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. : | 585-76-2 | MDL No. : | MFCD00002487 |
Formula : | C7H5BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VOIZNVUXCQLQHS-UHFFFAOYSA-N |
M.W : | 201.02 | Pubchem ID : | 11456 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.1 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.49 cm/s |
Log Po/w (iLOGP) : | 1.12 |
Log Po/w (XLOGP3) : | 2.87 |
Log Po/w (WLOGP) : | 2.15 |
Log Po/w (MLOGP) : | 2.36 |
Log Po/w (SILICOS-IT) : | 1.9 |
Consensus Log Po/w : | 2.08 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.27 |
Solubility : | 0.107 mg/ml ; 0.000534 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.31 |
Solubility : | 0.0978 mg/ml ; 0.000487 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.63 |
Solubility : | 0.473 mg/ml ; 0.00236 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.16 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
91% | With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 95℃; Inert atmosphere | General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide In 1,4-dioxane at 110℃; for 23 h; Stage #2: With hydrogenchloride; water In 1,4-dioxane at 20℃; |
A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 molpercent), 3- bromobenzoic acid (210 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and [BACKELLEDWITHARGON. TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine [(16) IL,] 0. 10mmol, 10 molpercent), 1,1, 1,3, 3,3-hexamethyldisilazane [(211, UL,] 1.00 mmol), and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature, poured into 10percent aq HCl (20 mL), and extracted with dichloromethane [(3X 15] mL). The combined organic phases were dried [(NA2SO4)] and concentrated. The residue was dissolved in dichloromethane (50 mL) and washed with an aqueous solution of 1percent HCl and 1percent [NA2SO3.] The aqueous phase was extracted with with dichloromethane [(2X20] mL). The organic phases were combined, dried (Na2SO4) and concentrated. The solid residue was washed with hexane [(3X15 ML)] and dried to provide 3-iodobenzoic acid (222 mg, 90percent yield) as white, fine needles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-iodo-succinimide; [4,4’-bis(tert-butyl)-2,2’-bipyridine]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl]iridium(III) hexafluorophosphate; iodine; caesium carbonate In 1,2-dichloro-ethane at 50℃; for 24 h; Inert atmosphere; Irradiation; Sealed tube | General procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), NIS (1.5mmol, 337.5 mg) and I2 (60 μmol, 20 molpercent) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry DCE was added through a syringer under argon.The tube was sealed with Parafilm Mr® and placed in an oil bath with a contact thermometer, andthe reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λmax = 455 nm).After 24 h or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and thesilica was washed with DCM) (50 mL). The filtrate was collected and the solvent was removed invacuo. The crude residue was purified by silica gel flash column chromatography to provide thetarget product (2). (Note: The reaction was very sensitive to moisture, and the yields sharplydecreased to less than 5percent when 0.01 equivalent of H2O was added to the reaction system). |
61% | With 1-iodo-3,5,5-trimethylhydantoin In tetrachloromethane for 15 h; Reflux; Irradiation | [00216] A mixture of 3 -bromobenzoic acid (0.40 g, 2.0 mmol), l-iodo-3,5,5- trimethylhydantoin (0.80 g, 3.0 mmol), and CC (10 mL) was refluxed under irradiation with tungsten lamp for 15 h. The cold reaction mixture was washed with 1 M aq Na2S03 (2 x 5 mL), dried over Na2S04, filtered through short neutral alumina pad and concentrated in vacuo to give 0.35 g (61percent) of 3- bromoiodobenzene. The combine aq sodium sulfite washings were extracted with DCM (3 x 10 mL), carefully acidified with cone, hydrochloric acid to pH 2 and stirred at 0-5 °C for 2 h. The precipitated solid was filtered off, washed on the filter with cold water and dried in vacuo to recover 0.12 g (30percent) of 3- bromobenzoic acid. The combine DCM extracts were dried over Na2S04, filtered and concentrated in vacuo to obtain 0.21 g (75percent) of 3,5,5-trimethylhydantoin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; acetonitrile at 0℃; for 0.166667 h; Inert atmosphere Stage #2: With ammonium hydroxide; ammonia; sodium hydroxide In dichloromethane; acetonitrile |
