Chemical Properties of (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene (CAS 7785-26-4)

InChI

InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1

InChI Key

GRWFGVWFFZKLTI-IUCAKERBSA-N

Formula

C10H16

SMILES

CC1=CC[C@H]2C[C@@H]1C2(C)C

Molecular Weight¹

136.24

CAS

7785-26-4

Other Names

• (-)-(1S)-pin-2-ene
• (-)-.alpha.-pinene
• (-)-2-pinene
• (-)-pin-2(3)-ene
• (-)-«alpha»-Pinene
• (1S)-(-)-.alpha.-pinene
• (1S)-(-)-«alpha»-Pinene
• (1S,5S)-(-)-.alpha.-pinene
• (S)-(-)-.alpha.-pinene
• (S)-2-pinene
• .alpha.-pinene, (1S)-(-)-
• 1S-(-)-a-pinene
• 1S-«alpha»-Pinene
• 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene-, (1S,5S)-
• 2-pinene, (1S,5S)-(-)-
• L-«alpha»-Pinene
• bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1S)-
• l-.alpha.-pinene
• «alpha»-Pinene, (-)-

• Δ_cH°_liquid : Standard liquid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• IE : Ionization energy (eV).
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_vap : Vapor pressure (kPa).
• ρ_l : Liquid Density (kg/m³).
• I_np : Non-polar retention indices.
• I_p : Polar retention indices.
• γ : Surface Tension (N/m).
• T_boil : Normal Boiling Point Temperature (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Contents

1. Physical Properties
2. Temperature Dependent Properties
3. Datasets
4. Correlations
5. Similar Compounds
6. Mixtures
7. Sources

Physical Properties

Property	Value	Unit	Source
ΔcH°liquid	-6150.50	kJ/mol	NIST
ΔfusH°	11.43	kJ/mol	Joback Calculated Property
ΔvapH°	43.96	kJ/mol	Relay (1.0) Calculated Property
IE	8.66	eV	Relay (1.0) Calculated Property
logPoct/wat	2.999		Crippen Calculated Property
McVol	125.740	ml/mol	McGowan Calculated Property
Inp	[922.57; 967.39]
Inp	941.76		NIST
Inp	945.19		NIST
Inp	948.69		NIST
Inp	952.30		NIST
Inp	955.94		NIST
Inp	959.63		NIST
Inp	963.45		NIST
Inp	Outlier 967.39		NIST
Inp	928.69		NIST
Inp	931.87		NIST
Inp	935.08		NIST
Inp	938.37		NIST
Inp	941.85		NIST
Inp	945.26		NIST
Inp	948.88		NIST
Inp	952.43		NIST
Inp	956.02		NIST
Inp	922.57		NIST
Inp	925.64		NIST
Inp	928.73		NIST
Inp	931.91		NIST
Inp	935.13		NIST
Inp	938.44		NIST
Inp	937.00		NIST
Inp	937.00		NIST
Inp	959.00		NIST
Inp	936.00		NIST
Inp	934.00		NIST
Inp	936.00		NIST
Inp	938.00		NIST
Inp	929.00		NIST
Inp	930.00		NIST
Inp	937.00		NIST
Inp	959.00		NIST
Ip	[1008.00; 1030.00]
Ip	1030.00		NIST
Ip	1030.00		NIST
Ip	Outlier 1008.00		NIST
Ip	1029.00		NIST
Ip	1029.00		NIST
Ip	1030.00		NIST
Tboil	428.20	K	NIST
Tc	644.00	K	IUPAC Vapor-Liquid Critical Properties of Elements and Compounds, part 6 Compiled value
Tfus	218.39 ± 0.15	K	NIST
Vc	0.454	m3/kmol	IUPAC Vapor-Liquid Critical Properties of Elements and Compounds, part 6 Compiled value

