13491-79-7

Basic information

• Product Name: 2-TERT-BUTYLCYCLOHEXANOL
• Synonyms: 2-tert-butylcyclohexanol,mixtureofisomers;ORTHO TERTIARY BUTYL CYCLOHEXANOL;O-TERT-BUTYL CYCLOHEXANOL;VERDOL;2-TERT-BUTYLCYCLOHEXANOL;2-TERT-BUTYLCYCLOHEXANOL, 99%, MIXTURE O F ISOMERS;Cyclohexanol, 2-(1,1-dimethylethyl)-;YLANATALKOHOL-ORTHO CA. 80 P.
• CAS NO: 13491-79-7
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.27
• EINECS: 236-806-6
• Product Categories: Pharmaceutical Raw Materials;C9 to C30;Oxygen Compounds;Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 13491-79-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 43-46 °C(lit.)
• Boiling Point: 209 °C
• Flash Point: 175 °F
• Appearance: white crystalline flakes and powder
• Density: 0.902 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0543mmHg at 25°C
• Refractive Index: 1.4583 (estimate)
• PKA: 15.33±0.40(Predicted)
• CAS DataBase Reference: 2-TERT-BUTYLCYCLOHEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-TERT-BUTYLCYCLOHEXANOL(13491-79-7)
• EPA Substance Registry System: 2-TERT-BUTYLCYCLOHEXANOL(13491-79-7)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN 1325 4.1/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 13491-79-7(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE FLAKES AND POWDER

Uses

2-tert-Butylcyclohexanol was used in the synthesis of 2-tert-butylcyclohexyl methacrylate via reaction with methacryloyl chloride in the presence of triethylamine.

General Description

2-tert-Butylcyclohexanol is the major metabolite of (+/-)-2-tert-butylcyclohexanone.

InChI:InChI=1/C10H20O/c1-10(2,3)8-6-4-5-7-9(8)11/h8-9,11H,4-7H2,1-3H3/t8-,9-/m1/s1

Synthetic route

2-tert-butylcyclohexanone → 2-tert-butylcyclohexan-1-ol (13491-79-7)

Conditions	Yield
With aluminum oxide; sodium tetrahydroborate In hexane at 40℃; for 3h;	100%
With sodium tetrahydroborate; silica gel In hexane at 40℃; for 5h;	96%
With hydrogenchloride; isopropyl alcohol; nickel for 33.05h; Heating;	75%
With tetrabutylammonium borohydride In various solvent(s) at 25℃; Reduction;

2-tert-Butylphenol (88-18-6) → 2-tert-butylcyclohexan-1-ol (13491-79-7)

Conditions	Yield
With hydrogen In water at 40℃; under 7500.75 Torr; for 6h; Autoclave;	99.2%
With nickel(II) oxide; hydrogen; palladium In hexane at 100℃; under 22502.3 Torr; for 8h;	92%
With 5%-palladium/activated carbon; hydrogen at 90 - 100℃; under 15001.5 Torr;

(2-tert-butyl-cyclohexyloxy)-trimethyl-silane → 2-tert-butylcyclohexan-1-ol (13491-79-7)

Conditions	Yield
With ammonium chloride In water; acetonitrile at 80℃; for 1h;	85%

cis-2-tert-butylcyclohexyl vinyl ether → 2-tert-butylcyclohexan-1-ol (13491-79-7) + (R,R)-2-tert-butylcyclohexyl vinyl ether + (S,S)-2-tert-butylcyclohexyl vinyl ether

Conditions	Yield
With water; C2H3O2(1-)*C36H53CoN2O2(1+) In methanol at 20℃; for 11h; Product distribution / selectivity;	A 77% B n/a C n/a
With water; [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) In methanol at 20℃; for 140h; Product distribution / selectivity;	A 75% B n/a C n/a
With water; C6H3N2O5(1-)*C36H53CoN2O2(1+) In methanol at 20℃; for 10h; Product distribution / selectivity;	A 73% B n/a C n/a
With water; C2H3O2(1-)*C36H53CoN2O2(1+) In methanol at -10℃; for 103h; Product distribution / selectivity;	A 68% B n/a C n/a
With water; C6H3N2O5(1-)*C36H53CoN2O2(1+) In methanol at -10℃; for 77h; Product distribution / selectivity;	A 62% B n/a C n/a

tert-butyl alcohol (75-65-0) + cyclohexene (110-83-8) → 1,2-Cyclohexanediol (931-17-9) + 2-tert-butylcyclohexan-1-ol (13491-79-7)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; dihydrogen peroxide; methyltrioxorhenium(VII) In water Product distribution; Ambient temperature; without HMPA as well;

