beta-Pinene supplier | CasNO.127-91-3

Name
beta-Pinene
EINECS 204-872-5
CAS No. 127-91-3
Article Data26
CAS DataBase
Density 0.88 g/cm³
Solubility Insoluble in water, soluble in ethanol
Melting Point -61 °C
Formula C₁₀H₁₆
Boiling Point 166 °C at 760 mmHg
Molecular Weight 136.237
Flash Point 34.9 °C
Transport Information
Appearance Colorless transparent oily liquid
Safety 16
Risk Codes 10
Molecular Structure
Hazard Symbols R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.;
Synonyms 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane;2(10)-Pinene(8CI);Pseudopinen;Pseudopinene;NSC 21447;NSC 406265;NSC 59190;Nopinen;Nopinene;PC 600;Terebenthene;b-Pinene;beta-Pinene;
PSA 0.00000
LogP 2.99870

Synthetic route

: 74946-99-9
Diethyl (+)-Myrtene-10-phosphonate

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 4h;	93%

: 18680-26-7
pinane-2β,10-diol

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;	92%

: 7785-70-8
(+)-α-pinene

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
Stage #1: (+)-α-pinene With n-butyllithium; potassium tert-butylate In hexane at -78 - 20℃; for 45h; Stage #2: With Trimethyl borate In hexane at -78 - 20℃; Stage #3: With hydrogenchloride In hexane; water for 1h;	73%
With selenium(IV) oxide; ethanol
Yield given. Multistep reaction;
Stage #1: (+)-α-pinene With n-butyllithium; potassium tert-butylate at -78 - 20℃; for 48h; Stage #2: With Trimethyl borate In diethyl ether at -78 - 20℃; for 1h;
With borane

: 7785-70-8
(+)-α-pinene

A: 127-91-3
(1R,5R)-(+)-β-pinene

B: 190715-28-7
6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene

Conditions

Conditions	Yield
With selenium(IV) oxide; ethanol at 140 - 150℃; under 15 Torr;

: 7785-70-8
(+)-α-pinene

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

B: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
Yield given. Multistep reaction. Yields of byproduct given;

: diisopinocampheylborane

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
With benzaldehyde 1.) triglyme, 130 deg C, 12 h; 2.) 165-175 deg C, 2h; Yield given. Multistep reaction;

: 64-17-5
ethanol

: 23727-16-4
myrtenal

: 141-52-6
sodium ethanolate

: 7803-57-8
hydrazine hydrate

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
at 200℃;

...Expand

: 7446-08-4
selenium(IV) oxide

: 64-17-5
ethanol

: 7785-70-8
(+)-α-pinene

A: 23727-16-4
myrtenal

B: 127-91-3
(1R,5R)-(+)-β-pinene

C: 6712-78-3
myrtenol

D (-)-verbenene and dimyrtenyl selenide: (-)-verbenene and dimyrtenyl selenide

...Expand

: (+)-dimyrtenyl selenide

A: 127-91-3
(1R,5R)-(+)-β-pinene

B (-)-verbenene: (-)-verbenene

Conditions

Conditions	Yield
at 140 - 150℃; under 15 Torr;

bis-<(6.6-dimethyl-norpinen(2)-yl-(2)-methyl>-selenide: bis-<(6.6-dimethyl-norpinen(2)-yl-(2)-methyl>-selenide

A: 127-91-3
(1R,5R)-(+)-β-pinene

B: 190715-28-7
6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene

Conditions

Conditions	Yield
at 140 - 150℃; under 15 Torr;

: 74984-67-1
(+)-Myrtenyl Bromide

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / 12 h / 85 °C 2: 93 percent / Lithium aluminium hydride / diethyl ether / 4 h / 0 °C View Scheme

: 6712-78-3
myrtenol

: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 68 percent / Phosphorus (III) Bromide 2: 90 percent / 12 h / 85 °C 3: 93 percent / Lithium aluminium hydride / diethyl ether / 4 h / 0 °C View Scheme

: 7785-70-8
(+)-α-pinene

A: 99-87-6
4-methylisopropylbenzene

B: 508-32-7
tricyclane

C: 5794-04-7
camphene

D: 5989-54-8
(-)-(S)-limonene

E: 127-91-3
(1R,5R)-(+)-β-pinene

F: 190715-28-7
6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene

G: 7378-37-2
α-fenchene

Conditions

Conditions	Yield
With Co(2,6-Me2C5H3N)2Br2; oxygen In carbon dioxide; ethyl acetate at 220℃; under 95006.4 Torr; tubular reactor; Supercritical conditions;

