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[ CAS No. 105250-16-6 ]

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2D
Chemical Structure| 105250-16-6
Chemical Structure| 105250-16-6
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Product Details of [ 105250-16-6 ]

CAS No. :105250-16-6MDL No. :MFCD08062415
Formula : C7H9NO Boiling Point : 239.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :123.15Pubchem ID :9942144
Synonyms :

Computed Properties of [ 105250-16-6 ]

TPSA : 33.1 H-Bond Acceptor Count : 2
XLogP3 : 0.4 H-Bond Donor Count : 1
SP3 : 0.29 Rotatable Bond Count : 1

Safety of [ 105250-16-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 105250-16-6 ]

  • Upstream synthesis route of [ 105250-16-6 ]
  • Downstream synthetic route of [ 105250-16-6 ]

[ 105250-16-6 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 105250-16-6 ]
  • [ 63875-01-4 ]
YieldReaction ConditionsOperation in experiment
20% With pyridine; chromium(VI) oxide In dichloromethane at 20℃; for 0.5 h; A solution of chromium (Vl) oxide (2 g, 20 mmol), pyridine (4 mL, 50 mmol) and 20 mL of dichloromefhane was stirred at room temperature for 30 minutes. To this mixture, cooled with an ice water bath, (2-methyl-pyridin-4-yl)-methanol (48, 0.5 g, 4.0 mmol) in 5 mL of dichloromethane was added. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled with an ice water bath and diluted with ethyl acetate, then filtered through a pad of Celite, The filtrate was concentrated under vacuum and the residue was purified by silica gel chromatography eluting with hexanes and ethyl acetate to provide the desired compound as a colorless liquid (21b, 0.1 g, 20percent),
Reference: [1] Patent: WO2010/129467, 2010, A1, . Location in patent: Page/Page column 64
[2] Patent: WO2006/76644, 2006, A2, . Location in patent: Page/Page column 111
  • 2
  • [ 1122-45-8 ]
  • [ 108-24-7 ]
  • [ 42508-74-7 ]
  • [ 105250-16-6 ]
  • [ 27296-77-1 ]
Reference: [1] Pharmaceutical Bulletin, 1955, vol. 3, p. 413,415[2] Yakugaku Zasshi, 1956, vol. 76, p. 900[3] Chem.Abstr., 1957, p. 2770
  • 3
  • [ 67-56-1 ]
  • [ 1122-71-0 ]
  • [ 105250-16-6 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 317 - 326
  • 4
  • [ 152815-18-4 ]
  • [ 105250-16-6 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With hydrogen; triethylamine In ethyl acetate for 21 h;
Stage #2: With hydrogen In ethyl acetate for 5 h;
In a variation of the above procedure, a solution of 2-chloro-6-methylpyridine-4-carboxylic, palladium (0.20 g, 10 mol percent on carbon), ethyl acetate (45 mL), and triethylamine (2.8 mL, 20 mmol). The reaction mixture was placed under hydrogen at 1 atm for 21 hours. Additional Pearlman's catalyst (0.2 g) was added and the reaction was stirred under hydrogen for an additional 5 hours to effect dechlorination. The mixture was filtered through a pad of celite and concentrated. Purification by column chromatography (5:95 methanol:dichloromethane) gave (2-methyl-pyridin-4-yl)-methanol (1.48 g, 88percent). The (2-methyl-pyridin-4-yl)-methanol was used to prepare 2-amino-3-(2-methyl-pyridin-4-yl)-propionitrile, from which 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[cyano-(2-methyl-pyridin-4-ylmethyl)-methyl]-carbamoyl}-cyclohexyl)-amide was obtained (186 mg, 62percent) in the manner described above. MS: 444 (M+H).
Reference: [1] Patent: US2004/77646, 2004, A1, . Location in patent: Page 116
  • 5
  • [ 55485-90-0 ]