2-tert-butylcyclohexan-1-ol (13491-79-7) → 2-tert-butylcyclohexanone (1728-46-7)

Conditions	Yield
With chromium(VI) oxide; aluminum oxide In hexane at 39.9℃; for 15h;	95%
With water; fluorine; acetonitrile In chloroform at -10 - 0℃; for 3.5h;	90%
With cerium(III) sulfate; barium bromate In water; acetonitrile for 7h; Heating;	90%

2-tert-butylcyclohexan-1-ol (13491-79-7) → 6-t-butyl-2,2,6-trichlorocyclohexanone (116625-41-3)

Conditions	Yield
With chlorine In N,N-dimethyl-formamide at 55 - 70℃; for 2.33333h;	93%

2-tert-butylcyclohexan-1-ol (13491-79-7) → 1-tert-butyl-1-cyclohexene (3419-66-7)

Conditions	Yield
With triphenylphosphine dibromide 1:1 addition complex In N,N-dimethyl-formamide at 30℃; for 1h;	90%
With phosphoric acid

formaldehyde diethyl acetal (462-95-3) + 2-tert-butylcyclohexan-1-ol (13491-79-7) → 1-tert-Butyl-2-ethoxymethoxy-cyclohexane (80390-89-2)

Conditions	Yield
montmorillonite Heating;	78%

2-tert-butylcyclohexan-1-ol (13491-79-7) → C22H38O5

Conditions	Yield
In toluene	78%

acetic acid methyl ester (79-20-9) + 2-tert-butylcyclohexan-1-ol (13491-79-7) → 2-(1,1-dimethylethyl)cyclohexyl ethanoate (88-41-5)

Conditions	Yield
With 1,3-dicyclohexylimidazol-2-ylidene at 25℃; for 72h;	9%

2-tert-butylcyclohexan-1-ol (13491-79-7) + ethyl acetate (141-78-6) → 2-(1,1-dimethylethyl)cyclohexyl ethanoate (88-41-5)

Conditions	Yield
With 1,3-dicyclohexylimidazol-2-ylidene at 25℃; for 72h;	5%

2-tert-butylcyclohexan-1-ol (13491-79-7) → 1-tert-butyl-1-cyclohexene (3419-66-7) + (3S)-(+)-3-tert-butylcyclohexene (77242-41-2)

Conditions	Yield
With phosphoric acid Yield given. Yields of byproduct given;

2-tert-butylcyclohexan-1-ol (13491-79-7) → 1-tert-butyl-2-chloro-cyclohexane + 1-tert-butyl-1-cyclohexene (3419-66-7)

Conditions	Yield
With trichloroacetamide; triphenylphosphine In dichloromethane at 30℃; for 0.25h;

2-tert-butylcyclohexan-1-ol (13491-79-7) → 1-t-butyl-3,3-dichloro-2-methoxy-1,2-epoxycyclohexane (116625-43-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / chlorine gas / dimethylformamide / 2.33 h / 55 - 70 °C 2: methanol / 20 h View Scheme

2-tert-butylcyclohexan-1-ol (13491-79-7) → 1-(2-tert-butylcyclohexyloxy)-2-propanol

Conditions	Yield
In tetrahydrofuran; mineral oil

2-tert-butylcyclohexan-1-ol (13491-79-7) → (+/-) (1R,2R,6S) 1-(1,1-dimethylethyl)-7-oxabicyclo[4.1.0]heptan-2-ol

Conditions	Yield
With tert.-butylhydroperoxide; bis(acetylacetonate)oxidovanadium(IV) In decane; dichloromethane at 0℃; Inert atmosphere;

