2,6-Di-tert-butylpyridine supplier

Name
2,6-Di-tert-butylpyridine
EINECS 209-557-6
CAS No. 585-48-8
Article Data10
CAS DataBase
Density 0.885 g/cm³
Solubility Miscible with alcohol, acetone, and hexane. Immiscible with water.
Melting Point 2°C(lit.)
Formula C₁₃H₂₁N
Boiling Point 208.5 °C at 760 mmHg
Molecular Weight 191.316
Flash Point 72.2 °C
Transport Information UN 3267
Appearance dark brown liquid
Safety 37/39-26-36/37/39-36
Risk Codes 36/37/38-22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Pyridine,2,6-di-tert-butyl- (6CI,7CI,8CI);2,6-Bis(1,1-dimethylethyl)pyridine;2,6-Di-tert-butylpyridine;NSC 175805;
PSA 12.89000
LogP 3.67660

Synthetic route

: 5944-41-2
2-tert-butylpyridine

: 585-48-8
2,6-di-tert-butyl-pyridine

Conditions

Conditions	Yield
With diethyl ether; tert.-butyl lithium; Petroleum ether

: 2525-19-1
1,2,6-trimethylpyridinium iodide

: 74-88-4
methyl iodide

A: 6832-21-9
2,6-di(isopropyl)pyridine

B: 5402-34-6
2-isopropyl-6-t-butylpyridine

C: 585-48-8
2,6-di-tert-butyl-pyridine

D: 74701-47-6
2-ethyl-6-isopropyl pyridine

Conditions

Conditions	Yield
With sodium hydride 1.) Dioxan, 80 deg C, 1 h, then 100 deg C, 3 h, then heating, 2 h, 2.) 250-270 deg C; Multistep reaction;
With sodium hydride 1.) Dioxan, 80 deg C, 1 h, then 100 deg C, then 3 h, heating, 2 h, 2.) 250-270 deg C; Multistep reaction;

...Expand

: 85237-75-8
2,6-di-tert-butylpiperidine

: 585-48-8
2,6-di-tert-butyl-pyridine

Conditions

Conditions	Yield
at 170℃; for 1h;	40 %Spectr.

: C39H49Cl2N3Ru

: 2,6-di-tert-butylpyridinium tetrafluoroborate

A: 585-48-8
2,6-di-tert-butyl-pyridine

B: C68H88Cl4N4Ru2

C: pyridinium tetrafluoroborate

Conditions

Conditions	Yield
In dichloromethane-d2 at 25℃; Equilibrium constant; Inert atmosphere; Sealed tube;

...Expand

: dichloro(N,N'-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(pyridine)ruthenium(II)

: 2,6-di-tert-butylpyridinium tetrafluoroborate

A: 585-48-8
2,6-di-tert-butyl-pyridine

B: C56H64Cl4N4Ru2

C: pyridinium tetrafluoroborate

Conditions

Conditions	Yield
In dichloromethane-d2 at -10℃; Equilibrium constant; Inert atmosphere; Sealed tube;

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: 2C4H10O*C24BF20*H(1+)

: 1309604-77-0
2,6-di-tert-butylpyridininum tetrakis(pentafluorophenyl)borate

Conditions

Conditions	Yield
In dichloromethane for 2h; Inert atmosphere;	95%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 15602-41-2
sodium hexacarbonylvanadate

: 104437-79-8
2,6-di-t-butylpyridinium hexacarbonylvanadate

Conditions

Conditions	Yield
In water N2-atmosphere; pH=4-5; filtration, drying (over P4O10, reduced pressure); elem. anal.;	93%

: 585-48-8
2,6-di-tert-butyl-pyridine

: (pentafluorophenyl)xenon(II) hexafluoroarsenate

: 175907-31-0
[C6F5Xe(C5H3(C(CH3)3)2N)](1+)*[AsF6](1-)=[C6F5Xe(C5H3(C(CH3)3)2N)][AsF6]

Conditions

Conditions	Yield
In dichloromethane; acetonitrile Ar atm.; 10% excess of base, stirring (-78°C), pptn.; decantation, washing (CH2Cl2, -78°C), drying (8 h, -40°C, 0.1 mbar);	92%
In water Ar atm.; equimolar ratio, stirring (0°C), pptn.; decantation, washing (CH2Cl2, 0°C), drying (8 h, -20°C, 0.1 mbar);	70%
In dichloromethane Ar atm.; 10% excess of base, stirring (-78°C, 3 h); decantation, washing (CH2Cl2, -40°C), drying (vac., 8 h, -40°C, 0.1 mbar);	61%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 358-23-6
trifluoromethylsulfonic anhydride

