[ CAS No. 13466-35-8 ] {[proInfo.proName]}

Name: 13466-35-8|3-Chloro-2-hydroxypyridine|98%
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Quality Control of [ 13466-35-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 13466-35-8 ]

CAS No. :	13466-35-8	MDL No. :	MFCD01646109
Formula :	C₅H₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XTYNIPUFKBBALX-UHFFFAOYSA-N
M.W :	129.54	Pubchem ID :	582210
Synonyms :

Calculated chemistry of [ 13466-35-8 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.27
TPSA :	33.12 Å²

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) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.13
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	0.81
Log Po/w (SILICOS-IT) :	1.61
Consensus Log Po/w :	1.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.91
Solubility :	1.59 mg/ml ; 0.0123 mol/l
Class :	Very soluble
Log S (Ali) :	-1.42
Solubility :	4.93 mg/ml ; 0.0381 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.03
Solubility :	1.21 mg/ml ; 0.00938 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 13466-35-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13466-35-8 ]

* 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 [ 13466-35-8 ]
Downstream synthetic route of [ 13466-35-8 ]

[ 13466-35-8 ] Synthesis Path-Upstream 1~4

1
[ 13466-43-8 ]
[ 13466-35-8 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 37, p. 6695 - 6698

2
[ 6515-09-9 ]
[ 13466-35-8 ]

Reference： [1] Patent: CN107935921, 2018, A,

3
[ 98273-80-4 ]
[ 13466-35-8 ]

Reference： [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1616

4
[ 13466-35-8 ]
[ 58236-70-7 ]

Reference： [1] Patent: US5629428, 1997, A,

[ 13466-35-8 ] Synthesis Path-Downstream 1~31

1
[ 623-73-4 ]
[ 13466-35-8 ]
[ 79674-52-5 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1614

2
[ 98273-80-4 ]
[ 13466-35-8 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1616

3
[ 13466-43-8 ]
[ 13466-35-8 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6695 - 6698

4
[ 13466-35-8 ]
[ 189956-34-1 ]
3-(3-Chloro-2-pyridyloxy)-5,5-dimethyl-4-(4-methylsulfonyl)phenyl-5H-furan-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 3187 - 3192

5
2-butoxy-3-chloro-pyridine hydrochloride [ No CAS ]
[ 13466-35-8 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1287

6
[ 13466-35-8 ]
[ 79674-53-6 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1614

7
[ 13466-35-8 ]
[ 58236-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; sodium sulfite; In N-methyl-acetamide; water;	EXAMPLE 1 3-Chloro-5-octyl-2-(4-octyloxyphenyl)pyridine 10.5 ml (203.0 mmol) of bromine are added dropwise at 0° C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. STR13 m.p.: 168° C. (decomp.)

Reference： [1]Patent: US5629428,1997,A

8
[ 13466-35-8 ]
[ 536-74-3 ]
[ 24391-84-2 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 6023 - 6026

9
[ 13466-35-8 ]
[ 120277-69-2 ]
1-(5-bromopyridin-3-ylmethyl)-3-chloro-1-pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h;	General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.

Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 29

10
[ 109-04-6 ]
[ 13466-35-8 ]
6-(benzo[d]oxazol-2-yl)-3-chloro-2H-[1,2'-bipyridin]-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 10784 - 10788
Angew. Chem.,2014,vol. 126,p. 10960 - 10964,5

11
[ 109-04-6 ]
[ 13466-35-8 ]
[ 109822-14-2 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 10784 - 10788
Angew. Chem.,2014,vol. 126,p. 10960 - 10964,5
[2]Organic Letters,2016,vol. 18,p. 1064 - 1067

12
[ 13466-35-8 ]
[ 85217-69-2 ]
C₁₄H₁₂ClNO [ No CAS ]
C₁₄H₁₂ClNO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1873 - 1876
Angew. Chem.,2015,vol. 127,p. 1893 - 1896,4

13
[ 13466-35-8 ]
3-chloro-5-iodopyridin-2-ol [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 17744 - 17747

14
[ 109-04-6 ]
[ 13466-35-8 ]
11-benzoyl-3-chloroimidazo[1,2-a:3,4-a′]dipyridin-5-ium-4-olate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1064 - 1067

15
[ 13466-35-8 ]
[ 74-88-4 ]
[ 123062-64-6 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 296 - 303

16
[ 6515-09-9 ]
[ 13466-35-8 ]

Reference： [1]Patent: CN107935921,2018,A

17
sodium 3,6-dichloro-2-pyridinol [ No CAS ]
[ 13466-35-8 ]

Yield	Reaction Conditions	Operation in experiment
40g	With water; hydrogen; at 70℃;	Dechlorination reduction:70g of sodium 3,6-dichloro-2-pyridinolate and 550g of water and 0.7g of catalyst are heated to 70C to dissolve hydrogen,In the control,After the reaction is over,After concentrating to the original volume, cool down to 10C to crystallize.Get 3-chloro-2-hydroxypyridine,It is filtered, and the solid is washed with water and dried to 40 g.

