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[ CAS No. 638218-78-7 ] {[proInfo.proName]}

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Chemical Structure| 638218-78-7
Chemical Structure| 638218-78-7
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Product Details of [ 638218-78-7 ]

CAS No. :638218-78-7 MDL No. :MFCD16657880
Formula : C8H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :OXSDDDKLMCHNHF-UHFFFAOYSA-N
M.W : 216.08 Pubchem ID :22714301
Synonyms :

Calculated chemistry of [ 638218-78-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.56
TPSA : 33.12 ?2

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) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 1.62
Log Po/w (WLOGP) : 1.96
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.626 mg/ml ; 0.0029 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 2.55 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.13
Solubility : 0.159 mg/ml ; 0.000738 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 638218-78-7 ]

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 [ 638218-78-7 ]

* 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 [ 638218-78-7 ]

[ 638218-78-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 917-64-6 ]
  • [ 26218-75-7 ]
  • [ 638218-78-7 ]
YieldReaction ConditionsOperation in experiment
100% In diethyl ether; at 20℃; for 0.5h;Inert atmosphere; Dissolve methyl 6-bromopicolinate (Int-1-a) (5 g, 23.1 mmol) in diethyl ether (100 mL),Methyl magnesium iodide (17 mL, 50.8 mmol) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 0.5 hours.Water and 2N hydrochloric acid were added to the reaction solution, and extracted three times with ethyl acetate.The organic layers were combined and washed successively with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution.It was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain the title compound (5 g, yield: 100%) in this step.
85% In diethyl ether; at 20℃; for 0.0833333h;Inert atmosphere; Methylmagnesium iodide (3M in Et20, 1.50 ml, 4.48 mmol) was added to a solution of methyl 6-bromopyridine-2- carboxylate (0.430 g, 1.99 mmol) in dry Et20 (1 5 ml) under N2. After 5 min at RT the reaction was quenched with 1 M HCI (10 ml) and extracted with EtOAc (15 ml). The organic extract was washed with sat. NaHC03 solution (1 5 ml) and brine (10 ml), dried (MgS04) and concentrated in vacuo. The desired product was obtained as a yellow oil (0.365 g, 1.69 mmol, 85%). Rf 0.60 (1 :1 Hexane:EtOAc); I R (cm-1 ) 3420, 2975, 2930, 1731 , 1701 , 1 580, 1 553; 1 H NMR (400 MHz, DMSO-d6) 1.42 (6H, s, C(CH2)2), 5.33 (1 H, s, OH), 7.47 (1 H, dd, J = 7.7, 0.9 Hz, H-5), 7.67 (1 H, dd, J = 7.7, 0.9 Hz, H-3), 7.73 (1 H, dd, J = 7.7, 7.7 Hz, H-4); 13C N MR (125 MHz, DMSO-d6) 30.9 (C(CH2)2), 72.6 (C(CH2)2), 1 18.5 (Ar-C), 126.0 (Ar-C), 140.4 (Ar-C), 140.5 (Ar-C), 170.8 (Ar-C).
85% In diethyl ether; at 20℃; for 0.0833333h;Inert atmosphere; (0223) Synthesis of 2-(6-bromopyridin-2-yl)propan-2-ol. Methylmagnesium iodide (3M in Et20, 1.50 ml, 4.48 mmol) was added to a solution of methyl 6-bromopyridine-2- carboxylate (0.430 g, 1.99 mmol) in dry Et20 (15 ml) under N2. After 5 min at RT the reaction was quenched with 1 M HCI (10 ml) and extracted with EtOAc (15 ml). The organic extract was washed with sat. NaHC03 solution (15 ml) and brine (10 ml), dried (MgS04) and concentrated in vacuo. The desired product was obtained as a yellow oil (0.365 g,1.69 mmol, 85%). Rf 0.60 (1 :1Hexane:EtOAc); IR (cm 1) 3420, 2975, 2930, 1731, 1701, 1580, 1553; 1H NMR (400 MHz, DMSO-d6) 1.42 (6H, s, C(CH2)2), 5.33 (1H, s, OH), 7.47 (1H, dd, J = 7.7, 0.9 Hz, H-5), 7.67 (1H, dd, J = 7.7, 0.9 Hz, H-3), 7.73 (1H, dd, J = 7.7, 7.7 Hz, H-4); 13C NMR (100 MHz, DMSO- 6) 30.9 (C(CH2)2), 72.6 (C(CH2)2), 1 18.5 (Ar-C), 126.0 (Ar-C), 140.4 (Ar-C), 140.5 (Ar-C), 170.8 (Ar-C).
With hydrogenchloride; In diethyl ether; water; 1) Production of 2-(6-bromo-2-pyridinyl)-2-propanol In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2-carboxylate. Water and 2 N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain 8.51 g of crude 2-(6-bromo-2-pyridinyl)-2-propanol as a yellow oily substance. 1H-NMR (400 MHz, CDCl3) delta: 7.56 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=7.8, 1.0 Hz), 7.36 (1H, dd, J=7.8, 1.0 Hz), 1.55(6H, s). ESI-MS Found: m/z[M+H]+ 216, 218.
Reference Example 2:Production of 2-allyl-l -[6-(I -hydroxy- 1 -methyl ethyl)pyridin-2-yl] -6-{ [4-(4-methylpiperazin- 1- yl)phenyl]ammo>-l,2-dihvdro-3H-pyrazolo[3,4-dlpyrimidin-3-one1) Production of 2-(6-bromo-2-pyridinyl)-2-propanol:In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2- carboxylate. Water and 2 N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain 8.51 g of crude 2-(6-bromo-2-pyridinyl)-2- propanol as a yellow oily substance. iH-NMR (400 MHz, CDC13) 6: 7.56 (IH, t, J=7.8 Hz), 7.38 (IH, dd, J=7.8, 1.0 Hz), 7.36 (IH, dd, J=7.8, 1.0 Hz), 1.55(6H, s). ESI-MS Found: m/z[M+H]+ 216, 218.
In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2- carboxylate. Water and 2N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain 8.51 g of crude 2-(6-bromo-2-pyridinyl)-2- propanol as a yellow oily substance. iH-NMR (400 MHz, CDC13) delta: 7.56 (IH, t, J=7.8 Hz), 7.38 (IH, dd, J=7.8, 1.0 Hz), 7.36 (IH, dd, J=7.8, 1.0 Hz), 1.55(6H, s). ESI-MS Found: m/z[M+H]+ 216, 218.
With hydrogenchloride; In diethyl ether; water;Inert atmosphere; Step 1) Production of 2-(6-bromo-2-pyridinyl)-2-propanol: In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2- carboxylate. Water and 2 N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain 8.51 g of crude 2-(6-bromo-2-pyridinyl)-2- propanol as a yellow oily substance. iH-NMR (400 MHz, CDC13) delta: 7.56 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=7.8, 1.0 Hz), 7.36 (1H, dd, J=7.8, 1.0 Hz), 1.55(6H, s). ESI-MS Found: m/z[M+H]+ 216, 218.
In diethyl ether;Inert atmosphere; In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2-carboxylate. Water and 2 N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain crude 2-(6-bromo-2-pyridinyl)-2-propanol as a yellow oily substance. 1H-NMR (400 MHz, CDCl3) delta: 7.56 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=7.8, 1.0 Hz), 7.36 (1H, dd, J=7.8, 1.0 Hz), 1.55 (6H, s). ESI-MS Found: m/z[M+H]+ 216, 218.