: 1301256-39-2
2-(4-(N-methyl-N-tert-butoxycarbonylamino)phenyl)benzo[d]thiazol-6-ol

: 2-(4-(N-methyl-N-tert-butoxycarbonylamino)phenyl)-6-trifluoromethanesulfonyloxybenzo[d]thiazole

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	92%

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1493-13-6
trifluorormethanesulfonic acid

: 134967-72-9
2,6-di-tert-butylpyridin-1-ium trifluoromethanesulfonate

Conditions

Conditions	Yield
In dichloromethane at 20℃;	91%
In dichloromethane at 0℃; for 0.0833333h;	90%
In dichloromethane at 22 - 26℃; for 0.75h; Inert atmosphere;	90%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 420-37-1
trimethoxonium tetrafluoroborate

: 343566-71-2
(6-but-3-enyl-2-hydroxypyridin-3-yl)carbamic acid benzyl ester

: 343566-72-3
(6-but-3-enyl-2-methoxypyridin-3-yl)carbamic acid benzyl ester

Conditions

Conditions	Yield
In dichloromethane; ethyl acetate	91%

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1450-14-2
1,1,1,2,2,2-hexamethyldisilane

: C16H29NSi

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 65℃; Inert atmosphere;	90%

: 67969-82-8
tetrafluoroboric acid diethyl ether

: 585-48-8
2,6-di-tert-butyl-pyridine

: 2,6-di-tert-butylpyridinium tetrafluoroborate

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 0.166667h; Inert atmosphere;	89%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 73183-34-3
bis(pinacol)diborane

: 1392146-23-4
2,6-di-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 80℃; for 0.5h; Microwave irradiation;	88%
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 55℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-di-tert-butyl-pyridine In hexane at 55℃; for 72h; Inert atmosphere;	82%
Stage #1: bis(pinacol)diborane With 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In methyl t-butylether Inert atmosphere; Sealed vial; Stage #2: 2,6-di-tert-butyl-pyridine In methyl t-butylether at 80℃; for 2h;	60%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1865-01-6
(4-nitrophenyl) formate

: 181997-31-9
(5S)-N-((3-(4-amino-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide

: 324788-61-6
5-(S)-Acetamidomethyl-3-[4'-formamido-3'-fluorophenyl]oxazolidine-2-one

Conditions

Conditions	Yield
In tetrahydrofuran; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetone	85%

...Expand

: 324788-63-8
(S)-N-[3-[3-fluoro-4-N-methylaminophenyl]-2-oxo-5-oxazolidinylmethyl]acetamide

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1865-01-6
(4-nitrophenyl) formate

: 324788-66-1
5-(S)-acetamidomethyl-3-[4'-(N-methylformamido)-3'-fluorophenyl]oxazolidine-2-one

Conditions

Conditions	Yield
In tetrahydrofuran	85%

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoate

: 69739-34-0
t-butyldimethylsiyl triflate

: phenacyl 3-(t-butyldimethylsilyloxy)2-n-tetradecyl-11-icosenoate

Conditions

Conditions	Yield
In dichloromethane; water	82.6%

...Expand

: 35812-01-2
N-bromosaccharin

: 585-48-8
2,6-di-tert-butyl-pyridine

: C20H24N2O3S

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h; Inert atmosphere; Irradiation; chemoselective reaction;	79%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 108695-90-5, 178232-84-3, 186843-76-5
[ReOCl3(OPPh3)(SMe2)]

: 101821-30-1
2-(2′-hydroxyphenyl)-2-thiazoline

: C9H8Cl3NO2ReS(1-)*C13H22N(1+)

Conditions

Conditions	Yield
In ethanol at 78℃; for 0.25h;	78%

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: 20237-92-7
2-(2'-Hydroxyphenyl)-2-oxazolin

: 108695-90-5, 178232-84-3, 186843-76-5
[ReOCl3(OPPh3)(SMe2)]

: C9H8Cl3NO3Re(1-)*C13H22N(1+)

Conditions

Conditions	Yield
In ethanol at 78℃; for 0.25h;	76%

...Expand

: 196930-46-8
(4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid

: 675-14-9
trifluoro-[1,3,5]triazine

: 585-48-8
2,6-di-tert-butyl-pyridine

: 2976-75-2
1-Naphthoxyacetic acid

: (2RS,4R)-3-((1-naphthyloxy)acetyl)-2-phenylthiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
With pyridine In C2Cl2; dichloromethane	75%

