[ CAS No. 3475-21-6 ] {[proInfo.proName]}

Name: 3475-21-6|4-Methyl-2-phenylpyridine|97%
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3d Animation Molecule Structure of 3475-21-6

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Quality Control of [ 3475-21-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3475-21-6 ]

SDS Specification

Alternatived Products of [ 3475-21-6 ]

Product Details of [ 3475-21-6 ]

CAS No. :	3475-21-6	MDL No. :	MFCD00087695
Formula :	C₁₂H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WWMRJCUZPJJWBC-UHFFFAOYSA-N
M.W :	169.22	Pubchem ID :	77026
Synonyms :

Calculated chemistry of [ 3475-21-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.64
TPSA :	12.89 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) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	2.88
Log Po/w (WLOGP) :	3.06
Log Po/w (MLOGP) :	2.41
Log Po/w (SILICOS-IT) :	3.53
Consensus Log Po/w :	2.83

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.32
Solubility :	0.0809 mg/ml ; 0.000478 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.262 mg/ml ; 0.00155 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.92
Solubility :	0.00203 mg/ml ; 0.000012 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 3475-21-6 ]

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 [ 3475-21-6 ]

* 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 [ 3475-21-6 ]
Downstream synthetic route of [ 3475-21-6 ]

[ 3475-21-6 ] Synthesis Path-Upstream 1~7

1
[ 3475-21-6 ]
[ 55240-51-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With selenium(IV) oxide In pyridineHeating / reflux	2-phenyl-4-methylpyridine (6 g, 35.4 mmol) and SeO₂ (24 g, 216 mmol) were refluxed in pyridine (100 ml) overnight under argon. The mixture was then filtered through celite while hot. The Celite filter cake was rinsed with pyridine (3x50 ml) and the resulting filtrate evaporated to dryness. The solid thus obtained was triturated in water (200 ml) and filtered off. The resulting brown solid was suspended in a mixture of water (150 ml) and MeOH (200 ml) and made basic by addition of an aqueous NaOH solution. The mixture was then filtered over Celite to removed some insoluble materials. The filtrate was then acidified with concentrated HCl. MeOH was evaporated and the formed precipitate was filtered, washed with water, then small portions Of Et₂O (3x20 ml) and finally dried to afford 5.9 g (84percent) of the titled compound as a slightly brown solid.

Reference： [1] Patent: WO2007/4113, 2007, A2, . Location in patent: Page/Page column 24
[2] Dalton Transactions, 2012, vol. 41, # 9, p. 2582 - 2591
[3] Annali di Chimica Applicata, 1931, vol. 21, p. 553,556

2
[ 108-89-4 ]
[ 98-80-6 ]
[ 19352-29-5 ]
[ 3475-21-6 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 21, p. 5772 - 5775

3
[ 122-78-1 ]
[ 123-73-9 ]
[ 3256-88-0 ]
[ 46181-30-0 ]
[ 19352-29-5 ]
[ 3475-21-6 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 11, p. 1153 - 1156[2] Khimiya Geterotsiklicheskikh Soedinenii, 1980, vol. 16, # 11, p. 1516 - 1519

4
[ 536-74-3 ]
[ 123-73-9 ]
[ 3256-88-0 ]
[ 46181-30-0 ]
[ 19352-29-5 ]
[ 3475-21-6 ]

5
[ 108-89-4 ]
[ 108-86-1 ]
[ 19352-29-5 ]
[ 3475-21-6 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 37, p. 8065 - 8071

6
[ 108-89-4 ]
[ 94-36-0 ]
[ 1003-67-4 ]
[ 19352-29-5 ]
[ 3475-21-6 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 23, p. 4911 - 4920

7
[ 108-89-4 ]
[ 94-36-0 ]
[ 19352-29-5 ]
[ 92-52-4 ]
[ 3475-21-6 ]
[ 65-85-0 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 23, p. 4911 - 4920

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[ 3475-21-6 ]

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P233	Keep container tightly closed.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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Response
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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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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Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 - 20℃; for 12h;	General procedure: To a stirred solution of 2-phenylpyridines (6 mmol) in CHCl3 (2 mL) was added 70percent m-CPBA (1 equiv.), portionwise at 0°C. The resulting mixture was stirred at room temperature for 12 h, at which time complete consumption of starting material was observed by TLC. The reaction mixture was diluted with CHCl3, and solid K2CO3 (4 equiv.) was added. The resulting mixture was stirred for an additional 10 min. The solid was separated by filtration, and the filtrate was dried over Na2SO4 and concentrated under reduced pressure to afford the 2-phenylpyridine N-oxides in yields of 60-85percent.
	With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 - 20℃;	General procedure: To a stirred solution of N-heteroaromatic compounds in chloroform (0.5 M) was added meta-chloroperoxybenzoic acid (m-CPBA) (2.0 eq) in portions at 0 °C. After the completion of this course, the reaction mixture was allowed up to room temperature and stirred overnight. An aqueous solution of saturated K2CO3 was added to the mixture to neutralize residual m-CPBA. The resulting mixture was extracted with CHCl3 and isopropanol (volume ratio = 9:1) three times (3 x 30 mL). The organic phase were combined and washed with saturated NaCl solution (30 mL). The organic layer was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give crude products, which were purified by column chromatography. The new products were characterized by 1H NMR, 13C NMR and HRMS.

