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[ CAS No. 54232-03-0 ] {[proInfo.proName]}

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Chemical Structure| 54232-03-0
Chemical Structure| 54232-03-0
Structure of 54232-03-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54232-03-0 ]

CAS No. :54232-03-0 MDL No. :MFCD11519295
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :UGDSWVXJJFIVAH-UHFFFAOYSA-N
M.W : 143.57 Pubchem ID :12852015
Synonyms :

Calculated chemistry of [ 54232-03-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.24
TPSA : 33.12 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.612 mg/ml ; 0.00427 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 1.05 mg/ml ; 0.00732 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.43
Solubility : 0.535 mg/ml ; 0.00372 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 54232-03-0 ]

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 [ 54232-03-0 ]

* 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 [ 54232-03-0 ]
  • Downstream synthetic route of [ 54232-03-0 ]

[ 54232-03-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 38186-82-2 ]
  • [ 54232-03-0 ]
  • [ 38186-84-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 445 - 448
  • 2
  • [ 22280-56-4 ]
  • [ 7732-18-5 ]
  • [ 7439-89-6 ]
  • [ 54232-03-0 ]
  • [ 38186-82-2 ]
Reference: [1] Patent: US6133253, 2000, A,
  • 3
  • [ 54232-04-1 ]
  • [ 54232-03-0 ]
YieldReaction ConditionsOperation in experiment
89% at 20℃; for 1 h; Potassium carbonate (1.10 g, 0.0081 mol) was added to a stirred solution of 6- chloro-5-methylpyridine-3-yl acetate (750 mg, 0.004 mol) in MeOH (15 mL) at RT. The reaction mixture was stirred for lh at ambient temperature. The reaction mixture was concentrated under reduced pressure and the residue was diluted with minimum amounts of water and neutralized with 1N HCl (15 mL). After neutralization, the solution was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-chloro-5- methylpyridine-3-ol as a off white solid (500 mg, 89percent). MS m/z = 143.01 [M+H]+. 'H-NMR (300MHZ, DMSO-d6): δ 10.09 (s, 1H), 7.76 (d, J= 3Hz, 1H), 7.18 (d, J=3.6 Hz, 1H), 2.24 (s, 3H)
89% at 20℃; for 1 h; Potassium carbonate (1.1 g, 8.1 mmol) was added to a stirred solution of 6-chloro-5-methylpyridine-3-yl acetate (269B, 750 mg, 4.0 mmol) in MeOH (15 mL) at RT. The reaction mixture was stirred for 1 h at ambient temperature. The reaction mixture was concentrated under reduced pressure and the residue was diluted with minimum amounts of water and neutralized with 1 N HCl (15 mL). After neutralization, the solution was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-chloro-5-methylpyridine-3-ol (269C) as an off white solid (500 mg, 89percent). MS m/z = 143.01 [M+H]+. 1H-NMR (300MHz, DMSO-d6): δ 10.09 (s, 1 H), 7.76 (d, J= 3Hz, 1 H), 7.18 (d, J=3.6 Hz, 1 H), 2.24 (s, 3H).
Reference: [1] Patent: WO2014/138484, 2014, A1, . Location in patent: Page/Page column 157
[2] Patent: WO2016/22724, 2016, A1, . Location in patent: Page/Page column 297
[3] Patent: US2014/249104, 2014, A1, . Location in patent: Page/Page column
  • 4
  • [ 38186-82-2 ]
  • [ 54232-03-0 ]
Reference: [1] Patent: WO2014/138484, 2014, A1,
[2] Patent: WO2016/22724, 2016, A1,
[3] Patent: WO2005/123668, 2005, A1, . Location in patent: Page/Page column 46-47
  • 5
  • [ 22280-56-4 ]
  • [ 7732-18-5 ]
  • [ 7439-89-6 ]
  • [ 54232-03-0 ]
  • [ 38186-82-2 ]
Reference: [1] Patent: US6133253, 2000, A,
  • 6
  • [ 38186-82-2 ]
  • [ 54232-03-0 ]
