[ CAS No. 6636-78-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 6636-78-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6636-78-8 ]

SDS Specification

Alternatived Products of [ 6636-78-8 ]

Product Details of [ 6636-78-8 ]

CAS No. :	6636-78-8	MDL No. :	MFCD00006235
Formula :	C₅H₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RSOPTYAZDFSMTN-UHFFFAOYSA-N
M.W :	129.54	Pubchem ID :	81136
Synonyms :		Chemical Name :	2-Chloro-3-hydroxypyridine

Calculated chemistry of [ 6636-78-8 ] Expand+

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 ?2

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) :	1.3
Log Po/w (XLOGP3) :	1.13
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	1.61
Consensus Log Po/w :	1.18

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 :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 6636-78-8 ]

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

Application In Synthesis of [ 6636-78-8 ]

* 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 [ 6636-78-8 ]
Downstream synthetic route of [ 6636-78-8 ]

[ 6636-78-8 ] Synthesis Path-Upstream 1~2

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

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

2
[ 6636-78-8 ]
[ 478148-60-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436
[2] Patent: WO2004/52894, 2004, A1,
[3] Patent: WO2004/52894, 2004, A1,
[4] Patent: WO2004/52894, 2004, A1,

[ 6636-78-8 ] Synthesis Path-Downstream 1~11

1
[ 6636-78-8 ]
[ 161511-85-9 ]
(S)-2-(2-Chloro-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3690 - 3698

2
[ 452972-11-1 ]
[ 6636-78-8 ]

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

3
[ 6636-78-8 ]
[ 478148-61-7 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4425 - 4436
[2]Patent: WO2004/52894,2004,A1
[3]Patent: WO2004/52894,2004,A1
[4]Patent: WO2004/52894,2004,A1

4
[ 6636-78-8 ]
[ 478148-60-6 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4425 - 4436
[2]Patent: WO2004/52894,2004,A1
[3]Patent: WO2004/52894,2004,A1
[4]Patent: WO2004/52894,2004,A1

5
[ 6636-78-8 ]
[ 478148-62-8 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4425 - 4436
[2]Patent: WO2004/52894,2004,A1
[3]Patent: WO2004/52894,2004,A1
[4]Patent: WO2004/52894,2004,A1

6
[ 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

7
[ 6636-78-8 ]
[ 1895-39-2 ]
[ 1206977-80-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 4h;	0097] As shown in step 3-i of Scheme 3, 2-chloro-3-hydroxypyridine (Compound 1005,2.0 g, 15.4 mmol, obtained from Aldrich Chemical Co.) was dissolved in 40 mL of DMF and5.0 mL of water along with sodium chlorodifluoroacetate (4.71 g, 30.9 mmol, obtained fromLancaster Synthesis, Inc.) and anhydrous potassium carbonate (2.56 g; 18.5 mmol). The reaction mixture was heated in an oil bath at 1000C for 2 hours. Another equivalent of sodium chlorodifluoroacetate and 1.2 equiv. of potassium carbonate were added and heating continued for an additional 2.0 hours. After this time, the reaction was cooled and the volatiles removed under reduced pressure. The residue was partitioned between brine and ethyl acetate and the organics washed once more with brine, dried over Na2SO4, filtered, and the volatiles removed under reduced pressure. The product was purified by silica gel chromatography, eluting with a hexanes/DCM to DCM gradient, to produce 2-chloro-3- (difluoromethoxy)pyridine as a white solid (Compound 1006, 2.0 g, 72% yield): ESMS (M+H) 180; 1H NMR (CDCl3) delta 8.05 (m, IH), 7.45(m, IH), 6.90(m,lH), 6.60(t, IH; J=75Hz), 4.0 l(s, 3H).
72%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 4h;	As shown in step 3-i of Scheme 3,2-chloro-3-hydroxypyridine (Compound 1005,2.0 g, 15.4 mmol, obtained from Aldrich Chemical Co.) was dissolved in 40 mL of DMF and5.0 mL of water along with sodium chlorodifluoroacetate (4.71 g, 30.9 mmol, obtained fromLancaster Synthesis, Inc.) and anhydrous potassium carbonate (2.56 g; 18.5 mmol). The reaction mixture was heated in an oil bath at 1000C for 2 hours. Another equivalent of sodium chlorodifluoroacetate and 1.2 equiv. of potassium carbonate were added and heating continued for an additional 2.0 hours. After this time, the reaction was cooled and the volatiles removed under reduced pressure. The residue was partitioned between brine and ethyl acetate and the organics washed once more with brine, dried over Na2SO4, filtered, and the volatiles removed under reduced pressure. The product was purified by silica gel chromatography, eluting with a hexanes/DCM to DCM gradient, to produce 2-chloro-3-(difluoromethoxy)pyridine as a white solid (Compound 1006, 2.0 g, 72% yield): ESMS (M+H) 180; 1H NMR (CDCl3) delta 8.05 (m, IH), 7.45(m, IH), 6.90(m,lH), 6.60(t, IH; J=75Hz), 4.0 l(s, 3H).
72%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 4h;	As shown in step 3(a)-i of Scheme 3(a), 2-chloro-3-hydroxypyridine (Compound 2005, 2.0 g, 15.4 mmol, obtained from Aldrich Chemical Co.) was dissolved in 40 mL of DMF and 5.0 mL of water along with sodium chlorodifluoroacetate (4.71 g, 30.9 mmol, obtained from Lancaster Synthesis, Inc.) and anhydrous potassium carbonate (2.56 g; 18.5 mmol). The reaction mixture was heated in an oil bath at 100C for 2 hours. Another equivalent of sodium chlorodifluoroacetate and 1.2 equiv. of potassium carbonate were added and heating continued for an additional 2.0 hours. After this time, the reaction was cooled and the volatiles removed under reduced pressure. The residue was partitioned between brine and ethyl acetate and the organics washed once more with brine, dried over Na2S04, filtered, and the volatiles removed under reduced pressure. The product was purified by silica gel chromatography, eluting with a hexanes/DCM to DCM gradient, to produce 2-chloro-3- (difluoromethoxy)pyridine as a white solid (Compound 2006, 2.0 g, 72% yield): ESMS (M+H) 180; 1H NMR (CDC13) delta 8.05 (m, 1H), 7.45(m, 1H), 6.90(m,lH), 6.60(t, 1H; J = 75Hz), 4.01(s, 3H).

