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. : | 69321-60-4 | MDL No. : | MFCD00013524 |
Formula : | C7H6Br2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OCSKCBIGEMSDIS-UHFFFAOYSA-N |
M.W : | 249.93 | Pubchem ID : | 34681 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.81 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.22 cm/s |
Log Po/w (iLOGP) : | 2.5 |
Log Po/w (XLOGP3) : | 3.67 |
Log Po/w (WLOGP) : | 3.52 |
Log Po/w (MLOGP) : | 4.1 |
Log Po/w (SILICOS-IT) : | 3.66 |
Consensus Log Po/w : | 3.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.2 |
Solubility : | 0.016 mg/ml ; 0.0000638 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.36 |
Solubility : | 0.109 mg/ml ; 0.000437 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.49 |
Solubility : | 0.00801 mg/ml ; 0.0000321 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.21 |
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 |
---|---|---|
35% | With pyridine In N,N-dimethyl-formamide; 3-bromo-5-fluorobenzonitrile | 3-Bromo-2-methylbenzonitrile. This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35percent) of 3-bromo-2-methylbenzonitrile. |
35% | With pyridine In N,N-dimethyl-formamide; 3-bromo-5-fluorobenzonitrile | 3-Bromo-2-methylbenzonitrile This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35percent) of 3-bromo-2-methylbenzonitrile. |
35% | With pyridine In N,N-dimethyl-formamide; 3-bromo-5-fluorobenzonitrile | 3-Bromo-2-methylbenzonitrile. This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35percent) of 3-bromo-2-methylbenzonitrile. |
35 % | With pyridine In N,N-dimethyl-formamide; 3-bromo-5-fluorobenzonitrile | EXAMPLE 178 6-(3-cyano-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 278, structure 4 of Scheme II, where R1 =3-cyano-2-methylphenyl) 3-Bromo-2-methylbenzonitrile. This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35 percent) of 3-bromo-2-methylbenzonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.4% | With tert.-butyl lithium In tetrahydrofuran; pentane at -80 - -76℃; | Example 27 3-Bromo-2-methylbenzoic acid To a solution of 1,3-dibromo-2-methylbenzene (6.57 g) in dry THF (100 mL), t-BuLi solution (1.5 M in pentane, 17 mL) was added dropwise at -80° C. Then reaction mixture was stirred between -76~-78° C. for 2 h. Then the mixture was cooled to below -80° C. and dry ice was added after which the mixture was warmed to room temperature naturally. Solvent was removed, 5percent NaOH solution (40 mL) added and the aqueous solution was washed with CH2Cl2 (10 mL*2). Then the aqueous layer was acidified with concentrated HCl to pH=1 and extracted with EtOAc (100 mL*2). The combined organic extracts were dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by silica column chomatography, (eluted with petrol. ether: EtOAc=8:1 to 1:1), to obtain 3.58 g of the product. Yield: 63.4percent. 1H NMR (400 MHz, CDCl3) δ 2.73 (s, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.77 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, 1H). |
63.4% | Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -80 - -76℃; Stage #2: at -80 - 20℃; |
Example 27 3-Bromo-2-methylbenzoic Acid To a solution of 1,3-dibromo-2-methylbenzene (6.57 g) in dry THF (100 mL), t-BuLi solution (1.5 M in pentane, 17 mL) was added dropwise at -80° C. Then reaction mixture was stirred between -76~-78° C. for 2 h. Then the mixture was cooled to below -80° C. and dry ice was added after which the mixture was warmed to room temperature naturally. Solvent was removed, 5percent NaOH solution (40 mL) added and the aqueous solution was washed with CH2Cl2 (10 mL*2). Then the aqueous layer was acidified with concentrated HCl to pH=1 and extracted with EtOAc (100 mL*2). The combined organic extracts were dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by silica column chomatography, (eluted with petrol. ether: EtOAc=8:1 to 1:1), to obtain 3.58 g of the product. Yield: 63.4percent. 1H NMR (400 MHz, CDCl3) δ 2.73 (s, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.77 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, 1H). |
