[ CAS No. 153034-94-7 ]

Name: 153034-94-7|2-Fluoro-4-iodo-5-picoline|98%
Brand: Ambeed
SKU: A355116
Price: 6.0 USD
Availability: InStock
Rating: 94 (28 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 153034-94-7

Structure of 153034-94-7 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 153034-94-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 153034-94-7 ]

SDS Specification

Alternatived Products of [ 153034-94-7 ]

Product Details of [ 153034-94-7 ]

CAS No. :	153034-94-7	MDL No. :	MFCD03095297
Formula :	C₆H₅FIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BVKQLNXPPQEELX-UHFFFAOYSA-N
M.W :	237.01 g/mol	Pubchem ID :	10060052
Synonyms :

Calculated chemistry of [ 153034-94-7 ]

Physicochemical Properties

Num. heavy atoms :	9
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 :	41.88
TPSA :	12.89 Å²

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) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	2.3
Log Po/w (WLOGP) :	2.55
Log Po/w (MLOGP) :	2.18
Log Po/w (SILICOS-IT) :	3.21
Consensus Log Po/w :	2.45

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.25
Solubility :	0.133 mg/ml ; 0.00056 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	1.47 mg/ml ; 0.00619 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.65
Solubility :	0.0533 mg/ml ; 0.000225 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 153034-94-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 153034-94-7 ]

* 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.

Upstream synthesis route of [ 153034-94-7 ]
Downstream synthetic route of [ 153034-94-7 ]

[ 153034-94-7 ] Synthesis Path-Upstream 1~3

1
[ 2369-19-9 ]
[ 153034-94-7 ]

Yield	Reaction Conditions	Operation in experiment
109.69 g	Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75 - -73℃; for 3.5 h; Inert atmosphere Stage #2: With iodine In tetrahydrofuran; hexane at -75℃; for 1.91667 h; Inert atmosphere	Diisopropylamine (92 mL) was added to THF (1.2 L), and the mixture was cooled to −18° C. under a nitrogen atmosphere. To this solution was added dropwise a solution (224 mL) of 2.69 M n-butyllithium in hexane. After the dropwise addition, the temperature was increased to −5° C. over 20 minutes while stirring this mixture. The reaction solution was cooled to −73° C. To this reaction solution was added dropwise a THF solution (240 mL) of 2-fluoro-5-methylpyridine (61 g). The reaction mixture was stirred at −75° C. for three and a half hours. To this reaction solution was added dropwise a THF solution (24 mL) of iodine (139 g). The reaction mixture was stirred at −75° C. for 1 hour and 55 minutes. After the reaction, water (220 mL) was added to the reaction solution at the same temperature. The mixture was stirred at the same temperature for 5 minutes. The reaction solution was brought back to room temperature, and then water (1.2 L) was added. To this mixture were added an aqueous solution (300 mL) of sodium thiosulfate pentahydrate (136 g) and water (300 mL), and the mixture was stirred for 10 minutes. This mixture was extracted with MTBE (1.2 L). The organic layer was washed with saturated saline (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. n-Heptane was added to the residue, and the mixture was cooled. The precipitated solid was collected by filtration. The solid was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. The procedure was repeated 5 times to give the title compound (109.69 g). (0167) ¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). (0168) ESI-MS m/z 238 [M+H]⁺

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 18, p. 4603 - 4606
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Patent: US2016/46623, 2016, A1, . Location in patent: Paragraph 0166-0168

2
[ 153034-78-7 ]
[ 153034-94-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With n-butyllithium; diisopropylamine In tetrahydrofuran	A solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78° C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na₂S₂O₃, water, and brine, dried (MgSO₄), filtered, and concentrated to provide 6.3 g (87percent) of the desired product. MS (DCI/NH₃) m/z 238 (M+H)⁺; ¹H NMR (CDCl₃) δ7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).
87%	With n-butyllithium; diisopropylamine In tetrahydrofuran	A solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78° C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na₂S₂O₃, water, and brine, dried (MgSO₄), filtered, and concentrated to provide 6.3 g (87percent) of the desired product. MS (DCI/NH₃) m/z 238 (M+H)⁺; ¹H NMR (CDCl₃) δ 7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 18, p. 4603 - 4606
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Patent: US2003/87940, 2003, A1,
[4] Patent: US2002/115640, 2002, A1,

3
[ 153034-94-7 ]
[ 1227581-81-8 ]

Yield	Reaction Conditions	Operation in experiment
27%	With ammonium hydroxide In water; dimethyl sulfoxide at 140℃; for 4 h; Microwave irradiation	A white suspension of 2-fluoro-4-iodo-5-methylpyridine (3.00 g, 12.7 mmol) and concentrated aqueous ammonium hydroxide (3.5 mL, 90 mmol) in DMSO (17 mL) was subjected to microwave conditions (140° C., 4 h) and then cooled. The reaction was diluted with EtOAc and water, and the layers were separated. The aqueous layer was extracted with EtOAc (3×50 mL), and the combined organic layers were concentrated under reduced pressure. The resulting residue was adsorbed onto silica gel and purified by flash silica chromatography, elution gradient 0 to 10percent MeOH in DCM, to afford 4-iodo-5-methylpyridin-2-amine (800 mg, 27percent) as a white solid. ¹H NMR (300 MHz, DMSO-d₆, 27° C.) 2.13 (s, 3H) 5.81 (s, 2H) 6.99 (s, 1H) 7.75 (s, 1H). m/z: ES+[M+H]+ 235.

Reference： [1] Patent: US2016/376287, 2016, A1, . Location in patent: Paragraph 0957
[2] Patent: WO2011/26904, 2011, A1, . Location in patent: Page/Page column 131
[3] Patent: WO2012/87519, 2012, A1, . Location in patent: Page/Page column 122

[ 153034-94-7 ] Synthesis Path-Downstream 1~59

1
[ 153034-94-7 ]
[ 450840-75-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4603 - 4606
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1571 - 1574

2
[ 153034-94-7 ]
4-(3-chloro-phenyl)-5-methyl-1-oxy-pyridine-2-carbonitrile [ No CAS ]