470-08-6

Basic information

• Product Name: (1S,2R,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol
• Synonyms: (-)-beta-Fenchol;(1S,2R,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptane-2-ol;(1S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptane-2β-ol;[1S,4R,(-)]-1,3,3-Trimethylbicyclo[2.2.1]heptane-2β-ol;(1S,2R,4R)-1,3,3-trimethylnorbornan-2-ol;(1S,4R,6R)-1,5,5-trimethylbicyclo[2.2.1]heptan-6-ol
• CAS NO: 470-08-6
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• Mol File: 470-08-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 202.9°Cat760mmHg
• Flash Point: 73.9°C
• Appearance: /
• Density: 0.992g/cm³
• Vapor Pressure: 0.0693mmHg at 25°C
• Refractive Index: 1.502
• PKA: 15.38±0.60(Predicted)
• CAS DataBase Reference: (1S,2R,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol(470-08-6)
• EPA Substance Registry System: (1S,2R,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol(470-08-6)

Safety Data

• Hazardous Substances Data: 470-08-6(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1S,2R,4R)-1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-ol" is a bicyclic monoterpene alcohol with the molecular formula C10H18O. It is also known as α-terpineol and is commonly found in the essential oils of various plant species, including eucalyptus, pine, and tea tree. α-Terpineol has a pleasant, floral odor and is often used in the fragrance and flavor industry. It has also been studied for its potential antimicrobial, anti-inflammatory, and antioxidant properties, making it a valuable compound for medicinal and industrial applications. Additionally, it has been used as a solvent and a reagent in organic chemistry. Overall, α-terpineol is a versatile and valuable compound with a wide range of practical uses.

InChI:InChI=1/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1

Synthetic route

fenchone (4695-62-9) + aluminum isopropoxide (555-31-7) → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

Conditions	Yield
With isopropyl alcohol

fenchone (4695-62-9) → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

Conditions	Yield
With copper chromite; ethanol at 110℃; under 73550.8 Torr; Hydrogenation;
With nickel at 110℃; Hydrogenation;
With methanol; nickel Hydrogenation;
With aluminum isopropoxide In isopropyl alcohol for 420h; Heating;	A n/a B 1.52 g

oxalic acid bis-((1S)-1,3,3-trimethyl-norbornan-2-yl ester) (124118-33-8) → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

Conditions	Yield
Hydrolysis;

fenchone (4695-62-9) + aluminum isopropoxide (555-31-7) + isopropyl alcohol (67-63-0) → (-)-β-fenchol (470-08-6)

9-fluorenone (486-25-9) + 9-Fluorenol (1689-64-1) + (-)-α-fenchol (512-13-0) + tert-butyl alcohol (75-65-0) + sodium tert.-butylate → (-)-β-fenchol (470-08-6)

Conditions	Yield
at 160 - 180℃; Epimerisierung;

fenchone (4695-62-9) + Raney nickel → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

Conditions	Yield
at 110℃; unter Druck.Hydrogenation;

methanol (67-56-1) + fenchone (4695-62-9) + Raney nickel → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

Conditions	Yield
at 110℃; unter Druck.Hydrogenation;

ethanol (64-17-5) + fenchone (4695-62-9) + sodium → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

fenchone (4695-62-9) + sodium + LiAlH4 → (-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6)

fenchone (4695-62-9) → (-)-β-fenchol (470-08-6) + l-α-fenchol

Conditions	Yield
With ethanol; sodium

p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (916497-81-9) + (-)-β-fenchol (470-08-6) → (+)-fenchyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Conditions	Yield
With trifluorormethanesulfonic acid; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -78℃; for 3h; Molecular sieve;	97%

(-)-β-fenchol (470-08-6) → fenchone (4695-62-9)

Conditions	Yield
With oxone; C18H17IN2O7PolS(1-)*Na(1+); tetra(n-butyl)ammonium hydrogensulfate In acetonitrile at 70℃; for 3h; Reagent/catalyst; Solvent; Sealed tube; Green chemistry;	85%

(-)-β-fenchol (470-08-6) + propargyl bromide (106-96-7) → (1S,2R,4R)-2-[(Prop-2-yn-1-yl)oxy]-1,3,3-trimethylbicyclo[2.2.1]heptane

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 72h; Williamson ether synthesis;	81%

(-)-β-fenchol (470-08-6) + N-benzyloxycarbonyl-D-alanine (26607-51-2) → N-benzyloxycarbonyl-D-alanine (-)-β-fenchyl ester (376585-09-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6.5h;	69%

(-)-α-fenchol (512-13-0) + (-)-β-fenchol (470-08-6) → (+)-O-(3.5-dinitro-benzoyl)-β-fenchol; compound with (1S)-2endo-(3.5-dinitro-benzoyloxy)-1.3.3-trimethyl-norbornane

(-)-β-fenchol (470-08-6) → (+)-O-(4-Nitro-benzoyl)-β-fenchol (18679-59-9, 117404-51-0)

(-)-β-fenchol (470-08-6) → α-fenchene (116724-26-6)

Conditions	Yield
With kaolin
With zinc(II) chloride
With potassium hydrogensulfate

(-)-β-fenchol (470-08-6) → succinic acid mono-((1S)-1,3,3-trimethyl-[2=x]norbornyl ester)

