[ CAS No. 68325-15-5 ] {[proInfo.proName]}

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Quality Control of [ 68325-15-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 68325-15-5 ]

SDS Specification

Alternatived Products of [ 68325-15-5 ]

Product Details of [ 68325-15-5 ]

CAS No. :	68325-15-5	MDL No. :	MFCD05663706
Formula :	C₆H₃ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JLLJPPBGJVCFGG-UHFFFAOYSA-N
M.W :	138.55	Pubchem ID :	10678306
Synonyms :		Chemical Name :	3-Chloro-4-cyanopyridine

Calculated chemistry of [ 68325-15-5 ] 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 :	0.0
Molar Refractivity :	33.96
TPSA :	36.68 ?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) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	1.15
Log Po/w (WLOGP) :	1.61
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	1.98
Consensus Log Po/w :	1.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.68 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (Ali) :	-1.51
Solubility :	4.23 mg/ml ; 0.0306 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.7
Solubility :	0.278 mg/ml ; 0.002 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 68325-15-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P305+P351+P338-P311	UN#:	3439
Hazard Statements:	H302+H312-H315-H319-H331-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 68325-15-5 ]

* 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 [ 68325-15-5 ]
Downstream synthetic route of [ 68325-15-5 ]

[ 68325-15-5 ] Synthesis Path-Upstream 1~3

1
[ 546-88-3 ]
[ 68325-15-5 ]
[ 114080-94-3 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	Intermediate 1 : lsoxazolo[5,4-cipyridin-3-ylamine.; To a solution of 3-chloro-isonicotinitrile (1.13 g, 8.36 mmol) in DMF (6.0 mL) were added potassium carbonate (1.69 g, 12.2 mmol) and acetohydroxamic acid (0.91 g, 12.2 mmol). The reaction mixture was stirred at rt overnight, diluted with EtOAc (200 mL) and extracted with saturated aqueous NaHCO₃ (200 mL) then saturated aqueous NaCI (100 mL). The aqueous layers were back extracted with EtOAc (200 mL) and the combined organic layers were dried (MgSO₄) and concentrated. The crude residue was purified (FCC, 2 N NH₃ in MeOH/DCM) to give isoxazolo[5,4-c]pyhdin-3-ylamine (0.447 g, 41 percent). MS (ESI⁺): calcd for C₆H₅N₃O m/z 135.04, found 136.2 (M+H)⁺. ¹H NMR (d₆-DMSO): 8.93 (d, J = 0.8, 1 H), 8.45 (d, J = 5.2, 1 H), 7.88-7.86 (dd, J = 5.2, 1.2, 1 H), 6.72 (br s, 2H).

Reference： [1] Patent: WO2010/68452, 2010, A1, . Location in patent: Page/Page column 26
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7357 - 7362

2
[ 68325-15-5 ]
[ 114080-94-3 ]

Yield	Reaction Conditions	Operation in experiment
41%	With acetylhydroxamic acid; potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere	Intermediate 1 : lsoxazolo[5,4-c1pyridin-3-ylamine.; To a solution of 3-chloro-isonicotinitrile (1.13 g, 8.36 mmol) in DMF (6.0 mL) were added potassium carbonate (1.69 g, 12.2 mmol) and acetohydroxamic acid (0.91 g, 12.2 mmol). The reaction mixture was stirred at rt overnight, diluted with EtOAc (200 mL) and extracted with saturated aqueous NaHCO₃ (200 mL) then saturated aqueous NaCI (100 mL). The aqueous layers were back extracted with EtOAc (200 mL) and the combined organic layers were dried (MgSO₄) and concentrated. The crude residue was purified (FCC, 2 N NH₃ in MeOH/DCM) to give isoxazolo[5,4-c]pyhdin-3-ylamine (0.447 g, 41 percent). MS (ESI⁺): calcd for C₆H₅N₃O m/z 135.04, found 136.2 (M+H)⁺. ¹H NMR (d₆-DMSO): 8.93 (d, J = 0.8, 1 H), 8.45 (d, J = 5.2, 1 H), 7.88-7.86 (dd, J = 5.2, 1.2, 1 H), 6.72 (br s, 2H).

