[ CAS No. 3883-39-4 ] {[proInfo.proName]}

Name: 3883-39-4|5-Methyl-2-vinylpyridine|95% mix TBC as stabilizer
Brand: Ambeed
SKU: A731082
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Quality Control of [ 3883-39-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 3883-39-4 ]

CAS No. :	3883-39-4	MDL No. :	MFCD08703184
Formula :	C₈H₉N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LCFYCLRCIJDYQD-UHFFFAOYSA-N
M.W :	119.16	Pubchem ID :	12503355
Synonyms :

Safety of [ 3883-39-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3883-39-4 ]

* 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 [ 3883-39-4 ]

[ 3883-39-4 ] Synthesis Path-Downstream 1~37

1
[ 151-50-8 ]
[ 3883-39-4 ]
[ 71858-93-0 ]

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

2
[ 3883-39-4 ]
[ 1193-02-8 ]
[ 136401-90-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1440 - 1445

3
[ 3883-39-4 ]
[ 76162-63-5 ]

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

4
[ 941-69-5 ]
[ 3883-39-4 ]
5-(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-8-methyl-2-phenyl-3a,4,5,9b-tetrahydro-pyrrolo[3,4-f]quinoline-1,3-dione [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 833 - 836
Khimiya Geterotsiklicheskikh Soedinenii,1980,p. 1075 - 1078

5
[ 30148-50-6 ]
[ 3883-39-4 ]
bis(trimethylsilyl) 2-(2-pyridyl)ethylphosphonite [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1996,vol. 66,p. 1999 - 2000
Zhurnal Obshchei Khimii,1996,vol. 66,p. 2055 - 2056

7
[ 3883-39-4 ]
[ 80379-05-1 ]
1-(3'-butenyl)-5-methyl-2-vinylpyridinium triflate [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4125 - 4127
[2]Journal of Organic Chemistry,2009,vol. 74,p. 4166 - 4176

8
[ 3883-39-4 ]
[ 136401-59-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1440 - 1445

9
[ 3883-39-4 ]
2-Bromo-3-{4-[2-(5-methyl-pyridin-2-yl)-ethylsulfanyl]-phenyl}-propionic acid methyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1440 - 1445

10
[ 3883-39-4 ]
[ 136401-80-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1440 - 1445

11
[ 3883-39-4 ]
[ 132554-32-6 ]

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

12
[ 3883-39-4 ]
[ 132554-28-0 ]

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

13
[ 3510-66-5 ]
[ 7486-35-3 ]
[ 3883-39-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 120℃; for 18.0h;	Step 1: Preparation of 5-methyl-2-vinylpyridine To a solution of 3 g (17.4 mmol) of 2-bromo-5-methylpyridine in 30 ml of dimethylformamide was successively added 2 g (1.7 mmol) of tetrakis (triphenylphosphine)palladium and 5.52 g (17.4 mmol) of tributyl(vinyl)tin. The reaction mixture was stirred at 120C for 18 hours. After cooling, the reaction mixture was poured into 50 ml of water saturated with potassium fluoride and stirred for 1 hour. The mixture was filtered on supersel and the aqueous phase was extracted with ethyl ether. The organic phase was washed twice with water saturated with potassium fluoride, once with water and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give 3.5 g of a crude mixture as a yellow oil. The mixture was purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 4/1) to give 5-methyl-2-vinylpyridine as a yellow oil: 0.9 g (43%); mass spectrum: 120 (M+1).

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 4166 - 4176
[2]Patent: EP1500651,2005,A1 .Location in patent: Page 29

14
[ 136918-14-4 ]
[ 3883-39-4 ]
2-[2-(5-methyl-2-pyridinyl)ethyl]-1H-isoindole-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With N-benzyl-trimethylammonium hydroxide; at 200℃; for 3.0h;	Step 2: Preparation of 2-[2-(5-methyl-2-pyridinyl)ethyl]-1-H-isoindole-1,3(2H)-dione 0.5 g (4.2 mmol) of <strong>[3883-39-4]5-methyl-2-vinylpyridine</strong> and 0.618 g (4.2 mmol) of phthalimide was added to 0.5 ml of benzyltrimethylammonium hydroxide (Triton B) and the mixture was heated at 200C for 3 hours. The mixture was allowed to cool to room temperature and was directly purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 5/1) to give 2-[2-(5-methyl-2-pyridinyl)ethyl]-1H-isoindole-1,3(2H)-dione as white crystals: 0.680 g (59%); mass spectrum: 267 (M+1).

