13959-34-7|4-Methyl-2-vinylpyridine| Ambeed

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Quality Control of [ 13959-34-7 ] Purity: 95% mix TBC as stabilizer SDS Specification

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Product Details of [ 13959-34-7 ]

CAS No. :	13959-34-7
Formula :	C₈H₉N
M.W :	119.16
SMILES Code :	CC1=CC(C=C)=NC=C1
MDL No. :	MFCD08703183
InChI Key :	WVNIWWGCVMYYJZ-UHFFFAOYSA-N
Pubchem ID :	11205741

Safety of [ 13959-34-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 13959-34-7 ]

* 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.

Downstream synthetic route of [ 13959-34-7 ]

[ 13959-34-7 ] Synthesis Path-Downstream 1~25

1
[ 110-91-8 ]
[ 13959-34-7 ]
4-[2-(4-methyl-[2]pyridyl)-ethyl]-morpholine [ No CAS ]

References: [1]CHEMTECH,1957,vol. 9,p. 96.

2
[ 13959-34-7 ]
[ 513-44-0 ]
[ 101589-63-3 ]

References: [1]CHEMTECH,1957,vol. 9,p. 96.

3
[ 13959-34-7 ]
[ 108-98-5 ]
[ 106320-21-2 ]

References: [1]CHEMTECH,1957,vol. 9,p. 96.

4
[ 13959-34-7 ]
[ 618-41-7 ]
[ 100710-97-2 ]

References: [1]CHEMTECH,1957,vol. 9,p. 96.

5
[ 4664-18-0 ]
[ 13959-34-7 ]

References: [1]CHEMTECH,1957,vol. 9,p. 96.

6
[ 13959-34-7 ]
[ 2295-31-0 ]
[ 32594-62-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1971,vol. 7,p. 559 - 560.
Khimiya Geterotsiklicheskikh Soedinenii,1971,vol. 7,p. 599 - 600.

7
[ 13959-34-7 ]
[ 151-50-8 ]
[ 71858-92-9 ]

References: [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 1016 - 1022.
Khimiya Geterotsiklicheskikh Soedinenii,1990,vol. 26,p. 1217 - 1225.

8
[ 13959-34-7 ]
[ 76162-65-7 ]

References: [1]Chemistry of Heterocyclic Compounds,1980,p. 945 - 950.
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 1248 - 1254.

11
[ 13959-34-7 ]
[ 132554-31-5 ]

References: [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 1016 - 1022.
Khimiya Geterotsiklicheskikh Soedinenii,1990,vol. 26,p. 1217 - 1225.

12
[ 13959-34-7 ]
[ 132554-27-9 ]

References: [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 1016 - 1022.
Khimiya Geterotsiklicheskikh Soedinenii,1990,vol. 26,p. 1217 - 1225.

13
[ 108-47-4 ]
[ 13959-34-7 ]

References: [1]CHEMTECH,1957,vol. 9,p. 96.

14
[ 4926-28-7 ]
[ 7486-35-3 ]
[ 13959-34-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With 2,6-di-tert-butyl-4-methyl-phenol;tetrakis(triphenylphosphine) palladium(0); In toluene; at 100℃; for 18.0h;	A yellow mixture of 2-bromo-4-methyl-pyridine (Aldrich, 5.2 g, 30.5 mmol, 1.0 eq), 2, 6-DI-TERT-BUTYL-4-METHYL-PHENOL (ALDRICH, 67 mg, 0.3 mmol, 1 MOL%), TRIBUTYL-VINYL- stannane (ALDRICH, 26.8 mL, 91.5 MMOL, 3.0 eq) and tetrakis (triphenylphosphine) palladium (0) (Strem, 1.8 g, 1.5 mmol, 5mol%) in toluene (100 mL) was degassed and purged with argon. An amber solution was obtained after the mixture was warmed to 100 C. The reaction mixture was quenched after 18 hours by the addition of 1.0 M HCI. The acidic extract was washed with ether, adjusted to pH 9 with solid sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product (3.7 g of a brown oil) was purified by flash chromatography (silica) and eluted with 0-5% ethyl acetate-dichloromethane, which gave a clear oil (1.9 g, 53%). 1H NMR (DMSO-D6, 300 MHz) 5 8.39 (1H, d, J = 4.9 HZ), 7.33 (1H, s), 7.10 (1H, dd, J = 5. 0, 0.8 Hz), 6.77 (1H, dd, 17.5, 10.8 HZ), 6.20 (1H, dd, J = 17.5, 1.7 Hz), 5.44 (1H, dd, J = 10.8, 1.8 Hz), 2.31 (3H, s). ESIMS m/z 120 (M + H)+.

References: [1]Patent: WO2004/56806,2004,A1 .Location in patent: Page 64.

