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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-
Article Data: 84
Cas Database
Molecular Structure:
Molecular Structure of 80-56-8 (Bicyclo[3.1.1]hept-2-ene,2,6,6-trimethyl-)
Formula: C10H16
Molecular Weight: 136.237
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;
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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.