Reference： [1] Patent: WO2010/68453, 2010, A1, . Location in patent: Page/Page column 30

3
[ 68325-15-5 ]
[ 87032-82-4 ]

Reference： [1] Patent: WO2007/89512, 2007, A1,

[ 68325-15-5 ] Synthesis Path-Downstream 1~4

1
[ 13220-33-2 ]
[ 68325-15-5 ]
[ 91832-82-5 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2178 - 2199

2
[ 13220-33-2 ]
[ 68325-15-5 ]
[ 110-17-8 ]
3-[(1-methyl-3-pyrrolidinyl)oxy]-4-pyridinecarbonitrile fumarate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; water; mineral oil;	Preparation 12 3-[(1-Methyl-3-pyrrolidinyl)oxy]-4-pyridinecarbonitrile fumarate [1:2] A solution of 55 g (0.55 mole) of <strong>[13220-33-2]1-methyl-3-pyrrolidinol</strong> in 55 ml of dry dimethylformamide was added dropwise to a suspension of 22 g (0.58 mole) of 60percent sodium hydride/40percent mineral oil in 300 ml of dimethylformamide. The mixture was stirred at room temperature for one hour and 73 g (0.53 mole) of 3-chloro-4-cyanopyridine in 200 ml of dimethylformamide was added dropwise with mild cooling to maintain a temperature of 30°-40° C. The solution was stirred 3 hours and an equal volume of water added. The solution was made acidic with dilute hydrochloric acid and extracted with isopropyl ether. The aqueous layer was made basic with sodium hydroxide and extracted 5 times with chloroform. The extracts were combined, dried over sodium sulfate and concentrated. The residue was treated with 50 g of fumaric acid in 400 ml of isopropyl alcohol and 40 ml of water. The resulting crystals (51 g; 21 percent) were collected. A 2 g sample was recrystallized from methyl isobutyl ketone. Yield of product was 1.5 g, m.p. 172°-174° C. Analysis: Calculated for C18 H21 N3 O9: C, 52.42; H, 4.86; N, 9.65. Found: C, 52.40; H, 4.90; N, 9.68.
	In N-methyl-acetamide; water; mineral oil;	PREPARATION 12 3-[(1-Methyl-3-pyrrolidinyl)oxy]-4-pyridinecarbonitrile fumarate [1:2] A solution of 55 g (0.55 mole) of <strong>[13220-33-2]1-methyl-3-pyrrolidinol</strong> in 55 ml of dry dimethylformamide was added dropwise to a suspension of 22 g (0.58 mole) of 60percent sodium hydride/40percent mineral oil in 300 ml of dimethylformamide. The mixture was stirred at room temperature for one hour and 73 g (0.53 mole) of 3-chloro-4-cyanopyridine in 200 ml of dimethylformamide was added dropwise with mild cooling to maintain a temperature of 30°-40° C. The solution was stirred 3 hours and an equal volume of water added. The solution was made acidic with dilute hydrochloric acid and extracted with isopropyl ether. The aqueous layer was made basic with sodium hydroxide and extracted 5 times with chloroform. The extracts were combined, dried over sodium sulfate and concentrated. The residue was treated with 50 g of fumaric acid in 400 ml of isopropyl alcohol and 40 ml of water. The resulting crystals (51 g; 21percent) were collected. A 2 g sample was recrystallized from methyl isobutyl ketone. Yield of product was 1.5 g, m.p. 172°-174° C. Analysis: Calculated for C19 H21 N3 O9: C, 52.42; H, 4.86; N, 9.65. Found: C, 52.40; H, 4.90; N, 9.68.

