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[ CAS No. 23056-36-2 ] {[proInfo.proName]}

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Chemical Structure| 23056-36-2
Chemical Structure| 23056-36-2
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Product Details of [ 23056-36-2 ]

CAS No. :23056-36-2 MDL No. :MFCD00661454
Formula : C5H3ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LIEPVGBDUYKPLC-UHFFFAOYSA-N
M.W : 158.54 Pubchem ID :735152
Synonyms :

Calculated chemistry of [ 23056-36-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.07
TPSA : 58.71 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : -0.13
Log Po/w (SILICOS-IT) : -0.09
Consensus Log Po/w : 0.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.23
Solubility : 0.925 mg/ml ; 0.00583 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.518 mg/ml ; 0.00327 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.01
Solubility : 1.55 mg/ml ; 0.00979 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 23056-36-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23056-36-2 ]

* 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 [ 23056-36-2 ]
  • Downstream synthetic route of [ 23056-36-2 ]

[ 23056-36-2 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 23056-36-2 ]
  • [ 17368-12-6 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 4, p. 577 - 579
  • 2
  • [ 23056-36-2 ]
  • [ 14432-12-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Journal of the Chinese Chemical Society, 2003, vol. 50, # 2, p. 267 - 271
[3] Organic Letters, 2017, vol. 19, # 18, p. 4746 - 4749
[4] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2016, vol. 46, # 10, p. 1499 - 1505
  • 3
  • [ 14432-16-7 ]
  • [ 23056-36-2 ]
YieldReaction ConditionsOperation in experiment
78% With phosphorus trichloride In chloroform at 20℃; Heating / reflux Reference Example 17: 2-Chloro-4-nitro-pyridine. Phosphorus trichloride (4.2 mL, 48.7 mmol) was-added_to a solution of 2- chloro-4-nitro-pyridine-l -oxide (1.70 g, 9.74 mmol) in dry chloroform (25 mL) at r.t.The reaction mixture was then heated to reflux and maintained at this temperature overnight. The reaction was cooled to r.t. then poured onto ice, basified to between pH7-8 with saturated aq. sodium bicarbonate solution and extracted with chloroform (x 2).The combined organic phase was washed with water and brine, dried over sodium sulfate and concentrated. Drying under high vacuum afforded 2-chloro-4-nitro-pyridine(1.2 g, 78 percent) as a solid.
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7441 - 7448
[2] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 114
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 2674
  • 4
  • [ 109-09-1 ]
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Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 2674
  • 5
  • [ 2402-95-1 ]
  • [ 23056-36-2 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 2674
  • 6
  • [ 23056-36-2 ]
  • [ 35980-77-9 ]
Reference: [1] Patent: WO2012/3283, 2012, A1,
  • 7
  • [ 67-56-1 ]
  • [ 23056-36-2 ]
  • [ 17228-69-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 433 - 447
[2] Tetrahedron Letters, 2001, vol. 42, # 4, p. 735 - 737
[3] European Journal of Organic Chemistry, 2004, # 16, p. 3477 - 3483
  • 8
  • [ 23056-36-2 ]
  • [ 34851-41-7 ]
  • [ 17228-69-2 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 4, p. 577 - 579
  • 9
  • [ 23056-36-2 ]
  • [ 124-41-4 ]
  • [ 17228-69-2 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 42, p. 7575 - 7578
[2] Inorganic Chemistry, 2012, vol. 51, # 4, p. 2263 - 2271
  • 10
  • [ 23056-36-2 ]
  • [ 141-52-6 ]
  • [ 52311-50-9 ]
