Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 6952-59-6 | MDL No. : | MFCD00001796 |
Formula : | C7H4BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | STXAVEHFKAXGOX-UHFFFAOYSA-N |
M.W : | 182.02 | Pubchem ID : | 23381 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 38.86 |
TPSA : | 23.79 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) : | -6.15 cm/s |
Log Po/w (iLOGP) : | 1.91 |
Log Po/w (XLOGP3) : | 1.77 |
Log Po/w (WLOGP) : | 2.32 |
Log Po/w (MLOGP) : | 2.21 |
Log Po/w (SILICOS-IT) : | 2.5 |
Consensus Log Po/w : | 2.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.58 |
Solubility : | 0.482 mg/ml ; 0.00265 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.89 |
Solubility : | 2.36 mg/ml ; 0.013 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.33 |
Solubility : | 0.0842 mg/ml ; 0.000462 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
85% | With C20H24ClNO2Ru; sodium hydroxide In isopropyl alcohol at 79.84℃; for 4 h; Inert atmosphere; Schlenk technique | General procedure: To a stirred solution of half-sandwich ruthenium complex (0.25molpercent) in 2.0mL of isopropanol were added NaOH (0.3mmol) and benzonitrile (0.3mmol) followed by stirring for 4h at 353K. After completion of the reaction (monitored by TLC), the resulting solution was evaporated to dryness at reduced pressure. The crude products loaded directly onto a column of silica gel and purified by column chromatography to yield the corresponding amides [15]. |
82% | With dihydrogen peroxide; potassium carbonate In water; dimethyl sulfoxide at 0 - 20℃; for 0.5 h; | Step 54a: 3-Bromobenzamide (Compound 0601-142)To a solution of m-bromobenzonitrile (2 g, 10 mol) in DMSO (6 mL) was added 30percent H202 (5 g, 13 mmol) and K2C03 at 0°C, and stirred at room temperature for 30 min. The mixture was poured into water and filtered, the solid was washed with water, dried to got the compound 0601-142 (1.8 g, 82percent) as a white solid. LCMS: 200 [M+l]+; 1H NMR (400 MHz, DMSO-de) δ 7.41 (t, J= 8.0 Hz, 1H), 7.50 (s, 1H), 7.70(dd, J = 8.0, 0.8 Hz, 1H), 7.85 (d, J= 8.0 Hz, 1H), 8.03 (t, J= 1.6 Hz, 1H), 8.06 (s, 1H). |
82% | With dihydrogen peroxide; potassium carbonate In water; dimethyl sulfoxide at 0 - 20℃; for 0.5 h; | Step 54a: 3-Bromobenzamide (Compound 0601-142)[0425]To a solution of m-bromobenzonitrile (2 g, 10 mol) in DMSO (6 mL) was added 30percent H2O2 (5 g, 13 mmol) and K2CO3 at 0° C., and stirred at room temperature for 30 min. The mixture was poured into water and filtered, the solid was washed with water, dried to got the compound 0601-142 (1.8 g, 82percent) as a white solid. LCMS: 200 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 7.41 (t, J=8.0 Hz, 1H), 7.50 (s, 1H), 7.70 (dd, J1,2=8.0, 0.8 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 8.03 (t, J=1.6 Hz, 1H), 8.06 (s, 1H) |
82% | With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide at 0 - 20℃; for 0.5 h; | To a solution of DMSO (6mL) in m- bromobenzonitrile (2g, 10mol), with the addition of 30percent H2O2 (5g, 13mmol) and K2CO3 at 0 , and the mixture was stirred for 30 minutes at room temperature. The mixture was filtered and poured into water and the solid was washed with water, dried, The compound was prepared 0601-142 as a white solid solid (1.8g, 82percent). |
81% | at 120℃; for 15 h; Green chemistry | General procedure: Ni NPs/HT (0.05 g) is placed in a heavy-walled pressure tube, followed by the addition of water (4 ml) and benzonitrile (1 mmol), and the reaction mixture is vigorously stirred at 120 °C in an oil bath for the specified time in tables. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture is extracted with ethyl acetate, after the extraction, the catalyst is removed by filtration, and the filtrate is cooled to 0 °C, and white crystals are precipitated from the filtrate. The crystalline product was obtained by simple filtration and dried in vacuo at room temperature to give analytically amide product. In cases where the product not precipitated out, the reaction mixture was extracted with ethyl acetate, subsequent purification by column chromatography on silica gel provided amide product.#10;#10; |