(-)-β-fenchol (470-08-6) → (+)-O-(3.5-dinitro-benzoyl)-β-fenchol (1167-25-5, 57526-38-2, 57526-40-6)

(-)-β-fenchol (470-08-6) + acetic anhydride (108-24-7) → exo-fenchyl acetate (76109-40-5)

Conditions	Yield
With pyridine

(-)-β-fenchol (470-08-6) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid-((1S)-1,3,3-trimethyl-[2exo]norbornyl ester) (1156-31-6, 1920-98-5, 94959-50-9)

Conditions	Yield
With pyridine

9-fluorenone (486-25-9) + 9-Fluorenol (1689-64-1) + (-)-β-fenchol (470-08-6) + tert-butyl alcohol (75-65-0) + sodium tert.-butylate → (-)-α-fenchol (512-13-0)

Conditions	Yield
at 165℃; Epimerisierung;

(-)-β-fenchol (470-08-6) + Cr2O3-H2SO4 → fenchone (4695-62-9)

sulfuric acid (7664-93-9) + (-)-β-fenchol (470-08-6) + acetic acid (64-19-7) → exo-fenchyl acetate (76109-40-5)

oxalyl dichloride (79-37-8) + (-)-β-fenchol (470-08-6) → oxalic acid bis-((1S)-1,3,3-trimethyl-norbornan-2-yl ester) (124118-33-8) + (+)-oxalic acid bis-<(1S)-1.3.3-trimethyl-norbornyl-(2exo)-ester>

Conditions	Yield
With pyridine; diethyl ether

oxalyl dichloride (79-37-8) + (-)-β-fenchol (470-08-6) → oxalic acid bis-((1S)-1,3,3-trimethyl-norbornane-2exo-yl ester) (124118-33-8) + oxalic acid bis-<(1S)-1.3.3-trimethyl-norbornyl-(2)-ester>-substance of F. 91-92 degree

Conditions	Yield
With pyridine; diethyl ether

(-)-β-fenchol (470-08-6) → D-alanine (-)-β-fenchyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 6.5 h / 0 - 20 °C 2: H2 / 5 percent Pd/C / methanol / 5 h / 20 °C View Scheme

(-)-β-fenchol (470-08-6) → L-aspartyl-D-alanine (-)-β-fenchyl ester

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 69 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 6.5 h / 0 - 20 °C 2.1: H2 / 5 percent Pd/C / methanol / 5 h / 20 °C 3.1: N-hydroxy-endo-5-norbornene-2,3-dicarboximide; dicyclohexylcarbodiimide / dioxane / 4 h / 20 °C 3.2: 77 percent / dioxane / 16 h / 20 °C 4.1: 79 percent / H2 / 5 percent Pd/C / methanol / 5 h / 20 °C / atmospheric pressure View Scheme

Upstream product

• 1195-79-5 1,3,3-trimethyl-2-norbornanone 
• 4695-62-9 fenchone 
• 7785-70-8 (+)-α-pinene 
• 144-62-7 oxalic acid 
• 79-11-8 chloroacetic acid 
• 7785-26-4 (-)-α-pinene 
• 108-24-7 acetic anhydride 
• 177698-19-0 Beta-pinene 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 108-88-3 toluene 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 486-25-9 9-fluorenone 

Downstream Products

• 7462-24-0 fenchyl salicylate 
• 26405-07-2 Cyclohexyl-carbamic acid 1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 103300-59-0 (2-Nitro-phenylsulfanylamino)-phenyl-acetic acid (1R,2S,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 103300-59-0 (2-Nitro-phenylsulfanylamino)-phenyl-acetic acid (1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 103300-59-0 N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine (-)-α-fenchyl ester 
• 488-97-1 cyclofenchene 
• 4695-62-9 fenchone 
• 512-13-0 (-)-α-fenchol 
• 376585-09-0 N-benzyloxycarbonyl-D-alanine (-)-β-fenchyl ester 
• 13851-11-1 α-fenchyl acetate 
• 7787-20-4 (1R)-fenchone 
• 103300-55-6 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 
• 103300-55-6 (S)-3-Benzyloxycarbonylamino-N-[phenyl-((1S,2R,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxycarbonyl)-methyl]-succinamic acid benzyl ester 
• 103366-56-9 L-aspartyl-D-phenylglycine (-)-α-fenchyl ester 

Relevant articles and documents

Stereochemical equilibration of alcohols.

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Synthesis and kinetic regularities of the thermal decomposition of new hydrotrioxides of cyclic alcohols

Cyclic hydrotrioxides were synthesized by low-temperature (?78 °C) ozonolysis of a series of cyclic alcohols and identified using 1H NMR spectra. The kinetic regularities of the thermal decomposition of the synthesized hydrotrioxides were studied. The experimental proof of the induced decomposition of alcohol hydrotrioxides was obtained for the first time using cyclohexanol hydrotrioxide as an example. The influence of cyclic substituents on the thermal stability of the hydrotrioxides is shown.

Chiral β- and γ-aminoalcohols derived from (+)-camphor and (-)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

The addition of Me3SiCN and LiCH2CN to (+)-camphor and (-)-fenchone, respectively, followed by reduction leads to chiral β- and γ-aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et2Zn to benzaldehyde were lower than those obtained using the corresponding δ-aminoalcohols.