In a round-bottomed two-neck flask 820 mg 3-bromobenzoic acid (4.0 mmol) were suspended in 14 mL of a 6: 1 DCM/MeCN mixture under argon and 600 mg HOBt (4.44 mmol) and 861 mg EDOHCI (4.4 mmol) were added under stirring. After 10 min the mixture became clear and was cooled to 0°C in an ice bath. In a round-bottomed flask 1.64 g NaOH (40 mmol) were added to 2.8 mL of a 28 percent NH4OH solution (20 mmol) and the resulting gaseous NH3 was bubbled into the reaction vessel after passing through a NaOH trap. After NH3-bubbling had ceased, the mixture was concentrated under reduced pressure, taken-up in AcOEt (60 mL), washed with 5 percent KHSO4 (2x30 mL), H20 (20 mL), 5 percent NaHC03 (3x20 mL) and brine (20 mL), dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. 700 mg 3-bromobenzamide were obtained (87 percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With boron trifluoride diethyl etherate In toluene at 20℃; for 0.5 h; | Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.94% | With sulfuric acid; nitric acid In water at 0 - 20℃; for 1 h; | A suspension of 3-bromobenzoic acid (249 g, 1.24 mol, 1.0 eq.) in conc.sulfuric acid (800 mL) was cooled at 0° C. Conc. nitric acid (57.1 mL, 1.2 mol) was added dropwise and the mixture was warmed to 20° C. and stirred 1 hr. The mixture was poured into poured into ice-water (2 L). The precipitate was collected by filtration, washed with water (1000 mL*2) and dried to give 5-bromo-2-nitrobenzoic acid (280 g, 1.14 mol, 91.94percent yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=14.12 (br. s., 1H), 8.00 (d, J=1.8 Hz, 1H), 7.98-7.90 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; Inert atmosphere | To a degassed souDon of 1,4-doxane (0.1 M), under an atmosphere of ntrogen,was addedthe benzoc acid (1 eq.), bs(pnacoato)dthoron (1 .5 eq.), and KOAc (4.4 eq.) sequenUafly.The mixture was degassed once again and then PdC2(dppf) (5 mopercent) was added. Theresutng souUon was heated to 110°C overnight. The sovent was removed in vacuo to givea dark gummy residue, which was taken up nto EtOAc and H20. The organic ayer was separated and the aqueous was further extracted with EtOAc (2x). The combined organic ayers were washed with 2 M HC, dried over MgSO4 and concentrated in vacuo to give a dark brown sohd. The resutng sohd was trtu rated wth petroeum benzne to afford the Uflecompound. The foHowng compounds were made by the 8uzuk couphng method E Bl,Os 0BCO2HFaint brown scUd (89percent). 1H NMR (400 MHz,CDC3) 68.57 (s, 1H), 8.19 (ddd, J= 21.9, 11.8,10.1 Hz, 1 H), 8.09 7.98 (m, 1 H), 7.57 7.38(m, 1H), 1.37 (s, 12H). 13C NMR (101 MHz,CDC3)6 171.66, 139.98, 136.60, 132.84,128.71, 127.93, 84.21, 24.89. LCM8 B rt 3.67mn, m/z249.2 [M + H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With palladium 10% on activated carbon; sodium carbonate In water; isopropyl alcohol at 20 - 70℃; for 4.5 h; | The Suzuki coupling was carried out according to the method of Dyer et al. (Tetrahedron Letters, 2001, 42, 1765-1767). Commercially available 4-(Trifluoromethyl)phenylboronic acid (95.9g, 505 mmol) and 3-bromobenzoic acid (100.5g, 500 mmol) were suspended in 2-propanol:water (1:4, 500 mL). 10percent Pd/C (4.8g) was added. Aqueous Na2CO3 (250 mL, 20percent by wt.) was then added slowly (to control CO2 evolution) to the above mixture while vigorously stirring. The resulting mixture was stirred at room temperature for 30 min and then heated at 70C for 4 hours. The Pd/C was filtered and rinsed with 20percent aqueous Na2CO3 solution (20mL). The filtrate was acidified to pH~4 with 6N HCl, and the resulting white solid was collected by filtration and dried in vacuo. The crude product was dissolved in acetone (1.4L) then an equal volume of distilled water was added. The resulting white precipitate was collected by filtration and dried in vacuo. 120.2 g of coupled product 8.1 was acquired (yield: 90percent). MS ESI m/e: 267 (M-H). 1H NMR (500MHz) (DMSO) 13.17 (1H, s); 8.25 (1H, s); 8.03-7.99 (2H, m); 7.95 (2H, d); 7.85 (2H, d); 7.66 (1H, t). mp: 197 °C - 200 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 95℃; Inert atmosphere | General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product. |
[ 74346-19-3 ]
4-Bromo-2,6-dimethylbenzoic acid
Similarity: 0.93
[ 74346-19-3 ]
4-Bromo-2,6-dimethylbenzoic acid
Similarity: 0.93
[ 74346-19-3 ]
4-Bromo-2,6-dimethylbenzoic acid
Similarity: 0.93