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[ CAS No. 84459-32-5 ] {[proInfo.proName]}

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Chemical Structure| 84459-32-5
Chemical Structure| 84459-32-5
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Product Details of [ 84459-32-5 ]

CAS No. :84459-32-5 MDL No. :MFCD00462865
Formula : C7H4BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LJASZNNBVOTAAN-UHFFFAOYSA-N
M.W : 230.02 Pubchem ID :11138942
Synonyms :

Calculated chemistry of [ 84459-32-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.35
TPSA : 62.89 Ų

Pharmacokinetics

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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 2.49
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.195 mg/ml ; 0.000846 mol/l
Class : Soluble
Log S (Ali) : -3.46
Solubility : 0.0805 mg/ml ; 0.00035 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.597 mg/ml ; 0.00259 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 84459-32-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 84459-32-5 ]

* 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 [ 84459-32-5 ]
  • Downstream synthetic route of [ 84459-32-5 ]

[ 84459-32-5 ] Synthesis Path-Upstream   1~8

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  • [ 2999-46-4 ]
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  • [ 16732-57-3 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2036 - 2039
  • 2
  • [ 332883-48-4 ]
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YieldReaction ConditionsOperation in experiment
78% With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1,10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 54 - 55
[2] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087
[3] Patent: US6514964, 2003, B1,
[4] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7916 - 7925
  • 3
  • [ 6630-33-7 ]
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YieldReaction ConditionsOperation in experiment
94% at 0℃; for 4.66667 h; To a solution of 2-bromobenzaldehyde (10.0 g, 53.7 mmol) in H2SO4 (100 mL) was added K O3 (5.43 g, 53.7 mmol) in portions over 1 h at 0°C. The mixture was stirred for 40 min and additional K O3 (0.72 g) was added. The reaction mixture was stirred at 0°C for 3 h then poured into ice water. The resulting precipitate was collected by filtration, rinsed with water and recrystallized from EtOAc/Pentane to give 2-bromo-5-nitrobenzaldehyde (11.7 g, 94percent yield) as a white solid. MS (ESI) calcd for C7H4BrN03: 228.9
94% at 0℃; for 3.67 h; To a solution of 2-bromobenzaldehyde (10.0 g, 53.7 mmol) in H2SO4 (100 mL) was added KNO3 (5.43 g, 53.7 mmol) in portions over 1 h at 0° C. The mixture was stirred for 40 min and additional KNO3 (0.72 g) was added. The reaction mixture was stirred at 0° C. for 3 h then poured into ice water. The resulting precipitate was collected by filtration, rinsed with water and recrystallized from EtOAc/Pentane to give 2-bromo-5-nitrobenzaldehyde (11.7 g, 94percent yield) as a white solid. MS (ESI) calcd for C7H4BrNO3: 228.9.
83% at 0℃; for 3 h; KNO3 (1.09 g, 10.8 mmol) was added slowly to a stirred red solution of 2-bromobenzaldehyde (2.0 g, 10.8 mmol) in H2SO4 (10 mL) at 0 °C. After 30 minutes extra portion of KNO3 (0.16 g, 1.6 mmol) was added, and the reaction mixture was stirred for 2.5 hours at 0 °C. Then the reaction mixture was poured over ice water (50 mL), extracted with Et2O (3×25 mL). Combined organic layers were washed with water (30 mL), brine (40 mL) and dried over Na2SO4. Solvents were evaporated in vacuo. The residual yellow solid was recrystallized from EtOAc/hexane (1/2, 40 mL) to give pure nitroaldehyde SI-1e (1.32 g, 5.7 mmol, 53percent). Further recrystallization of evaporated mother liquor from EtOAc/hexane (1/3, 15 mL) gives additional nitroaldehyde SI-1e (0.75 g, 3.2 mmol, 30percent) of the same purity.
55% at 5 - 20℃; for 1.5 h; A mixture of concentrated sulfuric acid (17.01 mL) andfuming nitric acid (2.250 mL) was cooled to 5 °C followedby the dropwise addition of 2—bromobenzaldehyde (3.15 mL,27.0 mmol) over a period of 30 minutes. The mixture wasthen allowed to warm to room temperature and stirred for60 minutes. The reaction mixture was poured intoice/water (200 mL) and the precipitated solid isolated by filtration, washed with water and sucked dry to give a pale yellow solid. This was recrystallised from 50:50 cyclohexane:ethyl acetate (30 mL) to give the title compound as an off—white solid (3.39 g, 55percent) . ‘H NMR(300 MHz, CDC13) : 3 10.39 (s, 1H) , 8.72 (d, 1H) , 8.29 (dd,1H) , 7.89 (d, 1H)
54.6% at 0℃; for 4.66667 h; Intermediate 17: l-(2-bromo-5-nitrophenyl)-N-methylmethanamine; Intermediate 17A:; [00237] Potassium nitrate (2.59 mL, 54.0 mmol) was added portionwise to a stirred and chilled (ice bath) solution of 2-bromobenzaldehyde (10 g, 54.0 mmol) in sulfuric acid (50 mL, 938 mmol) over 1 h. After 40 min an additional portion of KNO3 (0.72 g) was added. After 3 h stirring at 0 0C, the mixture was poured over ice water, and the product was filtered and washed with water. The crude pale yellow solid was recrystallized from 1 : 1 ethyl acetate/hexane (-60 mL) to give Intermediate 17A (6.789 g, 29.5 mmol, 54.6 percent yield). MS (ESI) m/z 230, 232 (M+H)+.

Reference: [1] Patent: WO2014/186313, 2014, A1, . Location in patent: Page/Page column 173-174
[2] Patent: US2015/152108, 2015, A1, . Location in patent: Paragraph 0881; 0882
[3] Tetrahedron Letters, 2016, vol. 57, # 1, p. 11 - 14
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1355 - 1362
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 20, p. 5051 - 5057
[6] Patent: WO2015/92431, 2015, A1, . Location in patent: Page/Page column 303
[7] Patent: WO2008/79836, 2008, A2, . Location in patent: Page/Page column 106
[8] European Journal of Organic Chemistry, 2011, # 28, p. 5626 - 5635
[9] Molecules, 2000, vol. 5, # 3, p. 227 - 239
[10] Patent: US5062884, 1991, A,
  • 4
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Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7125 - 7137
  • 5
  • [ 943-14-6 ]
  • [ 84459-32-5 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 18, p. 4563 - 4572
[2] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7916 - 7925
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7125 - 7137
  • 6
  • [ 33499-33-1 ]
  • [ 84459-32-5 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 7
  • [ 99-61-6 ]
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Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 8
  • [ 80887-01-0 ]
  • [ 84459-32-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7125 - 7137
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