[ CAS No. 52764-11-1 ] {[proInfo.proName]}

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2D 3D

Structure of 52764-11-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 52764-11-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52764-11-1 ]

SDS Specification

Alternatived Products of [ 52764-11-1 ]

Product Details of [ 52764-11-1 ]

CAS No. :	52764-11-1	MDL No. :	MFCD11044319
Formula :	C₅H₃Cl₂NO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	CDDCESLWCVAQMG-UHFFFAOYSA-N
M.W :	163.99	Pubchem ID :	104317
Synonyms :

Calculated chemistry of [ 52764-11-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
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 :	36.28
TPSA :	33.12 ?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) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	1.79
Log Po/w (WLOGP) :	2.09
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	2.23
Consensus Log Po/w :	1.75

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.546 mg/ml ; 0.00333 mol/l
Class :	Soluble
Log S (Ali) :	-2.1
Solubility :	1.29 mg/ml ; 0.00787 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.67
Solubility :	0.348 mg/ml ; 0.00212 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 52764-11-1 ]

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

Application In Synthesis of [ 52764-11-1 ]

* 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 [ 52764-11-1 ]
Downstream synthetic route of [ 52764-11-1 ]

[ 52764-11-1 ] Synthesis Path-Upstream 1~3

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

2
[ 6636-78-8 ]
[ 52764-11-1 ]

Reference： [1] Patent: US4404020, 1983, A,
[2] Patent: US4067725, 1978, A,

3
[ 2402-78-0 ]
[ 52764-11-1 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 6, p. 1417 - 1421

[ 52764-11-1 ] Synthesis Path-Downstream 1~12

1
[ 2402-78-0 ]
[ 52764-11-1 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 1417 - 1421

2
[ 52764-11-1 ]
[ 535-11-5 ]
[ 62804-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In acetonitrile;	EXAMPLE 1 2-[(2,6-dichloro-3-pyridyl)oxy]propionic acid ethyl ester 164 g (1 mole) of 2,6-dichloro-3-pyridinol, 1500 ml of acetonitrile, 253.4 g (1.4 moles) of 2-bromopropionic acid ethyl ester and 127.2 (1.2 moles) of sodium carbonate were refluxed for 3 hours. The reaction mixture was then cooled, filtered and concentrated in a rotary evaporator. The residue was taken up in ether and washed with 2 N sodium hydroxide solution. After drying with magnesium sulphate and concentration of the solution by evaporation, distillation was performed, with a clear oil distilling at 110-140/0.1 torr; yield: 200 g; nD25:1.5200. Crystallisation from benzene/petroleum ether yielded a product having the melting point 41-46. The 2,6-dichloro-3-pyridinol required as starting material was produced as follows:
	With sodium carbonate; In acetonitrile;	b. 2-[(2,6-dichloro-3-pyridyl)oxy]propionic acid ethyl ester 164 g (1 mole) of 2,6-dichloro-3-pyridinol, 1500 ml of acetonitrile, 253.4 g (1.4 moles) of 2-bromopropionic acid ethyl ester and 127.2 (1.2 moles) of sodium carbonate are refluxed for 3 hours. The reaction mixture is then cooled, filtered, and concentrated in a rotary evaporator. The residue is taken up in ether and washed with 2N sodium hydroxide solution. After drying with magnesium sulphate, the solution is concentrated by evaporation and distilled in vacuo; a clear oil distills at 110-140/0.1 torr; yield: 200 g; i nD25: 1.5200. Crystallisation from benzene/petroleum ether yields a product having a melting point of 41-46;