69%

With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 1h;

This reaction was carried out 3 times. A mixture of potassium carbonate (282 g, 2.04 mol) and N,N-dimethylformamide (750 mL) was heated to 100 C and slowly treated, in a drop-wise manner over 1 hour, with a solution of 2-chloropyridin-3-ol (66.7 g, 515 mmol) and sodium chloro(difluoro)acetate (200 g, 1.31 mol) in N,N-dimethylformamide (750 mL). After completion of the addition, the reaction mixture was stirred at 100 C for 1 hour, then cooled to 25 C and partitioned between water (10 L) and tert-butyl methyl ether (5 L). The aqueous layer was extracted with ethyl acetate (4 x 2.5 L), and the combined organic layers were washed with saturated aqueous sodium chloride solution (6 x 2.5 L), dried over sodium sulfate, filtered, and concentrated in vacuo. The combined crude products from the three reactions were purified via distillation at reduced pressure (30-40 C, 1-5 mm Hg) to provide the product as a colorless oil. Yield: 192 g, 1.07 mol, 69%. LCMS m/z 180.0 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.26-8.30 (m, 1 H), 7.60 (br d, J=8.2 Hz, 1 H), 7.28 (br dd, J=8.0, 4.8 Hz, 1 H), 6.60 (t, JHF=72.5 Hz, 1 H).

Reference： [1]Patent: WO2010/96389,2010,A1 .Location in patent: Page/Page column 39-40; 42
[2]Patent: WO2010/135014,2010,A1 .Location in patent: Page/Page column 47-49
[3]Patent: WO2011/87776,2011,A1 .Location in patent: Page/Page column 51; 53
[4]Patent: WO2014/207601,2014,A1 .Location in patent: Page/Page column 88

8
[ 75-46-7 ]
[ 6636-78-8 ]
[ 1206977-80-1 ]

Yield	Reaction Conditions	Operation in experiment
51%		General procedure: Using an apparatus previously described for method B [21] , potassium hydroxide (2.52 g, 45 mmol, 15 equiv) and water (2.52 g) were added to the reaction vessel and the mixture was allowed to stir until the potassium hydroxide was almost completely dissolved. Then, 2-bromo-3-pyridinol (0.354 g, 3 mmol) was added and the mixture stirred for 30 min, after which acetonitrile (10 mL) was added via syringe and the mixture stirred at room temperature. Fluoroform was then bubbled slowly into the mixture for 2 h, after which the resulting mixture was stirred for one additional hour. After being quenched with water and extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated solution on sodium hydroxide, separated and concentrated. Additional impurities were removed via column chromatography on silica gel using an 80:20 mixture of hexanes/methylene chloride to give a 53% yield of the liquid product, 2-bromo-3-difluoromethoxypyridine (3d):

Reference： [1]Journal of Fluorine Chemistry,2014,vol. 168,p. 34 - 39

9
[ 6636-78-8 ]
[Cu(1,10-phenanthroline)₂][O₂CCF₂Cl] [ No CAS ]
[ 1206977-80-1 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 2075 - 2084

10
[ 6636-78-8 ]
[ 13472-83-8 ]

Reference： [1]Tetrahedron,2019,vol. 75,p. 3178 - 3185
[2]Patent: JP2019/99518,2019,A

11
[ 6636-78-8 ]
[ 161511-85-9 ]
(S)-2-(2-Chloro-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethyl acetate;	121a. 2-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine To a solution of triphenylphosphine (1.73 g, 6.6 mmol) in THF (26 mL) was added diethyl azodicarboxylate (1.04 mL, 6.6 mmol) at 0 C., and the reaction mixture was stirred for 15 minutes. 1-BOC-2-(S)-azetidinemethanol (1.03 g, 5.5 mmol) and 2-chloro-3-pyridinol (785 mg, 6.0 mmol, Aldrich Chemical Co.) were then added. The reaction mixture was allowed to warm slowly to room temperature and stir overnight. Solvent was removed, and the residue was dissolved in ethyl acetate. The solution was washed with saturated aqueous K2 CO3 and brine, dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluding with ethyl acetate:hexane (1:4 to 1:1) to afford the title compound (611 mg). MS (DCI/NH3) m/z 299 (M+H)+.

Reference： [1]Patent: US6133253,2000,A

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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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[ 6636-78-8 ]

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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. 6636-78-8 ] {[proInfo.proName]}

Quality Control of [ 6636-78-8 ]

Related Doc. of [ 6636-78-8 ]

Product Details of [ 6636-78-8 ]

Calculated chemistry of [ 6636-78-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6636-78-8 ]

Application In Synthesis of [ 6636-78-8 ]

[ 6636-78-8 ] Synthesis Path-Upstream 1~2

[ 6636-78-8 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 6636-78-8 ]

Chlorides

Alcohols

Related Parent Nucleus of [ 6636-78-8 ]

Pyridines

Precautionary Statements-General

Prevention

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Storage

Disposal

Physical hazards

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Inquiry

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[ 6636-78-8 ]

Related Parent Nucleus of
[ 6636-78-8 ]