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[ CAS No. 100848-70-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 100848-70-2
Chemical Structure| 100848-70-2
Chemical Structure| 100848-70-2
Structure of 100848-70-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 100848-70-2 ]

CAS No. :100848-70-2 MDL No. :MFCD06200799
Formula : C7H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :HGRXBKDKSYDWLD-UHFFFAOYSA-N
M.W : 123.15 Pubchem ID :14223472
Synonyms :

Calculated chemistry of [ 100848-70-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.7
TPSA : 22.12 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) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 1.21
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 1.8
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.79
Solubility : 1.98 mg/ml ; 0.0161 mol/l
Class : Very soluble
Log S (Ali) : -1.27
Solubility : 6.59 mg/ml ; 0.0535 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.395 mg/ml ; 0.00321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 100848-70-2 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 100848-70-2 ]

* 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 [ 100848-70-2 ]
  • Downstream synthetic route of [ 100848-70-2 ]

[ 100848-70-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 695-34-1 ]
  • [ 624-91-9 ]
  • [ 3678-62-4 ]
  • [ 100848-70-2 ]
YieldReaction ConditionsOperation in experiment
69.5%
Stage #1: With hydrogenchloride In methanol at 10 - 30℃; for 1.5 h;
Stage #2: at 20 - 30℃; for 13 h;
Stage #3: With sodium hydroxide In water at 30℃;
(a); Into a 2L four-necked flask equipped a stirrer, a thermometer and a gas introduction tube (inlet), 324 g (3.00 mol) of 2-amino-4-methylpyridine and 485 g of methanol were charged and mixed for dissolution, and while keeping the temperature in the system at from 10 to 30°C, 361.4 g (9.90 mol) of hydrogen chloride gas was introduced over a period of one and a half hours. Then, in a 2L four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and an introduction tube (outlet) equipped with a bubble counter having a gas generation apparatus and a diazotization apparatus connected, 414 g (6.00 mol) of sodium nitrite, 211 g (6.60 mol) of methanol and 454 g of water were mixed, and 812.4 g (3.15 mol) of a 38percent sulfuric acid aqueous solution was dropwise added over a period of 5 hours while keeping the temperature in the system at from 20 to 30°C. In the methyl nitrite generation apparatus, simultaneously with dropwise addition of the 38percent sulfuric acid aqueous solution, methyl nitrite gas in an equivalent amount was generated and introduced to the diazotization apparatus through the bubble counter. Further, for diazotization, the reaction apparatus was cooled with water so that the temperature in the system would be kept at from 20 to 30°C. After completion of the introduction of the methyl nitrite gas, stirring was carried out at the same temperature for 13 hours and the reaction was completed. After methanol was distilled off under reduced pressure, 648 g of water was charged, and 518 g of a 40percent sodium hydroxide aqueous solution was dropwise added at 30°C or below to adjust the pH in the system to 12. The formed oil was extracted with 910 g of diethyl ether, the aqueous layer was separated out, and the solvent was distilled off under reduced pressure to obtain 375.3 g of an oil. The oil (crude product) had a composition comprising 70.7percent (yield: 69.5percent) of 2-chloro-4-methylpyridine, 26.6percent (yield: 27.2percent) of 2-methoxy-4-methylpyridine and 2.6percent of 2-amino-4-methylpyridine.
Reference: [1] Patent: EP1679003, 2006, A1, . Location in patent: Page/Page column 20-21
  • 2
  • [ 13466-41-6 ]
  • [ 74-88-4 ]
  • [ 100848-70-2 ]
YieldReaction ConditionsOperation in experiment
71% With silver carbonate In chloroform at 20℃; for 48 h; To a stirred solution OF 2-HYDROXY-4-METHYLPYRIDINE (10 g, 92 mmol) in chloroform (350 mL) was added at room temperature silver carbonate (34.2 g, 124 mmol) and iodomethane (130 g, 920 mmol). The reaction mixture was stirred in the dark for 48 h, and then filtered through Celite and washed with ether. The filtrate was concentrated below 20 oC, and the residue was purified by chromatography with PENTANE/ETHER (5: 1) to afford 2-methoxy-4-methylpyridine as a colorless oil (8.0 g, 71percent). LH NMR (CDC13) 8 8. 02 (d, 1H, J = 5.4 Hz), 6.69 (d, 1H, J= 5.4 Hz), 6.55 (s, 1H), 3.91 (s, 3H), 2. 28 (s, 3H) ;"C NMR (CDC13) 8 164.40, 149. 72,146. 31, 118. 21,110. 88,53. 17, 20. 81. MS M/Z (percent): 123 (M+, 76), 122 (100).
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 35, p. 6153 - 6156
[2] Patent: WO2005/806, 2005, A2, . Location in patent: Page 72
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 921 - 924
  • 3
  • [ 695-34-1 ]
  • [ 624-91-9 ]
  • [ 3678-62-4 ]
  • [ 100848-70-2 ]
YieldReaction ConditionsOperation in experiment
