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80-56-8

Basic Information
CAS No.: 80-56-8
Name: Bicyclo[3.1.1]hept-2-ene,2,6,6-trimethyl-
Molecular Structure:
Molecular Structure of 80-56-8 (Bicyclo[3.1.1]hept-2-ene,2,6,6-trimethyl-)
Formula: C10H16
Molecular Weight: 136.26
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;
EINECS: 201-291-9
Density: 0.879 g/cm3
Melting Point: - 55°C
Boiling Point: 157.883 °C at 760 mmHg
Flash Point: 32.222 °C
Solubility: insoluble in water
Appearance: liquid with a turpentine odour
Hazard Symbols: HarmfulXn; DangerousN
Risk Codes: 10-36/37/38-51/53-65
Safety: 16-26-29-37/39-61
Transport Information: UN 2368 3/PG 3
PSA: 0.00000
LogP: 2.99870
Synthetic route
422567-10-0

dithiocarbonic acid S-methyl ester-O-pinan-3-yl ester

A

74-93-1

methylthiol

B

463-58-1

carbon oxide sulfide

80-56-8

rac-α-pinene

Conditions
ConditionsYield
at 170 - 190℃; pinocamphylxanthogenic acid methyl ester from inactive pinocampheol;
177698-19-0

Beta-pinene

65-85-0

benzoic acid

80-56-8

rac-α-pinene

Conditions
ConditionsYield
at 125 - 130℃; levorotatory form;
at 125 - 130℃; levorotatory form;
127-91-3

(1R,5R)-(+)-β-pinene

A

99-86-5

1-methyl-4-isopropyl-1,3-cyclohexadiene

B

99-87-6

4-methylisopropylbenzene

C

99-85-4

crithmene

565-00-4

dl-camphene

80-56-8

rac-α-pinene

Conditions
ConditionsYield
With pyridine; hydrogen; platinum-alumina(0.6 percentPt) at 300℃; for 0.79h; Product distribution; effects of partial pressures of N2, H2, pyridine;
127-91-3

(1R,5R)-(+)-β-pinene

A

99-86-5

1-methyl-4-isopropyl-1,3-cyclohexadiene

B

99-87-6

4-methylisopropylbenzene

80-56-8

rac-α-pinene

Conditions
ConditionsYield
With hydrogen; platinum-alumina(0.6 percent Pt) at 300℃; Yield given;
177698-19-0

Beta-pinene

69-72-7

salicylic acid

80-56-8

rac-α-pinene

B

138-86-3

limonene.

C

bornyl ester

bornyl ester

D

terpinene

terpinene

Conditions
ConditionsYield
at 160℃; levorotatory form;
79-92-5

camphene

80-56-8

rac-α-pinene

Conditions
ConditionsYield
dl-camphene;
hydrazone of (+)-pinocamphone

hydrazone of (+)-pinocamphone

A

24031-99-0

(-)-trans-δ-pinene

80-56-8

rac-α-pinene

Conditions
ConditionsYield
With ethanol; mercury(II) oxide
Conditions
ConditionsYield
With hydrogen; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In benzene at 120℃; under 67505.4 Torr; for 4h;
177698-19-0

Beta-pinene

201230-82-2

carbon monoxide

80-56-8

rac-α-pinene

cis-10-formylpinane

trans-10-formylpinane

Conditions
ConditionsYield
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;
177698-19-0

Beta-pinene

98-86-2

acetophenone

80-56-8

rac-α-pinene

cis-10-formylpinane

trans-10-formylpinane

Conditions
ConditionsYield
di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In benzene-d6 at 100℃; under 67505.4 Torr; for 4h;
201230-82-2

carbon monoxide

127-91-3

(1R/S,5R/S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane

80-56-8

rac-α-pinene

cis-10-formylpinane

trans-10-formylpinane

Conditions
ConditionsYield
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.
Conditions
ConditionsYield
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%
80-56-8

rac-α-pinene

22466-73-5

(1S,2S,3S)-pinane-2,3-diol

Conditions
ConditionsYield
With pyridine; trimethylamine-N-oxide; osmium(VIII) oxide In water; tert-butyl alcohol for 17h; Heating;93%
60805-71-2

phenylselenyl benzenesulfonate

80-56-8

rac-α-pinene

phenyl (1RS,2RS,3RS,5SR)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl selenide