Reference： [1]Patent: EP1500651,2005,A1 .Location in patent: Page 29

15
[ 137729-45-4 ]
[ 3883-39-4 ]
(BH(C₃H₃N₂)3)RuCl(NOC₂H₂NC₅H₃CH₃) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 10508 - 10509

16
[ 3883-39-4 ]
[ 93102-05-7 ]
[ 1257521-42-8 ]

Yield	Reaction Conditions	Operation in experiment
35%	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 2.0h;	Step 2; To a stirred solution of <strong>[3883-39-4]5-methyl-2-vinylpyridine</strong> (600 mg, 1.87 mmol) in dry CH2CI2 (6 mL) was added N-benzyl-1-methoxy-N- ((trimethylsilyl)methyl)methanamine (1.42 g, 6.0 mmol) and TFA (570 mg, 5.0 mmol) at 00C. The mixture was stirred at rt for 2 TLC showed the disappearance of starting material. The mixture was quenched with satd aq NaHCO3 (15 mL) and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with water (40 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column on silica cartridge eluted with PE/EA=5:1 to afford 2-(1-benzyl-pyrrolidin-3-yl)-5-methyl-pyridine (450 mg, 35%) as a yellow oil

Reference： [1]Patent: WO2010/141424,2010,A1 .Location in patent: Page/Page column 55

17
[ 3510-66-5 ]
[ 92988-08-4 ]
[ 3883-39-4 ]

Yield	Reaction Conditions	Operation in experiment
75.6%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 100℃;Inert atmosphere;	Step 1; To a stirred mixture of 2-bromo-5-methyl-pyridine (1.7 g, 10 mmol), 2,4,6- trivinyl-cyclotriboroxanein (1.20 g, 5 mmol) and Na2CO3 (3.73 g, 35.2 mmol) in toluene (15 mL) / EtOH (10 mL) / H2O (5 mL) was added Pd(PPh3)4 (300 mg, 0.25 mmol) under N2. The mixture was stirred at 100 0C overnight. The resulting mixture was quenched with water (20 mL) and extracted with EtOAc (30 mL x 3).The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column (PE:EA=50:1 ) to afford 5-methyl-2-vinyl-pyridine (900 mg, 75.6%) as a yellow oil.

Reference： [1]Patent: WO2010/141424,2010,A1 .Location in patent: Page/Page column 54-55

18
[ 4985-92-6 ]
[ 2065-66-9 ]
[ 3883-39-4 ]

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

19
Dihydroxy-styryl-boran [ No CAS ]
[ 3883-39-4 ]
1-phenyl-4-(5-methyl-2-pyridyl)-1-butene [ No CAS ]

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

20
[ 3510-66-5 ]
potassium vinyltrifluoroborate [ No CAS ]
[ 3883-39-4 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; at 100℃; for 2.0h;Inert atmosphere;	To a stirred solution of 2-bromo-5-methylpyridine (23.8 g, 138.0 mmol) and potassium vinyl trifluoroborate (20.39 g, 152.0 mmol) in dioxane (235 mL) under nitrogen was added Pd(dppf)2Cl2 (11.30 g, 13.8 mmol), cesium carbonate (135.0 g, 415.0 mmol), and water (41.5 mL). The resulting mixture heated to 100C for 2 hours. The reaction was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 0-30% ethyl acetate/ hexane gradient gave E-1 as a volatile oil, which was carried on directly to next step.

Reference： [1]Chemical Science,2020,vol. 11,p. 5205 - 5212
[2]Patent: WO2013/28590,2013,A1 .Location in patent: Page/Page column 37; 38

21
[ 3883-39-4 ]
[ 1424376-33-9 ]