15
[ 13959-34-7 ]
[ 717134-81-1 ]
[ 717135-02-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine;palladium diacetate; In DMF (N,N-dimethyl-formamide); at 100℃; for 18.0h;	A suspension of <strong>[13959-34-7]4-Methyl-2-vinyl-pyridin</strong>e (Example 23) (1.9g, 15. 97MMOL), 6- Nitro-1-(tetrahydro-pyran-2-yl)-3-vinyl-1H-indazole (4. 96g, 13. 3MMOL), Pd (OAc) 2 (149mg, 0. 66MOL), P (O-TOLYL) 3, and DIEA (3. 5MOI, 19. 96MMOL) in degassed DMF (50ml) was heated under argon at 100C for 18HR. The reaction mixture was cooled and the solids removed by filtration washing with EtOAc. The filtrate was diluted wih EtOAc and washed with brine (2x), dried (MGS04) and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting Hexanes: EtOAc (3: 1) to give 3.40g (70%) of a bright yellow solid. 'H NMR (CDCI3) No. 8.56 (1H, S), 8.50 (1H, d, J = 5.0 Hz), 8.11 (2H, m), 7.89 (1H, d, J = 16.3 Hz), 7.61 (1 H, s), 7.03 (1H, d, J = 4.3 HZ), 5.83 (1H, dd, J = 2.6, 9.0 HZ), 4.06 (1H, m), 3.82 (1H, m), 2.58 (1H, m), 2.39 (3H, s), 2.18 (2H, m), 1.78 (3H, M). ANAL. CALCD for C2OH2ON403 : C, 65.92 ; H, 5.53 ; N, 15.38. Found: C, 65.80 ; H, 5.52 ; N, 15.15.

References: [1]Patent: WO2004/56806,2004,A1 .Location in patent: Page 64-65.

16
[ 13959-34-7 ]
Dihydroxy-styryl-boran [ No CAS ]
1-phenyl-4-(4-methyl-2-pyridyl)-1-butene [ No CAS ]

References: [1]Chemistry - An Asian Journal,2011,vol. 6,p. 669 - 673.

17
[ 53547-60-7 ]
[ 2065-66-9 ]
[ 13959-34-7 ]

References: [1]Chemistry - An Asian Journal,2011,vol. 6,p. 669 - 673.

18
[ 13959-34-7 ]
[ 7677-24-9 ]
[ 4559-70-0 ]
2-(4-methylpyridin-2-yl)-3-diphenylphosphinylpropionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With manganese(II) acetate; copper(ll) bromide; In acetic acid; at 40℃;Inert atmosphere;	The reaction procedure is as follows: 2-vinyl-4-methylpyridine and diphenyloxyphosphine as starting materials,2-vinyl-4-methylpyridine (0.048 g, 0.4 mmol), diphenylphosphine oxide (0.162 g,0.8 mmol), trimethylcyanosilane (0.079 g, 0.8 mmol), CuBr2 (0.176 g, 0.08 mmol), manganese acetate(0.322 g, 1.2 mmol) and glacial acetic acid (3 mL) under argon at 40 C;TLC tracks the reaction until it ends completely;The crude product obtained after the completion of the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1: 1) to give the desired product(Yield 82%).

References: [1]Patent: CN106432329,2017,A .Location in patent: Paragraph 0050.

19
[ 13959-34-7 ]
[ 2369-31-5 ]
2-([1,1'-biphenyl]-4-yl)-1,1,1-trifluoro-4-(4-methylpyridin-2-yl)butan-2-ol [ No CAS ]

References: [1]Chemical Communications,2018,vol. 54,p. 11017 - 11020.

20
[ 13959-34-7 ]
[ 100-52-7 ]
(R)-3-(4-methylpyridin-2-yl)-1-phenylpropan-1-ol [ No CAS ]
3-(4-methylpyridin-2-yl)-1-phenylpropan-1-ol [ No CAS ]

References: [1]Journal of the American Chemical Society,2019,vol. 141,p. 5437 - 5443.

21
[ 13959-34-7 ]
[ 98-86-2 ]
(R)-4-(4-methylpyridin-2-yl)-2-phenylbutan-2-ol [ No CAS ]
4-(4-methylpyridin-2-yl)-2-phenylbutan-2-ol [ No CAS ]

References: [1]Journal of the American Chemical Society,2019,vol. 141,p. 5437 - 5443.

