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[ CAS No. 4214-79-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4214-79-3
Chemical Structure| 4214-79-3
Structure of 4214-79-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4214-79-3 ]

CAS No. :4214-79-3 MDL No. :MFCD00040278
Formula : C5H4ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :SZFUWUOHDRMCKD-UHFFFAOYSA-N
M.W : 129.54 Pubchem ID :77889
Synonyms :
Chemical Name :5-Chloropyridin-2(1H)-one

Calculated chemistry of [ 4214-79-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.07
TPSA : 32.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 0.55
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.54
Solubility : 3.7 mg/ml ; 0.0285 mol/l
Class : Very soluble
Log S (Ali) : -0.81
Solubility : 20.0 mg/ml ; 0.154 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.4 mg/ml ; 0.00309 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 4214-79-3 ]

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 [ 4214-79-3 ]

* 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 [ 4214-79-3 ]
  • Downstream synthetic route of [ 4214-79-3 ]

[ 4214-79-3 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 142-08-5 ]
  • [ 4214-79-3 ]
Reference: [1] Synthesis, 2012, vol. 44, # 7, p. 1074 - 1078
  • 2
  • [ 16110-09-1 ]
  • [ 4214-79-3 ]
Reference: [1] Patent: US1778784, 1928, ,
  • 3
  • [ 1072-98-6 ]
  • [ 4214-79-3 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[2] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
  • 4
  • [ 504-29-0 ]
  • [ 4214-79-3 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 689[2] Chem. Zentralbl., 1928, vol. 99, # II, p. 1671
  • 5
  • [ 4214-79-3 ]
  • [ 16110-09-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1370 - 1380
  • 6
  • [ 4214-79-3 ]
  • [ 40473-01-6 ]
Reference: [1] Patent: US2003/236270, 2003, A1, . Location in patent: Page 44
  • 7
  • [ 4214-79-3 ]
  • [ 21427-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637
  • 8
  • [ 4214-79-3 ]
  • [ 21427-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987
  • 9
  • [ 4214-79-3 ]
  • [ 21427-61-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987
  • 10
  • [ 4214-79-3 ]
  • [ 137628-16-1 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: With bromine In acetic acid at 20℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
A mixture of 5-CHLORO-2-HYDROXYPYRIDINE (20.1 g, 155.4 MMOL) and bromine (11.9 ml) in acetic acid (250 m) was stirred at r. t. for 2 hours. Then, the solvent was evaporated in vacuo and ethyl acetate (600 ML) and saturated sodium bicarbonate (300 ML) were added. The organic layer was washed with saturated sodium bicarbonate (2X200 ML), brine and was dried (NA2SO4) and concentrated to give a solid that was crystallized from hexane/ diethyl ether. The solid 3-bromo-5-chloro-2-hydroxypyridine (21.3 g, 66percent) so obtained was used in the subsequent reaction.
4.4 g at 20℃; To a stirred solution of 5-chloropyridin-2-ol (4 g, 31 mmol) in acetic acid (35 mL) at room temperature was added bromine (2.55 mL, 49.6 mmol) dropwise. After stirring the reaction mixture for overnight at room temperature, water was added and the mixture was extracted twice with ethyl acetate (2 x 150 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and was concentrated under reduced pressure to afford crude product. The crude product was purified by column chromatography by using silica (100-200 mesh) using 22percent EtOAc-hexane as eluent to afford the 3-bromo-5-chloropyridin-2-ol (4.4 g) as yellow solid.
Reference: [1] Patent: WO2004/72037, 2004, A1, . Location in patent: Page 11
[2] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2777 - 2782
[3] Patent: US5861419, 1999, A,
[4] Patent: US6245797, 2001, B1,
[5] Patent: WO2014/141110, 2014, A2, . Location in patent: Page/Page column 83; 84
[6] Patent: WO2004/39753, 2004, A2, . Location in patent: Page 83-84
[7] Patent: US2010/204257, 2010, A1, . Location in patent: Page/Page column 6
  • 11
  • [ 4214-79-3 ]
  • [ 138006-41-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2777 - 2782
  • 12
  • [ 75-46-7 ]
  • [ 4214-79-3 ]
  • [ 1214323-40-6 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With potassium hydroxide In water for 0.5 h;
Stage #2: at 20℃; for 3 h;
General procedure: Using an apparatus previously described for method B
[21]
, potassium hydroxide (2.52 g, 45 mmol, 15 equiv) and water (2.52 g) were added to the reaction vessel and the mixture was allowed to stir until the potassium hydroxide was almost completely dissolved.
Then, 2-bromo-3-pyridinol (0.354 g, 3 mmol) was added and the mixture stirred for 30 min, after which acetonitrile (10 mL) was added via syringe and the mixture stirred at room temperature.
Fluoroform was then bubbled slowly into the mixture for 2 h, after which the resulting mixture was stirred for one additional hour.
After being quenched with water and extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated solution on sodium hydroxide, separated and concentrated.
Additional impurities were removed via column chromatography on silica gel using an 80:20 mixture of hexanes/methylene chloride to give a 53percent yield of the liquid product, 2-bromo-3-difluoromethoxypyridine (3d):
Reference: [1] Journal of Fluorine Chemistry, 2014, vol. 168, p. 34 - 39
  • 13
  • [ 4214-79-3 ]
  • [ 1895-39-2 ]
  • [ 1214323-40-6 ]
Reference: [1] Patent: WO2012/3283, 2012, A1, . Location in patent: Page/Page column 226
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