696-30-0

Basic information

• Product Name: 4-Isopropylpyridine
• Synonyms: 4-(1-methylethyl)-pyridin;4-(1-Methylethyl)pyridine;4-(1-methylethyl)-pyridine;Pyridine, 4-(1-methylethyl)-;4-ISOPROPYLPYRIDINE;Isopropylpyridine,98%;gamma-Isopropylpyridine;4-ISOPROPYLPYRIDINE (GAMMA-) 98+%
• CAS NO: 696-30-0
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• EINECS: 211-794-5
• Mol File: 696-30-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: -54.9°C
• Boiling Point: 178 °C
• Flash Point: 66°C
• Appearance: /
• Density: 0,93 g/cm3
• Vapor Pressure: 1.421mmHg at 25°C
• Refractive Index: 1.4940 to 1.4970
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: pK1:6.02(＋1) (25°C)
• CAS DataBase Reference: 4-Isopropylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropylpyridine(696-30-0)
• EPA Substance Registry System: 4-Isopropylpyridine(696-30-0)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 696-30-0(Hazardous Substances Data)

Usage

Uses

4-Isopropylpyridine serves as a reagent in the synthesis of Bis(alkylpyridinium) with antifungal and cytotoxic properties.

Chemical Properties

Liquid. Solubility in 100 g, 19.4 g at 20C.

InChI:InChI=1/C8H11N/c1-7(2)8-3-5-9-6-4-8/h3-7H,1-2H3

Synthetic route

(pyridin-4-yl)-α-methylstyrene (17755-30-5) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
With (bis-1,2-diphenylphosphinoethane)Co(CH2SiMe3)2; hydrogen In toluene at -196.15 - 25℃; under 3040.2 Torr; for 6h; Reagent/catalyst; Sealed tube;	68%
With hydrogen; palladium(II) hydroxide/carbon In methanol; ethyl acetate at 20℃; for 41.5h;

4-Isopropylpiperidine (19678-58-1) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
In octane at 120℃; under 760.051 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	95 %Chromat.

2-bromo-2-(4-pyridyl)propane → 4-s-propylpyridine (696-30-0) + 2,3-dimethyl-2,3-di-4-pyridylbutane (25128-23-8)

Conditions	Yield
With chromium chloride; lithium borohydride In tetrahydrofuran at 25℃; for 15h; Yields of byproduct given;	A n/a B 64%

2-(1-(methoxycarbonyl)-1,4-dihydropyridin-4-yl)-2-methylpropanoic acid (455258-20-5) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
With air In toluene Heating;	80%

1-(2,5-Dimethyl-pyrrol-1-yl)-4-isopropyl-1,4-dihydro-pyridine → 4-s-propylpyridine (696-30-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran for 20h; Heating;	74%

4-Ethylpyridine (536-75-4) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
With ammonia; potassium amide anschliessend Behandeln mit Methylchlorid;

picoline (108-89-4) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amide; liquid ammonia 2: potassium amide; liquid ammonia / anschliessend Behandeln mit Methylchlorid View Scheme

1-(4-Isopropyl-4H-pyridin-1-yl)-ethanone → 4-s-propylpyridine (696-30-0)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 1.16667h; Inert atmosphere;	0.41 g

pyridine (110-86-1) + 2-iodo-propane (75-30-9) → 4-s-propylpyridine (696-30-0) + 2-isopropylpyridine (644-98-4)

Conditions	Yield
at 200 - 240℃; for 16h; autoclave;	A 7% B 5%
at 300℃;

