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CAS No. : | 376646-62-7 | MDL No. : | MFCD01310789 |
Formula : | C8H10BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CRDQDMSHRCFAAW-UHFFFAOYSA-N |
M.W : | 200.08 | Pubchem ID : | 2735592 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.78 |
TPSA : | 26.02 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) : | -6.21 cm/s |
Log Po/w (iLOGP) : | 2.05 |
Log Po/w (XLOGP3) : | 1.84 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 2.61 |
Log Po/w (SILICOS-IT) : | 2.57 |
Consensus Log Po/w : | 2.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.62 |
Solubility : | 0.483 mg/ml ; 0.00241 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.01 |
Solubility : | 1.97 mg/ml ; 0.00984 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.69 |
Solubility : | 0.0411 mg/ml ; 0.000206 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
100% | Stage #1: With borane In tetrahydrofuran at 0 - 80℃; Inert atmosphere Stage #2: With hydrogenchloride In 1,4-dioxane; ethyl acetate for 0.0833333 h; |
[0617j To a solution of 4-bromo-2-methylbenzonitrile (3.0 g, 15 mmol) in anhydrous THF (20 mL) under nitrogen at 0 °C was added 1.0 M solution of borane in THF (46 mL). The reaction mixture was stirred at 0 °C for 1 h, and heated at 80 °C overnight. The reaction mixture was cooled to 0 °C and slowly quenched with MeOH, concentrated in vacuo. The crude product was treated with EtOAc (20 mL) and 4 M of HC1 in 1,4-dioxane (8.0 mL, 32 mmol) for 5 mm. The solid was filtered, rinsed with diethyl ether, dried to give the title compound as a white powder (3.24 g, yield: 100percent). LCMS: RT 0.75 mm.; MH+ 200.0. ‘H NMR (300 MHz, DMSOd6) 5: 8.28 (br. s., 2H), 7.42 - 7.54 (m, 2H), 7.34 (d, J = 7.93 Hz, 1H), 3.99 (d, J = 4.15 Hz, 2H), 2.35 (s, 3H). |
90% | With THF·BF3 In tetrahydrofuran at 0 - 80℃; for 17 h; | [0114] To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL), BH3 THF (45 mL, 45 mmol) was added. The solution was stirred at 0 °C for 1 h and heated to 80 °C for 16 h. Then the mixture was quenched with MeOH. After concentrated, the residue was stirred with saturated HCl/EtOAc solution and filtered. The filter cake was rinsed with ether (20 mL x3) and dried under vacuum to afford (4-bromo-2-methylphenyl)methanamine (3.2 g, yield: 90percent) as white solid. ESI-MS (M+H)+: 200.1 Preparation of tert-butyl 4-bromo-2-methylbenzylcarbamate |
69% | With borane-THF In tetrahydrofuran at 0 - 80℃; for 3 h; | To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL) was added BH3·THF (45 mL, 45 mmol) at 0 °C. The solution was stirred for 1 h and heated to 80 °C for 2 h. The mixture was quenched with H2O and extracted with EtOAc (50 mL x 3). The organic layer was concentrated in vacuo to afford a residue which was suspended in saturated HCl/EtOAc and filtered. The filter cake was washed with diethyl ether (20 mL x 3) and dried under vacuum to afford the desired product (2.1 g, yield 69percent) as white solid. ESI-MS (M+H)+: 200.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With borane-THF; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux; | General procedure: Following general procedure P, 4-bromo-2,6-difluorobenzonitrile (350 mg, 1 .61 mmol) yielded (4- bromo-2,6-difluoro-phenyl)methanamine (260 mg,1 .17 mmol, 73percent yield) as a yellow liquid. LC-MS (ES+, method 2): 1 .33 min, m/z 221 .9 [M]+ 1 M borane THF complex (5.0 eq.) was added dropwise under nitrogen to a stirred solution of nitrile derivative (1 .0 eq.) in anhydrous THF (0.10 M). The reaction mixture was then heated at reflux for 4 h before being cooled to room temperature. Methanol was added carefully dropwise until evolution of gas ceased. The solvent was removed under reduced pressure and the residue was dissolved in methanol and treated with cone. aq. HCI. The resultant mixture was heated at reflux for 10 min and then cooled to room temperature. The solvent