  • 2
  • [ 638218-78-7 ]
  • [ 638218-62-9 ]
  • [ 638218-76-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; water; at 80℃; for 0.25h; [ A MIXTURE OF QUINOLINE 4 (L. OEQ. ), 2- (6-BROMO-PYRIDIN-2-YL)-PROPAN-2- OL (1. 2EQ. ), NA2CO3 (3.5EQ. ; 2M IN H20), PD (OAC) 2 (0.05EQ.) AND PPH3 (0. 15EQ.) IN N-] propanol [(0.] 1M) was stirred at [80C] for [15MIN.] The mixture was cooled to rt, poured in water and extracted with EtOAc (2x). The combined organic extracts were washed with brine, dried over [NA2SO4,] filtered and concentrated. Flash chromatography (Tol: Ace; 9: 1) afforded the title compound as a white [SOLID. 1H] NMR (500 MHz, acetone-d6) : [8] 8.95 (dd, 1H), 8.53 (t, 1H), 8.48 (dd, 1H), 8.32 (d, 1H), 8.26 (d, 1H), 8.20 (dt, 1H), 7.92-7. 81 (m, 3H), 7.65-7. 58 (m, 3H), 4.83 (s, OH), 2.76 (s, 3H), 2.03 (s, 6H), 1.58 (s, 6H).
  • 3
  • [ 626-05-1 ]
  • [ 638218-78-7 ]
YieldReaction ConditionsOperation in experiment
Step 1: 2-Bromo-6-(1-hydroxy-1-methylethyl)pyridine. Following the procedure of Step 1 of EXAMPLE 27, but substituting 2,6-dibromopyridine for 2,5-dibromopyridine, the 2-Bromo-6-(1-hydroxy-1-methylethyl)pyridine compound was obtained as a solid.
  • 4
  • [ 626-05-1 ]
  • [ 67-64-1 ]
  • [ 638218-78-7 ]
YieldReaction ConditionsOperation in experiment
98% Place a 1.6 M solution of n-butyl lithium in hexane (31.2 niL, 50 mmol) in a dry 250 rnL round bottomed flask fitted with a stir bar, septum and temperature probe. Cool in a dry- ice acetone bath to -76 0C. Add THF (30 mL) to the solution, then add a solution of 2,6- dibromopyridine (11.5 g, 50 mmol) in THF (60 mL) slowly via syringe maintaining the temperature under -600C. Stir the dark yellow-brown solution for 30 minutes in the dry- ice bath, then add acetone (6 mL, 80 mmol). Stir the deep green solution in the dry-ice bath for 15 minutes then allow the reaction to warm to room temperature. After an hour add a 5% aqueous solution of ammonium chloride (50 mL) carefully. Extract with dichloromethane, evaporate to give 2-(6-bromo-pyridin-2-yl)-propan-2-ol (10.6 g, 98%) as an orange oil. MS (m/z): 216 and 218 (M+H) +.
94.3% With n-butyllithium; In tetrahydrofuran; hexane; at -76 - 20℃; for 1.25h;Cooling with ice; Step 1 2-(6-Bromopyridin-2-yl)propan-2-ol A dry 250 mL round bottomed flask fitted with a stir bar and septum was charged with n-buthyllithium 1.6 M in hexane (30.3 mL, 48.5 mmol), the flask was cooled in a dry-ice acetone bath to -76 C. and added THF (30 mL) to the solution, then added a solution of 2,6-dibromopyridine (11.5 g, 48.5 mmol) in THF (60 mL) slowly via cannula over 15 min. The dark yellow-brown solution was stirred for 30 minutes in the dry-ice bath, then added propan-2-one (4.75 g, 6 mL, 81.7 mmol). The deep green solution was stirred in the dry-ice bath for 15 minutes and then allowed to warm to room temperature. After an hour, added carefully a saturated aqueous solution of ammonium chloride (100 mL) and product extracted with dichloromethane (3*200), combined organics dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (silica gel 50 mum, 150 g, Analogix) eluting with 0 to 50% over 20 min dichloromethane/hexanes, obtained 2-(6-bromopyridin-2-yl)propan-2-ol (9.9 g, 94.3% yield) as a light yellow clear liquid. 1H NMR (CHLOROFORM-d) delta: 7.52-7.59 (m, 1H), 7.33-7.40 (m, 2H), 4.05 (br. s., 1H), 1.55 (s, 6H); LC-MS 216.1, 218.1 [M+H]+.
