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[ CAS No. 3222-49-9 ] {[proInfo.proName]}

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Chemical Structure| 3222-49-9
Chemical Structure| 3222-49-9
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Product Details of [ 3222-49-9 ]

CAS No. :3222-49-9 MDL No. :MFCD00829036
Formula : C7H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DJDHHXDFKSLEQY-UHFFFAOYSA-N
M.W : 137.14 Pubchem ID :256208
Synonyms :

Calculated chemistry of [ 3222-49-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.16
TPSA : 50.19 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) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : -0.78
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.53
Solubility : 4.01 mg/ml ; 0.0292 mol/l
Class : Very soluble
Log S (Ali) : -1.37
Solubility : 5.81 mg/ml ; 0.0424 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.76
Solubility : 2.41 mg/ml ; 0.0175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.11

Safety of [ 3222-49-9 ]

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 [ 3222-49-9 ]

* 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 [ 3222-49-9 ]
  • Downstream synthetic route of [ 3222-49-9 ]

[ 3222-49-9 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 3222-49-9 ]
  • [ 407-21-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 2
  • [ 3222-49-9 ]
  • [ 3430-19-1 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 3
  • [ 591-22-0 ]
  • [ 3222-49-9 ]
YieldReaction ConditionsOperation in experiment
59.4% With potassium permanganate In water at 25 - 45℃; for 20 h; Step 1.
Preparation of 5-methyl-nicotinic acid (B15-1): A solution of 3,5 lutidine (100 g, 934.57 mmol) in water at 25° C. was treated portion-wise over 5 hours with KMnO4 (221.1 g, 1401.86 mmol).
The reaction mixture was then heated at 45° C. for about 20 hours.
The reaction mixture was filtered and washed with water.
The resultant filtrates were concentrated, and the resultant residue was diluted with ethanol (3*500 mL), boiled, and filtered.
The filtrate was then concentrated under reduced pressure to provide B15-1 as a white solid. Yield: 76 g, 59.4percent. 1H NMR (D2O): δ 8.6-8.7 (s, 1H), 8.3-8.4 (m, 1H), 7.92 (s, 1H) and 2.3 (s, 3H). Mass: (M+1) 138 calculated for C7H7NO2.
Reference: [1] Patent: US2009/54395, 2009, A1, . Location in patent: Page/Page column 42
[2] Patent: EP1193265, 2002, A2, . Location in patent: Page 72
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 17, p. 2697 - 2703
[4] Journal of Chemical Research, Miniprint, 1987, # 9, p. 2360 - 2384
  • 4
  • [ 42972-46-3 ]
  • [ 3222-49-9 ]
Reference: [1] Carbohydrate Research, 1980, vol. 78, p. 235 - 242
  • 5
  • [ 591-22-0 ]
  • [ 3222-49-9 ]
  • [ 499-81-0 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 6
  • [ 612-58-8 ]
  • [ 3222-49-9 ]
Reference: [1] Chemische Berichte, 1933, vol. 66, p. 1338,1341, 1342
  • 7
  • [ 112945-08-1 ]
  • [ 3222-49-9 ]
Reference: [1] Chemische Berichte, 1933, vol. 66, p. 1338,1341, 1342
  • 8
  • [ 3222-49-9 ]
  • [ 402-66-4 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 9
  • [ 3222-49-9 ]
  • [ 455-70-9 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 10
  • [ 591-22-0 ]
  • [ 3222-49-9 ]
  • [ 499-81-0 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 11
  • [ 67-56-1 ]
  • [ 3222-49-9 ]
  • [ 29681-45-6 ]
YieldReaction ConditionsOperation in experiment
96% at 60 - 65℃; Inert atmosphere Example-1:
Synthesis of 5-Methyl-nicotinic acid methyl ester (Formula-8) from 5-Methyl-nicotinic acid (Formula-7)
Under nitrogen atmosphere, Thionyl chloride (110.0 ml; 1.50 moles) is added drop wise at 20-25°C to a suspension of 5-methyl nicotinic acid (100.0g; 0.73 moles) in methanol (500.0 ml) kept under nitrogen atmosphere at 20-25°C and heated the reaction mixture to 60-65°C for 2-3 hrs. On completion of the reaction is monitored by TLC. After completion of the reaction methanol is evaporated under reduced pressure to get a residue. Chilled water (150.0 ml) is added to the residue and pH of the reaction mass is adjusted to 7.0 using ammonia. The reaction mass is extracted using MDC (250.0 ml x 2). The organic layers were combined and washed with brine (150.0 ml), dried over anhydrous sodium sulfate and filtered. The filtrate is evaporated under reduced pressure to obtain the title intermediate compound (150.0 g; Yield=96percent) HPLC purity- 99.00percent
96.5% at 82℃; for 6.33333 h; S1, Preparation of methyl 5-methyl nicotinate:According to the molar portion of a 5-methyl nicotinic acid,16 parts of methanol,Dropping 3 parts of thionyl chloride,Thionyl chloride was added dropwise within 20min,Warmed to 82 ° C,Insulation 6h,Dropping and insulation kept stirring process,Adjust the temperature to 55 ,Methanol and thionyl chloride were removed by evaporation under reduced pressure,Cool to room temperature,Add ice water to get solution A;In the ice bath,The pH of solution A was adjusted to 8 with aqueous ammonia,Add ethyl acetate extract,The ethyl acetate phase was added anhydrous sodium sulfate to dry to a moisture content of 0.3 wtpercentfilter,Take ethyl acetate phase by rotary evaporation to give methyl 5-methyl nicotinate;
Reference: [1] Patent: EP2824103, 2015, A1, . Location in patent: Paragraph 0039
[2] Patent: CN106560471, 2017, A, . Location in patent: Paragraph 0054; 0060; 0066; 0072; 0078; 0084; 0090; 0096
[3] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205
[4] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[5] Biochemistry, 2010, vol. 49, # 49, p. 10421 - 10439
[6] Synthetic Communications, 2008, vol. 38, # 1, p. 122 - 127
  • 12
  • [ 186581-53-3 ]
  • [ 3222-49-9 ]
  • [ 29681-45-6 ]
Reference: [1] Carbohydrate Research, 1980, vol. 78, p. 235 - 242
  • 13
  • [ 3222-49-9 ]
  • [ 64-17-5 ]
  • [ 20826-02-2 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1987, # 9, p. 2360 - 2384
[2] Patent: US6664271, 2003, B1, . Location in patent: Page column 20
  • 14
  • [ 3222-49-9 ]
  • [ 102074-19-1 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[2] Patent: WO2006/110668, 2006, A1, . Location in patent: Page/Page column 56
[3] Patent: WO2006/110668, 2006, A1, . Location in patent: Page/Page column 61
[4] Patent: EP1230232, 2004, B1, . Location in patent: Page 39; 40
[5] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 89
[6] Patent: EP2824103, 2015, A1,
[7] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205
  • 15
  • [ 3222-49-9 ]
  • [ 39891-04-8 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 16
  • [ 3222-49-9 ]
  • [ 100910-66-5 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[2] Biochemistry, 2010, vol. 49, # 49, p. 10421 - 10439
[3] Patent: WO2016/123392, 2016, A2,
  • 17
  • [ 3222-49-9 ]
  • [ 22620-32-2 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 18
  • [ 3222-49-9 ]
  • [ 1235342-53-6 ]
Reference: [1] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205
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