2-(4-pyridyl)propan-2-ol (15031-78-4) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
With phosphorus; hydrogen iodide at 140℃;
With phosphorus; hydrogen iodide at 150 - 160℃;

pyridine (110-86-1) + isopropylmercury(II) chloride (30615-19-1) → 4-s-propylpyridine (696-30-0) + 2-isopropylpyridine (644-98-4)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 40℃; for 12h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2-isopropylallyl alcohol (26903-66-2) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2, pyridine 2: 1.) Mg / 1) THF, 2 h, room temperature; 2) THF, night 3: H2, Et3N, RhCl(CO)(PPh3)2 / 36 h / 80 - 100 °C / 76000 Torr 4: NH2OH*HCl / ethanol; H2O / 12 h / Heating View Scheme
Multi-step reaction with 4 steps 1: SOCl2, pyridine 2: 1.) Mg / 1) THF, 2 h, room temperature; 2) THF, room temperature (night), reflux (6 d) 3: H2, Et3N, RhCl(CO)(PPh3)2 / 36 h / 80 - 100 °C / 76000 Torr 4: NH2OH*HCl / ethanol; H2O / 12 h / Heating View Scheme

2-i.propylallyl chloride (78156-21-5) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Mg / 1) THF, 2 h, room temperature; 2) THF, night 2: H2, Et3N, RhCl(CO)(PPh3)2 / 36 h / 80 - 100 °C / 76000 Torr 3: NH2OH*HCl / ethanol; H2O / 12 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 1.) Mg / 1) THF, 2 h, room temperature; 2) THF, room temperature (night), reflux (6 d) 2: H2, Et3N, RhCl(CO)(PPh3)2 / 36 h / 80 - 100 °C / 76000 Torr 3: NH2OH*HCl / ethanol; H2O / 12 h / Heating View Scheme

1,1-diethoxy-3-i.propylbut-3-ene (78156-23-7) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2, Et3N, RhCl(CO)(PPh3)2 / 36 h / 80 - 100 °C / 76000 Torr 2: NH2OH*HCl / ethanol; H2O / 12 h / Heating View Scheme

3-i.propyl-5,5-diethoxypentanal (78156-25-9) → 4-s-propylpyridine (696-30-0) + 3-isopropylpyridine (6304-18-3)

Conditions	Yield
With hydroxylamine hydrochloride In ethanol; water for 12h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

methyl (4-pyridyl) ketone (1122-54-9) → 4-s-propylpyridine (696-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 20 °C / Schlenk technique 1.2: 1 h / 20 °C / Schlenk technique 2.1: (bis-1,2-diphenylphosphinoethane)Co(CH2SiMe3)2; hydrogen / toluene / 6 h / -196.15 - 25 °C / 3040.2 Torr / Sealed tube View Scheme

pyridine (110-86-1) + 2-iodo-propane (75-30-9) → picoline (108-89-4) + 4-s-propylpyridine (696-30-0)

Conditions	Yield
at 200 - 240℃; for 16h; autoclave;	A 5% B 7%

pyridine (110-86-1) + petroleum ether → 4-s-propylpyridine (696-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 0.08 h / 0 °C View Scheme

pyridine (110-86-1) + 1-iodo-propane (107-08-4) → 4-s-propylpyridine (696-30-0) + 2-isopropylpyridine (644-98-4)

Conditions	Yield
at 300℃;

1-Iodo-4-isopropyl-pyridinium → 4-s-propylpyridine (696-30-0) + I(1+)

Conditions	Yield
at 59.9℃; Thermodynamic data; gas-phase;

2,3-dimethyl-2,3-di-4-pyridylbutane (25128-23-8) → (pyridin-4-yl)-α-methylstyrene (17755-30-5) + 4-s-propylpyridine (696-30-0)

Conditions	Yield
With 9,10-dihydroanthracene In toluene at 225℃; Kinetics; Thermodynamic data; thermolysis; various temp.; ΔG(excit.), ΔH(excit.), ΔS(excit.);

N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium tetrafluoroborate + i-PrMgHal → 4-s-propylpyridine (696-30-0) + 4'-Isopropyl-2,6-dimethyl-4'H-[1,1']bipyridinyl-4-one (76160-95-7)

