated to reflux for 24 hours. After cooling to room temperature, the water layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate, concentrated, and the residue was purified by silica gel chromatography. The obtained crystals were recrystallized Intermediate 16 (11.6g) in hexane. The yield was 45%. |
42% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; toluene; at 100℃; for 12.0h; | 1,3-dibromo-2,6-dimethoxybenzene in the reactor, 50 g (169 mmol), fluorophenylboronic acid 52 g (372 mmol),Tetrakis (triphenylphosphine) palladium (0) 3.9 g (3 mmol), Potassium carbonate46.7 g (338 mmol), 1,4-dioxane 250 ml,Toluene250 ml, 50 ml of distilled water was put into the mixture and was stirred at100 for 12hours. When the reaction is completed it is cooled at room temperature, theorganic layer was extracted and concentrated under reduced pressure to obtain23 g of a compound represented by .4-a (Yield 42%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; water; for 2h;Inert atmosphere; Reflux; | 3.18 g (10.0 mmol) of <strong>[132178-78-0]1,5-dibromo-2,6-dihydroxynaphthalene</strong>, 7.00 g (50.0 mmol) of 2-fluorophenylboronic acid, 458 mg (0.50 mmol) of tris(dibenzylideneacetone)dipalladium, 820 mg (2.00 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl, 8.49 g (40.0 mmol) of potassium phosphate, 35 mL of THF, and 17.5 mL of water were mixed and refluxed under heating in a nitrogen atmosphere for 2 hours. The reaction liquid was cooled to room temperature, to which ethyl acetate and water were then added, and the organic layer was extracted. The organic layer was concentrated, then purified by silica gel column chromatography (toluene/ethyl acetate=9/1), and further rinsed out with methanol, thereby providing 2.0 g of a synthesis intermediate 1 as a white solid matter (yield: 57%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Into a 500-mL three-neck flask were put 10 g (46 mmol) of <strong>[16932-45-9]2-bromo-1,3-dimethoxybenzene</strong>, 7.2 g (51 mmol) of 2-fluorophenylboronic acid, 66 mL of toluene, 66 mL of diethylene glycol dimethyl ether (diglyme), and 76 mL of a sodium carbonate aqueous solution (2.0 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 1.1 g (0.95 mmol) of tetrakis(trismethylphenylphosphine)palladium(0), and the mixture was stirred for 5 hours. After the stirring, the obtained mixture was cooled down to room temperature. Then, 3.2 g (23 mmol) of 2-fluorophenylboronic acid and 1.0 g (0.87 mmol) of tetrakis(trismethylphenylphosphine)palladium(0) were added to the mixture. The mixture was degassed by being stirred while the pressure in the flask was reduced. The atmosphere in the flask was replaced with nitrogen, and the mixture was stirred at 80 C. for 8 hours. After the stirring, the mixture was cooled down to the room temperature. Then, 5.2 g (37 mmol) of 2-fluorophenylboronic acid, 0.19 g (0.46 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl, and 50 mg (0.22 mmol) of palladium(II) acetate were added to the mixture. The mixture was degassed by being stirred while the pressure in the flask was reduced. The atmosphere in the flask was replaced with nitrogen, and the mixture was stirred at 80 C. for 4 hours. After the stirring, this mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a brown oily substance. The obtained oily substance was purified by silica gel column chromatography (a developing solvent was subjected to a gradient to change from hexane to chloroform gradually) and was then recrystallized with toluene/hexane to give 8.4 g (36 mmol) of a target solid at a yield of 78%. A synthesis scheme of the above synthesis method is shown in (C-1) below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81% and its NMR data was as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 2-fluorophenylboronic acid (0.56?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol) and Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14c as a white solid (0.36?g, 43%); Rf?=?0.00 (EtOAc 9: acetone 1); 1H NMR (DMSO-d6, 400?MHz) delta 2.89-3.09 (m, NH3CH2CH2), 7.24-7.52 (m, 8 ArH), 8.32 (s, NH3); 13C NMR (DMSO-d6, 100?MHz) delta 33.1 (NCH2CH2), 116.6 (d, JC-F?=?22.4?Hz), 120.3, 125.4 (d, JC-F?=?3.5?Hz), 129.4, 129.5, 129.9 (d, JC-F?=?8.2?Hz), 131.1 (d, JC-F?=?3.3?Hz), 131.5, 131.9, 137.5 (d, JC-F?=?21.9?Hz), 159.6 (d, JC-F?=?244.2?Hz) (12 ArC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine; In toluene; at 110℃; for 7h;Inert atmosphere; | Into a 200-mL three-neck flask were put 3.0 g (8.7 mmol) of<strong>[105404-89-5]3,6-dibromo-2,7-dimethoxynaphthalene</strong>, 1.2 g (8.7 mmol) of 2-fluorophenylboronic acid, 2.4 g(17 mmol) of potassium carbonate, and 0.13 g (0.43 mmol) of tris(2-methylphenyl)phosphine.5 To this mixture was added 90 mL of toluene. The resulting mixture was degassed by beingstirred while the pressure was reduced. To the mixture was added 19 mg (87 IJ.mol) ofpalladium(II) acetate, and stirring was performed under a nitrogen stream at 110 oc for 7 hours.After the stirring, toluene was added to the mixture, and the resulting mixture wassuction-filtered through Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog10 No. 540-00135), Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No.531-16855), and alumina to give a filtrate. The filtrate was concentrated to give a solid. Thissolid was purified by silica gel column chromatography (as the developing solvent, first, tolueneand hexane in a ratio of 1:2 were used, and then toluene and hexane in a ratio of 1:1 were used)to give 1.1 g of a white solid which was an objective substance in a yield of 34 %. A synthesis15 scheme of Step 1 is shown below |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.8% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere; | Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, 19.0 g (0.136 mol) of 2-fluorophenylboronic acid, 15.0 g of potassium carbonate in a four-necked flask, and add 100 g of DMF and 40 g of water in a nitrogen atmosphere. A catalytic amount of tetrakis(triphenylphosphine)palladium was added thereto, and the temperature was raised to 105 C, and the reaction was carried out for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, diluted with water, and extracted with ethyl acetate. The extract was dried, suction filtered, concentrated and weighed. Crystallization gave 13.5 g of gray solid 1, yield 82.8%, purity 99.94% |
82.8% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere; | Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, respectively.19.0 g (0.136 mol) of 2-fluorophenylboronic acid,15.0g of potassium carbonate in a four-necked bottle,Add 100g DMF and 40g water,A catalytic amount of tetrakis(triphenylphosphine)palladium is added under a nitrogen atmosphere.Warming up to 105 C,Reaction for 20h,After the reaction is over,Down to room temperature,Dilute with water,Extracted with ethyl acetate,The extract is dried,Filtering,concentrate,Recrystallization gave 13.5 g of a gray solid 1,The yield is 82.8%.Purity 99.94%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
Tags: 2-Fluorophenylboronic acid | Fluorinated Building Blocks | Organoboron | Aryls | Boronic Acids | Organic Building Blocks | Boronic Acids/Esters | Organometallic Reagents | 1993-03-9
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
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.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL