(1S)-(-)-alpha-Pinene supplier

Name
(1S)-(-)-alpha-Pinene
EINECS 232-077-3
CAS No. 7785-26-4
Article Data33
CAS DataBase
Density 0.879 g/cm³
Solubility insoluble in water
Melting Point -64 °C(lit.)
Formula C₁₀H₁₆
Boiling Point 157.9 °C at 760 mmHg
Molecular Weight 136.237
Flash Point 32.2 °C
Transport Information UN 2368 3/PG 3
Appearance clear colourless liquid
Safety 26-36/37-61-16-60
Risk Codes 10-36/37/38-43-50-65-51/53-20/21/22
Molecular Structure
Hazard Symbols Xi,N,Xn
Synonyms 2-Pinene,(1S,5S)-(-)- (8CI);Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1S)-;(-)-(1S)-a-Pinene;(-)-2-Pinene;(-)-a-Pinene;(1S)-(-)-a-Pinene;(1S,5S)-(-)-a-Pinene;(S)-(-)-a-Pinene;1S-a-Pinene;l-a-Pinene;
PSA 0.00000
LogP 2.99870

Synthetic route

: 18172-67-3, 19902-08-0
beta-pinene

: 7785-26-4
(-)-α-pinene

Conditions

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

: 7785-26-4
(-)-α-pinene

Conditions

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

: 18172-67-3, 19902-08-0
beta-pinene

A: 7785-26-4
(-)-α-pinene

B: 7785-70-8
(+)-α-pinene

C: 2,4,4-Trimethyl-8-methylene-3-aza-bicyclo[3.3.1]non-2-ene

Conditions

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

...Expand

: 55527-89-4
(-)-myrtenyl bromide

: 7785-26-4
(-)-α-pinene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

: 80-56-8
rac-α-pinene

A: 7785-26-4
(-)-α-pinene

B: 7785-70-8
(+)-α-pinene

Conditions

Conditions	Yield
Leiten des Dampfes durch Gelatine-Hydrosol;

: 18172-67-3, 19902-08-0
beta-pinene

: 144-62-7
oxalic acid

: 7785-26-4
(-)-α-pinene

: 7647-01-0
hydrogenchloride

: 60-29-7
diethyl ether

: 35519-42-7
2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

A: 7785-26-4
(-)-α-pinene

B: 138-86-3
limonene.

C (1R)-2endo-chloro-1,3,3-trimethyl-norbornane(?): (1R)-2endo-chloro-1,3,3-trimethyl-norbornane(?)

D (1S)-2endo-chloro-bornane: (1S)-2endo-chloro-bornane

Conditions

Conditions	Yield
Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

...Expand

: 7647-01-0
hydrogenchloride

: 60-29-7
diethyl ether

: 35408-04-9
2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

A: 7785-26-4
(-)-α-pinene

B: 1195-77-3, 3372-12-1, 90976-73-1
(1S)-2-endo-chlorofenchane

C: 138-86-3
limonene.

Conditions

Conditions	Yield
Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

...Expand

bis: bis

A: 7785-26-4
(-)-α-pinene

: 4080-46-0, 23733-90-6, 30460-81-2
(+)-dehydro-β-pinene

Conditions

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

: 201230-82-2
carbon monoxide

: 18172-67-3, 19902-08-0
beta-pinene

: 111-92-2
dibutylamine

A: 7785-26-4
(-)-α-pinene

B: 199445-88-0
2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)acetaldehyde

C: C19H35N

D: 1350552-88-3
C19H37N

Conditions

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

...Expand

: 201230-82-2
carbon monoxide

: 18172-67-3, 19902-08-0
beta-pinene

: 111-92-2
dibutylamine

A: 7785-26-4
(-)-α-pinene

B: 1350552-88-3
C19H37N

Conditions

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

...Expand

: 2-((1S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-1-phenylethan-1-one

A: 7785-26-4
(-)-α-pinene

B: 98-86-2
acetophenone

Conditions

Conditions	Yield
In methanol for 1h; Photolysis;

: 127-91-3
(1R,5R)-(+)-β-pinene

A: 7785-26-4
(-)-α-pinene

B: α-dihydropinene

Conditions

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

: 7785-26-4
(-)-α-pinene

(1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid: (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 21947-87-5
L-diisopinocampheylborane

Conditions

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

: 7785-26-4
(-)-α-pinene

: 34413-88-2
pinocarvone

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 264881-99-4
methyl 2-(4-bromophenyl)-2-diazoacetate

: (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

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

: 7785-26-4
(-)-α-pinene

: 1686-14-2
(1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.2,4]octane

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 5,7,7-trimethyl-3-oxa-tricyclo[4.1.1.02,4]octane

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 20536-51-0
(+)-α-pinanediol

Conditions

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

: 7785-26-4
(-)-α-pinene

: 19894-98-5
6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol

Conditions

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%

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 7785-26-4
(-)-α-pinene

: C19H20O3

Conditions

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

: 7785-26-4
(-)-α-pinene

: 303801-38-9
(1S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions

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.