Conditions
ConditionsYield
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%
1212-08-4

S-Phenyl benzenethiosulfonate

80-56-8

rac-α-pinene

phenyl (1RS,2RS,3RS,5SR)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl sulfide

Conditions
ConditionsYield
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%
80-56-8

rac-α-pinene

(1RS,2RS,3RS,5SR)-3-bromomethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions
ConditionsYield
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%
80-56-8

rac-α-pinene

80-57-9, 1196-01-6, 5480-12-6, 18309-32-5

(+/-)-2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide; cobalt(II) ethyl phosphonate In acetonitrile at 50℃; for 48h;88%
80-56-8

rac-α-pinene

(1RS,2RS,3RS,5SR)-3-iodomethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions
ConditionsYield
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%
16601-01-7

benzenethiosulfonic acid S-benzyl ester

80-56-8

rac-α-pinene

(1RS,2RS,3RS,5SR)-3-benzylsulfanyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions
ConditionsYield
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%
80-56-8

rac-α-pinene

(1RS,2RS,3RS,5SR)-3-chloromethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

Conditions
ConditionsYield
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%
1212-08-4

S-Phenyl benzenethiosulfonate

80-56-8

rac-α-pinene

phenyl (1RS,2RS,3RS,5SR)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl sulfide

Conditions
ConditionsYield
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%
80-56-8

rac-α-pinene

538342-26-6

7-nitro-3-methoxycarbonyl-4H-1,2-benzoxazine

C17H21NO3

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;78%
1000847-61-9

5-trifluoromethyl-3-methoxycarbonyl-4H-1,2-benzoxazine

80-56-8

rac-α-pinene

C18H21F3O

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;72%
80-56-8

rac-α-pinene

51152-11-5

(1R*,2R*,3R*,5S*)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol

Conditions
ConditionsYield
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;
932399-74-1

8-nitro-3-methoxycarbonyl-4H-1,2-benzoxazine

80-56-8

rac-α-pinene

C17H21NO3

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;70%
67-66-3

chloroform

80-56-8

rac-α-pinene

18675-44-0, 32549-14-7, 33059-79-9, 49752-36-5

3,3-dichloro 2,7,7-trimethyl tricyclo<4.1.1.02,4>octane

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate at 0℃; for 0.75h;60%
80-56-8

rac-α-pinene

538342-18-6

7-bromo-3-methoxycarbonyl-4H-1,2-benzoxazine

C17H21BrO

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;56%
80-56-8

rac-α-pinene

108-24-7

acetic anhydride

Conditions
ConditionsYield
With sodium perchlorate; sodium acetate In acetic acid at 20℃; electrochemically - Pt electrodes; 2.0 A/dm2;55%
80-56-8

rac-α-pinene

538342-24-4

7-trifluoromethyl-3-methoxycarbonyl-4H-1,2-benzoxazine

C18H21F3O

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

C12H11NO5

80-56-8

rac-α-pinene

C19H24O3

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;51%
80-56-8

rac-α-pinene

538342-22-2

3,7-dimethoxycarbonyl-4H-1,2-benzoxazine

C19H24O3

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

C10H8BrNO3

80-56-8

rac-α-pinene

C17H21BrO

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;48%
80-56-8

rac-α-pinene

538342-25-5

7-cyano-3-methoxycarbonyl-4H-1,2-benzoxazine

C18H21NO

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;44%
80-56-8

rac-α-pinene

538342-19-7

6-chloro-3-methoxycarbonyl-4H-1,2-benzoxazine

C17H21ClO

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;43%
80-56-8

rac-α-pinene

538342-17-5

7-chloro-3-methoxycarbonyl-4H-1,2-benzoxazine

C17H21ClO

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

C10H8FNO3

80-56-8

rac-α-pinene

C17H21FO

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;38%
4233-33-4

4-Phenyl-1,2,4-triazolidine-3,5-dione

80-56-8

rac-α-pinene

A

82934-23-4

7,8,8-Trimethyl-N-phenyl-4,5-diazatricyclo<4.2.1.03,7>nonan-4,5-dicarboximide

82934-22-3

1-(6,6-Dimethyl-2-methylenbicyclo<3.1.1>hept-3-yl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Conditions
ConditionsYield
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%
932399-72-9

