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[ CAS No. 108166-02-5 ] {[proInfo.proName]}

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Product Details of [ 108166-02-5 ]

CAS No. :108166-02-5 MDL No. :MFCD06659066
Formula : C11H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :HLFYJILNIBADGG-UHFFFAOYSA-N
M.W : 173.21 Pubchem ID :2795481
Synonyms :

Safety of [ 108166-02-5 ]

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 [ 108166-02-5 ]

* 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.

  • Downstream synthetic route of [ 108166-02-5 ]

[ 108166-02-5 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 42074-68-0 ]
  • (2-methyl-6-quinolinyl)methanol [ No CAS ]
  • [ 196814-73-0 ]
  • (S)-2-(2-Benzoyl-phenylamino)-3-[4-(2-methyl-quinolin-6-ylmethoxy)-phenyl]-propionic acid [ No CAS ]
  • 2
  • [ 108166-02-5 ]
  • [ 945496-34-4 ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 23℃; 153.b b) 6-(azidomethyl)-2-methylquinoline To a solution of (2-methyl-6-quinolinyl)methanol (100 mg, 0.560 mmol) and DBU (0.152 ml, 1.008 mmol) in DMF (4 ml) was added DPPA (0.205 ml, 0.952 mmol). The reaction mixture was stirred overnight at 23° C. Reaction mixture was poured into water and extracted twice with ethyl acetate. Organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated to afford a crude material, which was purified by silicagel chromatography (cyclohexane:ethyl acetate from 100:0 to 0:100) to afford the title compound. HPLC (Method G) Rt=1.048 min; MS (Method F) [M+H]+=199.2
  • 3
  • [ 108166-02-5 ]
  • [ 1357954-34-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 23 °C 2: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol / 1.5 h / 23 °C 3: trifluoroacetic acid / dichloromethane / 23 °C
  • 4
  • [ 108166-02-5 ]
  • [ 1357957-37-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 23 °C 2: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol / 1.5 h / 23 °C
  • 5
  • [ 108166-02-5 ]
  • [ 1393580-26-1 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In dichloromethane at 20℃; for 2h; 1 6-(Chloromethyl)-2-methylquinoline hydrochloride SLA 47080B To a stirred solution of (2-methylquinolin-6-yl)methanol SLA 47080A (0.973 g, 5.62 mmol) in dry CH2Cl2 (40 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (8.15 mL, 112 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 6-(chloromethyl)-2-methylquinoline hydrochloride SLA 47080B as a yellow solid (1.30 g, quant). MW: 228.12; Yield: 100%; Yellow Solid; Mp (° C.): 134.0. MS-ESI m/z (% rel. Int.): 194 ([MH]+, 37Cl, 34), 192 ([MH]+, 35Cl, 100).
  • 6
  • [ 108166-03-6 ]
  • (2-methyl-6-quinolinyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% (2-Methylquinolin-6-yl)methanol SLA 47080A To a stirred solution of <strong>[108166-03-6]2-methylquinoline-6-carbaldehyde</strong> (1.00 g, 5.8 mmol) in THF (60 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.221 g, 5.8 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (10 mL). After stirring for 15 min at RT, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40 C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give (2-methylquinolin-6-yl)methanol SLA 47080A as a yellow oil (1.056 g, quant.). MW: 173.21; Yield: 100%; Yellow Oil. 1H NMR (CDCl3, delta): 2.60 (broad s, 1H, OH), 2.70 (s, 3H, CH3), 4.87 (s, 2H, CH2), 7.27 (d, 1H, J=8.5 Hz, ArH), 7.63 (dd, 1H, J=2.1 & 8.7 Hz, ArH), 7.72-7.74 (m, 1H, ArH), 7.96-8.02 (m, 2H, 2*ArH). 13C-NMR (CDCl3, delta): 25.2, 64.9, 122.2, 124.8, 126.3, 128.7, 128.8, 136.1, 138.4, 147.4, 158.9. MS-ESI m/z (% rel. Int.): 174 ([MH]+, 100).
  • 7
  • [ 108166-02-5 ]
  • [ 1393580-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / 20 °C 2: lithium hydroxide / water; tetrahydrofuran / 1.5 h / 160 °C / microwave irradiation
  • 8
  • [ 108166-02-5 ]
  • [ 1393580-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / 20 °C 2: lithium hydroxide / water; tetrahydrofuran / 1.5 h / 160 °C / microwave irradiation
  • 9