: 7785-26-4
(-)-α-pinene

: 67-63-0
isopropyl alcohol

: 3(2),3(2),7-trimethyl-2,5-dioxo-6-oxa-3(1,3)-cyclobutanaoctaphane

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 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
(+)-isopinocampheol

Conditions

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;

: 7785-26-4
(-)-α-pinene

: 475290-10-9
1-methyl-4-(1-methyl-1-nitrooxy-ethyl)-cyclohexene

Conditions

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

: 7785-26-4
(-)-α-pinene

: 123-73-9
crotonaldehyde

: C14H22O

Conditions

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

: 7785-26-4
(-)-α-pinene

: 2525-55-5
(prop-2-ene-1,2-diyldisulfonyl)dibenzene

A: (1S,5S)-3-(2-Benzenesulfonyl-allyl)-2,6,6-trimethyl-bicyclo[3.1.1]heptane

B: phenyl 1-{[(1S,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methyl}vinyl sulfone

Conditions

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%

...Expand

: 7785-26-4
(-)-α-pinene

: 2999-42-0
1,1’-(2,4,6-trihydroxy-5-methyl-1,3-phenylene)di(ethan-1-one)

: 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

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%

: 7785-26-4
(-)-α-pinene

: 22422-34-0
(1R,2R,3S,5R)-2,3-pinane diol

Conditions

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: RuCl2 (PPh3)3

: 7785-26-4
(-)-α-pinene

: 109-76-2
Trimethylenediamine

: (-)-(2E)-2-ethyl-4-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol

Conditions

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

...Expand

: 7785-26-4
(-)-α-pinene

: 29333-10-6
(1S,2R,3R, 5S)-pinanediol

Conditions

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

: 623-73-4
diazoacetic acid ethyl ester

: 7785-26-4
(-)-α-pinene

: C14H22O2

Conditions

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%

: 67-56-1
methanol

: 7785-26-4
(-)-α-pinene

: 52305-35-8
methyl 2-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]acetate

Conditions

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

: 67-66-3
chloroform

: 7785-26-4
(-)-α-pinene

: (1R,6R)-3,3-Dichloro-2,7,7-trimethyl-tricyclo[4.1.1.02,4]octane

Conditions

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

: 7785-26-4
(-)-α-pinene

: 85931-57-3
1,3-dithiol-2,4,5-trithione

: (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

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

: 1189-71-5
isocyanate de chlorosulfonyle

: 7785-26-4
(-)-α-pinene

: C13H21NO

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 13292-87-0
dimethylsulfide borane complex

: 21947-87-5
L-diisopinocampheylborane

Conditions

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℃;

: 110-18-9
N,N,N,N,-tetramethylethylenediamine

: 7785-26-4
(-)-α-pinene

: 13292-87-0
dimethylsulfide borane complex

: 67826-92-0
(R)-alpine-boramine

Conditions

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%

...Expand

: 7785-26-4
(-)-α-pinene

: 127-65-1
chloroamine-T

: N-((1R,2R,3S,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-methyl-benzenesulfonamide

Conditions

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%

: 7785-26-4
(-)-α-pinene

: 89295-32-9
2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone

A: 2-((1S,5S)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-acrylic acid ethyl ester

B: 2-((1S,2R,3R,5S)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-acrylic acid ethyl ester

Conditions

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%

...Expand

(1S)-(-)-alpha-Pinene Specification

The Bicyclo[3.1.1]hept-2-ene,2,6,6-trimethyl-, (1S,5S)-, with the CAS registry number 7785-26-4 and EINECS registry number 232-077-3, has the systematic name of (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene. It is a kind of clear colourless liquid, and belongs to the product categories: Industrial/Fine Chemicals; API intermediates; Bicyclic Monoterpenes; Biochemistry; Terpenes. The molecular formula of the chemical is C₁₀H₁₆.

The characteristics of Bicyclo[3.1.1]hept-2-ene,2,6,6-trimethyl-, (1S,5S)- are as followings: (1)ACD/LogP: 4.37; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 0; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 0; (6)Polar Surface Area: 0 Å²; (7)Index of Refraction: 1.479; (8)Molar Refractivity: 43.96 cm³; (9)Molar Volume: 154.9 cm³; (10)Polarizability: 17.42×10^-24cm³; (11)Surface Tension: 25.3 dyne/cm; (12)Density: 0.879 g/cm³; (13)Flash Point: 32.2 °C; (14)Enthalpy of Vaporization: 37.83 kJ/mol; (15)Boiling Point: 157.9 °C at 760 mmHg; (16)Vapour Pressure: 3.49 mmHg at 25°C.

Uses of Bicyclo[3.1.1]hept-2-ene,2,6,6-trimethyl-, (1S,5S)-: It can be used to produce (1S,3R)-pin-2(10)-en-3-yl hydroperoxide. This reaction will need reagent methylene Blue, methylene Blue, isopropyl alcohol and oxygen.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: C\1=C(\[C@@H]2C[C@H](C/1)C2(C)C)C
(2)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
(3)InChIKey: GRWFGVWFFZKLTI-IUCAKERBBG

Product Name

(1S)-(-)-alpha-Pinene

Synthetic route

(1S)-(-)-alpha-Pinene Specification

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