Reference： [1]Patent: US4404020,1983,A
[2]Patent: US4067725,1978,A

3
[ 6636-78-8 ]
[ 52764-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; In N-methyl-acetamide; water;	(a) 2,6-dichloro-3-pyridinol 100 g (0.77 mole) of 2-chloro-3-pyridinol (I) was dissolved in 350 ml of dimethylformamide. 70 ml of chlorine (measured at -80; 0.93 mole) was introduced in the course of 1.5 hours into the stirred solution at 0. The reaction mixture was then stirred for 1.5 hours at 20 C. and subsequently concentrated in a rotary evaporator (bath: 50; 10 torr). 400 ml of water and 100 ml of ether were added to the residue; the two phases were separated and the aqueous phase was extracted 5 times with 100 ml of ether each time. The combined ether phases were washed with water and dried. The solvent was removed in vacuo; the semisolid residue was stirred with 1.6 liters of water, and the resulting suspension was adjusted to pH 3. The suspension was heated to boiling, and after a few minutes the solution was decanted from an oily residue. The solution was purified with active charcoal, and the yellow product obtained on cooling was recrystallized from water; m.p. 136-138 C.; yield 42 g.
	With chlorine; In N-methyl-acetamide; water;	a. 2,6-dichloro-3-pyridinol 100 g (0.77 mole) of 2-chloro-3-pyridinol is dissolved in 350 ml of dimethylformamide. In the course of 1.5 hours, 70 ml of chlorine (measured at -80; 0.93 mole) is introduced at 0 into the stirred solution. The reaction mixture is subsequently stirred for 1.5 hours at 20 C and afterwards concentrated in a rotary evaporator (bath: 50; 10 torr). To the residue are added 400 ml of water and 100 ml of ether. The two phases are separated, and the aqueous phase is extracted 5 times with 100 ml of ether each time.

Reference： [1]Patent: US4404020,1983,A
[2]Patent: US4067725,1978,A

4
[ 52764-11-1 ]
[ 2315-36-8 ]
[ 62843-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; dimethyl sulfoxide;	EXAMPLE 1 N,N-diethyl-(2,6-dichloro-3-pyridyl)-oxy-acetic acid amide A solution of 4.6 g of sodium methylate (0.2 mole) in 50 ml of absolute methanol is slowly added at room temperature to 33.4 g (0.2 mole) of <strong>[52764-11-1]2,6-dichloropyridin-3-ol</strong>. There is then added, with gentle heating, 100 to 150 ml of dimethylsulphoxide until the cloudy solution becomes clear. The solution is then heated to 80-90 and methanol is distilled off. The reaction solution is cooled and an addition is slowly made dropwise at 0-10 C of a solution of 60 g (0.2 mole) of chloroacetic acid diethylamide (dissolved in 300 ml of dimethylsulphoxide). After the dropwise addition is completed, the reaction mixture is stirred at room temperature for a further hour. The solvent is distilled off under reduced pressure; the oil remaining is taken up in ether, washed with water, dried and freed from solvent to leave N,N-diethyl-(2,6-dichloro-3-pyridyl)-oxy-acetic acid amide, which boils at 137/0.4 torr; yield: 35 g (62% of theory).

Reference： [1]Patent: US4067725,1978,A

5
[ 52764-11-1 ]
[ 75-61-6 ]
[ 1258190-77-0 ]

Yield	Reaction Conditions	Operation in experiment
58%		3-(Bromodifluoromethoxy)-2,6-dichloropyridine (15); At 0 0C, sodium hydride (60%, 1.8 g, 45.7 mmol, 1.5 eq) is added portion wise to a solution of <strong>[52764-11-1]2,6-dichloro-3-hydroxypyridine</strong> (5.0 g, 30.5 mmol) in DMF (50 mL). The reaction mixture is then vigorously stirred for 1 h at 25 0C and 30 min at 55C. At 0 0C, a solution of dibromodifluoromethane (25.7 g, 11.2 mL, 122 mmol, 4 eq) in DMF (10 mL) is added dropwise and the reaction mixture is allowed to reach 25 0C during 2 h. At 0 0C, potassium tert-butoxide (3.6 g, 33.5 mmol, 1.1 eq) is then added portion wise and the reaction mixture is vigorously stirred for 16 h at 70 0C in a closed reactor. After addition of water (100 mL) the organic phase is separated and the aqueous layer is extracted with diethyl ether (3 * 50 mL). The combined organic layers are dried over sodium sulfate before being evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate / cyclohexane (2 : 98) as eluent which afforded pure 3-(bromodifluoromethoxy)-2,6-dichloropyridine (15, 4.1 g, 17.7 mmol, 58 %) as a pale yellow oil.1H NMR (CDCl3, 300 MHz): delta = 7.60 (d, J = 8.5 Hz, 1 H), 7.26 (d, J = 8.5 Hz, 1 H). - 13C NMR (CDCl3, 75 MHz): delta = 148.1, 144.4, 143.2, 133.4, 124.3, 114.7 (t, J= 113 Hz). - MS(EI): m/z = 292 [M+], 212 [M+-Br].