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: potassium (3-hydroxy-3-methylbut-1-yl)trifluoroborate

: C18H31NO

Conditions

Conditions	Yield
With manganese(III) triacetate dihydrate; acetic acid; trifluoroacetic acid In 2,2,2-trifluoroethanol at 60℃; for 4h; Minisci Aromatic Substitution; Schlenk technique; Inert atmosphere;	74%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 20089-07-0, 110549-12-7, 1878-18-8
2-methyl-1-butanethiol

: 2,6-di-tert-butyl-4-pyridyl 2-methyl-1-butyl sulfide

Conditions

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: 2-methyl-1-butanethiol With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	72%

: 67-56-1
methanol

: 585-48-8
2,6-di-tert-butyl-pyridine

: 38222-83-2
2,6-di-tert-butyl-4-methylpyridine

Conditions

Conditions	Yield
With hydrogenchloride; 2,4-diphenylquinoline In water for 24h; Inert atmosphere; UV-irradiation;	71%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1142-19-4
4,4'-dichlorodiphenyl disulfide

: 1393715-67-7
2,6-di-tert-butyl-4-pyridyl 4-chlorophenyl sulfide

Conditions

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; Stage #2: 4,4'-dichlorodiphenyl disulfide With [2,2]bipyridinyl; copper(l) chloride In water; dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; regioselective reaction;	68%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1666-13-3
diphenyl diselenide

: 2,6-di-tert-butyl-4-pyridyl phenyl selenide

Conditions

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: diphenyl diselenide With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	66%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: N,2,6-tri-tert-butylisonicotinamide

Conditions

Conditions	Yield
With sodium persulfate In acetonitrile at 120℃; for 24h; Sealed tube;	66%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 98-89-5
Cyclohexanecarboxylic acid

: 2,6-di-tert-butyl-4-cyclohexylpyridine

Conditions

Conditions	Yield
With hydrogenchloride; cerium(III) chloride heptahydrate; tetrabutyl-ammonium chloride In 2,2,2-trifluoroethanol; water for 17h; Schlenk technique; Inert atmosphere; Electrochemical reaction; Irradiation;	63%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1885-29-6
anthranilic acid nitrile

: Dimethyl N-[2-(cyano)phenyl]-(S)-aspartate

Conditions

Conditions	Yield
In CH3 Cl; hexane	62%
In CH3Cl; CH3Cl-hexane; hexane	62%

: 585-48-8
2,6-di-tert-butyl-pyridine

: (1-diazo-2-ethoxy-2-oxoethyl)(2-(2-ethoxy-2-oxoethoxy)carbonylphenyl)iodonium trifluoromethanesulfonate

: C17H25N3O2

Conditions

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; sodium hydrogencarbonate In acetonitrile at 20℃; for 2h; Irradiation;	56%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 112-55-0
1-dodecylthiol

: 2,6-di-tert-butyl-4-pyridyl dodecyl sulfide

Conditions

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: 1-dodecylthiol With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	53%
Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 80℃; for 1h; Inert atmosphere; Glovebox; Microwave irradiation; Stage #2: 1-dodecylthiol With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 1.5h; Inert atmosphere; Microwave irradiation; regioselective reaction;	46%

Yield

Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Schlenk technique; Inert atmosphere;
Stage #2: 1-dodecylthiol With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;

53%

Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 80℃; for 1h; Inert atmosphere; Glovebox; Microwave irradiation;
Stage #2: 1-dodecylthiol With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 1.5h; Inert atmosphere; Microwave irradiation; regioselective reaction;

46%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 7101-31-7
dimethyl diselenide

: 2,6-di-tert-butyl-4-pyridyl methyl selenide

Conditions

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-pyridine With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: dimethyl diselenide With pyridine; copper diacetate In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	53%

: 136918-14-4
phthalimide

: 585-48-8
2,6-di-tert-butyl-pyridine

: 1620204-80-9
2-(2,6-di-tert-butylpyridin-3-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 20℃; for 12h; Irradiation;	53%

: 585-48-8
2,6-di-tert-butyl-pyridine

: 27490-33-1
tri-n-butylstannylmethanol

: 333-27-7
methyl trifluoromethanesulfonate

: 207741-57-9
tert-Butyl-((3aR,6R,7S,7aR)-6-ethylsulfanyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-silane