...Expand

: 177698-19-0
Beta-pinene

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

B: 127-91-3
(1R,5R)-(+)-β-pinene

Conditions

Conditions	Yield
With MEGA-DEX-DET Resolution of racemate;	A n/a B n/a

: 127-91-3
(1R,5R)-(+)-β-pinene

: 77982-63-9
nopinone

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With ozone In methanol Stage #2: With Iron(III) nitrate nonahydrate In methanol at 20℃; for 1h;	97%
With sodium periodate; rhodium(III) chloride hydrate In tetrachloromethane; water; acetonitrile at 20℃; for 2h;	91%
With ozone In methanol at -78℃; for 2.5h;	78%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 1118071-19-4
2-chloromethyl-6,6-dimethylbicyclo[3.1.1]heptane

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-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;	94%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 473-01-8, 514-99-8, 15358-91-5, 15358-92-6, 51152-12-6, 53369-17-8, 73136-30-8, 132203-71-5
cis-myrtanol

Conditions

Conditions	Yield
With C11H7F17S(1+)B(1-)H3; 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methyl sulfide In FC-72; dichloromethane	93%
Stage #1: (1R,5R)-(+)-β-pinene With dimethyl sulfide borane In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; ethanol; water at 0 - 35℃; for 1h; Heating / reflux;	93%
Stage #1: (1R,5R)-(+)-β-pinene With borane-THF In tetrahydrofuran at 25℃; for 0.0138889h; Flow reactor; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; ethanol; water at 20℃; for 0.00555556h; Reagent/catalyst; Temperature; Solvent; Flow reactor;	92%

: 1016985-26-4
dithiocarbonic acid S-(3,3-dimethoxy-2-oxo-propyl) ester O-ethyl ester

: 127-91-3
(1R,5R)-(+)-β-pinene

: 1016985-35-5
C18H30O4S2

Conditions

Conditions	Yield
With dilauryl peroxide In 1,2-dichloro-ethane Heating;	92%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 6931-54-0
trans-2,10-epoxypinane

Conditions

Conditions	Yield
With dihydrogen peroxide; potassium hydrogencarbonate; dicyclohexyl-carbodiimide In methanol; water for 24h; Ambient temperature; other reagents: H2O2/Na3PO4*12H2O/dicyclohexylcarbodiimide, H2O2/Amberlite IRC-50/dicyclohexylcarbodiimide, H2O2/KHCO3/benzonitrile;	91%
With dihydrogen peroxide; sodium acetate; acetic anhydride; sodium carbonate In toluene at 50℃; for 4h;	90%
With dihydrogen peroxide; potassium hydrogencarbonate; benzonitrile In methanol for 24h; Ambient temperature;	35%
With C44H44IrN5; N-(benzenesulfonyl)-3-phenyloxaziridine In dichloromethane for 48h; optical yield given as %de;

: 127-91-3
(1R,5R)-(+)-β-pinene

: diallyl(methyliden)ammonium trifluoroacetate

: N-Myrtanylmethyl-N,N-diallylamine

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With dimethylsulfide borane complex; diethylzinc In tetrahydrofuran Metallation; Stage #2: diallyl(methyliden)ammonium trifluoroacetate In tetrahydrofuran; dichloromethane at 25℃; for 0.5h; Addition; Aminomethylation;	91%

: 5324-64-1
2-(benzenesulfonyl)ethynylbenzene

: 127-91-3
(1R,5R)-(+)-β-pinene

: 6,6-dimethyl-2-(3-phenylprop-2-ynyl)bicyclo[3.1.1]heptane

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Heating; Stage #2: 2-(benzenesulfonyl)ethynylbenzene With di-tert-butoxydiazene In dichloromethane at 40℃;	89%

: 78104-88-8
1-Methylcyclopropancarbonsaeurenitril

: 127-91-3
(1R,5R)-(+)-β-pinene

: 1-methyl-1-cyano-2-(10'-α-pinenyl)cyclopropane

Conditions

Conditions	Yield
at 120℃; for 2h; Alder-ene reaction;	88%

: 1066-35-9
dimethylmonochlorosilane

: 127-91-3
(1R,5R)-(+)-β-pinene

: 666832-74-2
(+)-(1R,2R,5R)-myrtanyl dimethyl silicon chloride

Conditions

Conditions	Yield
dihydrogen hexachloroplatinate at 0 - 35℃; for 13h;	88%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 1118071-24-1
2-iodomethyl-6,6-dimethylbicyclo[3.1.1]heptane