  • [ 105250-16-6 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 24 h; (2-Methyl-pyridin-4-yl)-methanol:; Acetic acid 2-methyl-pyridin-4-ylmethyl ester (5.1 g, 31 mmol) was stirred with ammonium hydroxide (10 ml) in methanol (25 ml) at room temperature. After 24 hr., the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA) to afford 3.56 g (94percent) of (2-methyl-pyridin-4-yl)-methanol as a pale yellow solid. m.p. 58-59° C. 1H NMR (200 MHz, CDCl3) δ 2.45(3H, s), 4.66 (2H, s), 7.06 (1H, d, J=5.2 Hz), 7.14 (1H, s), 8.25 (1H, d, J=5.2 Hz).
Reference: [1] Patent: US2008/70920, 2008, A1, . Location in patent: Page/Page column 97
  • 6
  • [ 16830-24-3 ]
  • [ 105250-16-6 ]
Reference: [1] Patent: US5962458, 1999, A,
[2] Patent: US6362336, 2002, B1, . Location in patent: Example 63
[3] Patent: WO2011/38086, 2011, A2, . Location in patent: Page/Page column 86
  • 7
  • [ 108-47-4 ]
  • [ 105250-16-6 ]
Reference: [1] Synthesis, 2002, # 4, p. 483 - 486
[2] Patent: WO2008/142376, 2008, A1, . Location in patent: Page/Page column 69-70; 131
  • 8
  • [ 16830-24-3 ]
  • [ 7732-18-5 ]
  • [ 105250-16-6 ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide In acetonitrile A.
Preparation of 4-Hydroxymethyl-2-methylpyridine STR240
To a suspension of 95percent lithium aluminum hydride (2.4 g, 0.06 mol) in 150 mL of anhydrous ether was added a solution of methyl 2-methylisonicotinate1 (14.0 g, 0.093 mol) in 50 mL of anhydrous ether, at -5° C. under N2.
The resulting mixture was stirred at room temperature for 30 min and was then refluxed for 2 h.
An additional 1.2 g (0.03 mole) of lithium aluminum hydride was added portionwise and refluxing was continued for 1 h.
The reaction mixture was then cooled at 0° C. and treated successively with 3.75 mL H2 O, 3.75 mL 15percent aqueous NaOH and finally 11.25 mL of H2 O.
This suspension was then filtered and the filter cake was washed with ether and then ethyl acetate.
The filtrate was evaporated to give a dark yellow oil which was taken up in acetonitrile and then filtered through a pad of silica gel (elution with acetonitrile and then acetone).
This gave the product (7.7 g, 67percent) as a yellow oil: 1 Hnmr (CDCl3) δ8.30, 7.10 (ABq, J=5 Hz, 2H), 7.17 (s, 1H), 5.42 (s, --OH), 4.70 (s, CH2), 2.50 (s, CH3).
Reference: [1] Patent: US4644061, 1987, A,
  • 9
  • [ 1254928-94-3 ]
  • [ 105250-16-6 ]
Reference: [1] Patent: WO2010/129467, 2010, A1, . Location in patent: Page/Page column 64
  • 10
  • [ 4021-11-8 ]
  • [ 105250-16-6 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3322 - 3330
  • 11
  • [ 22282-99-1 ]
  • [ 105250-16-6 ]
Reference: [1] Patent: WO2011/38086, 2011, A2,
  • 12
  • [ 63875-01-4 ]
  • [ 105250-16-6 ]
Reference: [1] Synthesis, 2002, # 4, p. 483 - 486
  • 13
  • [ 931-19-1 ]
  • [ 105250-16-6 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 317 - 326
  • 14
  • [ 1122-45-8 ]
  • [ 105250-16-6 ]
Reference: [1] Pharmaceutical Bulletin, 1955, vol. 3, p. 413,415[2] Yakugaku Zasshi, 1956, vol. 76, p. 900[3] Chem.Abstr., 1957, p. 2770
  • 15
  • [ 67-56-1 ]
  • [ 1122-71-0 ]
  • [ 105250-16-6 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 317 - 326
  • 16
  • [ 1122-45-8 ]
  • [ 108-24-7 ]
  • [ 42508-74-7 ]
  • [ 105250-16-6 ]
  • [ 27296-77-1 ]
Reference: [1] Pharmaceutical Bulletin, 1955, vol. 3, p. 413,415[2] Yakugaku Zasshi, 1956, vol. 76, p. 900[3] Chem.Abstr., 1957, p. 2770
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