Yield	Reaction Conditions	Operation in experiment
95%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; at 60℃; for 12h;Schlenk technique; Inert atmosphere;	To Schlenk bottle was added 2-bromo-4-methyl-pridine (1720 mg, 10 mmol), phenylboronic acid (1332 mg, 11 mmol), K2CO3 (2760 mg, 20 mmol), Pd(Ph3P)2Cl2 (701 mg, 1 mmol) and THF (60 mL). The solution was stirred and refluxed at 60 C for 12 h under Ar. Then the reaction solution was cooled to room temperature and poured into 200 mL of EtOAc and 200 mL of water. The solution was separated into two phases, the upper EtOAc was dried by Na2SO4 and then concentrated under vacuum. After evaporation, the residue was purified by column chromatography on silica with (eluten: PE/EtOAc=50:1) to give the light yellow oil liquid 4-methyl-2-phenyl-pridine (1605 mg, 95 %).
85%	With palladium diacetate; potassium carbonate; triphenylphosphine; In methanol; acetonitrile; at 65℃; for 24h;Inert atmosphere;	General procedure: Method B: The preparation of 2-Bromopyridines with arylboronic acids was according to literature procedures.[1] To a 50-mL fire-dried flask was charged with 2-Bromopyridines (5 mmol, 1.0 eq), arylboronic acid (5.5 mmol, 1.5 eq), K2CO3 (1.38 g, 10.0 mmol, 2.0 eq), Pd(OAc)2 (56.0 mg, 0.25 mmol, 5.0 mol% ), PPh3 (131.0 mg, 0.5 mmol, 10.0 mol% ), CH3CN (10.0 mL) and methanol (5.0 mL). The mixture was degassed through a freeze-thaw-pump thread for three times. The reaction was stirred at 65 C for 24 hours. To the reaction mixture was added brine (15 mL) and ethyl acetate (15 mL). The phase was separated and the aqueous phase was extracted with ethyl acetate (4 × 15 mL). The combined organic phase was dried over Na2SO4 and concentrated under vacuum. The product was isolated by flash-column chromatography on silica gel (300-400 mesh).

Yield	Reaction Conditions	Operation in experiment
78%	With SiO2; In 1,2-dimethoxyethane; hexane; water; ethyl acetate;	Synthesis of 4-methyl-2-phenylpyridine A 1 L round bottom flask was charged with 2-chloro-4-methylpyridine (25 g, 196 mmol), phenylboronic acid (23.9 g, 196 mmol), potassium carbonate (81 g, 588 mmol), Pd(PPh3)4 (2.3 g, 1.9 mmol), dimethoxyethane (500 mL) and water (150 mL). The reaction mixture was degassed with nitrogen and heated to reflux for 22 h. After cooling, the aqueous layer was extracted with EtOAc; the organic portion was combined and subjected to column chromatography (SiO2, 5percent EtOAc in hexane to 10percent EtOAc in hexane) to give 28 g (78percent) of 4-methyl-2-phenylpyridine. The product was confirmed by NMR and GC/MS.
78%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; for 22h;Inert atmosphere; Reflux;	to 1 L round bottom flask was fed into the 2-chloro-4-methylpyridine (25 g, 196 mmol), phenyl acid (23.9 g, 196 mmol), potassium carbonate (81 G, 588 mmol), of Pd (PPh33)4(2.3 G, 1.9 mmol), dimethoxyethane (500 mL) and water (150 mL).The reaction mixture was degassed with nitrogen and heated to reflux for 22 h.After cooling, the aqueous layer was extracted with EtOAc; the organic portion of the organic portion and so through column chromatography (of SiO2, 5percent EtOAc in hexanes to 10percent EtOAc in hexanes) to obtain 28 g (78percent) methyl-2-phenylpyridine.The product is confirmed by NMR and GC / MS.
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 48h;	A mixture of 2-chloro-4-methylpyridine (25 mmol), boronic acids (30 mmol), Pd(PPh3)4 (0.86 g, 3 molpercent) in mixture of toluene (75 mL), ethanol (10 mL) and potassium carbonate (2.0 M in water, 28mL) was stirred at 80°C for 48 h. The mixture was added brine (40 mL) and extracted four times with ethyl acetate (4 x 25 mL), the solvent was evaporated under reduced pressure and the product was isolated by short column chromatography using ethyl acetate and petroleum as eluent.

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. 3475-21-6 ] {[proInfo.proName]}

Quality Control of [ 3475-21-6 ]

Related Doc. of [ 3475-21-6 ]

Product Details of [ 3475-21-6 ]

Calculated chemistry of [ 3475-21-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3475-21-6 ]

Application In Synthesis of [ 3475-21-6 ]

[ 3475-21-6 ] Synthesis Path-Upstream 1~7

[ 3475-21-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 3475-21-6 ]

Aryls

Related Parent Nucleus of [ 3475-21-6 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3475-21-6 ]

Related Parent Nucleus of
[ 3475-21-6 ]