Conditions	Yield
In tetrahydrofuran Heating; Title compound not separated from byproducts;

diisopropylamine (108-18-9) + trans-β-(p-nitrophenylsulphonyl)vinyl-4-isopropylpyridinium chloride → 4-s-propylpyridine (696-30-0) + p-nitrophenyl trans-β-diisopropylaminovinyl sulfone

Conditions	Yield
With pyridine In acetonitrile at 25℃; Rate constant; var. concentr. of the reagent and diisopropylamine;

isopropylmagnesium bromide (920-39-8) + t-butyldimethylsilylpyridinium triflate → 4-s-propylpyridine (696-30-0) + 2-isopropylpyridine (644-98-4)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium tetrafluoroborate + i-PrMgHal → 4-s-propylpyridine (696-30-0) + 2,6-dimethyl-1H-pyridin-4-one (7516-31-6)

Conditions	Yield
1.) THF, reflux, overnight, 2.) MeCN, reflux, 10 h; Yield given. Multistep reaction;

4-Ethylpyridine (536-75-4) → pyridine (110-86-1) + picoline (108-89-4) + (pyridin-4-yl)-α-methylstyrene (17755-30-5) + 4-s-propylpyridine (696-30-0)

Conditions	Yield
With γ-Al2O3 at 500℃; Product distribution; Further Variations:; Reagents; Temperatures;	A 0.7% B 19.9% C 0.5% D 15.8%

picoline (108-89-4) + ammonia (7664-41-7) + sodium amide → 4-Ethylpyridine (536-75-4) + 4-tert-butylpyridine (3978-81-2) + 4-s-propylpyridine (696-30-0)

Conditions	Yield
Product distribution; anschliessend Behandeln mit Methylchlorid;

N-i-propylpyridinium iodide (6992-92-3) → 4-s-propylpyridine (696-30-0) + 2-isopropylpyridine (644-98-4)

Conditions	Yield
at 290 - 300℃; im Rohr;

(pyridin-4-yl)-α-methylstyrene (17755-30-5) + hydrogen iodide (10034-85-2) → 4-s-propylpyridine (696-30-0)

2-[4]pyridyl-allyl alcohol (57360-16-4) + hydrogen iodide (10034-85-2) → 4-s-propylpyridine (696-30-0)

4-s-propylpyridine (696-30-0) + benzyl bromide (100-39-0) → 1-benzyl-4-isopropylpyridin-1-ium bromide (87321-22-0)

Conditions	Yield
In acetone at 55℃;	100%
In dichloromethane Heating;

4-s-propylpyridine (696-30-0) + p-nitrophenyl trans-β-chlorovinyl sulfone (57992-01-5) → trans-β-(p-nitrophenylsulphonyl)vinyl-4-isopropylpyridinium chloride

Conditions	Yield
In acetonitrile at 25℃; for 1h; Rate constant;	95%
In acetonitrile at 25℃; for 1h;	95%

4-s-propylpyridine (696-30-0) → 4-isopropylpyridine 1-oxide (22581-87-9)

Conditions	Yield
With dihydrogen peroxide; acetic acid In water for 4h; Heating / reflux;	94%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 22h; Inert atmosphere; Cooling with ice;	31%
With dihydrogen peroxide; acetic acid

4-s-propylpyridine (696-30-0) + formaldehyd (50-00-0) → 2-methyl-2-(4-pyridyl)-1-propanol (34995-28-3)

Conditions	Yield
In water Heating;	84%

4-s-propylpyridine (696-30-0) + 1,3-bis(triflyloxy)propane (63256-90-6) → 1,1'-(propane-1,3-diyl)bis(4-isopropylpyridin-1-ium) bis(trifluoromethanesulfonate)

Conditions	Yield
In neat (no solvent) at 20 - 50℃; for 1h; Inert atmosphere;	81%

4-chloro-2-oxo-2,3-dihydrothiazole-5-carbaldehyde (55359-96-1) + 4-s-propylpyridine (696-30-0) → C12H12N2O2S (85833-48-3)

Conditions	Yield
	80%

4-s-propylpyridine (696-30-0) + bis(μ-acetato)dicarbonyldichlorodiiridium(II) (259672-87-2) → [Ir2Cl2(CO)2(O2CCH3)2(NC5H4CH(CH3)2)2] (259672-92-9)

Conditions	Yield
In dichloromethane stirring (3 h); evapn. to dryness, dissoln. (CH2Cl2), chromy. (SiO2; CH2Cl2/hexane); elem. anal.;	78%

4-s-propylpyridine (696-30-0) + 4-chlorobenzoylmethyl bromide (536-38-9) → 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(propan-2-yl)pyridinium bromide (1215283-27-4)

Conditions	Yield
In acetonitrile at 23℃;	78%
In acetonitrile at 23℃;	78%

4-s-propylpyridine (696-30-0) + cobalt(II) chloride hydrate + butane-2,3-dione dioxime (95-45-4) → Co(dmgH)2Cl(4-iPr-Py)

Conditions	Yield
Stage #1: cobalt(II) chloride hydrate; butane-2,3-dione dioxime In acetone Stage #2: 4-s-propylpyridine In methanol for 0.5h;	78%

4-s-propylpyridine (696-30-0) + cobalt(II) chloride hydrate + benzildioxime (23873-81-6) → Co(dpgH)2Cl(4-iPr-Py)

Conditions	Yield
Stage #1: cobalt(II) chloride hydrate; benzildioxime In acetone Stage #2: 4-s-propylpyridine In methanol for 0.5h;	71%

4-s-propylpyridine (696-30-0) + chloro-methylsulfanyl-methane (2373-51-5) → 4-(1,1-dimethyl-2-(methylthio)ethyl)pyridine (103905-24-4)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In hexane at -78℃; for 12h;	62%

4-s-propylpyridine (696-30-0) + (meso-tetra-p-tolylporphyrinato)Mo=NC6H5*(H2NC6H5)(x) → trans-(4-isopropylpyridine)(meso-tetra-p-tolylporphyrinato)Mo=NPh (868666-08-4)

Conditions	Yield
In not given byproducts: C6H5NH2; recrystn. (toluene/hexane);	61%

4-s-propylpyridine (696-30-0) + phenyl chloroformate (1885-14-9) → 4-isopropyl-1-phenoxycarbonyl-1,2-dihydropyridine

Conditions	Yield
Stage #1: 4-s-propylpyridine With sodium tetrahydroborate In methanol at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenyl chloroformate In methanol at -78℃; for 3h; Inert atmosphere;	56%

4-s-propylpyridine (696-30-0) + 1,12-dibromododecane (3344-70-5) → 1,12-bis(4'-isopropylpyridinium)dodecane dibromide

Conditions	Yield
In 4-methyl-2-pentanone Reflux; Inert atmosphere;	50%
In 4-methyl-2-pentanone for 18h; Heating / reflux;	50%

4-s-propylpyridine (696-30-0) → 2-fluoro-4-isopropylpyridine (111887-69-5)

Conditions	Yield
With fluorine In 1,1,2-Trichloro-1,2,2-trifluoroethane at -25℃;	47%

4-s-propylpyridine (696-30-0) + formaldehyd (50-00-0) + dimethyl amine (124-40-3) → β,β-dimethyl-N,N-dimethyl-4-pyridineethanamine (167649-34-5)

Conditions	Yield
With acetic acid for 72h; Mannich reaction; Heating;	42%

4-s-propylpyridine (696-30-0) + perfluoro-cis-2-n-butyl-3-n-propyloxaziridine → 4-isopropylpyridine 1-oxide (22581-87-9) + 4-Isopropyl-N-(perfluorobutanoyl)pyridinium-1-aminide

Conditions	Yield
In chloroform; trichlorofluoromethane at -60℃; for 0.5h;	A 40% B 24%

