7785-26-4

Basic information

• Product Name: (1S)-(-)-alpha-Pinene
• Synonyms: (1s)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene;(1S)-(-)-a-pinene;(1S)-(-)-pin-2-ene;(1S)-(-)-α-pinene;(1S)-2,6,6-trimethylbicyclo[3.1.1]-2-heptene;(1S,5S)-(-)-α-pinene;(S)-(-)-α-pinene;1S-(-)-a-pinene
• CAS NO: 7785-26-4
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 232-077-3
• Product Categories: Industrial/Fine Chemicals;API intermediates;Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 7785-26-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: -64 °C(lit.)
• Boiling Point: 156-158 °C(lit.)
• Flash Point: 90 °F
• Appearance: Clear colorless/Liquid
• Density: 0.874 g/mL at 25 °C
• Vapor Density: 4.7 (vs air)
• Vapor Pressure: ~3 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.466
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Explosive Limit: 0.8%(V)
• Water Solubility: INSOLUBLE
• Merck: 14,7445
• BRN: 1903790
• CAS DataBase Reference: (1S)-(-)-alpha-Pinene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(-)-alpha-Pinene(7785-26-4)
• EPA Substance Registry System: (1S)-(-)-alpha-Pinene(7785-26-4)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 10-36/37/38-43-50-65-51/53-20/21/22
• Safety Statements: 26-36/37-61-16-60
• RIDADR: UN 2368 3/PG 3
• WGK Germany: 1
• RTECS: DT 7000000
• F: 10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 7785-26-4(Hazardous Substances Data)

Usage

Chemical Properties

(1S)-(-)-alpha-Pinene is clear colourless liquid

Uses

Different sources of media describe the Uses of 7785-26-4 differently. You can refer to the following data:
1. (1S)-(-)-alpha-Pinene is used in the preparation of hydroxy ketones such as hydroxycarvones.
2. (1S)-(-)-α-Pinene is used in the preparation of hydroxy ketones such as hydroxycarvones.

General Description

α-Pinene is a monoterpene used in industries like fragrance, pharmaceuticals, flavor, and cosmetics. It is a major component of pine oil and turpentine oil. Isomerization of α-pinene yields industrially important compounds like camphene, limonene, and p-cymene.

Purification Methods

Purify as for 1R,5S--Pinene above. [Beilstein 5 III 366, 5 IV 455.]

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

beta-pinene (18172-67-3, 19902-08-0) → (-)-α-pinene (7785-26-4)

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium carbonate; cobalt(II) aceylacetonate In N,N-dimethyl-formamide at 25℃; for 16h; Irradiation;	98%
With potassium hydride; Trimethylenediamine In mineral oil at 25℃; for 24.25h; Temperature; Inert atmosphere;	93%
isomerization;	86%

C20H35B → (-)-α-pinene (7785-26-4)

Conditions	Yield
With boron trifluoride diethyl etherate; benzaldehyde at 100℃; for 1h; Inert atmosphere;	95%

beta-pinene (18172-67-3, 19902-08-0) → (-)-α-pinene (7785-26-4) + (+)-α-pinene (7785-70-8) + 2,4,4-Trimethyl-8-methylene-3-aza-bicyclo[3.3.1]non-2-ene

Conditions	Yield
With chloranil In dichloromethane; acetonitrile Irradiation; Yield given;	A n/a B n/a C 5%

(-)-myrtenyl bromide (55527-89-4) → (-)-α-pinene (7785-26-4)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

rac-α-pinene (80-56-8) → (-)-α-pinene (7785-26-4) + (+)-α-pinene (7785-70-8)

Conditions	Yield
Leiten des Dampfes durch Gelatine-Hydrosol;

beta-pinene (18172-67-3, 19902-08-0) + oxalic acid (144-62-7) → (-)-α-pinene (7785-26-4)

hydrogenchloride (7647-01-0) + diethyl ether (60-29-7) + 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (35519-42-7) → (-)-α-pinene (7785-26-4) + limonene. (138-86-3) + (1R)-2endo-chloro-1,3,3-trimethyl-norbornane(?) + (1S)-2endo-chloro-bornane