Reference: [1] Patent: US4329351, 1982, A,
[2] Patent: US4374140, 1983, A,
  • 7
  • [ 1003043-40-0 ]
  • [ 54232-03-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2536 - 2548
  • 8
  • [ 22280-56-4 ]
  • [ 54232-03-0 ]
Reference: [1] Patent: WO2014/138484, 2014, A1,
[2] Patent: WO2016/22724, 2016, A1,
[3] Patent: WO2005/123668, 2005, A1,
  • 9
  • [ 38186-82-2 ]
  • [ 54232-03-0 ]
  • [ 38186-84-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 445 - 448
  • 10
  • [ 54232-03-0 ]
  • [ 74650-70-7 ]
YieldReaction ConditionsOperation in experiment
95% With NaH In N,N-dimethyl-formamide Into a flame dried flask under N2 was placed DMF (150 mL), NaH (50percent oil dispersion, 4.0 g, 0.08 mol) and 2-chloro-5-hydroxy-3-methylpyridine (11.7 g, 0.08 mol).
The solution was stirred at 0°-5° C. until the evolution of H2 ceased and then a solution of CH3 I (5.6 mL, 0.09 mol) in DMF (50 mL) was added dropwise.
After the addition, the solution was allowed to stir at room temperature overnight.
The resulting slurry was added to H2 O and extracted with Et2 0 (3*).
The organic layer was concentrated and the residue distilled at 85° C. (0.6 mm) to yield 12.8 g of 2-chloro-5-methoxy-3-methylpyridine (95percent) as an oil; 1 H NMR (CDCl3) δ2.35 (3H, s), 3.8 (3H, s), 7.1 (1H, d, J=3) and 7.9 (1H, d, J=3); MS m/e (M+) 157.
95% With NaH In N,N-dimethyl-formamide Into a flame dried flask under N2 was placed DMF (150 mL), NaH (50percent oil dispersion, 4.0 g, 0.08 mol) and 2-chloro-5-hydroxy-3-methylpyridine (11.7 g, 0.08 mol).
The solution was stirred at 0°-5° C. until the evolution of H2 ceased and then a solution of CH3 I (5.6 mL, 0.09 mol) in DMF (50 mL) was added dropwise.
After the addition, the solution was allowed to stir at room temperature overnight.
The resulting slurry was added to H2 O and extracted with Et2 O (3X).
The organic layer was concentrated and the residue distilled at 85° C. (0.6 mm) to yield 12.8 g of 2-chloro-5-methoxy-3-methylpyridine (95percent) as an oil; 1 H NMR (CDCl3) δ 2.35 (3H, s), 3.8 (3H, s), 7.1 (1H, d, J=3) and 7.9 (1H, d, J=3); MS m/e (M+) 157.
Reference: [1] Patent: US4329351, 1982, A,
[2] Patent: US4374140, 1983, A,
  • 11
  • [ 54232-03-0 ]
  • [ 74-88-4 ]
  • [ 74650-70-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 445 - 448
  • 12
  • [ 54232-03-0 ]
  • [ 74650-73-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 445 - 448
  • 13
  • [ 557-21-1 ]
  • [ 54232-03-0 ]
  • [ 228867-86-5 ]
YieldReaction ConditionsOperation in experiment
32% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 110℃; for 21 h; Inert atmosphere; Sealed tube A resealable vessel was charged with Pd2dba3 (0.893 g, 0.975 mmol, Strem), dicyclohexyl(2',6'-dimethoxy-[l,l '-biphenyl]-2-yl)phosphine (0.858 g, 2.090 mmol, Strem), dicyanozinc (1.636 g, 13.93 mmol), and 6-chloro-5-methylpyridin-3-ol (2.00 g, 13.93 mmol,step 3 intermediate 34). The solids were taken up in DMF (45 mL) and the reaction mixture was purged with Argon. The vessel was sealed and heated in a 1 10 °C oil bath. After 21 h, the reaction was filtered through Celite and the filter cake was rinsed with 5percent MeOH-DCM. The filtrate was concentrated and the residue was purified by silica gel chromatography, eluting with 40percent to 50percent EtOAc-hexane to afford the title compound (676 mg, 32percent). MS m/z = 135 (M+H) +
Reference: [1] Patent: WO2014/138484, 2014, A1, . Location in patent: Page/Page column 165
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