2-(2-Methylpropyl)pyridine Chemical Properties

Boiling point:

180-185 °C

Density 

0.899

FEMA 

3370 | 2-(2-METHYLPROPYL)PYRIDINE

storage temp. 

Inert atmosphere,Room Temperature

pka

5.83±0.19(Predicted)

Odor

at 0.10 % in dipropylene glycol. strong aromatic bell pepper

Odor Type

aromatic

JECFA Number

1311

LogP

2.60

CAS DataBase Reference

6304-24-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

MSDS

• Language:English Provider:ALFA

2-(2-Methylpropyl)pyridine Usage And Synthesis

Description

May be prepared from 2-pycolyllithium and isopropyl bromide; from 2-methyl pyridine and isopropyl bromide in liquid ammonia in the presence of potassium metal and ferric nitrate.

Preparation

From β-picoline with NaNH2 and alkyl chloride or bromide.

Definition

ChEBI: 2-(2-Methylpropyl)pyridine is a member of pyridines.

Synthesis

The methylation reaction was carried out by General Method 2 using 2-ethylpyridine and trimethylcyclotriboroxane as raw materials. Upon completion of the reaction, the products were purified by column chromatography to give two products: 21 (2-propylpyridine) as a colorless oil (19.1 mg, 79% yield) and 13a (2-isobutylpyridine) as a colorless oil (3.0 mg, 11% yield). The NMR data for 21 (2-propylpyridine) are as follows: 1H NMR (400 MHz, CDCl3) δ 8.53 (d, J = 4.8 Hz, 1H), 7.58 (td, J = 7.6, 1.6 Hz, 1H), 7.14 (d, J = 8.0 Hz, 1H), 7.11-7.08 (m, 1H), 2.77 (t, J = 7.6 Hz, 2H), 1.81-1.71 (m, 2H), 0.97 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 162.35, 149.26, 136.25, 122.83, 120.94, 40.49, 23.19, 13.94; HRMS (EI): calculated value C8H11N (M+) 121.0891, measured value 121.0893. The NMR data of 13a (2-isobutylpyridine) are as follows: 1H NMR (400 MHz, CDCl3) δ 8.53 (d, J = 4.4 Hz, 1H), 7.58 (td, J = 7.6, 1.6 Hz, 1H), 7.12-7.08 (m, 2H), 2.65 (d, J = 7.6 Hz, 2H), 2.15-2.05 (m, 1H), 0.93 (d, J = 6.8 Hz, 6H); 13C NMR (100 MHz). 13C NMR (100 MHz, CDCl3) δ 161.89, 149.50, 136.34, 123.81, 121.19, 47.93, 29.57, 22.74; HRMS (EI): calculated value C9H13N (M+) 135.1048, measured value 135.1046. Reaction conditions: in a 40 mL reaction tube, the substrate (0.2 mmol, 1 eq.), Pd(OAc)2 (4.5 mg, 0.02 mmol, 10 mol%), methyl cycloboroxane (55.7 μL, 0.4 mmol, 2 eq.), Cu(OAc)2 (72.8 mg, 0.4 mmol, 2 eq.) and benzoquinone (43.2 mg, 0.4 mmol, 2 eq.) were mixed together. 0.4 mmol, 2 eq.) were dissolved in 1 mL of acetic acid and reacted under oxygen atmosphere. The reaction tube was sealed with a PTFE-lined cap and the reaction mixture was stirred at 100 °C for 24 hours. After completion of the reaction, it was neutralized to pH=8-9 with 4N NaOH aqueous solution and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a diatomaceous earth pad and the diatomaceous earth was washed with 20 mL of dichloromethane. The filtrate was washed twice with saturated brine and the organic layer was dried with Na2SO4 and concentrated in vacuum. The residue was purified by silica gel column chromatography (eluent: hexane:ether=10:1) to give the methylated product.

References

[1] Journal of the American Chemical Society, 2006, vol. 128, # 39, p. 12634 - 12635
[2] Patent: WO2008/24953, 2008, A2. Location in patent: Page/Page column 6; 62; 67-68
[3] Patent: WO2008/24953, 2008, A2. Location in patent: Page/Page column 6; 62; 67-68

2-(2-Methylpropyl)pyridine(6304-24-1)Related Product Information

• SERPENTINE HYDROGEN TARTRATE
• 3-ISOBUTYLPYRIDINE
• 9-AMINO-3,3-DIMETHYL-3,4-DIHYDRO-1(2H)-ACRIDINONE
• 2-AMINO-4-(2-CHLOROPHENYL)-6-ISOBUTYLNICOTINONITRILE
• 2,3-BIS[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]PROPANENITRILE
• 2-AMINO-4-(2,3-DICHLOROPHENYL)-6-ISOBUTYLNICOTINONITRILE
• N-(1,10-PHENANTHROLIN-5-YL)BROMOACETAMIDE
• 5-(4-CHLOROPHENYL)-3-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-3AH-PYRROLO[3,4-D]ISOXAZOLE-4,6(5H,6AH)-DIONE
• 2-AMINO-4-(4-CHLOROPHENYL)-6-ISOBUTYLNICOTINONITRILE
• 2-AMINO-7,7-DIMETHYL-7,8-DIHYDRO-5H-PYRANO[4,3-B]PYRIDINE-3-CARBOXYLIC ACID
• 2-AMINO-4-(3-CHLOROPHENYL)-6-ISOBUTYLNICOTINONITRILE
• DIETHYL 2-(ACETYLAMINO)-2-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]METHYL)MALONATE
• AURORA KA-3427
• 4-(1,3-DIOXO-1,3-DIHYDRO-2H-INDEN-2-YLIDEN)-2-PHENYL-6-(2-PYRIDINYL)TETRAHYDROPYRROLO[3,4-C]PYRROLE-1,3(2H,3AH)-DIONE
• 2,3-DI(2-PYRIDYL)OXIRANE-2-CARBOXAMIDE
• SERPENTINE TARTRATE
• N-(1,10-PHENANTHROLIN-5-YL)IODOACETAMIDE
• 2,3-DI-2-PYRIDYL-2,3-BUTANEDIOL, 99%, MIXTURE OF (+/-) AND MESO