Conditions	Yield
Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

hydrogenchloride (7647-01-0) + diethyl ether (60-29-7) + 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (35408-04-9) → (-)-α-pinene (7785-26-4) + (1S)-2-endo-chlorofenchane (1195-77-3, 3372-12-1, 90976-73-1) + limonene. (138-86-3)

Conditions	Yield
Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

bis → (-)-α-pinene (7785-26-4) + (+)-dehydro-β-pinene (4080-46-0, 23733-90-6, 30460-81-2)

Conditions	Yield
at 150 - 170℃; under 0.07 Torr;

carbon monoxide (201230-82-2) + beta-pinene (18172-67-3, 19902-08-0) + dibutylamine (111-92-2) → (-)-α-pinene (7785-26-4) + 2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)acetaldehyde (199445-88-0) + C19H35N + C19H37N (1350552-88-3)

Conditions	Yield
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 4h; Inert atmosphere;

carbon monoxide (201230-82-2) + beta-pinene (18172-67-3, 19902-08-0) + dibutylamine (111-92-2) → (-)-α-pinene (7785-26-4) + C19H37N (1350552-88-3)

Conditions	Yield
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 4h; Inert atmosphere;

2-((1S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-1-phenylethan-1-one → (-)-α-pinene (7785-26-4) + acetophenone (98-86-2)

Conditions	Yield
In methanol for 1h; Photolysis;

(1R,5R)-(+)-β-pinene (127-91-3) → (-)-α-pinene (7785-26-4) + α-dihydropinene

Conditions	Yield
With C5H14NO(1+)*C10H12NO4S(1-)*Pd; hydrogen In glycerol at 80℃; under 15001.5 Torr; for 2h; Inert atmosphere; Schlenk technique; Autoclave;

(-)-α-pinene (7785-26-4) → (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 20℃; for 24h; Oxidation;	100%
Stage #1: (-)-α-pinene With oxygen; ozone; acetic acid In dichloromethane at 0 - 20℃; Stage #2: With hydrazine hydrochloride In dichloromethane at 20℃; for 96h; Reagent/catalyst; Inert atmosphere;	88%
Stage #1: (-)-α-pinene With ammonium sulfate; potassium permanganate In water at 5℃; for 5h; Stage #2: With sulfuric acid In water at 5℃; for 0.5h;	56%

(-)-α-pinene (7785-26-4) → L-diisopinocampheylborane (21947-87-5)

Conditions	Yield
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane hydroboration;	99%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; Inert atmosphere;	73%
With sodium tetrahydroborate; boron trifluoride diethyl etherate

(-)-α-pinene (7785-26-4) → pinocarvone (34413-88-2)

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin; acetic anhydride; dmap In dichloromethane at 20℃; for 6h;	99%
With pyridine; dmap; oxygen; tetraphenyl pyrophosphate In dichloromethane; acetic anhydride at 20℃; for 48h; Irradiation;	98%
With pyridine; dmap; 5,10,15,20-tetrakisphenylporphyrin; oxygen; acetic anhydride at 20℃; for 16h;	95%
With pyridine; dmap; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane; acetic anhydride for 2h; Irradiation;	95%
With pyridine; dmap; oxygen; 5,15,10,20-tetraphenylporphyrin; acetic anhydride In dichloromethane at 20℃; for 16h; Irradiation;	82%

(-)-α-pinene (7785-26-4) + methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4) → (S)-(4-Bromo-phenyl)-((1R,2R,5S)-4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-yl)-acetic acid methyl ester

Conditions	Yield
With Rh2(R-DOSP)4 In various solvent(s) at 20℃;	99%

(-)-α-pinene (7785-26-4) → (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.2,4]octane (1686-14-2)