80% | With sodium perborate In 1,4-dioxane; water at 80℃; for 16 h; | 3-Bromobenzoic acid amide. To a solution [OF 3-BROMOBENZONITRILE (0. 91] g, 5 mmol) in dioxane (19 mL), [NABO3 4H2O] (2.12 g, 13.78 mmol) and [HA0] (19 mL) were added. The mixture was stirred at [80 C] 16 hours (h), cooled, added [OF H2O] and extracted with [CH2CK.] The combined organic layers were dried over [NA2S04] and evaporated. Purification of the residue by column chromatography (hexane/EtOAc 2: 8) and recrystallization gave the desired product as colorless tablets. Yield 80percent (EtOH). Mp: [156-7 C] (lit. [156 C)] (Pearson, D. E. et al., J. Org. [CLTEM.,] 28: 3147-3149, (1963) ). MS [(EI)] : mlz 199 (M+); 183 (100percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With palladium diacetate In 1-methyl-pyrrolidin-2-one at 20 - 140℃; for 24 h; Inert atmosphere | General procedure: An oven-dried Schlenk-tube (10 mL) was charged with Pd source (1 mol percent), and ethyl potassium oxalate (0.75 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL) were added by syringe under a counter flow of argon at room temperature. The reaction vessel was closed and then placed under stirring in a preheated oil bath. The reaction mixture was stirred for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate, and analyzed by gas chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With 1H-imidazole; palladium diacetate; triethylamine; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; magnesium chloride In tetrahydrofuran at 90℃; for 0.5 h; Microwave irradiation | To a stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 molpercent), Xantphos (5 mol percent), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90°C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.17% | Stage #1: With triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 20℃; for 0.25 h; Stage #2: at 20℃; for 0.0833333 h; Stage #3: at 180℃; for 0.25 h; Microwave |
Palladium (II) acetate (13.5 mg, 0.06 mmol), tri (o-tolyl) phosphine (40.2 mg, 0.132 mmol), and triethylamine (0.825 ml, 6.0 mmol) were dissolved in acetonitrile (9 ml) and stirred at room temperature for 15 minutes. 3-Bromo-benzonitrile (1.1 g, 6.0 mmol) was added and the reaction mixture was stirred for an extra 5 minutes at room temperature. Then, acrylic acid was added and the reaction mixture was stirred at 180° C. for 15 minutes in a microwave. The precipitate was filtered off and treated with water to yield a grey solid. The filtrate was concentrated and the residue was treated with water to yield a yellow solid. Each product was separately dissolved in ethanol and dichloromethane, and filtered through celite using ethanol. The filtrate was concentrated in vacuo to yield a light grey solid (552.5 mg, 53.17percent). 1H NMR (300 MHz, DMSO): δ (ppm)=12.59 (s, 1H); 8.24 (m, 1H); 8.06 (m, 1H); 7.87 (m, 1H); 7.62 (m, 2H); 6.71 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1 h; Stage #2: With hydrogenchloride In water |
4.2.17 3-Bromobenzimidamide hydrochloride (23) Beige solid; yield: 81percent. 1H NMR (400 MHz, d6-DMSO): δ 9.74 (s, 2H), 9.50 (s, 2H), 8.12 (t, J = 1.8 Hz, 1H), 7.88-7.96 (m, 2H), 7.56 (t, J = 8.1 Hz, 1H). 13C NMR (101 MHz, d6-DMSO): δ 165.0 (C), 136.9 (CH), 131.5 (CH), 131.3 (CH), 130.4 (C), 127.8 (CH), 122.4 (C). IR (neat, ν/cm-1): 3239 (br s), 3027 (br s), 1673 (s), 1519 (s), 1465 (s), 1080 (m), 884 (m), 796 (m), 710 (s), 659 (s). HRMS (ES-TOF+) calculated for C7H8N2Br 198.9871, found 198.9873. |
78% | Stage #1: With trimethylaluminum; ammonium chloride In hexane; toluene at 80℃; Stage #2: With methanol In hexane; toluene at 0 - 20℃; |
1. 18 g (22 mmol, 2 equiv.) ammonium chloride are suspended in 40 ml of dry toluene under an argon atmosphere, and the mixture is cooled to 0°C. 11 ml (22 mmol, 2 equiv. ) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evolution of gas is observed. After addition of 2.0 g (11 mmol, 1 equiv. ) 3-bromobenzonitrile, the mixture is stirred at 80°C bath temperature over night. It is then cooled down to 0°C, and 50 ml of methanol are added with subsequent stirring for 1 hour at room temperature. After filtration, the solid is washed with methanol for several times, the solution is evaporated to dryness in vacuo and the residue washed with methanol. Yield: 2.02 g (78percent) H-NMR (DMSO-d6, 300 MHz): 8 = 7.6 (m, 1H), 7. 8 (m, 1H), 8.0 (m, 1H), 8.1 (s, 1H) ppm. |