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-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;	88%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 1118071-22-9
2-bromomethyl-6,6-dimethylbicyclo[3.1.1]heptane

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-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;	85%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 65861-96-3, 71564-06-2
(+)-3-chloro-2(10)-pinene

Conditions

Conditions	Yield
With N-chloro-succinimide; bis(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)selenide; triethylamine In dichloromethane at 20℃; for 5h;	83%

: 127-91-3
(1R,5R)-(+)-β-pinene

: (aS)-N-hydroxy-2'-methoxy-1,1'-binaphthalene-2-carboximidoyl chloride

: C32H31NO2

Conditions

Conditions	Yield
With triethylamine In chloroform for 72h; Ambient temperature;	79%

: 19158-51-1
P-toluenesulfonyl cyanide

: 127-91-3
(1R,5R)-(+)-β-pinene

: (6,6-dimethylbicyclo[3.1.1]hept-2-yl)acetonitrile

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Heating; Stage #2: P-toluenesulfonyl cyanide With di-tert-butoxydiazene In dichloromethane at 40℃;	75%

: 52843-77-3
phenylethynyl trifluoromethyl sulfone

: 127-91-3
(1R,5R)-(+)-β-pinene

: (3-methyl-3-(4-(2,2,2-trifluoroethyl)cyclohex-3-en-1-yl)but-1-yn-1-yl)benzene

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethyl acetate at 80℃; for 12h; Schlenk technique; Inert atmosphere;	75%

: 127-91-3
(1R,5R)-(+)-β-pinene

: N,N-dibenzyliminium trifluoroacetate salt

: N-Myrtanylmethyl-N,N-dibenzylamine

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With dimethylsulfide borane complex; diethylzinc In tetrahydrofuran Metallation; Stage #2: N,N-dibenzyliminium trifluoroacetate salt In tetrahydrofuran; diethyl ether at 25℃; for 0.5h; Addition; Aminomethylation;	73%

: 127-91-3
(1R,5R)-(+)-β-pinene

: ethyl 2-diazobut-3-enoate

: 1453109-29-9
(E)-ethyl 5-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)pent-2-enoate

Conditions

Conditions	Yield
With IPrAuNTf2 In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; regioselective reaction;	73%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 51152-12-6
(-)-cis-myrtanol

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With dimethylsulfide borane complex In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; ethanol; water at 20 - 80℃; for 2.5h; Inert atmosphere; diastereoselective reaction;	73%

: 127-91-3
(1R,5R)-(+)-β-pinene

: bis(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)selenide

Conditions

Conditions	Yield
With selenium(IV) oxide; triethylamine In dichloromethane at 20℃; for 72h; Solvent;	71%

: 127-91-3
(1R,5R)-(+)-β-pinene

A: 99-89-8
4-Isopropylphenol

B: 77982-63-9
nopinone

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With ozone In methanol Stage #2: With iron(III) chloride hexahydrate In methanol at 60℃; for 2h;	A 15% B 70%

: 19158-51-1
P-toluenesulfonyl cyanide

: 127-91-3
(1R,5R)-(+)-β-pinene

: 112033-25-7
1-(p-tolylsulphonylmethyl)-4-(1-cyano-1-methylethyl)-1-cyclohexene

Conditions

Conditions	Yield
With Eosin Y In dimethyl sulfoxide for 12h; Irradiation; Sealed tube; Inert atmosphere; regioselective reaction;	68%

: 1415115-03-5
C7H6FIO2S

: 127-91-3
(1R,5R)-(+)-β-pinene

: 98-80-6
phenylboronic acid

A: 51229-66-4
[fluoro(phenyl)(phenylsulfonyl)]methane

B: C17H21FO2S

Conditions

Conditions	Yield
With bis(acetylacetonate)nickel(II); potassium carbonate; triphenylphosphine In dichloromethane at 100℃; for 24h; Inert atmosphere; Sealed tube;	A 8% B 66%

...Expand

: 50-00-0
formaldehyd

: 2999-10-2
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(3-methylbutan-1-one)

: 127-91-3
(1R,5R)-(+)-β-pinene

: 1017239-46-1
6,8-bis(3-methylbutanoyl)-3,4-dihydro-5,7-dihydroxy-6',6'-dimethyl-spiro-2H-benzopyran-2,2'-bicyclo[3.1.1]heptane

