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Chemical Structure| 131747-63-2
Chemical Structure| 131747-63-2
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Product Details of [ 131747-63-2 ]

CAS No. :131747-63-2 MDL No. :MFCD08690697
Formula : C6H4BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :CKVQWOKUEZYWRQ-UHFFFAOYSA-N
M.W : 186.01 Pubchem ID :14761472
Synonyms :

Calculated chemistry of [ 131747-63-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.32
TPSA : 29.96 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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.66
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 1.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.01 mg/ml ; 0.00544 mol/l
Class : Soluble
Log S (Ali) : -1.57
Solubility : 5.0 mg/ml ; 0.0269 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.278 mg/ml ; 0.00149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 131747-63-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 131747-63-2 ]

* 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 [ 131747-63-2 ]
  • Downstream synthetic route of [ 131747-63-2 ]

[ 131747-63-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 131747-63-2 ]
  • [ 22282-99-1 ]
Reference: [1] Patent: US2007/4730, 2007, A1, . Location in patent: Page/Page column 12
  • 2
  • [ 1005342-94-8 ]
  • [ 131747-63-2 ]
YieldReaction ConditionsOperation in experiment
89% With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1 h; 4-bromo-N-methoxy-N-methylpicolinamide (42; 5.84 g, 23.8 mmol) was dissolved in anhydrous THF (100 ml) and cooled to -78° C and 1.0 M lithium aluminum hydride in THF (14.3 ml, 14.3 mmol) was added via syringe and then the resulting mixture was stirred for 1 hour. 1 M NaOH (20 ml) and water (20 ml) was added carefully to the reaction mixture, and then the resulting solution was stirred for 30 minutes. Ethyl acetate and water was added, the organic phase was washed with water and brine, dried over Na2SO4 and concentrated to give A- bromopicolinaldehyde 43 as a yellow oil (3.95 g, yield: 89percent). MS calcd for C6H4BrNO: 186; found: 187 [M+l].
Reference: [1] Patent: WO2010/101949, 2010, A1, . Location in patent: Page/Page column 124
  • 3
  • [ 131747-45-0 ]
  • [ 131747-63-2 ]
YieldReaction ConditionsOperation in experiment
100% With manganese(IV) oxide In chloroform for 0.75 h; Reflux Example 29i
4-Bromopicolinaldehyde
Manganese(IV) oxide (22.19 g, 255.29 mmol) was added to a solution of (4-bromopyridin-2-yl)methanol (4.00 g, 21.27 mmol) in chloroform (80 mL) and the reaction mixture was stirred under reflux for 45 min.
After the mixture had cooled to room temperature the solids were removed by filtration through a pad of Celite.(R)..
The solvent was removed in vacuo and the residue (3.96 g, quant.) was used without further purification in the next step.
1H NMR (500 MHz, DMSO-d6) δ ppm 9.97 (s, 1H) 8.80 (d, 1H) 7.98 (d, 1H) 7.88 (dd, 1 H); MS (APCI+): m/z 186, 188 [M+H]+.
75% With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -65 - -60℃; for 1.5 h; Inert atmosphere Under the protection of nitrogen,Add 3L DCM to the 5L three-neck bottle to cool down.240g of oxalyl chloride was added dropwise during cooling;At -60 ° C,295.6 g of Dimethyl sulfoxide (DMSO) was added dropwise to the reaction solution.Keep warm for 30min;At -60 ° C,237.5 g of Cpd 3 was added dropwise to the reaction solution.The reaction was carried out at -65 ° C for 1 hour;At this temperature, 3.5 eq of triethylamine (TEA) was added dropwise.After the solution was allowed to stand, the plate was measured.Through the column, the product 4-bromopyridine-2-carbaldehyde is obtained.(Cpd 4) 177.2g,The yield was 75percent.
Reference: [1] Patent: US2010/125082, 2010, A1, . Location in patent: Page/Page column 24
[2] Tetrahedron, 1997, vol. 53, # 24, p. 8257 - 8268
[3] Patent: CN108516953, 2018, A, . Location in patent: Paragraph 0067-0068; 0074-0075; 0076-0083
[4] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[5] MedChemComm, 2015, vol. 6, # 7, p. 1252 - 1259
[6] Patent: WO2008/17691, 2008, A1, . Location in patent: Page/Page column 27-28
[7] Chemical Science, 2013, vol. 4, # 8, p. 3269 - 3274
  • 4
  • [ 1885-14-9 ]
  • [ 131747-63-2 ]
Reference: [1] Patent: US2007/4730, 2007, A1, . Location in patent: Page/Page column 12
  • 5
  • [ 108338-19-8 ]
  • [ 131747-63-2 ]
Reference: [1] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[2] Tetrahedron Letters, 2008, vol. 49, # 51, p. 7274 - 7275
  • 6
  • [ 22282-99-1 ]
  • [ 131747-63-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1239 - 1245
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Chemical Science, 2013, vol. 4, # 8, p. 3269 - 3274
  • 7
  • [ 100367-74-6 ]
  • [ 131747-63-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 24, p. 8257 - 8268
[2] Chemical Science, 2013, vol. 4, # 8, p. 3269 - 3274
