[ CAS No. 148493-34-9 ] {[proInfo.proName]}

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Quality Control of [ 148493-34-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 148493-34-9 ]

SDS Specification

Alternatived Products of [ 148493-34-9 ]

Product Details of [ 148493-34-9 ]

CAS No. :	148493-34-9	MDL No. :	MFCD03094989
Formula :	C₅H₄BCl₂NO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	XBBLBQZAVMHEER-UHFFFAOYSA-N
M.W :	191.81	Pubchem ID :	2762712
Synonyms :

Calculated chemistry of [ 148493-34-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	44.08
TPSA :	53.35 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.68
Log Po/w (WLOGP) :	0.07
Log Po/w (MLOGP) :	-0.13
Log Po/w (SILICOS-IT) :	0.17
Consensus Log Po/w :	0.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.72 mg/ml ; 0.00376 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.738 mg/ml ; 0.00385 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.15
Solubility :	1.35 mg/ml ; 0.00706 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.27

Safety of [ 148493-34-9 ]

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

Application In Synthesis of [ 148493-34-9 ]

* 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 [ 148493-34-9 ]
Downstream synthetic route of [ 148493-34-9 ]

[ 148493-34-9 ] Synthesis Path-Upstream 1~1

1
[ 148493-34-9 ]
[ 52764-11-1 ]

Yield	Reaction Conditions	Operation in experiment
91.4%	With dihydrogen peroxide In dichloromethane; water at 0 - 20℃; for 0.15 h;	Preparation of Compound 1Step 1 - Synthesis of 2,6-dichloropyridin-3-olΗ₂0₂ (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6- dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH₂CI₂ (30 mL) at 0 °C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na₂S203 aqueous (50 mL) and adjusted to pH < 7 with IN HC1. The mixture was extracted with EtOAc (40 mL x 3). The organic layer was washed with brine (100 mL), dried over Na₂S0₄, filtered and the solvent was evaporated to provide2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4percent). 1H-NMR (CDC1₃, 400 MHz) δ 7.30 (d, / = 8.4 Hz, 1H), 7.19 (d, / = 8.4 Hz, 1H), 5.70 (br, 1H).
91.4%	With dihydrogen peroxide In dichloromethane at 0 - 20℃; for 15 h;	H202 (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6- dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH2C12 (30 mL) at 0 °C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na2S203 aqueous (50 mL) and adjusted to pH < 7 with IN HC1. The mixture was extracted with EtOAc (40 mL x 3). The organic layer was washed with brine (100 mL), dried over Na2S04, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4percent). 1H- MR (CDC13, 400 MHz) δ 7.30 (d, J= 8.4 Hz, 1H), 7.19 (d, J= 8.4 Hz, 1H), 5.70 (br, 1H). MS (M+H)+: 164 / 166 / 168.
91.4%	With dihydrogen peroxide In dichloromethane at 0 - 20℃; for 15 h;	Step 1-Synthesis of 2,6-dichloropyridin-3-ol H₂O₂ (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6-dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH₂Cl₂ (30 mL) at 0° C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na₂S₂O₃ aqueous (50 mL) and adjusted to pH<7 with 1N HCl. The mixture was extracted with EtOAc (40 mL*3). The organic layer was washed with brine (100 mL), dried over Na₂SO₄, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4percent). ¹H-NMR (CDCl₃, 400 MHz) δ 7.30 (d, J=8.4 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 5.70 (br, 1H). MS (M+H)⁺: 164/166/168.

Reference： [1] Tetrahedron, 2005, vol. 61, # 6, p. 1417 - 1421
[2] Patent: WO2013/33900, 2013, A1, . Location in patent: Page/Page column 27
[3] Patent: WO2013/33971, 2013, A1, . Location in patent: Page/Page column 32-33
[4] Patent: US2014/213571, 2014, A1, . Location in patent: Paragraph 0223

[ 148493-34-9 ] Synthesis Path-Downstream 1~13

1
[ 609-73-4 ]
[ 148493-34-9 ]
2,6-Dichloro-3-(2-nitro-phenyl)-pyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 2127 - 2130

2
[ 615-43-0 ]
[ 148493-34-9 ]
2-(2,6-Dichloro-pyridin-3-yl)-phenylamine [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 2127 - 2130

3
[ 615-43-0 ]
[ 148493-34-9 ]
[ 26869-12-5 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 2127 - 2130

4
[ 19591-17-4 ]
[ 148493-34-9 ]
[ 148493-40-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	A mixture of N-(2-iodophenyl)acetamide (261 mg, 1.0 mmol), <strong>[148493-34-9](2,6-dichloropyridin-3-yl)boronic acid</strong> (230 mg, 1.2 mmol), palladium acetate (11 mg, 0.05 mmol), PPh3 (26 mg, 0.1 mmol) and Et3N (303 mg, 3.0 mmol) in DMF was degassed with nitrogen, heated to 100 C. and stirred for 16 hours. The mixture was cooled to r.t, diluted with water and extracted with EA. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-(2,6-dichloropyridin-3-yl)phenyl)acetamide (180 mg, 69% yield) as a white solid. LC/MS (ESI, m/z): [M+1]+=282.1
68%	With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 6h;Inert atmosphere;	Step 1: Synthesis of N-[2-(2,6-dichloro-3-pyridinyl)phenyl]acetamide First, 18.94 g of 2-iodophenylacetamide, 20.73 g of <strong>[148493-34-9]2,6-dichloropyridin-3-boronic acid</strong>, 1.18 g of triphenylphosphine, 0.49 g of palladium acetate, 30 mL of triethylamine, and 290 mL of dry DMF were put into a three-neck flask equipped with a reflux pipe, and the air in the flask was replaced with nitrogen. After that, stirring was performed at 100 C. for 6 hours. Water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline and dried with magnesium sulfate, and then purified by silica gel column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 2:1 to give an objective substance as yellow-white powder in a yield of 68%. A synthesis scheme of Step 1 is shown in (a-1).

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 2127 - 2130
[2]Patent: US2020/10468,2020,A1 .Location in patent: Paragraph 0725; 0727; 0885; 0887
[3]Patent: US2017/62738,2017,A1 .Location in patent: Paragraph 0250

5
C₂₅H₄₃F₃O₅SSi [ No CAS ]
[ 148493-34-9 ]
C₂₉H₄₅Cl₂NO₂Si [ No CAS ]