Reference： [1]Patent: WO2010/40461,2010,A1 .Location in patent: Page/Page column 26
[2]European Journal of Organic Chemistry,2010,p. 6043 - 6066

6
[ 52764-11-1 ]
[ 463-71-8 ]
C₆H₂Cl₃NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In chloroform; water; at 0℃;	2,6-Dichloro-3-trichloromethoxypyridine (3); At 0 0C, thiophosgene (4.3 g, 2.9 mL, 36.6 mmol, 1 eq) in chloroform (22 mL) is added dropwise to a solution of <strong>[52764-11-1]2,6-dichloro-3-hydroxypyridine</strong> (6.0 g, 36.6 mmol) in aqueous sodium hydroxide (5%, 32 mL). The reaction mixture is vigorously stirred for 2 h at 0 0C before being extracted with chloroform (3 x 20 mL). The combined organic layers are washed with diluted hydrochloric acid (1 N, 20 mL) and water (20 mL), dried over sodium sulfate before being filtrated. At 25 0C, the filtrate is then saturated with chlorine until the reaction mixture begins to warm up. After 2 h at 25 0C, another excess of chlorine is added until a yellow solution is obtained. After 24 h at 25 0C excess of chlorine is removed by a stream of Ar gas and the solvent is evaporated. The crude pale yellow oil is distilled under vacuum to afford pure 2,6- dichloro-3-trichloromethoxypyridine (3, 7.1 g, 25.4 mmol, 70%) as colorless crystals; b.p. 78- 81 0C / 0.5 mbar; m.p. 41-43 0C.1H NMR (CDCl3, 300 MHz): delta = 8.02 (d, J = 8.5 Hz, 1 H), 7.37 (d, J = 8.5 Hz, 1 H). - 13C NMR (CDCl3, 75 MHz): delta = 144.7, 143.4, 132.9, 123.6, 115.0, 112.2. - MS(EI): m/z = 281 [M+], 245 [M+-Cl].

Reference： [1]Patent: WO2010/40461,2010,A1 .Location in patent: Page/Page column 18
[2]European Journal of Organic Chemistry,2010,p. 6043 - 6066

7
[ 17228-74-9 ]
[ 52764-11-1 ]
[ 75-45-6 ]
[ 1214379-42-6 ]
[ 1214349-42-4 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 6043 - 6066

8
[ 52764-11-1 ]
[ 1418153-16-8 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 6940 - 6952

9
[ 74-96-4 ]
[ 52764-11-1 ]
[ 1418153-04-4 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 6940 - 6952

10
[ 52764-11-1 ]
[ 1426960-48-6 ]

Reference： [1]Patent: WO2013/33900,2013,A1
[2]Patent: US2014/213571,2014,A1
[3]Patent: WO2013/33971,2013,A1

11
[ 52764-11-1 ]
[ 1426960-49-7 ]

Reference： [1]Patent: WO2013/33900,2013,A1
[2]Patent: US2014/213571,2014,A1
[3]Patent: WO2013/33971,2013,A1

12
[ 52764-11-1 ]
[ 1426960-50-0 ]

Reference： [1]Patent: WO2013/33900,2013,A1
[2]Patent: US2014/213571,2014,A1
[3]Patent: WO2013/33971,2013,A1

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Technical Information

? Alkyl Halide Occurrence ? Appel Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation

Historical Records

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P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 52764-11-1 ] {[proInfo.proName]}

Quality Control of [ 52764-11-1 ]

Related Doc. of [ 52764-11-1 ]

Product Details of [ 52764-11-1 ]

Calculated chemistry of [ 52764-11-1 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

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Medicinal Chemistry

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Application In Synthesis of [ 52764-11-1 ]

[ 52764-11-1 ] Synthesis Path-Upstream 1~3

[ 52764-11-1 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 52764-11-1 ]

Chlorides

Alcohols

Related Parent Nucleus of [ 52764-11-1 ]

Pyridines

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[ 52764-11-1 ]

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[ 52764-11-1 ]