  • 8
  • [ 931-19-1 ]
  • [ 131747-63-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
  • 9
  • [ 5470-66-6 ]
  • [ 131747-63-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
  • 10
  • [ 192642-94-7 ]
  • [ 131747-63-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 24, p. 8257 - 8268
  • 11
  • [ 13508-96-8 ]
  • [ 131747-63-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 12
  • [ 98197-88-7 ]
  • [ 131747-63-2 ]
Reference: [1] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
  • 13
  • [ 30766-03-1 ]
  • [ 131747-63-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 14
  • [ 131747-63-2 ]
  • [ 865156-50-9 ]
Reference: [1] Chemical Science, 2013, vol. 4, # 8, p. 3269 - 3274
  • 15
  • [ 131747-63-2 ]
  • [ 1211580-54-9 ]
YieldReaction ConditionsOperation in experiment
54% at 20℃; for 16 h; [0207] Step 1: 4-Bromo-2-(difluoromethyl)pyridine : To a 4- bromopicolinaldehyde (5.0 g, 26.88 mmol) was added diethylaminosulfur trifluoride (7.03 mL, 53.7 mmol), and the mixture was stirred at rt for 16 h. The reaction was quenched with aq. sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3 X 100 mL). The combined organic layers were washed with brine (2 X 50 mL), dried over sodium sulfate, filtered, concentrated and purified by column chromatography (100- 200 silica) using 5percent ethyl acetate in hexane as eluent to afford 4-bromo-2- (difluoromethyl)pyridine (3.0 g, 14.492 mmol, 54percent yield ). lH NMR (400 MHz, CDC13) δ = 8.48 (d, J = 4.9 Hz, 1H), 7.82 (d, J = 1.5 Hz, 1H), 7.66-7.50 (m, 1H), 6.60 (t, 1H). LCMS: 207.9 [M+H]+.
49.7% With diethylamino-sulfur trifluoride In chloroform at 0 - 20℃; for 12 h; DAST (0.620 mL, 4.69 mmol) was added dropwise to a solution of 4-bromopicolinaldehyde (700 mg, 3.76 mmol) in Chloroform (21 mL) at 0° C. The reaction mixture was stirred at 20° C. for 12 h. The reaction mixture was poured in to saturated NaHCO3 solution (20 mL), and was extracted with DCM (2×20 mL). The DCM layer was dried over anhydrous Na2SO4, filtered and filtrate was evaporated to afford 4-bromo-2-(difluoromethyl)pyridine (400 mg, 1.870 mmol, 49.7percent yield) as light yellow solid, LCMS (m/z) 208.0 [M+H]+.
49.7% With N,N-diethyltrifluoromethanesulfenamide In chloroform at 0 - 20℃; for 12 h; DAST (0.620 mL, 4.69 mmol) was added dropwise to a solution of 4- bromopicolinaldehyde (700 mg, 3.76 mmol) in Chloroform (21 mL) at 0 °C. The reaction mixture was stirred at 20 °C for 12h. The reaction mixture was poured in to saturated NaHC03 solution (20 mL), and was extracted with DCM (IX 20 mL). The DCM layer was dried over anhydrous Na2S04, filtered and filtrate was evaporated to afford 4-bromo- 2-(difluoromethyl)pyridine (400 mg, 1.870 mmol, 49.7 percent yield) as light yellow solid, LCMS (m/z) 208.0 [M+H]+.
32% With diethylamino-sulfur trifluoride In chloroform at 0 - 20℃; Inert atmosphere Example 30i
4-Bromo-2-(difluoromethyl)pyridine
Diethylaminosulphur trifluoride (4.08 mL, 33.31 mmol) was added to 4-bromopicolinaldehyde (0.267 M in chloroform) (100 mL, 26.7 mmol) at 0° C. under an atmosphere of argon.
The reaction mixture was stirred over night while the temperature was raised to room temperature.
The reaction was quenched by addition of aqueous sodium bicarbonate (sat.) and was further diluted with dichloromethane.
The solids were filtered off through a pad of Celite.(R)..
The organic layer was collected and the water phase was extracted with dichloromethane (*3).
The organic layers were pooled, dried (Na2SO4), filtered and concentrated.
Purification by silica chromatography using 0 to 60percent diethyl ether in pentane gave the title compound (1.78 g, 32percent).
1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (d, 1H) 7.98 (d, 1H) 7.90 (dt, 1H) 6.98 (t, 1 H); MS (APCI+) m/z 208, 210 [M+H]+.
800 mg With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; Inert atmosphere Description 1284-Bromo-2-(difluoromethyl)pyridine (D128)To a solution of 4-bromopicolinaldehyde (1 g) in DCM (20 mL) stirred under nitrogen atmosphere at 0°C was added DAST (1.065 mL). The reaction mixture was stirred at RT overnight. To the mixture was added water, and then extracted with DCM (3 x50 mL). The organic phase was washed with saturated NaHCO3, water, and brine, then dried over MgSO4 and filtered to give the titlecompound (800 mg) as yellow oil. MS (ESI): C6H4BrF2N requires 207; found no mass.

Reference: [1] Patent: WO2016/161160, 2016, A1, . Location in patent: Paragraph 0207
[2] Patent: US2015/152108, 2015, A1, . Location in patent: Paragraph 0480; 0481
[3] Patent: WO2016/79709, 2016, A1, . Location in patent: Page/Page column 179
[4] Patent: US2010/125082, 2010, A1, . Location in patent: Page/Page column 24; 25
[5] Patent: WO2015/180612, 2015, A1, . Location in patent: Page/Page column 78
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