78% | With ammonium chloride In methanol; hexane; toluene | EXAMPLE 3A 3-Bromobenzenecarboximidamide Hydrochloride 1,18 g (22 mmol, 2 equiv.) ammonium chloride are suspended in 40 ml of dry toluene under an argon atmosphere, and the mixture is cooled to 0° C. 11 ml (22 mmol, 2 equiv.) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evolution of gas is observed. After addition of 2,0 g (11 mmol, 1 equiv.) 3-bromo-benzonitrile, the mixture is stirred at 80° C. bath temperature over night. It is then cooled down to 0° C. and 50 ml of methanol are added with subsequent stirring of 1 hour at room temperature. After filtration, the solid is washed with methanol for several times, the solution is evaporated to dryness in vacuo and the residue washed with methanol. Yield: 2.02 g (78percent) 1H-NMR (DMSO-d6, 300 MHz): δ=7,6 (m, 1H), 7,8 (m, 1H), 8,0 (m, 1H), 8,1 (s, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.5 h; Stage #2: Heating / reflux |
20 g of 3-bromobenzonitrile was dissolved in 100 ml of dry THF, and then mixed with 37.6 ml of triisopropoxyborane in the atmosphere of nitrogen. The solution was cooled at -78° C., and then 98.3 ml of a 1.6M n-butyl lithium hexane solution was dropwisely added to the cooled solution for about 30 minutes with stirring. The mixture was stirred at room temperature for 30 minutes, cooled at 0° C. and mixed with 220 ml of 4M sulfuric acid. The solution was heated and refluxed overnight, again cooled at 0° C., mixed with 340 ml of a 5M aqueous solution of sodium hydroxide, and then extracted with 200 ml of diethyl ether. The aqueous phase was separated, mixed with 6M hydrochloric acid until to give pH 2, and then twice extracted with 300 ml of ethyl acetate. The obtained ethyl acetate layer was dried over MgSO4, and the solvent was distilled away. The obtained crude product was recrystallized from DMF-water to obtain 11.6 g (72percent) of the title compound as needle-like pale yellow crystals. 1H NMR (270 MHz): δ (DMSO-d6) 8.5(brs, 2H), 8.3-7.6(m, 4H). |
62% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1 h; Inert atmosphere Stage #2: With sulfuric acid In tetrahydrofuran; diethyl ether; hexane at 0℃; Reflux |
3-bromobenzonitrile (20 g, 110 mmol) was dissolved in 100 mL of dry THF, and then mixed with triisopropoxyborane (71 ml, 309 mmol) in the atmosphere of nitrogen. The solution was cooled at -78° C., and then n-butyl lithium (76 mL, 121 mmol, 1.6M in hexane) was dropwisely added to the cooled solution for about 30 minutes with stirring. The mixture was stirred at room temperature for 30 min, cooled at 0° C. and mixed with 220 mL of 4M sulfuric acid. The solution was heated and refluxed overnight, again cooled at 0° C., mixed with 340 mL of a 5M aqueous solution of sodium hydroxide, and then extracted with 200 mL of diethyl ether. The aqueous phase was separated, mixed with 6M hydrochloric acid until to give pH 2, and then twice extracted with 300 mL of with 6M hydrochloric acid until to give pH4 2, and then twice extracted with 300 mL of ethyl acetate. The obtained ethyl acetate layer was dried over Na2SO4, and the solvent was distilled away. The obtained crude product was recrystallized from DMF-water to obtain (3-cyanophenyl)boronic acid (10.12 g, 62percent) as a solid.1H NMR (400 MHz, DMSO-d6): δ 8.39 (brs, 2H), 8.13 (s, 1H), 8.07 (d, J=7.6 Hz, 1H), 7.86 (d, J=7.6 Hz, 1H), 7.56 (t, J=7.6 Hz, 1H). |