69.5%
Stage #1: With hydrogenchloride In methanol at 10 - 30℃; for 1.5 h;
Stage #2: at 20 - 30℃; for 13 h;
Stage #3: With sodium hydroxide In water at 30℃;
(a); Into a 2L four-necked flask equipped a stirrer, a thermometer and a gas introduction tube (inlet), 324 g (3.00 mol) of 2-amino-4-methylpyridine and 485 g of methanol were charged and mixed for dissolution, and while keeping the temperature in the system at from 10 to 30°C, 361.4 g (9.90 mol) of hydrogen chloride gas was introduced over a period of one and a half hours. Then, in a 2L four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and an introduction tube (outlet) equipped with a bubble counter having a gas generation apparatus and a diazotization apparatus connected, 414 g (6.00 mol) of sodium nitrite, 211 g (6.60 mol) of methanol and 454 g of water were mixed, and 812.4 g (3.15 mol) of a 38percent sulfuric acid aqueous solution was dropwise added over a period of 5 hours while keeping the temperature in the system at from 20 to 30°C. In the methyl nitrite generation apparatus, simultaneously with dropwise addition of the 38percent sulfuric acid aqueous solution, methyl nitrite gas in an equivalent amount was generated and introduced to the diazotization apparatus through the bubble counter. Further, for diazotization, the reaction apparatus was cooled with water so that the temperature in the system would be kept at from 20 to 30°C. After completion of the introduction of the methyl nitrite gas, stirring was carried out at the same temperature for 13 hours and the reaction was completed. After methanol was distilled off under reduced pressure, 648 g of water was charged, and 518 g of a 40percent sodium hydroxide aqueous solution was dropwise added at 30°C or below to adjust the pH in the system to 12. The formed oil was extracted with 910 g of diethyl ether, the aqueous layer was separated out, and the solvent was distilled off under reduced pressure to obtain 375.3 g of an oil. The oil (crude product) had a composition comprising 70.7percent (yield: 69.5percent) of 2-chloro-4-methylpyridine, 26.6percent (yield: 27.2percent) of 2-methoxy-4-methylpyridine and 2.6percent of 2-amino-4-methylpyridine.
Reference: [1] Patent: EP1679003, 2006, A1, . Location in patent: Page/Page column 20-21
  • 4
  • [ 3678-62-4 ]
  • [ 124-41-4 ]
  • [ 100848-70-2 ]
YieldReaction ConditionsOperation in experiment
46% at 100℃; for 4 h; Step 1
2-Methoxy-4-methylpyridine
Procedure:
A mixture of 2-chloro-4-methylpyridine (20 g, 0.156 mol) and NaOCH3 (9.3 g, 0.172 mol) in DMSO (200 mL) was stirred at 100° C. for 4 hours.
The solution was added to H2O and then extracted with ethyl acetate (50 mL*2).
The organic layer was washed with H2O (300 mL) brine (300 mL) and dried concentrated to give 2-methoxy-4-methylpyridine (9 g, 46percent). LC-MS: 124 [M+H]+, tR=1.21 min.
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
[2] Patent: US2012/252777, 2012, A1, . Location in patent: Page/Page column 54
  • 5
  • [ 695-34-1 ]
  • [ 100848-70-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 3160,3164
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
  • 6
  • [ 4926-28-7 ]
  • [ 124-41-4 ]
  • [ 100848-70-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
  • 7
  • [ 3678-62-4 ]
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 100848-70-2 ]
Reference: [1] Patent: EP1679003, 2006, A1, . Location in patent: Page/Page column 21
  • 8
  • [ 13466-41-6 ]
  • [ 100848-70-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
  • 9
  • [ 100848-70-2 ]
  • [ 29342-05-0 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 2059 - 2066
  • 10
  • [ 100848-70-2 ]
  • [ 126717-59-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 3084 - 3092
  • 11
  • [ 100848-70-2 ]
  • [ 123506-66-1 ]
Reference: [1] Patent: WO2015/158427, 2015, A1,
  • 12
  • [ 100848-70-2 ]
  • [ 164513-39-7 ]
YieldReaction ConditionsOperation in experiment
40% With bromine; sodium acetate In ethyl acetate at 0 - 50℃; for 18 h; Sodium acetate (3.54g. 43.23mmol) was added to a solution of 2-methoxy-4-methylpyridine 54-5-1 (5.0g.3gmmol) in EtOAc (25mL). Br2 (1 .52mL, 58mmol) was added drop wise over 20 mm at 0°C. The RM wasstirred at 50°C for 18 h. The total reaction mass was cooled and after diluting with water, the pH was adjusted to 8 with aq. NaOH. The organic layer was separated and aq. layer extracted with EtOAc (250mL x 3). The combined extract was washed with water (300 mL), brine (200 mL), dried (Na2SO4) and concentrated under reduced pressure to get crude compound. The crude compound was purified by CC(silica gel 100-200mesh, 0-5percent EtOAc in PE) to obtain 5-bromo-2-methoxy-4-methylpyridine (2.82g. 40percent) as liquid.
Reference: [1] Patent: WO2015/158427, 2015, A1, . Location in patent: Page/Page column 84
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 3084 - 3092
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