A: (C4H9)3SnCH2OC8H12O3OH

B: (C4H9)3SnCH2OC8H12O3OH

Conditions

Conditions	Yield
In diethyl ether; dichloromethane Ar atmosphere; addn. of Sn-compd., butylpyridine, molecular seives and MeOTf to soln. of thioglycoside (stirring, 0°C, 12 h); concn. (vac.), chromy. (hexanes/EtOAc = 98:2), dissolving in THF, addn.of TBAF, stirring (2 h, room temp.), solvent removal (reduced pressure), chromy. (hexanes/EtOAc = 80:20);	A 45% B n/a

...Expand

: 585-48-8
2,6-di-tert-butyl-pyridine

: 21797-13-7
tetrakis(acetonitrile)palladium(II) tetrafluoroborate

: 75-52-5
nitromethane

: Pd(2,6-t-Bu2C5H2N)2(MeNO2)2(BF4)2

Conditions

Conditions	Yield
With styrene In nitromethane byproducts: polystyrene; dropwise addn. of 2,6-di-tert-butylpyridine to stirred soln. of Pd complex in CH3NO2, under anaerobic conditions; addn. of styrene after 1 d; stirring for 1 d;; filtration; addn. of (C2H5)2O/pentane; isolation of bottom layer; dissolving in small amt. of CH3NO2; pptn. by addn. of benzene/(C2H5)2O/pentane; pptn. in about 20 min; washing with pentane; drying under vac.; elem. anal.; detn. by gas chromy.;;	44%

Yield

With styrene In nitromethane byproducts: polystyrene; dropwise addn. of 2,6-di-tert-butylpyridine to stirred soln. of Pd complex in CH3NO2, under anaerobic conditions; addn. of styrene after 1 d; stirring for 1 d;; filtration; addn. of (C2H5)2O/pentane; isolation of bottom layer; dissolving in small amt. of CH3NO2; pptn. by addn. of benzene/(C2H5)2O/pentane; pptn. in about 20 min; washing with pentane; drying under vac.; elem. anal.; detn. by gas chromy.;;

44%

...Expand

2,6-Di-tert-butylpyridine Specification

The Pyridine, 2, 6-bis(1, 1-dimethylethyl)-, with the CAS registry number of 585-48-8, is also known as 2, 6-Bis(1, 1-dimethylethyl)pyridine. It belongs to the product categories of Pyridines, Pyrimidines, Purines and Pteredines; Heterocyclic Compounds; C9 to C46; Heterocyclic Building Blocks; Pyridines. Its EINECS registry number is 209-557-6. This chemical's molecular formula is C₁₃H₂₁N and molecular weight is 191.31. What's more, its IUPAC name is 2, 6-Ditert-butylpyridine. Besides, you must use this chemical in fume hood. Meanwhile, it should be avoided contact with strong acids, strong oxidizing agents.

Physical properties about Pyridine, 2, 6-bis(1, 1-dimethylethyl)- are: (1)ACD/LogP: 4.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.31; (4)ACD/LogD (pH 7.4): 4.07; (5)ACD/BCF (pH 5.5): 123.61; (6)ACD/BCF (pH 7.4): 724.15; (7)ACD/KOC (pH 5.5): 649.93; (8)ACD/KOC (pH 7.4): 3807.46; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 12.89 Å²; (13)Index of Refraction: 1.477; (14)Molar Refractivity: 61.11 cm³; (15)Molar Volume: 216 cm³; (16)Surface Tension: 28.1 dyne/cm; (17)Density: 0.885 g/cm³; (18)Flash Point: 72.2 °C; (19)Enthalpy of Vaporization: 42.66 kJ/mol; (20)Boiling Point: 208.5 °C at 760 mmHg; (21)Vapour Pressure: 0.307 mmHg at 25 °C.

Uses: it is used to produce other chemicals. For example, it is used to produce 2, 6-Di-tert-butylpyridine hydrotriflate. This reaction needs solvent CH₂Cl₂. The reaction time is 5 minutes with reaction temperature of 0 °C. The yield is about 90 %.

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. In addition, this chemical is harmful if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: n1c(cccc1C(C)(C)C)C(C)(C)C
(2) InChI: InChI=1/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3
(3) InChIKey: UWKQJZCTQGMHKD-UHFFFAOYAA

Product Name

2,6-Di-tert-butylpyridine

Synthetic route

2,6-Di-tert-butylpyridine Specification

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