80-56-8

Basic information

• Product Name: alpha-Pinene
• Synonyms: 2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene;2-Pinene;DL-Pin-2(3)-ene;2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
• CAS NO: 80-56-8
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23404
• EINECS: 201-291-9
• Mol File: 80-56-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: -55℃
• Boiling Point: 157.883 °C at 760 mmHg
• Flash Point: 32.222 °C
• Appearance: liquid with a turpentine odour
• Density: 0.879 g/cm³
• Vapor Pressure: 3.49mmHg at 25°C
• Refractive Index: 1.479
• Water Solubility: insoluble
• CAS DataBase Reference: alpha-Pinene(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Pinene(80-56-8)
• EPA Substance Registry System: alpha-Pinene(80-56-8)

Safety Data

• Hazard Codes: Xi:Irritant;; <
• Statements: R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.; R51/53:; R65:
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S23:Do not inhale gas/fumes/vapour/spray.; S26:; S29:
• Hazardous Substances Data: 80-56-8(Hazardous Substances Data)

Usage

General Description

Alpha-Pinene is a naturally occurring organic compound classified as a terpene, and is known for being the most widely distributed terpene in nature. It is a primary constituent in the essential oils of numerous plant species, including pine and conifer trees. It's known for its strong aroma, similar to that of pine forests. In terms of structure, it's a cyclic monoterpene, meaning it consists of two isoprene units. In regard to its industrial uses, alpha-Pinene is used as a base for both fragrances and flavors, where it often undergoes chemical modifications. It also exhibits potential medicinal and therapeutic properties, such as being anti-inflammatory and pain-relieving.

InChI:InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1

Synthetic route

dithiocarbonic acid S-methyl ester-O-pinan-3-yl ester (422567-10-0) → methylthiol (74-93-1) + carbon oxide sulfide (463-58-1) + rac-α-pinene (80-56-8)

Conditions	Yield
at 170 - 190℃; pinocamphylxanthogenic acid methyl ester from inactive pinocampheol;

Beta-pinene (177698-19-0) + benzoic acid (65-85-0) → rac-α-pinene (80-56-8)

Conditions	Yield
at 125 - 130℃; levorotatory form;
at 125 - 130℃; levorotatory form;

(1R,5R)-(+)-β-pinene (127-91-3) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 4-methylisopropylbenzene (99-87-6) + crithmene (99-85-4) + dl-camphene (565-00-4) + rac-α-pinene (80-56-8)

Conditions	Yield
With pyridine; hydrogen; platinum-alumina(0.6 percentPt) at 300℃; for 0.79h; Product distribution; effects of partial pressures of N2, H2, pyridine;

(1R,5R)-(+)-β-pinene (127-91-3) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 4-methylisopropylbenzene (99-87-6) + rac-α-pinene (80-56-8)

Conditions	Yield
With hydrogen; platinum-alumina(0.6 percent Pt) at 300℃; Yield given;

Beta-pinene (177698-19-0) + salicylic acid (69-72-7) → rac-α-pinene (80-56-8) + limonene. (138-86-3) + bornyl ester + terpinene

Conditions	Yield
at 160℃; levorotatory form;

camphene (79-92-5) + ozone (10028-15-6) → rac-α-pinene (80-56-8)

Conditions	Yield
dl-camphene;

hydrazone of (+)-pinocamphone → (-)-trans-δ-pinene (24031-99-0) + rac-α-pinene (80-56-8)

Conditions	Yield
With ethanol; mercury(II) oxide

Beta-pinene (177698-19-0) + carbon monoxide (201230-82-2) → rac-α-pinene (80-56-8) + (+)-3-formylpinane (60113-43-1) + trans-pinane (473-55-2, 4755-33-3, 4795-86-2, 4863-59-6, 6876-13-7, 10281-53-5, 33626-25-4, 112456-46-9, 112456-47-0) + trans-10-formylpinane

Conditions	Yield
With hydrogen; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In benzene at 120℃; under 67505.4 Torr; for 4h;

Beta-pinene (177698-19-0) + carbon monoxide (201230-82-2) → rac-α-pinene (80-56-8) + trans-pinane (473-55-2, 4755-33-3, 4795-86-2, 4863-59-6, 6876-13-7, 10281-53-5, 33626-25-4, 112456-46-9, 112456-47-0) + cis-10-formylpinane + trans-10-formylpinane

Conditions	Yield
With hydrogen; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In benzene at 100℃; under 67505.4 Torr; for 4h; Product distribution; Further Variations:; Reagents; Temperatures;
With hydrogen; 1,2-bis-(diphenylphosphino)ethane; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In benzene at 100℃; under 67505.4 Torr; for 4h;

Beta-pinene (177698-19-0) + acetophenone (98-86-2) → rac-α-pinene (80-56-8) + trans-pinane (473-55-2, 4755-33-3, 4795-86-2, 4863-59-6, 6876-13-7, 10281-53-5, 33626-25-4, 112456-46-9, 112456-47-0) + cis-10-formylpinane + trans-10-formylpinane

Conditions	Yield
di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In benzene-d6 at 100℃; under 67505.4 Torr; for 4h;

carbon monoxide (201230-82-2) + (1R/S,5R/S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane (127-91-3) → rac-α-pinene (80-56-8) + cis-10-formylpinane + trans-10-formylpinane

Conditions	Yield
With hydrogen; [rhodium(I)(1,5-cyclooctadiene)(2,2'-bipyridine)](BF4) In dichloromethane at 80℃; under 60004.8 Torr; for 24h; Title compound not separated from byproducts;	A 39 % Chromat. B 5 % Chromat. C 46 % Chromat.
With hydrogen; [Rh(COD)(4,4'-dimethoxy-2,2'-bipyridine)]BF4 In dichloromethane at 80℃; under 60004.8 Torr; for 24h; Title compound not separated from byproducts;	A 45 % Chromat. B 6 % Chromat. C 43 % Chromat.
With hydrogen; [Rh(COD)(4,4'-dinitro-2,2'-bipyridine)]BF4 In dichloromethane at 80℃; under 60004.8 Torr; for 24h; Title compound not separated from byproducts;	A 50 % Chromat. B 5 % Chromat. C 39 % Chromat.

rac-α-pinene (80-56-8) → 2α,3α-epoxypinane (1686-14-2, 14575-92-9, 19894-99-6, 32162-27-9, 38301-46-1, 94063-22-6, 95044-43-2)

Conditions	Yield
With sodium hypochlorite; manganese(II) 5,10,15,20-tetraphenylporphyrinate; 1-hexylimidazole In dichloromethane; water at 0℃; for 0.333333h; Product distribution; pH=9.5; further olefines, also in presence of methyl trioctyl ammonium chloride; selectivity;	99%
With sodium hypochlorite; Mn-TDClPP; Aliquat 336; 1-hexylimidazole In ethanol; water at 0℃; for 0.333333h; pH=9.5;	99%
With sodium hydrogencarbonate In dichloromethane at 5℃; for 1h;	85%

rac-α-pinene (80-56-8) → (1S,2S,3S)-pinane-2,3-diol (22466-73-5)

Conditions	Yield
With pyridine; trimethylamine-N-oxide; osmium(VIII) oxide In water; tert-butyl alcohol for 17h; Heating;	93%

phenylselenyl benzenesulfonate (60805-71-2) + rac-α-pinene (80-56-8) → phenyl (1RS,2RS,3RS,5SR)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl selenide

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: phenylselenyl benzenesulfonate With di-tert-butyl peroxide at 140℃; for 0.25h; Microwave irradiation;	93%

S-Phenyl benzenethiosulfonate (1212-08-4) + rac-α-pinene (80-56-8) → phenyl (1RS,2RS,3RS,5SR)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl sulfide