Reference： [1]Patent: US4592866,1986,A
[2]Patent: US4705853,1987,A

3
[ 13061-96-6 ]
[ 68325-15-5 ]
[ 7584-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 10h;Inert atmosphere;	Example 66A 3-methylisonicotinonitrile To a mixture of 3-chloroisonicotinonitrile (50 g) in toluene (1.5 L) was added K3PO4 (306 g), and the mixture was stirred for 10 minutes at 25 C. Methylboronic acid (32.4 g) and tricyclohexylphosphine (10.12 g) were added. After 5 minutes, 150 mL of water was added, and the mixture was stirred for 5 minutes at 25 C. Diacetoxypalladium (2.431 g) was added under a nitrogen atmosphere. The resulting mixture was stirred for 10 hours at 100 C. Eleven additional reactions were set up as described above. After cooling to 20 C., all twelve reaction mixtures were combined. 5 L of water was added to the mixture, and the layers were separated. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by silica gel chromatography using 1-20% ethyl acetate in heptanes as the eluent to provide the title compound. 1H NMR (400 MHz, chloroform-d) delta ppm 8.68 (s, 1H), 8.60 (d, 1H), 7.46 (d, 1H), 2.56 (s, 3H).

Reference： [1]Patent: US2019/55264,2019,A1 .Location in patent: Paragraph 0793

4
[ 68325-15-5 ]
[ 161511-85-9 ]
tert-butyl (2S)-2-[(4-cyanopyridin-3-yl)oxy]methyl}azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.01%		To a stirred solution of <strong>[161511-85-9]tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate</strong> (2.70 g, 14.436 mmol, 1 equiv) in DMF was added NaH (415.69 mg, 17.323 mmol, 1.2 equiv) in portions at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 0.5 h at room temperature under nitrogen atmosphere. To the above mixture was added 3-chloropyridine-4-carbonitrile (1.80 g, 12.992 mmol, 0.9 equiv) in portions at 0 degrees C. The resulting mixture was stirred for additional 16 h at room temperature. The reaction was quenched with Water/Ice at room temperature. The resulting mixture was extracted with DCM (4 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4.The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (1:1) to afford tert-butyl (2S)-2-[(4-cyanopyridin-3-yl)oxy]methyl}azetidine-1-carboxylate (3.3 g, 79.01%) as a yellow oil. LC-MS: M+H found: 290
79.01%		To a stirred solution of <strong>[161511-85-9]tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate</strong> (2.70 g, 14.436 mmol, 1 equiv) in DMF was added NaH (415.69 mg, 17.323 mmol, 1.2 equiv) in portions at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 0.5 h at room temperature under nitrogen atmosphere. To the above mixture was added 3-chloropyridine-4-carbonitrile (1.80 g, 12.992 mmol, 0.9 equiv) in portions at 0 degrees C. The resulting mixture was stirred for additional 16 h at room temperature. The reaction was quenched with Water/Ice at room temperature. The resulting mixture was extracted with DCM (4 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4.The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (1:1) to afford tert-butyl (2S)-2-[(4-cyanopyridin-3-yl)oxy]methyl}azetidine-1-carboxylate (3.3 g, 79.01%) as a yellow oil. LC-MS: M+H found: 290

Reference： [1]Patent: WO2022/66734,2022,A1 .Location in patent: Page/Page column 367
[2]Patent: WO2022/66734,2022,A1 .Location in patent: Page/Page column 367

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Blaise Reaction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction

Historical Records

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[ 68325-15-5 ]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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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. 68325-15-5 ] {[proInfo.proName]}

Quality Control of [ 68325-15-5 ]

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Calculated chemistry of [ 68325-15-5 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 68325-15-5 ]

[ 68325-15-5 ] Synthesis Path-Upstream 1~3

[ 68325-15-5 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 68325-15-5 ]

Chlorides

Nitriles

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Pyridines

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[ 68325-15-5 ]

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[ 68325-15-5 ]