[ CAS No. 78760-60-8 ] {[proInfo.proName]}

Name: 78760-60-8|5-(Benzyloxy)picolinonitrile|95%
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3d Animation Molecule Structure of 78760-60-8

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Quality Control of [ 78760-60-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 78760-60-8 ]

SDS Specification

Alternatived Products of [ 78760-60-8 ]

Product Details of [ 78760-60-8 ]

CAS No. :	78760-60-8	MDL No. :	MFCD11977436
Formula :	C₁₃H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FCECYLUEYDBZHV-UHFFFAOYSA-N
M.W :	210.23	Pubchem ID :	15574701
Synonyms :

Calculated chemistry of [ 78760-60-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.93
TPSA :	45.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.24
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	2.38
Log Po/w (MLOGP) :	1.07
Log Po/w (SILICOS-IT) :	2.84
Consensus Log Po/w :	2.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.99
Solubility :	0.213 mg/ml ; 0.00101 mol/l
Class :	Soluble
Log S (Ali) :	-2.97
Solubility :	0.223 mg/ml ; 0.00106 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.78
Solubility :	0.00349 mg/ml ; 0.0000166 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 78760-60-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 78760-60-8 ]

* 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 [ 78760-60-8 ]
Downstream synthetic route of [ 78760-60-8 ]

[ 78760-60-8 ] Synthesis Path-Upstream 1~2

1
[ 100-39-0 ]
[ 78760-60-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5 h; Stage #2: at 66℃; for 1 h;	Step l:5-Benzyloxy-pyridine-2-carbonitrile (3_60_2) [00482] A mixture of 5-hydroxy-pyridine-2-carbonitrile 3_60_1 (14 g, 116 mmol) and potassium carbonate (32.2 g, 233 mmol) in Ν,Ν-dimethylformamide (140 mL) was heated at 60°C for 0.5 hours. Benzylbromide (13.9 g, 116 mmol) was added and the mixture was stirred at 66°C for 1 hour, and filtered and the filtrate was concentrated, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The residue was triturated with diethyl ether and hexanes to give a precipitate, which was collected to give compound 3_60_2 (21 g, 85 percent yield) as a solid. [00483] NMR (400 MHz, DMSO-d₆): δ = 5.27 (s, 2H), 7.33-7.50 (m, 5H), 7.65 (dd, J=8.8, 2.9 Hz, 1H), 8.00 (d, J = 8.6 Hz, 1H), 8.50 (d, J = 3.2 Hz, 1H).

Reference： [1] Patent: WO2013/110643, 2013, A1, . Location in patent: Paragraph 00482; 00483

2
[ 41960-47-8 ]
[ 100-51-6 ]
[ 78760-60-8 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333

[ 78760-60-8 ] Synthesis Path-Downstream 1~9

1
[ 41960-47-8 ]
[ 100-51-6 ]
[ 78760-60-8 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333

2
5-hydroxypyridine-2-carbonitrile [ No CAS ]
[ 100-39-0 ]
[ 78760-60-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		Step l:5-Benzyloxy-pyridine-2-carbonitrile (3_60_2) [00482] A mixture of 5-hydroxy-pyridine-2-carbonitrile 3_60_1 (14 g, 116 mmol) and potassium carbonate (32.2 g, 233 mmol) in Nu,Nu-dimethylformamide (140 mL) was heated at 60C for 0.5 hours. Benzylbromide (13.9 g, 116 mmol) was added and the mixture was stirred at 66C for 1 hour, and filtered and the filtrate was concentrated, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The residue was triturated with diethyl ether and hexanes to give a precipitate, which was collected to give compound 3_60_2 (21 g, 85 % yield) as a solid. [00483] NMR (400 MHz, DMSO-d6): delta = 5.27 (s, 2H), 7.33-7.50 (m, 5H), 7.65 (dd, J=8.8, 2.9 Hz, 1H), 8.00 (d, J = 8.6 Hz, 1H), 8.50 (d, J = 3.2 Hz, 1H).

Reference： [1]Patent: WO2013/110643,2013,A1 .Location in patent: Paragraph 00482; 00483

3
[ 78760-60-8 ]
[ 1448674-60-9 ]