YieldReaction ConditionsOperation in experiment
92% at 0 - 25℃; for 12 h; A mixture of 2-chloro-4-nitropyridine (170 g 1070 mmol) in THF (2 L) was added NaOEt (109.45 g 1610 mmol) slowly at 0 . The mixture was stirred at 25 for 12 h. LCMS and TLC (PE/EA 51 Rf 0.6) showed the reaction was finished. The mixture was filtered and most solvent of the filtrate was removed in vacuo. The residue was extracted with EA (800 mL x 3) and the organic layer was washed with saturated NaCl solution (1 L) dried over Na2SO4and concentrated to give 2-chloro-4-ethoxypyridine (157 g 1.0 mol 92yield) as a solid1HNMR(400 MHz CD3OD) δ 8.15 (d J 6.0 Hz 1H) 6.99 (d J 2.0 Hz 1H) 6.91-6.89 (m 1H) 4.16-4.14 (m 2H) 1.41-1.38 (m 3H) ES-LCMS m/z 158 (M+H) .
92.4% at 0 - 25℃; for 12 h; Large scale To a mixture of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was added sodium ethanolate (109.45 g, 1610 mmol) slowly at 0 °C. The mixture was stirred at 25 °C for 12 h. LCMS and TLC analysis (PE/EA = 5:1, Rf= 0.6) showed the reaction wasfinished. The mixture was filtered, and most of the filtrate solvent was removed by reduced pressure. The mixture was quenched with water and extracted with EA, the organic layer was washed with brine, and then concentrated. Another six batches were34prepared following the same procedure to give 2-chloro-4-ethoxypyridine (1100 g, 7.01 mol, 92.4percent): ‘H NMR (400 MHz, CD3OD) 8.15 (d, J 6.0 Hz, 1H), 6.99 (d, J 2.0 Hz, 1H), 6.91-6.89 (m, 1H), 4.16-4.14 (m, 2H), 1.41-1.38 (m, 3H); ES-LCMS m/z: 158.1 (M+H).
92.4% at 0 - 25℃; for 12 h; Step 1 : 2-Chloro-4-ethoxypyridine To a mixture of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was added sodium ethanolate (109.45 g, 1610 mmol) slowly at 0 °C. The mixture was stirred at 25 °C for 12 h. LCMS and TLC analysis (PE/EA = 5: 1, Rf = 0.6) showed the reaction was finished. The mixture was filtered, and most of the filtrate solvent was removed by reduced pressure. The mixture was quenched with water and extracted with EA, the organic layer was washed with brine, and then concentrated. Another six batches were prepared following the same procedure to give 2- chloro-4-ethoxypyridine (1100 g, 7.01 mol, 92.4percent): lH NMR (400 MHz, CD3OD) δ 8.15 (d, J = 6.0 Hz, 1H), 6.99 (d, J = 2.0 Hz, 1H), 6.91-6.89 (m, 1H), 4.16-4.14 (m, 2H), 1.41-1.38 (m, 3H); ES-LCMS m/z: 158.1 (M+H).
57% at 25℃; for 10 h; To a mixture of 2-chloro-4-nitropyridine (20 g, 126 mmol) in THF (200 mL) was added sodium ethoxide (25.8 g, 378 mmol) in portions. The mixture was stirred at 25 °C for 10 h. The mixture was filtered and the filtrate was concentrated. The crude material was purified by silica column chromatography (PE/EA = 5: 1). All fractions found to contain product by TLC (PE/EA = 5: 1, Rf = 0.6) were combined and concentrated to yield a light yellow solid of 2-chloro-4-ethoxypyridine (13 g, 71.9 mmol, 57percent yield): lH NMR (400 MHz, CDC13) δ 8.18 (d, J = 5.2 Hz, 1H), 6.82 (d, J = 2.4 Hz, 1H), 6.73 (dd, J = 2.0, 6.0 Hz, 1H), 4.09 (q, J =7.2 Hz, 2H), 1.44 (t, J = 7.2 Hz, 3H); ES- LCMS m/z 158 (M+H).

Reference: [1] Patent: WO2016/37578, 2016, A1, . Location in patent: Page/Page column 71; 72
[2] Patent: WO2016/38519, 2016, A1, . Location in patent: Page/Page column 34; 35
[3] Patent: WO2016/38552, 2016, A1, . Location in patent: Page/Page column 49
[4] Patent: WO2014/141187, 2014, A1, . Location in patent: Page/Page column 112; 52; 53
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
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  • [ 34941-91-8 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 4, p. 577 - 579
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