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: S-Phenyl benzenethiosulfonate With di-tert-butyl peroxide at 140℃; for 0.25h; Microwave irradiation;	92%

rac-α-pinene (80-56-8) → (1RS,2RS,3RS,5SR)-3-bromomethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: With di-tert-butoxydiazene; benzenesulfonyl bromide In methanol; dichloromethane Reflux;	90%

rac-α-pinene (80-56-8) → (+/-)-2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one (80-57-9, 1196-01-6, 5480-12-6, 18309-32-5)

Conditions	Yield
With tert.-butylhydroperoxide; cobalt(II) ethyl phosphonate In acetonitrile at 50℃; for 48h;	88%

rac-α-pinene (80-56-8) → (1RS,2RS,3RS,5SR)-3-iodomethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: With p-toluenesulfonyl iodide; oxygen In dichloromethane; tert-butyl alcohol at 0℃; for 1.5h;	87%

benzenethiosulfonic acid S-benzyl ester (16601-01-7) + rac-α-pinene (80-56-8) → (1RS,2RS,3RS,5SR)-3-benzylsulfanyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: benzenethiosulfonic acid S-benzyl ester With di-tert-butoxydiazene In methanol; dichloromethane Reflux;	84%

rac-α-pinene (80-56-8) → (1RS,2RS,3RS,5SR)-3-chloromethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: With di-tert-butoxydiazene; benzenesulfonyl chloride In methanol; dichloromethane Reflux;	83%

S-Phenyl benzenethiosulfonate (1212-08-4) + rac-α-pinene (80-56-8) → phenyl (1RS,2RS,3RS,5SR)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl sulfide

Conditions	Yield
Stage #1: rac-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Inert atmosphere; Reflux; Stage #2: S-Phenyl benzenethiosulfonate With di-tert-butoxydiazene In methanol; dichloromethane Reflux;	81%

rac-α-pinene (80-56-8) + 7-nitro-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-26-6) → C17H21NO3

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	78%

5-trifluoromethyl-3-methoxycarbonyl-4H-1,2-benzoxazine (1000847-61-9) + rac-α-pinene (80-56-8) → C18H21F3O

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	72%

rac-α-pinene (80-56-8) → (1R*,2R*,3R*,5S*)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (51152-11-5)

Conditions	Yield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane Ambient temperature;	71%
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; acetic acid 1) THF, r.t., 12 h; Yield given. Multistep reaction;

8-nitro-3-methoxycarbonyl-4H-1,2-benzoxazine (932399-74-1) + rac-α-pinene (80-56-8) → C17H21NO3

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	70%

chloroform (67-66-3) + rac-α-pinene (80-56-8) → 3,3-dichloro 2,7,7-trimethyl tricyclo<4.1.1.02,4>octane (18675-44-0, 32549-14-7, 33059-79-9, 49752-36-5)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate at 0℃; for 0.75h;	60%

rac-α-pinene (80-56-8) + 7-bromo-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-18-6) → C17H21BrO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	56%

rac-α-pinene (80-56-8) + acetic anhydride (108-24-7) → (+/-)-trans-sobrenol diacetate (17177-64-9, 68754-15-4, 109845-98-9, 124434-99-7, 148040-86-2)

Conditions	Yield
With sodium perchlorate; sodium acetate In acetic acid at 20℃; electrochemically - Pt electrodes; 2.0 A/dm2;	55%

rac-α-pinene (80-56-8) + 7-trifluoromethyl-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-24-4) → C18H21F3O

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	52%

C12H11NO5 + rac-α-pinene (80-56-8) → C19H24O3

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	51%

rac-α-pinene (80-56-8) + 3,7-dimethoxycarbonyl-4H-1,2-benzoxazine (538342-22-2) → C19H24O3

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	48%

C10H8BrNO3 + rac-α-pinene (80-56-8) → C17H21BrO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	48%

rac-α-pinene (80-56-8) + 7-cyano-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-25-5) → C18H21NO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	44%

rac-α-pinene (80-56-8) + 6-chloro-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-19-7) → C17H21ClO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	43%

rac-α-pinene (80-56-8) + 7-chloro-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-17-5) → C17H21ClO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	42%

C10H8FNO3 + rac-α-pinene (80-56-8) → C17H21FO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	38%