Yield	Reaction Conditions	Operation in experiment
10 g	With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at 0 - 20℃; for 16h;	Step 2:5-Benzyloxy-pyridine-2-carboxamidine (3_60_3) [00484] Butyllithium (1.6N in hexane, 168 mL, 269 mmol) was added to a solution of hexamethyldisilazane (56.5 mL, 269 mmol) in tetrahydrofuran (250 mL) at 0C, and stirred at 0C for 1 hour to form lithium hexamethyldisilazide (LHMDS). A solution of compound 3_60_2 (22.6 g, 107.6 mmol) in tetrahydrofuran (250 mL) was added slowly at 0C, and the mixture was warmed to room temperature slowly and stirred for 16 hours at room temperature. A IN hydrochloric acid solution (300 mL) was added to the reaction mixture to give a precipitate which was collected to give pure compound 3_60_3 (17 g, 70 % yield). From the mother liquor an additional amount of crude compound 3_60_3 (10 g) was obtained as a gum. [00485] NMR (400 MHz, DMSO-d6): delta = 5.32 (s, 2H), 7.32-7.52 (m, 5H), 7.78 (dd, J = 8.8, 2.9 Hz, 1H), 8.25 (d, J = 8.6 Hz, 1H), 8.54 (d, J = 2.7 Hz, 1H), 9.18 (s, 2H), 9.32 (s, 2H).

Reference： [1]Patent: WO2013/110643,2013,A1 .Location in patent: Paragraph 00484; 00485

4
[ 78760-60-8 ]
[ 1448674-61-0 ]

Reference： [1]Patent: WO2013/110643,2013,A1

5
[ 78760-60-8 ]
[ 1448674-62-1 ]

Reference： [1]Patent: WO2013/110643,2013,A1

6
[ 78760-60-8 ]
[ 1448674-63-2 ]

Reference： [1]Patent: WO2013/110643,2013,A1

7
[ 78760-60-8 ]
[ 75-16-1 ]
[ 858597-92-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; for 3h;Inert atmosphere; Reflux;	To a reflux condenser 20mL round bottom flask was added 5mL anhydrous tetrahydrofuran solution, 0.5mmol <strong>[78760-60-8]5-benzyloxy-2-cyanopyridine</strong>,The mixture was stirred and replaced with nitrogen for three times. 1.5 mmol of methylmagnesium bromide was slowly added under the protection of nitrogen at room temperature. The whole system was heated to reflux and reacted for 3 hours.The whole reaction was poured into ice-water and extracted three times with dichloromethane, each time 20 mL, concentrated to give a white solid product, 102 mg, yield 90%.

Reference： [1]Patent: CN106397311,2017,A .Location in patent: Paragraph 0012-0018

8
[ 97483-77-7 ]
[ 100-51-6 ]
[ 78760-60-8 ]

Yield	Reaction Conditions	Operation in experiment
80.2%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 5℃; for 0.416667h;	Step C: at 0 ~ 5 , benzyl alcohol (7.68g, 71.0mmol) was added dropwise 60% sodium hydride (2.84g, 71.0mmol) in DMF (60mL) suspension.After the addition was completed, stirring was continued for 10 minutes, and then 5-bromo-2-cyanopyridine (10.0 g, 54.6 mmol) was added portionwise.The resulting mixture was stirred at this temperature for a further 15 minutes.Add water (180 mL), filter, and filter cake with water (100 mL)5-Benzyloxy-2-cyanopyridine (25) (9.2 g) was obtained. The yield was 80.2%.

Reference： [1]Patent: CN110183431,2019,A .Location in patent: Paragraph 0152-0153; 0156

9
[ 78760-60-8 ]
[ 925-90-6 ]
1-[5-(benzyloxy)pyridin-2-yl]propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.7%	In tetrahydrofuran; at -5 - 0℃; for 1h;	Step D: at -5 ~ 0 , a 2M ethylmagnesium bromide in THF (26.5mL, 53mmol) was added dropwise to compound 25 (8.6g, 40.9mmol) in THF (30 mL) solution. After the addition was completed, the resulting mixture was further stirred at this temperature for 1 hour. Slowly add water (90mL),Adjust the pH to 3~4 with 2M hydrochloric acid.Extracted with ethyl acetate (100 mL × 3),The combined organic phases were washed with water (50 mL) and brine brineThe solvent was evaporated under reduced pressure to give 1-(5-benzyloxypyridin-2-yl)propan-1-one (26) (9.74 g). The yield was 98.7%.

Reference： [1]Patent: CN110183431,2019,A .Location in patent: Paragraph 0152-0153; 0157

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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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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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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

[ CAS No. 78760-60-8 ] {[proInfo.proName]}

Quality Control of [ 78760-60-8 ]

Related Doc. of [ 78760-60-8 ]

Product Details of [ 78760-60-8 ]

Calculated chemistry of [ 78760-60-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 78760-60-8 ]

Application In Synthesis of [ 78760-60-8 ]

[ 78760-60-8 ] Synthesis Path-Upstream 1~2

[ 78760-60-8 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 78760-60-8 ]

Aryls

Ethers

Nitriles

Related Parent Nucleus of [ 78760-60-8 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 78760-60-8 ]

Related Parent Nucleus of
[ 78760-60-8 ]