4-s-propylpyridine (696-30-0) → 4-isopropylpyridine 1-oxide (22581-87-9) + 4-Isopropyl-N-(perfluorobutanoyl)pyridinium-1-aminide

Conditions	Yield
With perfluoro(cis-2-butyl-3-propyloxaziridine) In chloroform; trichlorofluoromethane at -60℃; for 0.5h;	A 40% B 24%

4-s-propylpyridine (696-30-0) + 2-amino-3-chloroquinoxaline (34117-90-3) → 2-Isopropyl-4a,5,10,11-tetraaza-benzo[b]fluorene (127376-20-9)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 48h;	38%
In N,N-dimethyl-formamide at 80℃; for 48h; Cyclization;	37.6%

4-s-propylpyridine (696-30-0) + acetic anhydride (108-24-7) + dimethyl sulfoxide (67-68-5) → 2-methyl-2-(4-pyridyl)-1-propanol (34995-28-3) + Acetic acid 2-methyl-2-pyridin-4-yl-propyl ester (120414-14-4)

Conditions	Yield
In acetic acid at 120℃; for 24h;	A 20% B 20%

piperidine (110-89-4) + 4-s-propylpyridine (696-30-0) + formaldehyd (50-00-0) → 1-[2-methyl-2-(4-pyridinyl)propyl]piperidine (478363-92-7)

Conditions	Yield
With acetic acid for 72h; Mannich reaction; Heating;	17%

4-s-propylpyridine (696-30-0) + formaldehyd (50-00-0) + piperidine hydrochloride (6091-44-7) → 1-[2-methyl-2-(4-pyridinyl)propyl]piperidine (478363-92-7)

Conditions	Yield
Stage #1: 4-s-propylpyridine; formaldehyd; piperidine hydrochloride In ethanol for 48h; Heating / reflux; Stage #2: With sodium hydroxide In water	17%

Upstream product

• 110-86-1 pyridine 
• 75-30-9 2-iodo-propane 
• 107-08-4 1-iodo-propane 
• 536-75-4 4-Ethylpyridine 
• 6992-92-3 N-i-propylpyridinium iodide 
• 455258-20-5 2-(1-(methoxycarbonyl)-1,4-dihydropyridin-4-yl)-2-methylpropanoic acid 
• 1631179-23-1 1,3-dioxoisoindolin-2-yl isobutyrate 
• 59137-44-9 3-carboxy-2-(pyridin-1-ium-1-yl)propanoate 
• 75-26-3 isopropyl bromide 
• 19678-58-1 4-Isopropylpiperidine 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 17755-30-5 (pyridin-4-yl)-α-methylstyrene 
• 108-89-4 picoline 
• 78156-23-7 1,1-diethoxy-3-i.propylbut-3-ene 

Downstream Products

• 15031-78-4 2-(4-pyridyl)propan-2-ol 
• 3978-81-2 4-tert-butylpyridine 
• 19678-58-1 4-Isopropylpiperidine 
• 22581-87-9 4-isopropylpyridine 1-oxide 
• 34995-28-3 2-methyl-2-(4-pyridyl)-1-propanol 
• 120414-14-4 Acetic acid 2-methyl-2-pyridin-4-yl-propyl ester 
• 111887-69-5 2-fluoro-4-isopropylpyridine 
• 55-22-1 pyridine-4-carboxylic acid 
• 108-89-4 picoline 
• 536-75-4 4-Ethylpyridine 
• 17755-30-5 (pyridin-4-yl)-α-methylstyrene 
• 187737-37-7 propene 
• 167710-59-0 1-[2-(4-chlorophenoxy)-2-methyl-1-oxopropyl]-β,β,N,N-tetramethyl-4-piperidineethaneamine 
• 478363-99-4 β,β,N,N-tetramethyl-1-[2-[4-(2-methylpropyl)phenyl]-1-oxopropyl]-4-piperidineethaneamine 

Relevant articles and documents

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