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[ CAS No. 189449-41-0 ]

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Chemical Structure| 189449-41-0
Chemical Structure| 189449-41-0
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Product Details of [ 189449-41-0 ]

CAS No. :189449-41-0 MDL No. :MFCD09743993
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :FYKNUGKDTZRYJM-UHFFFAOYSA-N
M.W :143.57 Pubchem ID :435084
Synonyms :

Calculated chemistry of [ 189449-41-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.37
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) : -6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 0.59
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.53
Solubility : 4.25 mg/ml ; 0.0296 mol/l
Class : Very soluble
Log S (Ali) : -0.86
Solubility : 19.9 mg/ml ; 0.138 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.514 mg/ml ; 0.00358 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 189449-41-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 189449-41-0 ]

* 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 [ 189449-41-0 ]
  • Downstream synthetic route of [ 189449-41-0 ]

[ 189449-41-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 114077-82-6 ]
  • [ 189449-41-0 ]
YieldReaction ConditionsOperation in experiment
42% With sodium borohydrid; acetic acid In tetrahydrofuran; methanol Example 5
4-chloro-3-hydroxymethylpyridine
To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1 mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol).
After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature.
The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) δ4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
42% With sodium borohydrid; acetic acid In tetrahydrofuran; methanol Example 5
4-chloro-3-hydroxymethylpyridine
To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol).
After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature.
The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) δ4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
42% With sodium borohydrid; acetic acid In tetrahydrofuran; methanol Example 5
4-chloro-3-hydroxymethylpyridine
To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1 mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol).
After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature.
The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) δ 4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).
42 % With sodium borohydrid; acetic acid In tetrahydrofuran; methanol Example 5
4-chloro-3-hydroxymethylpyridine
To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0 °C was added methanol (1mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol).
After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature.
The solid residue was chromatographed on silica gel column (1percent MeOH / dichloromethane) to afford 60 mg (42 percent) of the title compound. 1H NMR (CDCl3) δ 4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).

Reference: [1] Synthesis, 1999, # 8, p. 1294 - 1296
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 20, p. 5841 - 5863
[3] Tetrahedron, 2006, vol. 62, # 10, p. 2240 - 2246
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 13, p. 2832 - 2840
[5] Patent: US6025352, 2000, A,
[6] Patent: US6030965, 2000, A,
[7] Patent: US6057312, 2000, A,
[8] Patent: US6066630, 2000, A,
[9] Patent: US6087355, 2000, A,
[10] Patent: US5859256, 1999, A,
[11] Patent: EP1059293, 2000, A1,
[12] Synlett, 2013, vol. 24, # 1, p. 49 - 52
[13] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
  • 2
  • [ 37831-62-2 ]
  • [ 189449-41-0 ]
Reference: [1] Journal of Antibiotics, 2000, vol. 53, # 11, p. 1272 - 1281
[2] Patent: US2006/25433, 2006, A1, . Location in patent: Page/Page column 94
  • 3
  • [ 10177-29-4 ]
  • [ 189449-41-0 ]
Reference: [1] Patent: US2016/168139, 2016, A1, . Location in patent: Paragraph 0951-0955
  • 4
  • [ 626-61-9 ]
  • [ 189449-41-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 20, p. 5841 - 5863
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 13, p. 2832 - 2840
[3] Journal of Antibiotics, 2000, vol. 53, # 11, p. 1272 - 1281
[4] Synthesis, 1999, # 8, p. 1294 - 1296
  • 5
  • [ 7379-35-3 ]
  • [ 189449-41-0 ]
Reference: [1] Synlett, 2013, vol. 24, # 1, p. 49 - 52
  • 6
  • [ 189449-41-0 ]
  • [ 114077-82-6 ]
YieldReaction ConditionsOperation in experiment
480 mg With manganese(IV) oxide In ethyl acetate for 4 h; Reflux Manganese dioxide (1.53 g) was added to a solution of (4-chloro pyridin-3-yl)methanol (630 mg) in ethyl acetate (15 mL), followed by refluxing for 2 hours. Manganese dioxide (382 mg) was added thereto, followed by refluxing for 2 hours. The reaction mixture was cooled to room temperature, the insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (hexane:ethyl acetate=7:3→3:7), whereby 4-chloronicotinic aldehyde (480 mg) was obtained as a white solid
Reference: [1] Synlett, 2013, vol. 24, # 1, p. 49 - 52
[2] Patent: US2016/168139, 2016, A1, . Location in patent: Paragraph 0951; 0956; 0957
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