4-ISOPROPYLPYRIDINE

Name	4-isopropylpyridine
Synonyms	Isopropylpyridine 4-Isopropylpyridine 4-ISOPROPYLPYRIDINE 4-isopropylpyridine 4-(propan-2-yl)pyridine gamma-Isopropylpyridine 4-(1-methylethyl)-pyridin 4-(1-Methylethyl)pyridine 4-(1-methylethyl)-pyridine Pyridine, 4-(1-methylethyl)-
CAS	696-30-0
EINECS	211-794-5
InChI	InChI=1/C8H11N/c1-7(2)8-3-5-9-6-4-8/h3-7H,1-2H3

Molecular Formula	C8H11N
Molar Mass	121.18
Density	0,93 g/cm3
Melting Point	-54.9°C
Boling Point	178 °C
Flash Point	66°C
Vapor Presure	1.421mmHg at 25°C
pKa	pK1:6.02(＋1) (25°C)
Storage Condition	Inert atmosphere,Room Temperature
Refractive Index	1.4940 to 1.4970
MDL	MFCD00039719

Risk Codes	R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.

Use	4-isopropylpyridine is used as a reagent for the synthesis of bis (alkylpyridine), which is antifungal and cytotoxic.
Preparation method	The preparation of 4-isopropylpyridine is as follows: 1) At 0°C, to a mixture of 5.1g(14.3mmol)Ph3PhCH3Br in 25 mLHF, 11.0mLn-BuLi(1.6M hexane solution) is added dropwise within 20 minutes. After 1 hour, 1.5g(12.8mmol) of 1-(pyridine-4-yl) ethanone was added to 20mL of THF. The mixture was stirred at 0°C for 1 hour, then at room temperature for 50 minutes. The mixture was filtered through a Brinell funnel. Saturated NH4Cl and H2O were added to separate the layers. The organic layer was washed with brine, dried with Na2SO4, filtered and concentrated. Purified by rapid silica gel chromatography (54% EtOAc/hexane) to obtain isopropenylpyridine, which is a light yellow liquid. 2) At room temperature, stir a mixture of 4-(prop-1-en-2-yl) pyridine and 342mg 20% Pd(OH)2 in 15mLEtOAc and 10mLMeOH under an H2 balloon. After 24 hours, 305mg of 20% Pd(OH) was added for 2,6 hours, and the mixture was filtered through diatomite, filtered and concentrated. The crude product was dissolved in 15mLMeOH and 512mg 20% Pd(OH)2 was added. The mixture was stirred in a H2 balloon for 11.5 h at room temperature, filtered through diatomaceous earth, and concentrated to give 4-isopropylpyridine.
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)

Last Update：2024-04-10 22:29:15

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