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[ CAS No. 139042-59-4 ] {[proInfo.proName]}

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Chemical Structure| 139042-59-4
Chemical Structure| 139042-59-4
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Product Details of [ 139042-59-4 ]

CAS No. :139042-59-4 MDL No. :MFCD04974527
Formula : C7H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :MUKKGHQBUKOMTD-UHFFFAOYSA-N
M.W : 200.03 Pubchem ID :15668195
Synonyms :

Calculated chemistry of [ 139042-59-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.13
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) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 2.33
Consensus Log Po/w : 1.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.725 mg/ml ; 0.00362 mol/l
Class : Soluble
Log S (Ali) : -1.8
Solubility : 3.18 mg/ml ; 0.0159 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.22
Solubility : 0.121 mg/ml ; 0.000605 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 139042-59-4 ]

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 [ 139042-59-4 ]

* 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 [ 139042-59-4 ]
  • Downstream synthetic route of [ 139042-59-4 ]

[ 139042-59-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 624-28-2 ]
  • [ 127-19-5 ]
  • [ 139042-59-4 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78℃; for 4 h; Inert atmosphere
Step 1:
Synthesis of 1-(6-bromopyridin-3-yl)ethanone
To a stirred solution of 2,5-dibromopyridine (1.0 g, 4.219 mmol) in diethyl ether (10 mL) at -78° C. was added n-Butyl lithium (2.0 mL, 5.0 mmol, 2.5M in hexane) under nitrogen and stirred for 1 h at the same temperature.
Dimethyl acetamide (0.58 g, 6.3 mmol) was then added drop wise to the reaction mixture, stirred for 4 h at -78° C.
Progress of reaction was monitored by TLC.
After completion reaction mass was quenched with ice cold water and partitioned between saturated NH4Cl solution and EtOAc.
The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to give 1-(6-bromopyridin-3-yl) ethanone (0.4 g, 47percent) as yellow solid
MS: 200.1 [M++1]
Reference: [1] Molecules, 2008, vol. 13, # 4, p. 818 - 830
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6763 - 6770
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 3860 - 3874
[4] Patent: US2017/291894, 2017, A1, . Location in patent: Paragraph 0428
[5] Chemische Berichte, 1992, vol. 125, # 5, p. 1169 - 1190
  • 2
  • [ 624-28-2 ]
  • [ 139042-59-4 ]
Reference: [1] Patent: US5332757, 1994, A,
  • 3
  • [ 139042-59-4 ]
  • [ 358780-14-0 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 79, p. 75465 - 75469
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