  • [ 108166-02-5 ]
  • [ 1975198-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 1.2: 20 °C 2.1: trichloroisocyanuric acid / chloroform / 20 °C
  • 10
  • [ 108166-02-5 ]
  • [ 1975198-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 1.2: 20 °C 2.1: trichloroisocyanuric acid / chloroform / 20 °C 3.1: sodium iodide / N,N-dimethyl-formamide / 2 h / 60 °C
  • 11
  • [ 14267-92-6 ]
  • [ 108166-02-5 ]
  • [ 1975198-58-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (2-methyl-6-quinolinyl)methanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 1-chloro-4-pentyne In N,N-dimethyl-formamide at 20℃;
  • 12
  • [ 108166-02-5 ]
  • [ 1618699-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: phosphorus tribromide / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: caesium carbonate / N,N-dimethyl-formamide / 18 h / 50 °C / Inert atmosphere 3: water; hydrogenchloride / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere
  • 13
  • (2-methyl-6-quinolinyl)methanol [ No CAS ]
  • [ 141848-60-4 ]
YieldReaction ConditionsOperation in experiment
88% With phosphorus tribromide; In dichloromethane; at 20℃; for 18h;Inert atmosphere; (2-Methyl-quinolin-6-yl)-methanol (150mg, 0.87mmol) was dissolved in dichloromethane30 (SOmis). To this solution was added phosphorous tribromide (215mg, 2.13mmol) The reactionmixture was stirred at room temperature for 18 hours and diluted with CHCI3 (1 OOmls) the filtrate was washed with sat. NaHC03 (1x30mls), water (1x30mls), brine (1x30mls), dried(Na2S04) and evaporated in vacuo to give a white solid which was identified as 6-bromomethyl-2-methyl-quinoline (180mg, 0.76mmol, 88%).[M+Hr = 235.96
  • 14
  • [ 108166-02-5 ]
  • [ 1618648-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus tribromide / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: caesium carbonate / N,N-dimethyl-formamide / 18 h / 50 °C / Inert atmosphere
  • 15
  • [ 635-80-3 ]
  • (2-methyl-6-quinolinyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% 2-Methyl-quinoline-6-carboxylic acid (1.0g, 5.34mmol) was dissolved in THF (1 OOmls), thissolution was cooled to -20C, to this solution was added triethylamine (1.62g, 16.03mmol) andisobutyl chloroformate (875mg, 6.41 mmol). The reaction mixture was stirred at -20C for20 20mins and then poured into a solution of sodium borohydride (1.0g, 26.71mmol) in water(10mls) at 0C. The reaction mixture was stirred at OOC to room temperature for 18 hours anddiluted with EtOAc (200mls) 0.3M KHS04 (1x50mls), water (1x50mls), brine (1x50mls), dried(Na2S04) and evaporated in vacuo to give a white solid. The solid were triturated withEtOAc/Pet Ether 60-80Cto give a white solid identified as (2-methyl-quinolin-6-yl)-methanol25 (890mg, 5.14mmol, 96%).[M+Hr = 174.24
  • 16
  • [ 108166-02-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethylamino-sulfur trifluoride / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux; Inert atmosphere
  • 17
  • [ 108166-02-5 ]
  • [ 1818836-97-3 ]
YieldReaction ConditionsOperation in experiment
75% With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;
  • 18
  • [ 108166-02-5 ]
  • [ 1818837-10-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethylamino-sulfur trifluoride / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux; Inert atmosphere 3: sodium tetrahydroborate / ethanol; 1,4-dioxane / 3 h / 0 - 20 °C / Inert atmosphere
  • 19
  • [ 108166-02-5 ]
  • [ 1818837-55-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: diethylamino-sulfur trifluoride / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2.1: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux; Inert atmosphere 3.1: sodium tetrahydroborate / ethanol; 1,4-dioxane / 3 h / 0 - 20 °C / Inert atmosphere 4.1: triphenylphosphine; di-tert-butyl-diazodicarboxylate / 1,4-dioxane / 18 h / 60 °C / Inert atmosphere 4.2: Inert atmosphere
  • 20
  • [ 109-99-9 ]
  • [ 108166-02-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