2-tert-butylcyclohexan-1-ol (13491-79-7) → C10H21O2P + C10H21O2P

Conditions	Yield
With tetraphenoxysilane; hypophosphorous acid In acetonitrile for 2h; Inert atmosphere; Reflux;

2-tert-butylcyclohexan-1-ol (13491-79-7) + acetic anhydride (108-24-7) → 2-(1,1-dimethylethyl)cyclohexyl ethanoate (88-41-5)

Conditions	Yield
With toluene-4-sulfonic acid at 100 - 110℃;	110.9 g

2-tert-butylcyclohexan-1-ol (13491-79-7) + Diethyl carbonate (105-58-8) → carbonic acid 2-tert-butyl-cyclohexyl ester ethyl ester (67801-64-3)

Conditions	Yield
With toluene-4-sulfonic acid; sodium hydroxide at 100 - 110℃;	120.6 g

Upstream product

• 88-18-6 2-tert-Butylphenol 
• 75-65-0 tert-butyl alcohol 
• 108-95-2 phenol 
• 107932-21-8 2-t-butyl-2-cyclohexen-1-one 
• 1728-46-7 2-tert-butylcyclohexanone 
• 110-83-8 cyclohexene 

Downstream Products

• 3419-66-7 1-tert-butyl-1-cyclohexene 
• 67801-64-3 carbonic acid 2-tert-butyl-cyclohexyl ester ethyl ester 
• 88-41-5 2-(1,1-dimethylethyl)cyclohexyl ethanoate 
• 116625-43-5 1-t-butyl-3,3-dichloro-2-methoxy-1,2-epoxycyclohexane 
• 116625-41-3 6-t-butyl-2,2,6-trichlorocyclohexanone 
• 1728-46-7 2-tert-butylcyclohexanone 
• 77242-41-2 (3S)-(+)-3-tert-butylcyclohexene 
• 80390-89-2 1-tert-Butyl-2-ethoxymethoxy-cyclohexane 

Relevant articles and documents

Reactivity control via dihydrogen bonding: Diastereoselection in borohydride reductions of α-hydroxyketones [6]

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Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof

The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.

Synthesis method of tert-butyl cyclohexyl ethyl carbonate spice

The invention discloses a synthesis method of tert-butyl cyclohexyl ethyl carbonate spice and relates to the technical field of fine chemical engineering. The synthesis method includes: using phenol and tert-butanol as starting raw materials for alkylation reaction, hydrogenating, being in acetylation reaction with diethyl carbonate to generate tert-butyl cyclohexyl ethyl carbonate. The synthesismethod is easy-to-get in raw material and high in yield, a ratio of o-tert-butyl phenol and p-tert-butyl phenol generated by reaction of phenol and tert-butanol reaches 7:3, and p-tert-butyl phenol which is a byproduct can generate iris ester for use after being hydrogenated and esterified; the spice is high in purity and pure and gentle in fragrance and meets flavoring requirements of essence andspice.

Upgrading of aromatic compounds in bio-oil over ultrathin graphene encapsulated Ru nanoparticles

Fast pyrolysis of biomass for bio-oil production is a direct route to renewable liquid fuels, but raw bio-oil must be upgraded in order to remove easily polymerized compounds (such as phenols and furfurals). Herein, a synthesis strategy for graphene encapsulated Ru nanoparticles (NPs) on carbon sheets (denoted as Ru@G-CS) and their excellent performance for the upgrading of raw bio-oil were reported. Ru@G-CS composites were prepared via the direct pyrolysis of mixed glucose, melamine and RuCl3 at varied temperatures (500-800 °C). Characterization indicated that very fine Ru NPs (2.5 ± 1.0 nm) that were encapsulated within 1-2 layered N-doped graphene were fabricated on N-doped carbon sheets (CS) in Ru@G-CS-700 (pyrolysis at 700 °C). And the Ru@G-CS-700 composite was highly active and stable for hydrogenation of unstable components in bio-oil (31 samples including phenols, furfurals and aromatics) even in aqueous media under mild conditions. This work provides a new protocol to the utilization of biomass, especially for the upgrading of bio-oil.