94% Step 1 2-(6-Bromopyridin-2-yl)propan-2-ol A dry 250 mL round bottomed flask fitted with a stir bar and septum was charged with n- buthyllithium 1.6 M in hexane (30.3 mL, 48.5 mmol), the flask was cooled in a dry- ice acetone bath to -76 C then THF (30 mL) was added followed by a solution of 2,6-dibromopyridine (11.5 g, 48.5 mmol) in THF (60 mL) slowly via cannula over 15 min. The dark yellow-brown solution was stirred for 30 minutes in the dry- ice bath, then propan-2-one (4.75 g, 6 mL, 81.7 mmol) was added. The deep green solution was stirred in the dry- ice bath for 15 minutes then was warmed to room temperature over 1 hour. A saturated aqueous solution of ammonium chloride (100 mL) was carefully added and the mixture extracted with dichloromethane (3 x 200 mL). The combined organic extracts were dried over magnesium sulfate then concentrated in vacuo and purified by chromatography (silica gel 50 muiotaeta, 150g, Analogix, eluting with 0 to 50% dichloromethane in hexanes) to obtain 2-(6-bromopyridin-2-yl)propan-2-ol (9.9 g, 94 %) as a light yellow, clear liquid. 1H NMR (CHLOROFORM-d) delta: 7.52 - 7.59 (m, 1H), 7.33 - 7.40 (m, 2H), 4.05 (br. s., 1H), 1.55 (s, 6H); MS (EI/CI) m/z: 216.1, 218.1 [M + H].
To a suspension of 2,6-dibromopyridine [(L.] Oeq. ) in Et20 (0.2M) at -78C was added dropwise n-BuLi [(1.] [05EQ.).] The mixture was stirred at-78C for [45MIN] then acetone [(1.] 5eq.) was added. The final mixture was stirred for an extra [15MIN] at-78C and quenched with saturated aqueous NaHCO3,. The mixture was extracted with EtOAc (2x). The combined organic extracts were washed with, brine, dried over [MGS04,] filtered and concentrated to afford the title compound as a white solid which was used as such.
Place a 1.6 M solution ofn-BuLi in hexane (5.2 mL) in a dry 100 mL roundbottomed flask fitted with a stir bar, septum and temperature probe. Cool in adry- ice acetone bath to -76 C. Add THF (5 mL) to the solution, then add asolution of2,6- dibromopyridine (2.0 g) in THF (10 mL) slowly via syringemaintaining the temperature below -60 C. Stir the solution for 30 min in thedry- ice bath, then add acetone (13.5 mL). Stir the solution in the dry-ice bathfor 15 min then allow the reaction to warm to room temperature. After 1 h thereaction mixture was quenched with a 5% aqueous solution ofNH4Cl, andextracted with EtOAc. The combined organic layer was washed with brine anddried over Na2S04? It was filtered and concentrated in vacuo. The residue waspurified by silica gel column chromatography (Heptane:CH2Cb=70:30 toCH2Cb) to obtain compound 4-1 as an orange oil.
Place a 1.6 M solution of n-BuLi in hexane (5.2 mL) in a dry 100 rnL round bottomed flask fitted with a stir bar, septum and temperature probe. Cool in a dry- ice acetone bath to -76 C. Add THF (5 mL) to the solution, then add a solution of 2,6- dibromopyridine (2.0 g) in THF (10 mL) slowly via syringe maintaining the temperature under -60 C. Stir the solution for 30 min in the dry- ice bath, then add acetone (13.5 mL). Stir the solution in the dry-ice bath for 15 min then allow the reaction to warm to room temperature. After an h the reaction mixture was quenched with a 5% aqueous solution of NH4C1, and extracted with EtOAc. The combined organic layer was washed with brine and dried over Na2S04. It was filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (Heptane:CH2Cl2=70:30 to 0:100) to obtain compound 21-1 as a orange solid.

