[ CAS No. 399-88-2 ] {[proInfo.proName]}

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Quality Control of [ 399-88-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 399-88-2 ]

SDS Specification

Alternatived Products of [ 399-88-2 ]

Product Details of [ 399-88-2 ]

CAS No. :	399-88-2	MDL No. :	MFCD04114226
Formula :	C₆H₆FN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WZMOEPZZTTWDIA-UHFFFAOYSA-N
M.W :	111.12	Pubchem ID :	345367
Synonyms :

Calculated chemistry of [ 399-88-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.16
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.61
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.95
Log Po/w (MLOGP) :	1.24
Log Po/w (SILICOS-IT) :	2.28
Consensus Log Po/w :	1.68

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.35 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (Ali) :	-1.19
Solubility :	7.15 mg/ml ; 0.0643 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.63
Solubility :	0.261 mg/ml ; 0.00235 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.21

Safety of [ 399-88-2 ]

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

Application In Synthesis of [ 399-88-2 ]

* 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.

Downstream synthetic route of [ 399-88-2 ]

[ 399-88-2 ] Synthesis Path-Downstream 1~10

1
[ 399-88-2 ]
[ 393-53-3 ]

Reference： [1]Journal of Organic Chemistry,1955,vol. 20,p. 1729,1731

3
[ 3430-27-1 ]
aq.-ethanolic tetrafluoroboric acid [ No CAS ]
[ 399-88-2 ]

Reference： [1]Journal of Organic Chemistry,1955,vol. 20,p. 1729,1731

4
[ 372-47-4 ]
[ 74-88-4 ]
[ 399-88-2 ]

Yield	Reaction Conditions	Operation in experiment
47%		3-Fluoro-4-methylpyridine To a cooled (-780C) solution of Lambda/,Lambda/-diisopropylamine (15.92mL, 113.4mmol) in THF (14OmL) a solution of BuLi 2.5M in hexane (45.4ml, 113.4 mmol) was added dropwise over 30 minutes under an atmosphere of Argon. The mixture was stirred for 30 min. at - 780C and a solution of 3-fluoropyridine (1 Og1 103.1 mmol) in THF (5ml) was added. After 1h at -780C, the mixture was treated with MeI (7 ml, 113.4mmol) and then was allowed to reach 250C. A solution of NaHCO3 saturated (30ml) was added and the aqueous phase was extracted with diethyl ether. The organic layer was dried (MgSO4) and upon distillation the product was collected as a colourless liquid, bp 1300C, yield 5.3 g (47percent) delta 1 H-NMR (CDCI3): 8.25 (s, 1 H), 8.18 (m, 1 H), 7.02 (m, 1 H). ESI/MS m/e: 112 ([M+H]+, C6H6FN)
	With diisopropylamine;	3-Fluoro-4-methylpyridine (5-1) To a stirred solution of LDA (5.5 mmol) at -78° C., was added 3-fluoropyridine (486 mg, 5.0 mmol) dropwise. After stirring for 4h at -78° C., methyl iodide was added dropwise (0.343 mL, 5.5 mmol). The reaction was quenched after stirring at -78° C. for 2 h, by the addition of 20 mL of sat. aq. NH4Cl. This mixture was extracted with EtOAc (3*25 mL), the combined organics dried and concentrated to afford the product as a yellow solid 5-1: 1H NMR (CDCl3) delta 8.36 (br s, 1H), 8.27 (d, 1H, 4.8 Hz), 7.15 (br dd, 1H, 5.7, 5.7 Hz), 2.32 (s, 3H).
		To a solution of diisopropylamine in THF (200 mL) was added a 2.44 M H-BuLi in THF (116 mL) at 0 0C and the mixture was stirred at 0 0C for 20 min. The mixture was cooled to -60 0C and a solution of 3-fluoropyridine (25.0 g) in THF (100 mL) was added. The mixture was stirred at -60 0C for 3 h and a solution of iodomethane (17.6 mL) in THF (100 mL) was added. The mixture was stirred at -60 0C for 30 min and the reaction was quenched with saturated aqueous NH4CI (100 mL). The aqueous layer was extracted with EtOAc (three times). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure to give a colorless oil (14.6 g). To a solution of the above oil (14.6 g) in CHCl3 (145 mL) was added a suspension of m-chloroperbenzoic acid (34.8 g) in CHCl3 (145 mL) at 0 0C and the mixture was stirred at ambient temperature for 3 h. To the mixture was added saturated aqueous Na2S2psi3 and the organic layer was separated. The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was washed with IM aqueous NaOH and saturated aqueous NaCl, dried over MgSO4, filtered, concentrated under reduced pressure EPO <DP n="102"/>and purified by medium-pressure liquid chromatography (silica gel, 2percent to 4percent MeOH in CHCl3) to give the title compound (3.47 g).1HNMR (SOO MHz, CDCl3, delta): 2.28-2.32 (m, 3H), 7.06-7.13 (m, IH), 7.96-8.00 (m, IH), 8.11 (dd,J= 4.9, 1.8 Hz, IH); ESI MS m/z 150 (M++23, 100percent).

Reference： [1]Patent: WO2007/17096,2007,A1 .Location in patent: Page/Page column 70-71
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 461 - 473
[3]Patent: US6455532,2002,B1
[4]Patent: US6350745,2002,B1 .Location in patent: Page column 15;16
[5]Patent: WO2006/35967,2006,A1 .Location in patent: Page/Page column 98-99

5
[ 399-88-2 ]
[ 33252-59-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 - 20℃; for 3h;	To a solution of diisopropylamine in THF (200 mL) was added a 2.44 M H-BuLi in THF (116 mL) at 0 0C and the mixture was stirred at 0 0C for 20 min. The mixture was cooled to -60 0C and a solution of 3-fluoropyridine (25.0 g) in THF (100 mL) was added. The mixture was stirred at -60 0C for 3 h and a solution of iodomethane (17.6 mL) in THF (100 mL) was added. The mixture was stirred at -60 0C for 30 min and the reaction was quenched with saturated aqueous NH4CI (100 mL). The aqueous layer was extracted with EtOAc (three times). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure to give a colorless oil (14.6 g). To a solution of the above oil (14.6 g) in CHCl3 (145 mL) was added a suspension of m-chloroperbenzoic acid (34.8 g) in CHCl3 (145 mL) at 0 0C and the mixture was stirred at ambient temperature for 3 h. To the mixture was added saturated aqueous Na2S2psi3 and the organic layer was separated. The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was washed with IM aqueous NaOH and saturated aqueous NaCl, dried over MgSO4, filtered, concentrated under reduced pressure EPO <DP n="102"/>and purified by medium-pressure liquid chromatography (silica gel, 2percent to 4percent MeOH in CHCl3) to give the title compound (3.47 g).1HNMR (SOO MHz, CDCl3, delta): 2.28-2.32 (m, 3H), 7.06-7.13 (m, IH), 7.96-8.00 (m, IH), 8.11 (dd,J= 4.9, 1.8 Hz, IH); ESI MS m/z 150 (M++23, 100percent).

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 461 - 473
[2]Patent: WO2006/35967,2006,A1 .Location in patent: Page/Page column 98-99
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

6
[ 399-88-2 ]
[ 312904-99-7 ]