was removed under reduced pressure and the residue was treated cautiously with excess aq. sodium bicarbonate solution. The resultant suspension was extracted with ethyl acetate and the organic layer was dried, filtered and evaporated under reduced pressure to yield the corresponding amine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | To a solution of acid (185 mg, 1.0 mmol) in DMF (5 mL) was added HBTU (455 mg, 1.2 mmol) and DIPEA (387 mg, 3.0 mmol) and stirred at rt for 15 min, followed by the addition of 4-bromo-2-methylphenyl)methanamine (300 mg, 1.5 mmol), and the solution was stirred at rt for 16 h. Diluted with water (40 mL), the mixture was extracted with EtOAc (80 mL x 2). The organic phase was concentrated in vacuo to afford a residue which was purified by silica gel column chromatography (peteroleum ether/EtOAc = 10:1~4:1) to give the title compound (220 mg, yield: 60percent) as a yellow solid. ESI-MS (M+H)+: 367.1.1H NMR (400 MHz, CDCl3) : 8.20 (s, 1H), 7.35 (d, J = 1.6 Hz, 1H), 7.32 (dd, J = 8.0, 1.6 Hz, 1H), 7.17 (d, J = 8.4 Hz, 1H), 4.55 (d, J = 5.6 Hz, 2H), 2.34 (s, 3H), 1.47 (s, 9H). | |
60% | [0196j A mixture of 2-(tert-butyl)thiazole-5-carboxylic acid (185 mg, 1.0 mmol), HBTU (455 mg, 1.2 mmol) and DIPEA (387 mg, 3.0 mmol) in DMF (5 mL) was stirred at rt for 15 mill. Then <strong>[376646-62-7](4-bromo-2-methylphenyl)methanamine</strong> (300 mg, 1.5 mmol) was added. The resulting mixture was stirred at rt for 16 h. After diluted with water (40 mL), the mixture was extracted with EtOAc (80 mL x 2). The organic phase was concentrated and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 10:1 4: 1) to give N-(4-bromo-2- methylbenzyl)-2-(tert-butyl)thiazole-5-carboxamide (220 mg, yield: 60percent) as a yellow solid. ESIMS (M+H) : 367.1. ?H NMR (400 MHz, CDC13) 5: 8.20 (s, 1H), 7.35 (d, J = 1.6 Hz, 1H), 7.32 (dd,J= 8.0, 1.6 Hz, 1H), 7.17 (d,J= 8.4 Hz, 1H), 4.55 (d,J= 5.6 Hz, 2H), 2.34 (s, 3H), 1.47 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
150 mg | To a solution of tert-butyl 3-isopropoxyazetidine-1-carboxylate (345 mg, 1.6 mmol) in MeOH (30 mL) was dropwise added SOCl2 (1.88 g, 16 mmol, 10 eq). The mixture was stirred at 65 °C for 1 h and the solvent was evaporated to afford a residue which was dissolved in DCM (6 mL) and treated with triphosgene (189 mg, 0.64 mmol) and TEA (800 mg, 8.0 mmol). After the mixture was stirred at rt for 0.5 h 4-bromo-2-methylbenzyl amine (312 mg, 1.57 mmol, 1 eq) was added and the mixture was stirred for another 3 h. The solvent was concentrated in vacuo to afford a residue which was purified by prep-HPLC (CH3CN/H2O with 0.05percent TFA as mobile phase) to give the title compound (150 mg, 27percent) as a yellow solid. ESI-MS (M+H)+: 341.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triethylamine; In dichloromethane; at 20℃; for 1h; | To a solution of amine (1.2 g, 6 mmol) in CH2Cl2(30 mL) were added TEA (1.82 g, 18 mmol) and Boc2O (1.43 g, 6.6 mmol). The mixture was stirred at rt for 1h, diluted with water (50 mL) and extracted with CH2Cl2(50 mL x 2). The organic phase was washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford the title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H)+: 300.1. |
88% | With sodium hydrogencarbonate; In 1,4-dioxane; at 20℃; | To a round bottom flask were added di-tert-butyl dicarbonate (11.60 mL, 50.0 mmol), NaHCO3 (10.50 g, 125 mmol), <strong>[376646-62-7](4-bromo-2-methylphenyl)methanamine</strong> (5 g, 24.99 mmol) and dioxane (54.9 mL). The reaction mixture was stirred at room temperature overnight, then filtered and concentrated. The residue was purified by (silica) column chromatography, eluting with a gradient of 5-30percent EtOAc in heptane to give the title compound as a white solid (6.581 g, 88percent). ESI-MS m/z [M+Hj 300.2. |