  • 5
  • [ 49669-13-8 ]
  • [ 75-16-1 ]
  • [ 638218-78-7 ]
YieldReaction ConditionsOperation in experiment
98% Preparation 31 Synthesis of 2-(6-bromo-pyridin-2-yl)-propan-2-ol Add a solution of methyl magnesium bromide (3.0 M, 9.7 mL, 29.09 mmol) in tetrahydrofuran dropwise over 20 min to a cooled solution of 1-(6-bromo-pyridin-2-yl)-ethanone (5 g, 24.25 mmol) in anhydrous tetrahydrofuran (48.5 mL) at 0 C. Upon completion of the reaction, add water (exothermic), dilute with ethyl acetate (50 mL) and separate the layers. Extract the aqueous layer once with ethyl acetate (50 mL). Dry the combined organic layers over sodium sulfate, filter and concentrate to give the title compound as a pale yellow liquid (5.69 g, 98%) that is used without further purification. 1H NMR (CDCl3) delta 1.55 (s, 6H), 4.07 (s, 1H), 6.59 (t, 1H), 7.37 (t, 2H), 7.55 (t, 1H).
98% In tetrahydrofuran; at 20℃; for 16h; To a solution of l-(6-bromo-pyridin-2-yl)-ethanone (4.0 g, 20 mmol) in anhydrous THF (50 mL) at 0 C was added a solution of methyl magnesium bromide (3.0 M, 8.0 mL, 24 mmol, 1.2 eq) in THF dropwise over 20 min. The mixture was stirred at rt for 16 h, quenched with H20 (30 mL) and extracted by EA (4 x 30 mL). The organic phase was washed with brine (30 mL) and dried over Na2S04. After filtration and concentration, the residue was directly used for next step without further purification. 4.2 g, Y: 98%. ESI-MS (M+H)+: 216.
A solution of l-(6~bromorhoyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 ml) at 00C was treated with methyl magnesium bromide (8.33 ml, 25.0 mmol). After 3 hours, water was added to quench excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound. LRMS (APCI) calc'd for C8H1 jBrNO [M+H]+: 216, Found: 216.
In diethyl ether; at 0℃; for 3h; A solution of l-(6-bromopyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 mL) at 0C was treated with methyl magnesium bromide (8.33 mL, 25.0 mmol). After 3 hours, water was added to quench the excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound.Calc'd for C8HnBrNO [M+H]+: 216, Found: 216.

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