Conditions	Yield
With dihydrogen peroxide; microencapsulated polystyrene 2 percent cross-linked; methyltrioxorhenium(VII) In dichloromethane; water; acetonitrile at 25℃; for 1.5h;	98%
With 3,3-dimethyldioxirane In dichloromethane; acetone at -5 - 0℃; for 2h;	95%
With sodium peroxoborate tetrahydrate; Biliton; acetonitrile In water at 20℃; for 18h;	91%

(-)-α-pinene (7785-26-4) → 5,7,7-trimethyl-3-oxa-tricyclo[4.1.1.02,4]octane

Conditions	Yield
With dihydrogen peroxide; potassium carbonate; tin(IV) oxide; hydrazine at 55℃; for 3.5h; Reagent/catalyst; Temperature;	96.5%
With tert.-butylhydroperoxide; C11H13MoNO6 In water; 1,2-dichloro-ethane at 80℃; Reagent/catalyst;	96%
With C36H44IrN5; N-(benzenesulfonyl)-3-phenyloxaziridine In dichloromethane for 48h; optical yield given as %de;	78%

(-)-α-pinene (7785-26-4) → (+)-α-pinanediol (20536-51-0)

Conditions	Yield
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol for 24h; Reflux;	96.5%
Multi-step reaction with 2 steps 1: KMnO4 2: LiAlH4 View Scheme

(-)-α-pinene (7785-26-4) → 6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol (19894-98-5)

Conditions	Yield
Stage #1: (-)-α-pinene With oxygen; Nafilon-supported Pt(II) terpyridyl In dichloromethane; water-d2 at 20℃; for 2h; Irradiation; Stage #2: With sodium hydrogensulfite In dichloromethane; water-d2	95%
Stage #1: (-)-α-pinene With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Stage #2: With aluminum isopropoxide In toluene for 5h; Reflux;	68%
Stage #1: (-)-α-pinene With 5,15,10,20-tetraphenylporphyrin In chloroform for 0.166667h; Stage #2: With triphenylphosphine In chloroform at 0 - 20℃; for 0.5h;	63%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + (-)-α-pinene (7785-26-4) → C19H20O3

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile for 4h; Ambient temperature;	94%

(-)-α-pinene (7785-26-4) → (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane (303801-38-9)

Conditions	Yield
Stage #1: (-)-α-pinene With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: With hydrogen In tetrahydrofuran at 60℃; under 7500.75 Torr; for 3h;	94%
With sodium tetrahydroborate; hydrogen; nickel dichloride In isopropyl alcohol at 50℃; under 760.051 Torr; for 5h; Temperature;	45%
With [Fe3(1,1,1,3,3,3-hexamethyldisilazan-2-ide)4]Fe(η6-toluene); hydrogen at 20℃; under 1425.14 Torr; for 3h; Inert atmosphere; Glovebox; diastereoselective reaction;	95 %Chromat.
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; under 30003 Torr; for 0.5h; Flow reactor; Green chemistry;	> 99 %Chromat.

(-)-α-pinene (7785-26-4) + isopropyl alcohol (67-63-0) → 3(2),3(2),7-trimethyl-2,5-dioxo-6-oxa-3(1,3)-cyclobutanaoctaphane

Conditions	Yield
Stage #1: (-)-α-pinene With oxygen; ozone In isopropyl alcohol at 0℃; Stage #2: isopropyl alcohol With semicarbazide hydrochloride at 0 - 20℃; Inert atmosphere;	93%

(-)-α-pinene (7785-26-4) → (+)-isopinocampheol (1196-00-5, 2734-31-8, 19889-94-2, 19889-95-3, 25465-65-0, 25465-95-6, 27779-29-9, 35997-96-7, 35998-01-7, 36129-11-0, 51152-11-5, 73366-08-2, 125473-76-9, 473-61-0, 24041-60-9)

