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[ CAS No. 6940-57-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6940-57-4
Chemical Structure| 6940-57-4
Chemical Structure| 6940-57-4
Structure of 6940-57-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6940-57-4 ]

CAS No. :6940-57-4 MDL No. :MFCD06658293
Formula : C8H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :FPQMUQPPAYCAME-UHFFFAOYSA-N
M.W : 135.16 Pubchem ID :138872
Synonyms :

Calculated chemistry of [ 6940-57-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.4
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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 0.46
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 1.88 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -1.5
Solubility : 4.29 mg/ml ; 0.0318 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.26 mg/ml ; 0.00192 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 6940-57-4 ]

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 [ 6940-57-4 ]

* 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 [ 6940-57-4 ]
  • Downstream synthetic route of [ 6940-57-4 ]

[ 6940-57-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 71777-66-7 ]
  • [ 6940-57-4 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -75℃; for 1.33333 h;
Stage #2: With triethylamine In dichloromethane at -75 - 20℃; for 2 h;
To a -75°C solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at-75°C for 10 min, and then slowly treated with a solution of [1- (6-] methyl-pyridin-2-yl) -ethanol (28 [G,] 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1. [02 MOL, 5APOS;EQUIV).] The resulting, mixture was warmed to [20° OVER] 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3: 1 hexanes/ethyl acetate) yielded [1- (6-METHYL-PYRIDIN-2-YL)-ETHANONE] (25.36 g, 92percent).
Reference: [1] Patent: WO2004/26863, 2004, A1, . Location in patent: Page 54
  • 2
  • [ 79-37-8 ]
  • [ 71777-66-7 ]
  • [ 6940-57-4 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine In dichloromethane; dimethyl sulfoxide Step B
Preparation of 1-(6-Methyl-pyridin-2-yl)-ethanone
To a -75° C. solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour.
The resulting solution was stirred at -75° C. for 10 min, and then slowly treated with a solution of 1-(6-methyl-pyridin-2-yl)-ethanol of Step A (28 g, 204 mmol, 1 equiv) in methylene chloride (600 mL).
The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1.02 mol, 5 equiv).
The resulting mixture was warmed to 20° over 2 hours, and then quenched with water (500 mL).
The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material.
Silica gel chromatography (3:1 hexanes/ethyl acetate) yielded the title compound (25.36 g, 92percent).
Reference: [1] Patent: US2004/176390, 2004, A1,
  • 3
  • [ 5315-25-3 ]
  • [ 127-19-5 ]
  • [ 6940-57-4 ]
Reference: [1] Journal of the Chemical Society - Dalton Transactions, 1999, # 3, p. 349 - 355
[2] Journal of the American Chemical Society, 1997, vol. 119, # 24, p. 5606 - 5617
[3] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2481 - 2487
  • 4
  • [ 1620-75-3 ]
  • [ 75-16-1 ]
  • [ 6940-57-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 36, p. 9418 - 9426
  • 5
  • [ 1620-75-3 ]
  • [ 917-54-4 ]
  • [ 6940-57-4 ]
Reference: [1] Polyhedron, 2012, vol. 43, # 1, p. 55 - 62
  • 6
  • [ 13602-11-4 ]
  • [ 6940-57-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 2, p. 583 - 587[2] Angew. Chem., 2014, vol. 127, # 2, p. 593 - 597,5
  • 7
  • [ 934-60-1 ]
  • [ 6940-57-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 2, p. 583 - 587[2] Angew. Chem., 2014, vol. 127, # 2, p. 593 - 597,5
  • 8
  • [ 1122-70-9 ]
  • [ 6940-57-4 ]
Reference: [1] Patent: US2624740, 1951, ,
  • 9
  • [ 7647-01-0 ]
  • [ 6940-57-4 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 4247
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