Home Cart 0 Sign in  

[ CAS No. 223519-08-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 223519-08-2
Chemical Structure| 223519-08-2
Structure of 223519-08-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 223519-08-2 ]

Related Doc. of [ 223519-08-2 ]

Alternatived Products of [ 223519-08-2 ]

Product Details of [ 223519-08-2 ]

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 :

Calculated chemistry of [ 223519-08-2 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.33

Safety of [ 223519-08-2 ]

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:

Application In Synthesis of [ 223519-08-2 ]

* 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.

  • Upstream synthesis route of [ 223519-08-2 ]
  • Downstream synthetic route of [ 223519-08-2 ]

[ 223519-08-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 223519-08-2 ]
  • [ 1527007-77-7 ]
  • [ 170487-40-8 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
  • 2
  • [ 223519-08-2 ]
  • [ 882679-96-1 ]
Reference: [1] Patent: WO2015/104677, 2015, A1,
  • 3
  • [ 223519-08-2 ]
  • [ 885518-47-8 ]
YieldReaction ConditionsOperation 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)
Reference: [1] Patent: WO2011/38579, 2011, A1, . Location in patent: Page/Page column 36
[2] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
[3] Patent: WO2017/36404, 2017, A1,
  • 4
  • [ 67-56-1 ]
  • [ 34545-20-5 ]
  • [ 223519-08-2 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
[2] Patent: WO2017/36404, 2017, A1, . Location in patent: Page/Page column 69; 80
[3] Patent: WO2011/38579, 2011, A1, . Location in patent: Page/Page column 35; 36
  • 5
  • [ 96-98-0 ]
  • [ 223519-08-2 ]
Reference: [1] Patent: WO2011/38579, 2011, A1,
[2] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
[3] Patent: WO2017/36404, 2017, A1,
  • 6
  • [ 223519-08-2 ]
  • [ 885523-43-3 ]
Reference: [1] Patent: WO2011/38579, 2011, A1,
[2] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
  • 7
  • [ 223519-08-2 ]
  • [ 223519-11-7 ]
YieldReaction ConditionsOperation 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
Reference: [1] Tetrahedron, 2014, vol. 70, # 2, p. 318 - 326
[2] Patent: WO2017/36404, 2017, A1, . Location in patent: Page/Page column 69; 70; 80; 81
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 223519-08-2 ]

Aryls

Chemical Structure| 135484-76-3

[ 135484-76-3 ]

Methyl 2-bromo-6-nitrobenzoate

Similarity: 0.96

Chemical Structure| 6307-87-5

[ 6307-87-5 ]

Methyl 3-bromo-5-nitrobenzoate

Similarity: 0.96

Chemical Structure| 34545-20-5

[ 34545-20-5 ]

3-Bromo-4-methyl-5-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 220514-28-3

[ 220514-28-3 ]

Methyl 5-bromo-2-methyl-3-nitrobenzoate

Similarity: 0.91

Chemical Structure| 885519-05-1

[ 885519-05-1 ]

Methyl 3-bromo-2-methyl-5-nitrobenzoate

Similarity: 0.91

Bromides

Chemical Structure| 135484-76-3

[ 135484-76-3 ]

Methyl 2-bromo-6-nitrobenzoate

Similarity: 0.96

Chemical Structure| 6307-87-5

[ 6307-87-5 ]

Methyl 3-bromo-5-nitrobenzoate

Similarity: 0.96

Chemical Structure| 34545-20-5

[ 34545-20-5 ]

3-Bromo-4-methyl-5-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 220514-28-3

[ 220514-28-3 ]

Methyl 5-bromo-2-methyl-3-nitrobenzoate

Similarity: 0.91

Chemical Structure| 885519-05-1

[ 885519-05-1 ]

Methyl 3-bromo-2-methyl-5-nitrobenzoate

Similarity: 0.91

Esters

Chemical Structure| 135484-76-3

[ 135484-76-3 ]

Methyl 2-bromo-6-nitrobenzoate

Similarity: 0.96

Chemical Structure| 6307-87-5

[ 6307-87-5 ]

Methyl 3-bromo-5-nitrobenzoate

Similarity: 0.96

Chemical Structure| 220514-28-3

[ 220514-28-3 ]

Methyl 5-bromo-2-methyl-3-nitrobenzoate

Similarity: 0.91

Chemical Structure| 885519-05-1

[ 885519-05-1 ]

Methyl 3-bromo-2-methyl-5-nitrobenzoate

Similarity: 0.91

Chemical Structure| 690260-94-7

[ 690260-94-7 ]

Ethyl 3-bromo-5-nitrobenzoate

Similarity: 0.91

Nitroes

Chemical Structure| 135484-76-3

[ 135484-76-3 ]

Methyl 2-bromo-6-nitrobenzoate

Similarity: 0.96

Chemical Structure| 6307-87-5

[ 6307-87-5 ]

Methyl 3-bromo-5-nitrobenzoate

Similarity: 0.96

Chemical Structure| 34545-20-5

[ 34545-20-5 ]

3-Bromo-4-methyl-5-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 220514-28-3

[ 220514-28-3 ]

Methyl 5-bromo-2-methyl-3-nitrobenzoate

Similarity: 0.91

Chemical Structure| 885519-05-1

[ 885519-05-1 ]

Methyl 3-bromo-2-methyl-5-nitrobenzoate

Similarity: 0.91