22
[ 13959-34-7 ]
[ 491-36-1 ]
3-(2-(4-methylpyridin-2-yl)ethyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With scandium tris(trifluoromethanesulfonate); In toluene; at 110℃; for 12.0h;Inert atmosphere;	General procedure: Typically, quinazolinone (0.5 mmol, 73.0 mg), 2-vinylpyridine (1.0 mmol, 105.0 mg), Sc(OTf)3 (0.05 mmol, 24.6 mg) were charged sequentially into the flask with 3 mL toluene. The flask was then evacuated under reduced pressure, followed by the attachment of a nitrogen balloon. The resulting mixture was stirred at 110 for 12 h. The progress of the reaction was monitored by TLC. After the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel (EA/MeOH = 250:1 150:1) to give the product 3a (103 mg, 82 %) as a white solid. 3-(2-(pyridin-2-yl)ethyl)quinazolin-4(3H)-one (3a). The title compound was prepared according to the general procedure as described above in 82 % yield as white powder, 103 mg.

References: [1]Tetrahedron Letters,2020,vol. 61.

23
[ 13959-34-7 ]
[ 491-36-1 ]
3-(2-(4-methylpyridin-2-yl)ethyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With scandium tris(trifluoromethanesulfonate); In toluene; at 110℃;Inert atmosphere;	4-Hydroxyquinazoline (1mmol), <strong>[13959-34-7]4-methyl-2-vinylpyridine</strong> (1.5mmol), scandium trifluoromethanesulfonate (0.1mmol) were added to a single-necked flask containing 4mL of toluene, and the flask The air was replaced with argon, and then stirred at 110C. The reaction process was monitored by thin layer chromatography. After the reaction was completed, it was quenched with water (15 mL). The reaction product was extracted with methylene chloride (3×20 mL), washed with saturated brine (20 mL), dehydrated with anhydrous Na 2 SO 4, filtered, and the resulting filtrate was concentrated and passed through a silica gel column (300-400 mesh, the developing agent was ethyl acetate/ Methanol = 450:1) chromatographic separation to obtain product 209.6mg, yield 79%.

References: [1]Patent: CN111116552,2020,A .Location in patent: Paragraph 0207-0214.

24
[ 13959-34-7 ]
[ 4452-11-3 ]
(R)-5-(4-methylpyridin-2-yl)-1,2-diphenylpentan-1-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2021,vol. 143,p. 4024 - 4031.

25
[ 13959-34-7 ]
[ 491-38-3 ]
2-(2-(4-methylpyridin-2-yl)ethyl)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,4-dihydropyridine; diphenyl hydrogen phosphate; 5,6-bis(5-methoxythiophen-2-yl)pyrazine-2,3-dicarbonitrile; In acetonitrile; at -78 - 25℃; for 8.0h;Schlenk technique; Inert atmosphere; Irradiation; Green chemistry;	General procedure: Take a dry 25 mL schlenk tube and add 87.6 mg (0.6 mmol) chromone I-1, 42.0 mg (0.4 mmol) vinylpyridine II-1, DPZ (2.8 mg, 0.008 mmol), diphenyl phosphate (20 mg, 0.08 mmol), 1,4-dihydropyridine (HZE, 182 mg, 0.72 mmol), then add 8 mL of toluene, cap the bottle, and degas with a vacuum pump at no higher than -78C 2-3 times, 5-10 minutes each time, pass in argon gas for protection, then place it at 25, irradiate it with a 3 W blue light with a wavelength of 410-510 nm at a distance of about 3 cm from the schlenk tube, and react for 8 hours. After the reaction is over, column chromatography (petroleum ether/ethyl acetate = 10~2:1, volume ratio), rotary evaporation and concentration, vacuum drying (drying at 25C for 1 hour) to obtain 83.0 mg of yellow oil 2- The yield of (2-(pyridin-2-yl)ethyl)chroman-4-one III-1 was 82%.

References: [1]Patent: CN112759580,2021,A .Location in patent: Paragraph 0013; 0020.

Historical Records

Technical Information

• Preparation of Amines

Related Functional Groups of
[ 13959-34-7 ]

Alkenyls

A515903 [75392-24-4]

2,4-Di(styryl)pyridine

Similarity: 0.90

A566697 [98436-74-9]

2-Vinylisonicotinonitrile

Similarity: 0.88

A731082 [3883-39-4]

5-Methyl-2-vinylpyridine

Similarity: 0.87

A139114 [1122-70-9]

6-Methyl-2-vinylpyridine

Similarity: 0.86

A797038 [104188-16-1]

4-Methyl-2-(2-methylprop-1-en-1-yl)pyridine

Similarity: 0.85

Related Parent Nucleus of
[ 13959-34-7 ]

Pyridines

A515903 [75392-24-4]

2,4-Di(styryl)pyridine

Similarity: 0.90

A566697 [98436-74-9]

2-Vinylisonicotinonitrile

Similarity: 0.88

A731082 [3883-39-4]

5-Methyl-2-vinylpyridine

Similarity: 0.87

A139114 [1122-70-9]

6-Methyl-2-vinylpyridine

Similarity: 0.86

A797038 [104188-16-1]

4-Methyl-2-(2-methylprop-1-en-1-yl)pyridine

Similarity: 0.85

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CAS No.: 13959-34-7

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