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 60℃; for 0.0666667h; microwave irradiation;	65%

...Expand

: 127-91-3
(1R,5R)-(+)-β-pinene

: O-ethyl S-(2-oxotetrahydrothiophen-3-yl)carbonodithioate

: C17H26O2S3

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene; O-ethyl S-(2-oxotetrahydrothiophen-3-yl)carbonodithioate In ethyl acetate at 80℃; for 0.25h; Inert atmosphere; Stage #2: With dilauryl peroxide In ethyl acetate for 1h; Inert atmosphere;	65%

: 963-16-6
(E)-1,2-bis(phenylsulfonyl)ethylene

: 127-91-3
(1R,5R)-(+)-β-pinene

: 2-(3-benzenesulfonylallyl)-6,6-dimethylbicyclo[3.1.1]heptane

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With N,N-dimethyl acetamide; benzo[1,3,2]dioxaborole In dichloromethane for 5h; Heating; Stage #2: (E)-1,2-bis(phenylsulfonyl)ethylene With di-tert-butoxydiazene In dichloromethane at 40℃;	59%

: 127-91-3
(1R,5R)-(+)-β-pinene

: 926-62-5
isobutylmagnesium bromide

: C14H24

Conditions

Conditions	Yield
Stage #1: (1R,5R)-(+)-β-pinene With N,N'-bis(phenylsulfonyl)sulfur diimide In 1,2-dimethoxyethane; diethyl ether at 0 - 4℃; for 6h; Stage #2: isobutylmagnesium bromide With copper(I) bromide dimethylsulfide complex In 1,2-dimethoxyethane; diethyl ether at -78 - -20℃; for 0.666667h;	57%

: 123-73-9
trans-Crotonaldehyde

: 127-91-3
(1R,5R)-(+)-β-pinene

: (1S,4R,5S)-2,2,6-Trimethyl-4-((E)-propenyl)-3-oxa-bicyclo[3.3.1]non-6-ene

Conditions

Conditions	Yield
With askanite-bentonite clay In dichloromethane at 20℃; for 0.25h;	56%

beta-Pinene Consensus Reports

Reported in EPA TSCA Inventory.

beta-Pinene Standards and Recommendations

ACGIH TLV: TWA 20 ppm (sensitizer); Not Classifiable as a Human Carcinogen

beta-Pinene Specification

The Pseudopinene with CAS registry number of 127-91-3 is also known as beta-Pinene. The IUPAC name is 6,6-Dimethyl-4-methylidenebicyclo[3.1.1]heptane. It belongs to product categories of Pharmaceutical Intermediates; Bicyclic Monoterpenes; Biochemistry; Terpenes; Flavor. Its EINECS registry number is 204-872-5. In addition, the formula is C₁₀H₁₆ and the molecular weight is 136.23. This chemical is a colorless transparent oily liquid and it is insoluble in water but soluble in ethanol. What's more, this chemical can be used for synthesis of a variety of spices and can be derived by fractionation of turpentine. During using it, keep away from sources of ignition as it is flammable.

Physical properties about Pseudopinene are: (1)ACD/LogP: 4.37; (2)ACD/LogD (pH 5.5): 4.37; (3)ACD/LogD (pH 7.4): 4.37; (4)ACD/BCF (pH 5.5): 1225.94; (5)ACD/BCF (pH 7.4): 1225.94; (6)ACD/KOC (pH 5.5): 5653.62; (7)ACD/KOC (pH 7.4): 5653.62; (8)Index of Refraction: 1.483; (9)Molar Refractivity: 43.76 cm³; (10)Molar Volume: 153 cm³; (11)Surface Tension: 27 dyne/cm; (12)Density: 0.88 g/cm³; (13)Flash Point: 34.9 °C; (14)Enthalpy of Vaporization: 38.59 kJ/mol; (15)Boiling Point: 166 °C at 760 mmHg; (16)Vapour Pressure: 2.4 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1(C2CCC(=C)C1C2)C
2. InChI: InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
3. InChIKey: WTARULDDTDQWMU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	4700mg/kg (4700mg/kg)	BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Food and Cosmetics Toxicology. Vol. 16, Pg. 859, 1978.

Product Name

beta-Pinene

Synthetic route

beta-Pinene Consensus Reports

beta-Pinene Standards and Recommendations

beta-Pinene Specification

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