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + rac-α-pinene (80-56-8) → 7,8,8-Trimethyl-N-phenyl-4,5-diazatricyclo<4.2.1.03,7>nonan-4,5-dicarboximide (82934-23-4) + 1-(6,6-Dimethyl-2-methylenbicyclo<3.1.1>hept-3-yl)-4-phenyl-1,2,4-triazolidine-3,5-dione (82934-22-3)

Conditions	Yield
In dichloromethane for 24h; Mechanism; Ambient temperature; protection from light;	A 14% B 37%
In dichloromethane for 24h; Ambient temperature; protection from light;	A 14% B 37%

7-fluoro-3-methoxycarbonyl-4H-1,2-benzoxazine (932399-72-9) + rac-α-pinene (80-56-8) → C17H21FO

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	32%

rac-α-pinene (80-56-8) + 3-methoxycarbonyl-4H-1,2-benzoxazine (538342-16-4) → C17H22O

Conditions	Yield
In toluene at 150℃; for 6h; Diels-Alder reaction;	28%

1,4-dioxane (123-91-1) + rac-α-pinene (80-56-8) + benzenesulfonic acid (98-11-3) → terpineol (98-55-5)

Conditions	Yield
at 40℃;

2-methyl-2-butylchloride (594-36-5) + rac-α-pinene (80-56-8) → 2-endo-chloro-bornane (464-41-5, 559-45-5, 6120-13-4, 27720-69-0, 30462-53-4, 33602-15-2, 73804-39-4, 91547-96-5)

Conditions	Yield
at 160℃;

Upstream product

• 18172-67-3 beta-pinene 
• 67-56-1 methanol 
• 14575-88-3 2αH-pinan-3α-yl toluene-p-sulphonate 
• 75-91-2 tert.-butylhydroperoxide 
• 148952-14-1 2,2,2-Trichloro-acetimidic acid 2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester 
• 177698-19-0 Beta-pinene 
• 22679-02-3 dimethylallyl pyrophosphate 
• 7647-01-0 hydrogenchloride 
• 115-10-6 Dimethyl ether 
• 515-00-4 myrtenol 
• 201230-82-2 carbon monoxide 
• 422567-10-0 dithiocarbonic acid S-methyl ester-O-pinan-3-yl ester 
• 65-85-0 benzoic acid 
• 127-91-3 (1R,5R)-(+)-β-pinene 

Downstream Products

• 98-55-5 terpineol 
• 464-41-5 bornyl chloride 
• 565-00-4 dl-camphene 
• 138-86-3 limonene. 
• 464-41-5 2-endo-chloro-bornane 
• 586-62-9 Terpinolene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 470-82-6 1,8-Cineole 
• 108-31-6 maleic anhydride 
• 110-16-7 maleic acid 
• 623-26-7 terephthalonitrile 
• 98-82-8 Isopropylbenzene 
• 79-91-4 terebic acid 
• 1195-32-0 1-methyl-4-isopropenylbenzene 

Relevant articles and documents

Amphiphilic polymeric nanoreactors containing Rh(i)-NHC complexes for the aqueous biphasic hydrogenation of alkenes

A rhodium(i) complex bearing a monodentate N-heterocyclic carbene ligand has been confined into the core of amphiphilic polymeric core-crosslinked micelles (CCMs). The Rh complex was covalently bound to the polymeric chains by incorporation of a polymerizable unit on the NHC ligand. Nanoreactor Rh-NHCmes@CCM5bhas been evaluated as a catalyst for the aqueous biphasic hydrogenation of styrene and other alkenes. It has shown a high activity with styrene at a low catalytic loading (10?000/1 substrate/Rh ratio), greater than that of an analogous molecular Rh(i) complex, and its evolution to Rh0is slower. This is attributed to several factors, among which the confinement effect and the favourable polyoxygenated environment of the nanoreactor core. Finally, the CCMs could be recycled up to four times with almost no loss of activity over 3 h cycles and the loss of rhodium per cycle was on average lower than 0.6 ppm.

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

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