63.4% | Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -80 - -76℃; Stage #2: at -80 - 20℃; |
Example 30 3-Bromo-2-methylbenzoic Acid To a solution of 1,3-dibromo-2-methylbenzene (6.57 g) in dry THF (100 mL), t-BuLi solution (1.5 M in pentane, 17 mL) was added dropwise at -80° C. After addition, the reaction mixture was stirred between -76~-78° C. for 2 h. After the mixture was cooled to below -80° C., dry ice was added, and then warmed to room temperature naturally. Solvent was removed, 5percent NaOH solution (40 mL) was added, washed with CH2Cl2 (10 mL*2). Then the aqueous layer was acidified with concentrated HCl to pH=1, extracted with EtOAc (100 mL*2). The combined organic phase was dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by silica column chromatography, (eluted with petrol ether:EtOAc=8:1 to 1:1), to obtain 3.58 g of the product. Yield: 63.4percent. 1H NMR (400 MHz, CDCl3): δ 2.73 (s, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.77 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, 1H). |
63.4% | Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -80 - -76℃; for 2 h; Stage #2: at -80℃; Stage #3: With hydrogenchloride In water |
Example 27 3-Bromo-2-methylbenzoic acidTo a solution of l,3-dibromo-2-methylbenzene (6.57 g) in dry THF (100 mL), t-BuLi solution (1.5 M in pentane, 17 mL) was added dropwise at -80 C. Then reaction mixture was <n="131"/>stirred between -76 - 78 C for 2 h. Then the mixture was cooled to below -80 C and dry ice was added after which the mixture was warmed to room temperature naturally. Solvent was removed, 5percent NaOH solution (40 mL) added and the the aqueous solution was washed with CH2Cl2 (10 mL x 2). Then the aqueous layer was acidified with concentrated HCl to pH=l and extracted with EtOAc (100 mL x 2). The combined organic extracts were dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by silica column chomatography, (eluted with petrol, ether: EtOAc=8: l to 1 : 1), to obtain 3.58 g of the product. Yield: 63.4percent. 1H NMR (400 MHz, CDCl3) δ 2.73 (s, 3 H), 7.15 (t, J=8.0 Hz, 1 H), 7.77 (dd, J=8.0 Hz, ./=1.2 Hz, 1 H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, I H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere Stage #2: for 0.5 h; |
n-BuLi (1.6M in hexanes, 28.5 mL, 45.6 mmol) was added dropwise to a solution of 1,3-dibromo-2-methylbenzene (9.50 g, 38.0 mmol) in THF (119 mL) at -78° C. and the reaction was maintained at this temperature for 30 minutes. N,N-Dimethylformamide (4.41 mL, 57.0 mmol) was added and the reaction was stirred for a further 30 min, before being allowed to warm to 0° C. over 1 hour. The reaction was quenched by addition of water, then was extracted with EtOAc. The organic phase was dried over magnesium sulfate and concentrated to dryness to afford 3-bromo-2-methylbenzaldehyde (7.19 g, 95percent) as a straw coloured oil. 1H NMR (500 MHz, CDCl3, 27° C.) 2.75 (3H, s), 7.18-7.37 (1H, m), 7.78 (2H, ddd), 10.26 (1H, s). |
95% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Stage #2: at -78 - 0℃; for 1.5 h; |
Preparation of 3-bromo-2-methylbenzaldehvde w-BuLi in hexanes (1.6M; 28.5 mL, 45.6 mmol) was added dropwise to a solution of 1,3- dibromo-2-methylbenzene (9.50 g, 38.0 mmol) in THF (119 mL) at -78 °C and the reaction was maintained at this temperature for 30 minutes. N,N-Dimethylformamide (4.41 mL, 57.0 mmol) was added and the reaction was stirred for a further 30 minutes before being allowed to warm to 0 °C over 1 hour. The reaction was quenched by addition of water and then was extracted with EtOAc. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness to afford 3-bromo-2-methylbenzaldehyde (7.19 g, 95percent) as a light yellow oil. lH NMR (500 MHz, CDC13, 27 °C) 2.75 (3H, s), 7.18 - 7.37 (1H, m), 7.78 (2H, ddd), 10.26 (1H, s). |
[ 1074-24-4 ]
1,4-Dibromo-2,5-dimethylbenzene
Similarity: 0.94
[ 100189-84-2 ]
2,5-Dibromo-1,3-dimethylbenzene
Similarity: 0.94
[ 1074-24-4 ]
1,4-Dibromo-2,5-dimethylbenzene
Similarity: 0.94
[ 100189-84-2 ]
2,5-Dibromo-1,3-dimethylbenzene
Similarity: 0.94