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[ CAS No. 3964-04-3 ] {[proInfo.proName]}

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Chemical Structure| 3964-04-3
Chemical Structure| 3964-04-3
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Product Details of [ 3964-04-3 ]

CAS No. :3964-04-3 MDL No. :MFCD07644514
Formula : C9H6BrN Boiling Point : -
Linear Structure Formula :- InChI Key :SUXIPCHEUMEUSV-UHFFFAOYSA-N
M.W :208.05 Pubchem ID :11735918
Synonyms :

Calculated chemistry of [ 3964-04-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.44
TPSA : 12.89 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) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 1.63
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 2.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.308 mg/ml ; 0.00148 mol/l
Class : Soluble
Log S (Ali) : -1.51
Solubility : 6.38 mg/ml ; 0.0307 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.56
Solubility : 0.00574 mg/ml ; 0.0000276 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 3964-04-3 ]

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:

Application In Synthesis of [ 3964-04-3 ]

* 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 [ 3964-04-3 ]
  • Downstream synthetic route of [ 3964-04-3 ]

[ 3964-04-3 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 611-36-9 ]
  • [ 3964-04-3 ]
YieldReaction ConditionsOperation in experiment
88% With phosphorus tribromide In N,N-dimethyl-formamide for 0.666667 h; Inert atmosphere Step 1 : To a stirred solution of quinolin-4-ol (4.00 g, 27.6 mmol) in dry DMF (30 mL) was added phosphorus tribromide (7.61 g, 28.2 mmol) dropwise for 10 min. The reddish colored suspension was stirred for 30 min under nitrogen atmosphere. After complete consumption of starting material, the reaction mixture was quenched with ice, stirred for anther 30 min, then basified to pH -10 with a solution of saturated sodium bicarbonate (20 mL). The reaction mixture was extracted with ethyl acetate (2 x 100 mL) and the combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified on silica gel column using dichloromethane / methanol (0percent to 10percent) as eluent to give 4-bromo- quinoline (5.04 g; 88percent) as a yellow solid; LCMS (ESI) 208 (M+H); H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.69 (d, J=4.69 Hz, 1 H), 8.20 (dd, J=8 39, 0.88 Hz, 1 H), 8.08 - 8.16 (m, 1 H), 7.78 (ddd, J=8.39, 6.98, 1 .37 Hz, 1 H), 7.71 (d, J=4.69 Hz, 1 H), 7.66 (ddd, J=8.31 , 7.04, 1.15 Hz, 1 H).
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 12, p. 5652 - 5661
[2] Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2232 - 2235
[3] Patent: WO2014/121883, 2014, A1, . Location in patent: Page/Page column 51
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 37, p. 9311 - 9316[5] Angew. Chem., 2012, vol. 124, # 37, p. 9445 - 9450,6
  • 2
  • [ 1613-37-2 ]
  • [ 2005-43-8 ]
  • [ 3964-04-3 ]
YieldReaction ConditionsOperation in experiment
48% With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 °C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
Reference: [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
  • 3
  • [ 529-37-3 ]
  • [ 41320-96-1 ]
  • [ 3964-04-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
[2] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
  • 4
  • [ 22614-98-8 ]
  • [ 3964-04-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 5
  • [ 56-57-5 ]
  • [ 3964-04-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 6
  • [ 56-57-5 ]
  • [ 3741-15-9 ]
  • [ 3964-04-3 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 1337,1340[2] Chem.Abstr., 1957, p. 6639
[3] Yakugaku Zasshi, 1955, vol. 75, p. 127[4] Chem.Abstr., 1956, p. 1817
[5] Yakugaku Zasshi, 1951, vol. 71, p. 1088,1090[6] Chem.Abstr., 1952, p. 5046
  • 7
  • [ 578-68-7 ]
  • [ 3964-04-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
  • 8
  • [ 56-57-5 ]
  • [ 7789-60-8 ]
  • [ 141-78-6 ]
  • [ 20151-40-0 ]
  • [ 3964-04-3 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 1337,1340[2] Chem.Abstr., 1957, p. 6639
  • 9
  • [ 578-68-7 ]
  • [ 7664-93-9 ]
  • [ 3964-04-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
[2] Journal fuer Praktische Chemie (Leipzig), 1897, vol. <2> 56, p. 192
  • 10
  • [ 578-68-7 ]
  • [ 10035-10-6 ]
  • [ 36825-36-2 ]
  • [ 3964-04-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
[2] Journal fuer Praktische Chemie (Leipzig), 1897, vol. <2> 56, p. 192
  • 11
  • [ 1613-37-2 ]
  • [ 2005-43-8 ]
  • [ 3964-04-3 ]
YieldReaction ConditionsOperation in experiment
48% With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 °C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
Reference: [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
  • 12
  • [ 3964-04-3 ]
  • [ 16560-43-3 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 10, p. 2033 - 2035
[2] Tetrahedron, 2003, vol. 59, # 43, p. 8629 - 8640
[3] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1731 - 1737
  • 13
  • [ 3964-04-3 ]
  • [ 2973-27-5 ]
YieldReaction ConditionsOperation in experiment
8.03 g at 180℃; for 3 h; Inert atmosphere Step A: Preparation of 4-cyanoquinolineTo a solution of N-methylpyrrolidinone (100 mL) and CuCN (21.5 g, 240 mmol) was added 4-bromoquinoline (25.0 g, 120 mmol) in one portion with vigorous stirring under nitrogen. The reaction was heated to 180 °C for 3 hours. The reaction mixture was allowed to cool, and then added to water (300 mL). The crude solid product was filtered and dried in a vacuum oven overnight to give the title product (8.03 g).‘HNMR(CDC13) ö 7.73-7.81 (m, 2 H) 7.89 (ddd, J=8.47, 7.01, 1.34 Hz, 1 H) 8.11-8.34 (m,2 H) 9.06 (d, J4.39 Hz, 1 H).
Reference: [1] Patent: WO2014/99837, 2014, A1, . Location in patent: Page/Page column 47
  • 14
  • [ 557-21-1 ]
  • [ 3964-04-3 ]
  • [ 2973-27-5 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 7040 - 7044
  • 15
  • [ 544-92-3 ]
  • [ 3964-04-3 ]
  • [ 2973-27-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 16
  • [ 56-57-5 ]
  • [ 7789-60-8 ]
  • [ 141-78-6 ]
  • [ 20151-40-0 ]
  • [ 3964-04-3 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 1337,1340[2] Chem.Abstr., 1957, p. 6639
  • 17
  • [ 578-68-7 ]
  • [ 10035-10-6 ]
  • [ 36825-36-2 ]
  • [ 3964-04-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
[2] Journal fuer Praktische Chemie (Leipzig), 1897, vol. <2> 56, p. 192
  • 18
  • [ 3964-04-3 ]
  • [ 10447-29-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2891 - 2898
  • 19
  • [ 3964-04-3 ]
  • [ 62484-52-0 ]
Reference: [1] Synthesis, 1983, # 4, p. 312 - 314
[2] Organic Letters, 2012, vol. 14, # 11, p. 2846 - 2849
  • 20
  • [ 3964-04-3 ]
  • [ 371764-64-6 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
  • 21
  • [ 73183-34-3 ]
  • [ 3964-04-3 ]
  • [ 1035458-54-8 ]
Reference: [1] Patent: WO2016/206101, 2016, A1, . Location in patent: Page/Page column 380; 381
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