With triethylamine; In dichloromethane; at 20℃; for 1h; | [0138j To a solution of<strong>[376646-62-7](4-bromo-2-methylphenyl)methanamine</strong> (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc2O (1.43 g, 6.6 mmol). The mixture was stirred at rt for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H): 300.1. |
With triethylamine; In dichloromethane; at 20℃; for 1h; | [0115] To a solution of <strong>[376646-62-7](4-bromo-2-methylphenyl)methanamine</strong> (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc20 (1.43 g, 6.6 mmol). The mixture was stirred at room temperature for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2S04), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H)+: 300.1. | |
With triethylamine; In dichloromethane; at 20℃; for 1h; | To a solution of <strong>[376646-62-7](4-bromo-2-methylphenyl)methanamine</strong> (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc2O (1.43 g, 6.6 mmol). The mixture was stirred at rt for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H): 300.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | [0617j To a solution of 4-bromo-2-methylbenzonitrile (3.0 g, 15 mmol) in anhydrous THF (20 mL) under nitrogen at 0 °C was added 1.0 M solution of borane in THF (46 mL). The reaction mixture was stirred at 0 °C for 1 h, and heated at 80 °C overnight. The reaction mixture was cooled to 0 °C and slowly quenched with MeOH, concentrated in vacuo. The crude product was treated with EtOAc (20 mL) and 4 M of HC1 in 1,4-dioxane (8.0 mL, 32 mmol) for 5 mm. The solid was filtered, rinsed with diethyl ether, dried to give the title compound as a white powder (3.24 g, yield: 100percent). LCMS: RT 0.75 mm.; MH+ 200.0. ?H NMR (300 MHz, DMSOd6) 5: 8.28 (br. s., 2H), 7.42 - 7.54 (m, 2H), 7.34 (d, J = 7.93 Hz, 1H), 3.99 (d, J = 4.15 Hz, 2H), 2.35 (s, 3H). | |
90% | With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 0 - 80℃; for 17h; | [0114] To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL), BH3 THF (45 mL, 45 mmol) was added. The solution was stirred at 0 °C for 1 h and heated to 80 °C for 16 h. Then the mixture was quenched with MeOH. After concentrated, the residue was stirred with saturated HCl/EtOAc solution and filtered. The filter cake was rinsed with ether (20 mL x3) and dried under vacuum to afford (4-bromo-2-methylphenyl)methanamine (3.2 g, yield: 90percent) as white solid. ESI-MS (M+H)+: 200.1 Preparation of tert-butyl 4-bromo-2-methylbenzylcarbamate |
69% | With borane-THF; In tetrahydrofuran; at 0 - 80℃; for 3h; | To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL) was added BH3·THF (45 mL, 45 mmol) at 0 °C. The solution was stirred for 1 h and heated to 80 °C for 2 h. The mixture was quenched with H2O and extracted with EtOAc (50 mL x 3). The organic layer was concentrated in vacuo to afford a residue which was suspended in saturated HCl/EtOAc and filtered. The filter cake was washed with diethyl ether (20 mL x 3) and dried under vacuum to afford the desired product (2.1 g, yield 69percent) as white solid. ESI-MS (M+H)+: 200.1. |
Tags: 376646-62-7 synthesis path| 376646-62-7 SDS| 376646-62-7 COA| 376646-62-7 purity| 376646-62-7 application| 376646-62-7 NMR| 376646-62-7 COA| 376646-62-7 structure
[ 1171381-49-9 ]
(4-Bromo-2-methylphenyl)methanamine hydrochloride
Similarity: 0.97
[ 26177-44-6 ]
(4-Bromophenyl)methanamine hydrochloride
Similarity: 0.92
[ 27298-97-1 ]
(S)-1-(4-Bromophenyl)ethanamine
Similarity: 0.87
[ 1171381-49-9 ]
(4-Bromo-2-methylphenyl)methanamine hydrochloride
Similarity: 0.97
[ 26177-44-6 ]
(4-Bromophenyl)methanamine hydrochloride
Similarity: 0.92
[ 27298-97-1 ]
(S)-1-(4-Bromophenyl)ethanamine
Similarity: 0.87
[ 1171381-49-9 ]
(4-Bromo-2-methylphenyl)methanamine hydrochloride
Similarity: 0.97
[ 26177-44-6 ]
(4-Bromophenyl)methanamine hydrochloride
Similarity: 0.92
[ 27298-97-1 ]
(S)-1-(4-Bromophenyl)ethanamine
Similarity: 0.87
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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 |
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