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. : | 223519-08-2 | MDL No. : | MFCD07367995 |
Formula : | C9H8BrNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NKUYYWCQLGHYLF-UHFFFAOYSA-N |
M.W : | 274.07 | Pubchem ID : | 24728006 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.21 |
TPSA : | 72.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.08 cm/s |
Log Po/w (iLOGP) : | 2.13 |
Log Po/w (XLOGP3) : | 2.66 |
Log Po/w (WLOGP) : | 2.45 |
Log Po/w (MLOGP) : | 1.88 |
Log Po/w (SILICOS-IT) : | 0.73 |
Consensus Log Po/w : | 1.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.31 |
Solubility : | 0.133 mg/ml ; 0.000486 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.83 |
Solubility : | 0.0409 mg/ml ; 0.000149 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.09 |
Solubility : | 0.221 mg/ml ; 0.000807 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.33 |
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 |
---|---|---|
61% | Stage #1: With iron; acetic acid In tetrahydrofuran for 10 h; Reflux Stage #2: for 10 h; Reflux |
To a mixture of 3(5.1 g,0.02mol) in 100 ml THF was added 10 mL acetic acid and 5.6g Fe. The reaction mixture was stirred and refluxed for 10 hours. After cooled down to room temperature the mixture was filtered, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layers was dried over Na2S04. Drying agent was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was treated with 100 ml acetic acid and sodium nitrite (1.52g,0.022mol) while stirring, and then refluxed for 10 hours. The reaction mixture was concentrated under reduced pressure to yield a residue which was diluted with water and extracted with ethyl acetate. The ethyl acetate layers was concentrated under reduced pressure, and the residue was purified by flash column chromatography to give 4 (3.1g, 61percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | at 0 - 90℃; for 12 h; | 3-Bromo-4-methyl-5-nitrobenzoic acid (7.10 g, 27.3 mmol) and methanol (100 mL) were added to a 250 mL single-neck flask, then dichloro sulfoxide (2.96 mL, 41.0 mmol) was added dropwise at 0°C. The reaction mixture was stirred for 12 h at 90°C. The resulting mixture was concentrated in vacuo to remove the solvent. To the residue was added saturated sodium bicarbonate (200 mL) and the mixture was extracted with ethyl acetate (100 mL x 2). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo, then the residue was purified by silica gel chromatography (ethyl acetate/petroleum ether (v/v) = 1/30) to give the title compound as a pale yellow solid (6.36 g, 85percent). |
82% | at -5℃; Reflux | Thiolyl chloride (7.2g, 0.06mol) was added into methanol(50ml) drop-wisely at -5°C, and then followed by the addition of 3-bromo-4-methyl-5-nitrobenzoic acid(13g, 0.05mol). The reaction mixture was stirred for 30min at rt, and then refluxed for 2h. The mixtuer was evaporated at reduced pressure and the residue was purified by column chromatograph to give the product 3 (1 1.2g, 82percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With iron; acetic acid In tetrahydrofuran at 75℃; for 12 h; | Methyl 3-bromo-4-methyl-S-nitrobenzoate (8.50 g, 31.0 mmol), acetic acid (20 mL) and tetrahydrofuran (170 mL) were added to a SOOmL single-neck flask, then the iron (8.68 g, 155 mmol) was added in portions. The reaction mixture was stirred for 12 h at 75°C. The resulting mixture was cooled to room temperature, filtered to remove the insoluble solid, and the filtrate was concentrated in vacuo. To the residue was added water (500 mL). The mixture was extracted with ethyl acetate (100 mL x 2). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether (v/v) = 1/10) to give the title compound as a pale yellow solid (5.52g, 73percent).MS (ES-API, pos. ion) m/z: 244.9 [M + 2]t |
[ 135484-76-3 ]
Methyl 2-bromo-6-nitrobenzoate
Similarity: 0.96
[ 6307-87-5 ]
Methyl 3-bromo-5-nitrobenzoate
Similarity: 0.96
[ 34545-20-5 ]
3-Bromo-4-methyl-5-nitrobenzoic acid
Similarity: 0.93
[ 220514-28-3 ]
Methyl 5-bromo-2-methyl-3-nitrobenzoate
Similarity: 0.91
[ 885519-05-1 ]
Methyl 3-bromo-2-methyl-5-nitrobenzoate
Similarity: 0.91
[ 135484-76-3 ]
Methyl 2-bromo-6-nitrobenzoate
Similarity: 0.96
[ 6307-87-5 ]
Methyl 3-bromo-5-nitrobenzoate
Similarity: 0.96
[ 34545-20-5 ]
3-Bromo-4-methyl-5-nitrobenzoic acid
Similarity: 0.93
[ 220514-28-3 ]
Methyl 5-bromo-2-methyl-3-nitrobenzoate
Similarity: 0.91
[ 885519-05-1 ]
Methyl 3-bromo-2-methyl-5-nitrobenzoate
Similarity: 0.91
[ 135484-76-3 ]
Methyl 2-bromo-6-nitrobenzoate
Similarity: 0.96
[ 6307-87-5 ]
Methyl 3-bromo-5-nitrobenzoate
Similarity: 0.96
[ 220514-28-3 ]
Methyl 5-bromo-2-methyl-3-nitrobenzoate
Similarity: 0.91
[ 885519-05-1 ]
Methyl 3-bromo-2-methyl-5-nitrobenzoate
Similarity: 0.91
[ 135484-76-3 ]
Methyl 2-bromo-6-nitrobenzoate
Similarity: 0.96
[ 6307-87-5 ]
Methyl 3-bromo-5-nitrobenzoate
Similarity: 0.96
[ 34545-20-5 ]
3-Bromo-4-methyl-5-nitrobenzoic acid
Similarity: 0.93
[ 220514-28-3 ]
Methyl 5-bromo-2-methyl-3-nitrobenzoate
Similarity: 0.91
[ 885519-05-1 ]
Methyl 3-bromo-2-methyl-5-nitrobenzoate
Similarity: 0.91