7-fluoro-3-methoxycarbonyl-4H-1,2-benzoxazine

80-56-8

rac-α-pinene

C17H21FO

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;32%
80-56-8

rac-α-pinene

538342-16-4

3-methoxycarbonyl-4H-1,2-benzoxazine

C17H22O

Conditions
ConditionsYield
In toluene at 150℃; for 6h; Diels-Alder reaction;28%
123-91-1

1,4-dioxane

80-56-8

rac-α-pinene

98-11-3

benzenesulfonic acid

98-55-5

terpineol

Conditions
ConditionsYield
at 40℃;
Conditions
ConditionsYield
at 160℃;
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    English name: alpha-Pinene English Synonyms: (±) -pin-2-ene, 6,6-Trimethyl-bicyclo [3.1.1] hept-2-ene; 2,6,6-trimethylbicyclo- (3,1,1) -2- Heptene; 2,6,6-Trimethylbicyclo (3.1.1) -2-hept-2-ene; 2,6,6-Trimethylbicyclo (3.1.1) 3.1.1) hept

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    alpha-Pinene Basic information Product Name: alpha-Pinene Synonyms: (±)-pin-2-ene;,6,6-Trimethyl-bicyclo[3.1.1]hept-2-ene;2,6,6-trimethylbicyclo-(3,1,1)-2-heptene;2,6,6-Trimethylb

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    Product Name: alpha-Pinene Synonyms: (±)-pin-2-ene;,6,6-Trimethyl-bicyclo[3.1.1]hept-2-ene;2,6,6-trimethylbicyclo-(3,1,1)-2-heptene;2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene;2,6,6-Trimethylbicyc

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*Required Fields

Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid
ACGIH TLV: TWA 20 ppm (sensitizer); Not Classifiable as a Human Carcinogen

Specification

The 2-Pinene, with the CAS registry number 80-56-8 and EINECS registry number 201-291-9, has the systematic name of 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene. And the molecular formula of this chemical is C10H16. It is a kind of liquid with a turpentine odour, and belongs to the following product categories: Alkenes; Cyclic; Organic Building Blocks.

The 2-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis).
 
The physical properties of 2-Pinene are as following: (1)ACD/LogP: 4.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.321; (4)ACD/LogD (pH 7.4): 4.321; (5)ACD/BCF (pH 5.5): 1131.583; (6)ACD/BCF (pH 7.4): 1131.583; (7)ACD/KOC (pH 5.5): 5338.61; (8)ACD/KOC (pH 7.4): 5338.61; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.479; (14)Molar Refractivity: 43.964 cm3; (15)Molar Volume: 154.905 cm3; (16)Polarizability: 17.429×10-24cm3; (17)Surface Tension: 25.341 dyne/cm; (18)Density: 0.879 g/cm3; (19)Flash Point: 32.222 °C; (20)Enthalpy of Vaporization: 37.831 kJ/mol; (21)Boiling Point: 157.883 °C at 760 mmHg; (22)Vapour Pressure: 3.489 mmHg at 25°C.

Preparation and uses of 2-Pinene: It can be obtained by the fractionation of Turpentine. And it is often used as the raw material of terpineol, linalool and sandal flavor. It is also used in perfume and deodorant. What's more, it is used in manufacture of camphor, insecticides, solvents, plasticizers, perfume bases, synthetic pine oil.

You should be cautious while dealing with this chemical. It is a kind of flammable chemical, and it irritates eyes, respiratory system and skin. It may cause sensitization by skin contact, and lung damage if swallowed. What's more, it is toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Keep away from sources of ignition - No smoking; Do not empty into drains; Avoid release to the environment. Refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: CC1=CCC2CC1C2(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
(3)InChIKey: GRWFGVWFFZKLTI-UHFFFAOYAF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LCLo inhalation 572ug/m3 (0.572mg/m3) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Food and Cosmetics Toxicology. Vol. 16, Pg. 853, 1978.
mouse LD intraperitoneal > 500mg/kg (500mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 4, Pg. 232, 1952.
rat LCLo inhalation 625ug/m3 (0.625mg/m3) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Food and Cosmetics Toxicology. Vol. 16, Pg. 853, 1978.
rat LD50 oral 3700mg/kg (3700mg/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. 853, 1978.