64% With silver nitrate; Selectfluor In water at 50℃; for 3h; 6 Example 6 2-methyl-6-oxomethyl-quinoline (1 mmol, 173 mg),Selectfluor (4 mmol, 1.4 g) and AgNO3 (0.2 mmol, 34 mg) were added to an aqueous solution of tetrahydrofuran (10 ml, THF:H 2 O = 3:1) and reacted at 50 ° C for 3 h.The mixture was neutralized with EtOAc EtOAc (EtOAc m. Column chromatography (eluent: ethyl acetate / n-hexane = 1:4)The product 2-methyl-6-oxomethyl-4-(tetrahydrofuran-2-yl)quinoline 155 mg was obtained in a yield of 64%.
  • 21
  • [ 108166-02-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: ethanol / 24 h / 20 °C 3: trityl tetrakis(pentafluorophenyl)borate; Cp*Sc(CH2C6H4NMe2-o)2 / toluene / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Glovebox; Sealed tube
  • 22
  • [ 108166-02-5 ]
  • [ 2559795-51-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: ethanol / 24 h / 20 °C 3: trityl tetrakis(pentafluorophenyl)borate; Cp*Sc(CH2C6H4NMe2-o)2 / toluene / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Glovebox; Sealed tube 4: hydrogenchloride / dichloromethane; toluene / 24 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox; Sealed tube
  • 23
  • (2-methyl-6-quinolinyl)methanol [ No CAS ]
  • [ 108166-03-6 ]
  • 24
  • [ 108166-02-5 ]
  • [ 2559795-91-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: ethanol / 24 h / 20 °C
  • 25
  • [ 93-35-6 ]
  • [ 77-78-1 ]
  • [ 108166-02-5 ]
  • [ 7143-01-3 ]
  • [ 2766027-87-4 ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: (2-methyl-6-quinolinyl)methanol; Methanesulfonic anhydride With pyridine; dmap In dichloromethane; acetonitrile at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 7-hydroxy-2H-chromen-2-one With caesium carbonate In dichloromethane; acetonitrile at 20℃; Schlenk technique; Inert atmosphere; Stage #3: dimethyl sulfate In toluene at 100℃; for 24h; Inert atmosphere;
  • 26
  • [ 1266118-78-8 ]
  • [ 108166-02-5 ]
  • [ 2765595-53-5 ]
YieldReaction ConditionsOperation in experiment
31% With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane In 1,4-dioxane at 95℃; for 3h; Inert atmosphere; 10.A Step A: Synthesis of tert-butyl 4-(6-(((2-methylquinolin-6-yl)methoxy)pyridin-2-yl)piperidine-1-carboxylate At room temperature, tert-butyl 4-(6-chloropyridin-2-yl)piperidine-1-carboxylate (150.0 mg, 0.50 mmol),(2-Methylquinolin-6-yl)methanol (130.0 mg, 0.75 mmol) and cesium carbonate (326.0 mg, 1.00 mmol) were added to dioxane (5.0 mL),Then add 2-dicyclohexylphosphorus-2,4,6-triisopropylbiphenyl (47.0 mg, 0.1 mmol),Tris(dibenzylideneacetone)dipalladium (46.0 mg, 0.05 mmol) was reacted under N 2 protection at 95 degrees Celsius for 3.0 hours. The reaction was completed, quenched by adding water, the mixture was extracted with ethyl acetate (30 mL×L), the organic phases were combined, the organic phase was washed with saturated brine (20 mL×L), and then dried over anhydrous sodium sulfate, Finally concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/1),67.0 mg of tert-butyl 4-(6-(((2-methylquinolin-6-yl)methoxy)pyridin-2-yl)piperidine-1-carboxylate was obtained as a pale yellow solid (yield: 31.0%).
  • 27
  • [ 108166-02-5 ]
  • [ 2765595-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane / 1,4-dioxane / 3 h / 95 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere
  • 28
  • [ 108166-02-5 ]
  • [ 2765595-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane / 1,4-dioxane / 3 h / 95 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere 3: Cs2CO3; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 50 °C / Inert atmosphere
  • 29
  • [ 108166-02-5 ]
  • [ 2765594-01-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane / 1,4-dioxane / 3 h / 95 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere 3: Cs2CO3; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 50 °C / Inert atmosphere 4: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 20 °C
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