Conditions	Yield
Stage #1: (-)-α-pinene With dimethylsulfide borane complex In tetrahydrofuran at 20℃; hydroboration; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; ethanol for 1h; Oxidation; decomplexation; Heating;	90%
Stage #1: (-)-α-pinene With 1-bromo-butane; sodium tetrahydroborate; Aliquat 336 at 20℃; for 16h; Addition; Hydroboration; Stage #2: With sodium hydroxide; dihydrogen peroxide at 40℃; for 1h; Oxidation;	80%
With dihydrogen peroxide; benzo[1,3,2]dioxaborole; samarium (III) iodide 1.) THF, r.t., 18 h; Yield given. Multistep reaction;

(-)-α-pinene (7785-26-4) → 1-methyl-4-(1-methyl-1-nitrooxy-ethyl)-cyclohexene (475290-10-9)

Conditions	Yield
With zeolite of β type; nitric acid In dichloromethane at -15℃; for 0.833333h;	90%

(-)-α-pinene (7785-26-4) + crotonaldehyde (123-73-9) → C14H22O

Conditions	Yield
With Silica-supported tungstophosphoric heteropoly acid; air In 1,2-dichloro-ethane at 25℃; for 3h; Catalytic behavior; Time; Reagent/catalyst;	90%

(-)-α-pinene (7785-26-4) + (prop-2-ene-1,2-diyldisulfonyl)dibenzene (2525-55-5) → (1S,5S)-3-(2-Benzenesulfonyl-allyl)-2,6,6-trimethyl-bicyclo[3.1.1]heptane + phenyl 1-{[(1S,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methyl}vinyl sulfone

Conditions	Yield
Stage #1: (-)-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Heating; Stage #2: (prop-2-ene-1,2-diyldisulfonyl)dibenzene With trans-di-O-tert-butyl hyponitrite In methanol; dichloromethane Heating;	A n/a B 89%

(-)-α-pinene (7785-26-4) + 1,1’-(2,4,6-trihydroxy-5-methyl-1,3-phenylene)di(ethan-1-one) (2999-42-0) → 1-(5-Acetyl-6,8-dihydroxy-2,14,14-trimethyl-3-oxatetracyclo[11.1.1.02,11.04,9]pentadeca-4,6,8-trien-7-yl)ethan-1-one

Conditions	Yield
With tetraethylammonium tosylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In nitromethane electrolysis: fibre coated Pt anode, Pt cathode, 0.45 V vs. SCE, 2.5 F;	88.2%

(-)-α-pinene (7785-26-4) → (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0)

Conditions	Yield
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In tert-butyl alcohol for 20h; Inert atmosphere; Reflux;	85%
With osmium(VIII) oxide; trimethylamine-N-oxide In pyridine; water; tert-butyl alcohol for 96h; Heating;	65%
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In tert-butyl alcohol for 42h; Heating;	65%

RuCl2 (PPh3)3 + (-)-α-pinene (7785-26-4) + Trimethylenediamine (109-76-2) → (-)-(2E)-2-ethyl-4-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol

Conditions	Yield
With potassium hydroxide In (R,E)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal; hexane	85%

(-)-α-pinene (7785-26-4) → (1S,2R,3R, 5S)-pinanediol (29333-10-6)

Conditions	Yield
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol for 24h; Reflux; Inert atmosphere;	85%

diazoacetic acid ethyl ester (623-73-4) + (-)-α-pinene (7785-26-4) → C14H22O2

Conditions	Yield
With C8H6Cl2CuN3OS*2H2O In 1,2-dichloro-ethane at 70℃; for 1.66667h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	84%

methanol (67-56-1) + (-)-α-pinene (7785-26-4) → methyl 2-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]acetate (52305-35-8)

Conditions	Yield
Stage #1: methanol; (-)-α-pinene With oxygen; ozone at 0℃; Stage #2: With hydrazinium sulfate at 20℃; for 168h; Inert atmosphere;	84%

chloroform (67-66-3) + (-)-α-pinene (7785-26-4) → (1R,6R)-3,3-Dichloro-2,7,7-trimethyl-tricyclo[4.1.1.02,4]octane

Conditions	Yield
With potassium hydroxide; tert-butylammonium hexafluorophosphate(V) In toluene at 45℃; for 6h;	83%
With potassium tert-butylate