72% | With hydrogenchloride; sodium hydroxide; n-butyllithium; sulfuric acid In tetrahydrofuran; hexane | Productive Example 1 Preparation of 3-cyanophenylboronic acid In 100 ml of anhydrous tetrahydrofuran, was dissolved 20 g of 3-bromobenzonitrile. To the resulting solution, was added 37.6 ml of triisopropoxyborane under a nitrogen atmosphere. The formed solution was cooled to -78° C., and 98.3 ml of a 1.6 M solution of n-butyllithium in hexane was dropped thereinto under stirring for about 30 minutes. After stirring the resulting mixture at room temperature for 30 minutes, the mixture was then cooled to 0° C., and 220 ml of a 4 M sulfuric acid was added. The prepared solution was refluxed overnight and subsequently recooled to 0C. To the cooled solution, was added 340 ml of a 5 M aqueous solution of sodium hydroxide. The resulting solution was extracted with 200 ml of diethyl ether, and an aqueous layer was separated. To the aqueous layer, was added a 6 M hydrochloric acid until pH attained 2. The resulting mixture was extracted with 300 ml of ethyl acetate twice. The extract was dried over magnesium sulfate, and the solvent was then evaporated. The resulting crude product was recrystallized from dimethylformamide-water to provide 11.6 g (72percent) of the title compound as a needlelike light-yellow crystal. 1H-NMR (270 MHz, DMSO-d6): δ 7.6-8.3 (m, 4H), 8.5 (brs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With hydrogenchloride In tetrahydrofuran; hexane | Part C. Preparation of 3-cyanophenylboronic Acid. 3-Bromobenzonitrile (10.0 g, 55 mmol) was dissolved in dry THF (100 mL) and cooled to -100° C. (Et2 O/N2). n-Butyllithium (24.2 mL, 2.5 M in hexane) was added over 30 minutes, maintaining the internal temp under -90°. After 20 minutes, triisopropylborate (18.0 mL) was added over 15 minutes, again maintaining the internal temperature. After the addition was complete, the reaction was allowed to warm slowly to room temperature over 1.5 hours. The reaction was stirred at room temp for 16 hours, then cooled to 15° C., after which 6 M HCl (25 mL) was added. After stirring vigorously for 3.5 hours, the reaction was partitioned between water and EtOAc. After extracting a second time with EtOAc, the combined organics were washed with 2 M NaOH. The aqueous extract was neutralized with 6 M HCl. The white precipitate was filtered, yielding the desired product (4.80 g, 60percent). 1 H NMR (DMSO-d6): δ 8.37 (s, 2H), 8.10 (s, 1H), 8.03 (dt, 1H, J=7.3, J'=1.1), 7.83 (dt, 1H, J=7.6, J'=1.4), 7.53 (t, 1H, J=7.7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.6% | at 0 - 20℃; for 20 h; Inert atmosphere | 3-Bromobenzonitrile (7.80 g, 42.9 mmol) was placed in a 50 mL two-necked flask The inside of the flask was purged with nitrogen and ice bath was added. To the 3-bromobenzonitrile in the flask, Trifluoromethanesulfonic acid (3.47 mL, 42.9 mmol) was added dropwise via a dropping funnel. Under a nitrogen gas flow, The temperature was gradually returned to room temperature from 0 ° C., And the mixture was stirred at room temperature for 20 hours. After stirring, The solid obtained by the reaction was added to 100 mL of 28percent aqueous ammonia and stirred. In this way, The solid changed from yellow to white. The solid in the aqueous ammonia was recovered by suction filtration, water, Methanol in order. The washed solid was added to 200 mL of methanol and irradiated with ultrasonic waves. After irradiation, The mixture was suction filtered to recover a solid, White powdery solid (2,4,6-tris (3-bromophenyl) -1,3,5-triazine) Was obtained in a yield of 7.78 g, In a yield of 99.6percent. |
93% | at 0 - 20℃; for 12.5 h; Inert atmosphere; Cooling with ice | (1) Synthesis of 2,4,6-tri(3-bromophenyl)-1,3,5-triazine To a two-neck flask having been substituted with nitrogen, trifluoromethanesulfonic acid (66.6 mmol, 9.99 g) was added, and cooled (0 to 5ºC) over an ice bath. 3-Bromobenzonitrile (19.6 mmol, 3.57 g) was added thereto, and the mixture was stirred for 30 minutes. Thereafter, the mixture was stirred at room temperature for 12 hours. Water was added to the mixture, which was then neutralized with NaOH, and then washed with a mixed solvent of chloroform and acetone (50/50), and the organic layer was extracted. The organic layer was dehydrated over anhydrous magnesium sulfate, and the solvent was distilled off, thereby providing 2,4,6-tri(3-bromophenyl)-1,3,5-triazine as the target product (yield amount: 3.32 g, yield: 93.0percent). |