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[ CAS No. 4965-34-8 ] {[proInfo.proName]}

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Chemical Structure| 4965-34-8
Chemical Structure| 4965-34-8
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Product Details of [ 4965-34-8 ]

CAS No. :4965-34-8 MDL No. :MFCD09787847
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :VEKOCCXFMXGRTF-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :12332896
Synonyms :

Calculated chemistry of [ 4965-34-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.41
TPSA : 12.89 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) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 3.31
Log Po/w (MLOGP) : 2.85
Log Po/w (SILICOS-IT) : 3.6
Consensus Log Po/w : 3.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.9
Solubility : 0.028 mg/ml ; 0.000126 mol/l
Class : Soluble
Log S (Ali) : -3.23
Solubility : 0.132 mg/ml ; 0.000595 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.95
Solubility : 0.00251 mg/ml ; 0.0000113 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 4965-34-8 ]

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 [ 4965-34-8 ]

* 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 [ 4965-34-8 ]
  • Downstream synthetic route of [ 4965-34-8 ]

[ 4965-34-8 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 591-19-5 ]
  • [ 123-63-7 ]
  • [ 4965-34-8 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: With hydrogenchloride In water at 0 - 20℃; for 4 h; Reflux
Stage #2: With sodium hydroxide In water at 0℃;
Doebner Miller synthesis: 3-Bromoaniline (10 mL, 92 mmol) was added to a solution of 37 percent HCl at 0 °C (200 mL). Paraldehyde (11 mL, 0.8 mol, 9 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, and then heated to reflux temperature for 3 hours. After cooling to 0 °C, a saturated aquous solution of sodium hydroxide (200 mL) was slowly added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, then dried over MgSO4, and concentrated under reduced pressure. The crude product was obtained as a mixture of 5-bromoquinaldine and 7-bromoquinaldine that were separated by column chromatography (SiO2, cyclohexane-AcOEt 9:1). The 7-bromoquinaldine regioisomer was obtained as a sand yellow solid (9,3 g, 46 percent). Molecular formula: C10H8BrN. Molecular weight: 222.08 g.mol-1. IR (film): 1610, 1494, 1264, 841, 736 cm-1. Tfusion: 57 °C. 1H NMR: δ 8.09 (s, 1H, H8), 7.80 (d, J = 8.2 Hz, 1H, H4), 7.39 (m, 2H, H5 et H7), 7.12 (d, J = 8.2 Hz, 1H, H3), 2.61 (s, 3H, H9). 13C NMR: δ 160.3 (s, C2), 148.6 (s, C8a), 136.2 (s, C4), 131.2 (s, C8), 129.4 (s, C5), 128.9 (s, C6), 125.3 (s, C4a), 123.7 (s, C7), 122.6 (s, C3), 25.7 (s, C9).
Reference: [1] Patent: EP2397466, 2011, A1, . Location in patent: Page/Page column 12
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 41, p. 9708 - 9711
[3] Journal of the American Chemical Society, 1921, vol. 43, p. 2257
[4] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 6, p. 1615 - 1623
  • 2
  • [ 50-00-0 ]
  • [ 591-19-5 ]
  • [ 4965-34-8 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: With hydrogenchloride In water at 0℃; for 4 h; Reflux
Stage #2: With sodium hydroxide In water at 0℃;
1) Preparation of 7-bromo-2-methyl-quinolineDoebner-Miller synthesis:3-bromoaniline (3 mL, 27 mmol), was added to a solution of 37percent HC1 at 0°C (24 mL). Paraldehyde (8 mL, 83 mmol, 3 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, then refluxed for 3 hours. After cooling to 0°C, sodium hydroxide (25 mL) was added dropwise and the mixture was extracted with dichloromethane. The organic layer was washed twice with water and brine, then dried over MgS04, and concentrated under reduced pressure. The product was purified by column chromatography (Si02, Cyclohexane-AcOEt 9/1) and obtained as a white solid (2.8 g, 46percent).Molecular formula: Ci0HgBrNMolecular weight: 222.08 g.mol"1 IR (film): 1610, 1494, 1264, 841, 736 cm-1 Melting point: 57°C1H NMR: 8), 7.80 (d, J = 8.2 Hz, 1H, 3/4), 7.39 (m, 2H, H5 and H7), 7.12 (d, J= 8.2 Hz, 1H, H3), 2.61 (s, 3H, H9).13C NMR: δ 160.3 (s, C2), 148.6 (s, C8a), 136.2 (s, C4), 131.2 (s, C8), 129.4 (s, C5), 128.9 (s, C6), 125.3 (s, C4a), 123.7 (s, C7), 122.6 (s, C3), 25.7 (s, C9).Rf= 0.33 (Cyclohexane/EtOAc: 2/1), 0.73 (Cyclohexane/EtOAc: 1/1).
Reference: [1] Patent: WO2011/86469, 2011, A1, . Location in patent: Page/Page column 32
  • 3
  • [ 591-19-5 ]
  • [ 123-63-7 ]
  • [ 4965-34-8 ]
  • [ 54408-52-5 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: With hydrogenchloride In water at 0℃; for 4 h; Reflux
Stage #2: With sodium hydroxide In water at 0℃;
3-Bromoaniline (10 mL, 92 mmol) was added to a solution of 37 percent HC1 at 0 °C (200 mL). Paraldehyde (1 1 mL, 0.8 mol, 9 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, and then heated to reflux temperature for 3 hours. After cooling to 0 °C, a saturated aquous solution of sodium hydroxide (200 mL) was slowly added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, then dried over MgS04, and concentrated under reduced pressure. The crude product was obtained as a mixture of 5-bromoquinaldine and 7-bromoquinaldine that were separated by column chromatography (Si02, cyclohexane- AcOEt 9: 1). The 7-bromoquinaldine regioisomer was obtained as a sand yellow solid (9,3 g, 46 percent).Molecular formula: CioH8BrN.Molecular weight: 222.08 g.mol"s.IR (film): 1610, 1494, 1264, 841, 736 cm"1.Tfusion: 57 °C.1H NMR: δ 8.09 (s, 1H, H8), 7.80 (d, J = 8.2 Hz, 1H, H4), 7.39 (m, 2H, H5 et H7), 7.12 (d, J= 8.2 Hz, 1H, H3), 2.61 (s, 3H, H9).13C NMR: δ 160.3 (s, C2), 148.6 (s, C8a), 136.2 (s, C4), 131.2 (s, C8), 129.4 (s, C5), 128.9(s, C6), 125.3 (s, C4a), 123.7 (s, C7), 122.6 (s, C3), 25.7 (s, C9).
Reference: [1] Patent: WO2011/158189, 2011, A1, . Location in patent: Page/Page column 14-15
  • 4
  • [ 123-73-9 ]
  • [ 591-19-5 ]
  • [ 4965-34-8 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 11, p. 1783 - 1785
  • 5
  • [ 70557-29-8 ]
  • [ 4965-34-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 30, p. 6349 - 6352
  • 6
  • [ 5551-12-2 ]
  • [ 4965-34-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 30, p. 6349 - 6352
  • 7
  • [ 4965-34-8 ]
  • [ 19490-87-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 6, p. 1615 - 1623
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