(-)-α-pinene (7785-26-4) + 1,3-dithiol-2,4,5-trithione (85931-57-3) → (4aR,5R,7S,8aS)-4a,5,6,7,8,8a-hexahydro-5,7-methano-4a,6,6-trimethyl-1,3-dithiolo[4,5-b][1,4]benzodithiin-2-thione

Conditions	Yield
In toluene for 13h; Heating;	83%

isocyanate de chlorosulfonyle (1189-71-5) + (-)-α-pinene (7785-26-4) → C13H21NO

Conditions	Yield
Stage #1: isocyanate de chlorosulfonyle; (-)-α-pinene In diethyl ether at 20℃; for 1h; Stage #2: With triethylamine In diethyl ether at 20℃; for 3h; Stage #3: With water In diethyl ether at 20℃;	83%

(-)-α-pinene (7785-26-4) + dimethylsulfide borane complex (13292-87-0) → L-diisopinocampheylborane (21947-87-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	82%
In tetrahydrofuran at 0℃; for 0.5h;	60%
In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;	52%
In tetrahydrofuran
In tetrahydrofuran at 0℃;

N,N,N,N,-tetramethylethylenediamine (110-18-9) + (-)-α-pinene (7785-26-4) + dimethylsulfide borane complex (13292-87-0) → (R)-alpine-boramine (67826-92-0)

Conditions	Yield
Stage #1: (-)-α-pinene; dimethylsulfide borane complex In diethyl ether for 1h; Reflux; Stage #2: N,N,N,N,-tetramethylethylenediamine In diethyl ether for 1h; Reflux;	81%
Stage #1: (-)-α-pinene; dimethylsulfide borane complex In diethyl ether for 1h; Reflux; Stage #2: N,N,N,N,-tetramethylethylenediamine In diethyl ether for 1h; Reflux;	68%

(-)-α-pinene (7785-26-4) + chloroamine-T (127-65-1) → N-((1R,2R,3S,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-methyl-benzenesulfonamide

Conditions	Yield
Stage #1: (-)-α-pinene; chloroamine-T In water; tert-butyl alcohol for 15h; Oxyamination; Heating; Stage #2: With sodium tetrahydroborate In water; tert-butyl alcohol at 20℃; for 1h; Reduction;	80%

(-)-α-pinene (7785-26-4) + 2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone (89295-32-9) → 2-((1S,5S)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-acrylic acid ethyl ester + 2-((1S,2R,3R,5S)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-acrylic acid ethyl ester

Conditions	Yield
Stage #1: (-)-α-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Heating; Stage #2: 2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone With trans-di-O-tert-butyl hyponitrite In methanol; dichloromethane Heating;	A n/a B 80%

Upstream product

• 763-10-0 geranyl diphosphate 
• 18172-67-3 beta-pinene 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 35519-42-7 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 35408-04-9 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 201230-82-2 carbon monoxide 
• 111-92-2 dibutylamine 
• 18172-67-3 (?)-β-pinene 
• 22321-84-2 pinocarveyl hydroperoxide 
• 547-61-5 pinocarveol 
• 177698-19-0 Beta-pinene 
• 35836-73-8 (1R)-(-)-nopol 
• 127-91-3 (1R,5R)-(+)-β-pinene 

Downstream Products

• 4695-62-9 Fenchol 
• 464-45-9 endo-borneol 
• 10281-53-5 trans-pinane 
• 4755-33-3 (1S)-(-)-cis-pinane 
• 473-55-2 trans-pinane 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 473-61-0 (+)-isopinocampheol 
• 5989-54-8 (-)-(S)-limonene 
• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 138-86-3 limonene. 
• 7216-56-0 4E,6Z-alloocimene 
• 92891-74-2 1-(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-propan-1-one 
• 92891-75-3 1-(5-Isopropylidene-2-methyl-cyclohex-2-enyl)-propan-1-one 
• 92891-73-1 1-(2,6,6-Trimethyl-bicyclo[3.1.1]hept-2-en-3-yl)-propan-1-one 

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