Reference： [1]Patent: CN107935921,2018,A .Location in patent: Paragraph 0077

18
[ 13466-35-8 ]
[ 2402-77-9 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With phosphorus pentachloride; In 1,2-dichloro-ethane; at 60 - 65℃; for 10.0h;	Equipped with a thermometer,Mechanical agitation,Add 150 grams of 1,2-dichloroethane to a 500-mL four-necked flask with a reflux condenser,26.0 g (0.2 mol) of <strong>[13466-35-8]3-chloro-2-hydroxypyridine</strong> (IV) prepared in Example 3,52.0 grams (0.25 moles) of phosphorus pentachloride,Stir the reaction at 60-65 for 10 hours,Then slowly pour the remainder into 200 grams of ice water,Stir well,Then 40wt% sodium hydroxide aqueous solution neutralizes the pH value to 7-8,Layered,Use 1,2-dichloroethane three times for the water layer,50 grams each time,Combine the organic phase,Wash with 30 grams of saturated saline,Then dry with 5 grams of anhydrous sodium sulfate,The solvent was removed by rotary evaporation to obtain 28.1 g of 2,3-dichloropyridine (I), Yield 94.9%, gas phase purity 99.9%.
94.9%	With phosphorus pentachloride; In 1,2-dichloro-ethane; at 60 - 65℃; for 10.0h;	To a 500 ml four-necked flask equipped with a thermometer, mechanical stirring, and a reflux condenser was added 150 g of 1,2-dichloroethane, 26.0 g (0.2 mol) of <strong>[13466-35-8]2-hydroxy-3-chloropyridine</strong> prepared in Example 3, 52.0 g (0.25 mole) of phosphorus pentachloride, stir the reaction at 60-65 C for 10 hours, then slowly pour the residue into 200 g of ice water, stir well, and then neutralize the pH value with a 40 wt% sodium hydroxide aqueous solution. 8. The layers were separated. The aqueous layer was 50g with 1,2-dichloroethane three times. The organic phases were combined, washed with 30g of saturated brine, and then dried with 5g of anhydrous sodium sulfate. The solvent was removed by rotary evaporation. 28.1 g of 2,3-dichloropyridine (I) with a yield of 94.9% and a gas phase purity of 99.9%.
43g	With trichlorophosphate; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;Reflux;	Chlorination: 40 g of <strong>[13466-35-8]3-chloro-2-hydroxypyridine</strong> and 100 g of dichloroethane,DMF0.3g,Phosphorus oxychloride 56g was added to the reaction flask and refluxed.In the control,After the reaction is over,Distilled ethylene dichloride,Slowly add cold water to the reaction solution.After fully hydrolyzing, adjust the pH to 4-5 and steam it.Get 2,3-dichloropyridine,Dry at room temperature and dry at 43gThe purity is 99.1%.

Reference： [1]Patent: CN110818621,2020,A .Location in patent: Paragraph 0052-0060
[2]Patent: CN110818622,2020,A .Location in patent: Paragraph 0041; 0059-0065
[3]Patent: CN107935921,2018,A .Location in patent: Paragraph 0078

19
[ 13466-35-8 ]
1-(tert-butyl) 3-methyl (E)-2-(3-chloro-2-oxopyridin-1(2H)-yl)-2-styrylmalonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1980 - 1984
Angew. Chem.,2019,vol. 131,p. 2002 - 2006,5

20
[ 13466-35-8 ]
[ 24424-99-5 ]
tert-butyl (3-chloropyridin-2-yl) carbonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1980 - 1984
Angew. Chem.,2019,vol. 131,p. 2002 - 2006,5

21
[ 13466-35-8 ]
[ 959-28-4 ]
(R)-2-(3-chloro-2-oxopyridin-1(2H)-yl)-1,4-diphenylbutane-1,4-dione [ No CAS ]