Cheméo can also estimate Critical Pressure, Enthalpy of formation at standard conditions, Standard Gibbs free energy of formation, Acentric Factor, Log10 of Water solubility in mol/l for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Pvap	[5.30e-03; 1.07]	kPa	[238.19; 308.18]
Pvap	5.30e-03	kPa	238.19	Thermodynamic study of selected monoterpenes
Pvap	5.30e-03	kPa	238.19	Thermodynamic study of selected monoterpenes
Pvap	5.30e-03	kPa	238.19	Thermodynamic study of selected monoterpenes
Pvap	8.74e-03	kPa	243.20	Thermodynamic study of selected monoterpenes
Pvap	8.74e-03	kPa	243.20	Thermodynamic study of selected monoterpenes
Pvap	8.75e-03	kPa	243.20	Thermodynamic study of selected monoterpenes
Pvap	0.02	kPa	253.19	Thermodynamic study of selected monoterpenes
Pvap	0.02	kPa	253.19	Thermodynamic study of selected monoterpenes
Pvap	0.02	kPa	253.19	Thermodynamic study of selected monoterpenes
Pvap	0.03	kPa	258.20	Thermodynamic study of selected monoterpenes
Pvap	0.03	kPa	258.20	Thermodynamic study of selected monoterpenes
Pvap	0.03	kPa	258.20	Thermodynamic study of selected monoterpenes
Pvap	0.05	kPa	263.19	Thermodynamic study of selected monoterpenes
Pvap	0.05	kPa	263.19	Thermodynamic study of selected monoterpenes
Pvap	0.05	kPa	263.19	Thermodynamic study of selected monoterpenes
Pvap	0.08	kPa	268.19	Thermodynamic study of selected monoterpenes
Pvap	0.08	kPa	268.19	Thermodynamic study of selected monoterpenes
Pvap	0.08	kPa	268.19	Thermodynamic study of selected monoterpenes
Pvap	0.12	kPa	273.65	Thermodynamic study of selected monoterpenes
Pvap	0.12	kPa	273.66	Thermodynamic study of selected monoterpenes
Pvap	0.12	kPa	273.66	Thermodynamic study of selected monoterpenes
Pvap	0.16	kPa	278.16	Thermodynamic study of selected monoterpenes
Pvap	0.16	kPa	278.16	Thermodynamic study of selected monoterpenes
Pvap	0.16	kPa	278.16	Thermodynamic study of selected monoterpenes
Pvap	0.23	kPa	283.15	Thermodynamic study of selected monoterpenes
Pvap	0.23	kPa	283.15	Thermodynamic study of selected monoterpenes
Pvap	0.23	kPa	283.15	Thermodynamic study of selected monoterpenes
Pvap	0.32	kPa	288.15	Thermodynamic study of selected monoterpenes
Pvap	0.32	kPa	288.15	Thermodynamic study of selected monoterpenes
Pvap	0.32	kPa	288.15	Thermodynamic study of selected monoterpenes
Pvap	0.44	kPa	293.15	Thermodynamic study of selected monoterpenes
Pvap	0.44	kPa	293.15	Thermodynamic study of selected monoterpenes
Pvap	0.44	kPa	293.15	Thermodynamic study of selected monoterpenes
Pvap	0.60	kPa	298.15	Thermodynamic study of selected monoterpenes
Pvap	0.60	kPa	298.15	Thermodynamic study of selected monoterpenes
Pvap	0.60	kPa	298.15	Thermodynamic study of selected monoterpenes
Pvap	0.81	kPa	303.15	Thermodynamic study of selected monoterpenes
Pvap	0.81	kPa	303.16	Thermodynamic study of selected monoterpenes
Pvap	0.81	kPa	303.16	Thermodynamic study of selected monoterpenes
Pvap	1.07	kPa	308.17	Thermodynamic study of selected monoterpenes
Pvap	1.07	kPa	308.17	Thermodynamic study of selected monoterpenes
Pvap	1.07	kPa	308.18	Thermodynamic study of selected monoterpenes
ρl	[853.88; 853.88]	kg/m3	[298.15; 298.15]
ρl	853.88	kg/m3	298.15	Ternary and quaternary (liquid + liquid) equilibria for (water + ethanol + a-pinene, +b-pinene, or +limonene) and (water + ethanol + a-pinene + limonene) at the temperature 298.15 K
ρl	853.88	kg/m3	298.15	Mutual Solubilities of Terpene in Methanol and Water and Their Multicomponent Liquid-Liquid Equilibria

Datasets

Mass density, kg/m3

Fixed		Measured
Temperature, K - Liquid	Pressure, kPa - Liquid	Mass density, kg/m3 - Liquid
283.15	20000.00	880.0
283.15	25000.00	883.2
283.15	30000.00	886.3
283.15	35000.00	889.4
283.15	40000.00	892.5
298.15	20000.00	868.8
298.15	25000.00	872.1
298.15	30000.00	875.3
298.15	35000.00	878.6
298.15	40000.00	881.9
313.15	20000.00	858.0
313.15	25000.00	861.3
313.15	30000.00	864.7
313.15	35000.00	867.9
313.15	40000.00	871.3
328.15	20000.00	846.7
328.15	25000.00	850.4
328.15	30000.00	854.0
328.15	35000.00	857.5
328.15	40000.00	861.1
343.15	20000.00	835.9
343.15	25000.00	839.7
343.15	30000.00	843.8
343.15	35000.00	847.7
343.15	40000.00	851.4
358.15	20000.00	825.0
358.15	25000.00	829.2
358.15	30000.00	833.3
358.15	35000.00	837.4
358.15	40000.00	841.5
Reference

Fixed		Measured
Temperature, K - Liquid	Pressure, kPa - Liquid	Mass density, kg/m3 - Liquid
283.15	20000.00	880.0
283.15	25000.00	883.2
283.15	30000.00	886.3
283.15	35000.00	889.4
283.15	40000.00	892.5
298.15	20000.00	868.8
298.15	25000.00	872.1
298.15	30000.00	875.3
298.15	35000.00	878.6
298.15	40000.00	881.9
313.15	20000.00	858.0
313.15	25000.00	861.3
313.15	30000.00	864.7
313.15	35000.00	867.9
313.15	40000.00	871.3
328.15	20000.00	846.7
328.15	25000.00	850.4
328.15	30000.00	854.0
328.15	35000.00	857.5
328.15	40000.00	861.1
343.15	20000.00	835.9
343.15	25000.00	839.7
343.15	30000.00	843.8
343.15	35000.00	847.7
343.15	40000.00	851.4
358.15	20000.00	825.0
358.15	25000.00	829.2
358.15	30000.00	833.3
358.15	35000.00	837.4
358.15	40000.00	841.5
Reference

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[160.26; 476.14]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-1.33780e+02
Coefficient B			1.39596e+00
Coefficient C			-1.31164e-03
Coefficient D			5.25600e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	160.26	J/mol×K	273.00	Calculated Property
Cp,gas	219.19	J/mol×K	353.78	Calculated Property
Cp,gas	268.29	J/mol×K	434.56	Calculated Property
Cp,gas	309.21	J/mol×K	515.33	Calculated Property
Cp,gas	343.61	J/mol×K	596.11	Calculated Property
Cp,gas	373.17	J/mol×K	676.89	Calculated Property
Cp,gas	399.54	J/mol×K	757.67	Calculated Property
Cp,gas	424.38	J/mol×K	838.44	Calculated Property
Cp,gas	449.36	J/mol×K	919.22	Calculated Property
Cp,gas	476.14	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
γ	[0.03; 0.01]	N/m	[212.15; 439.15]	Jasper (1972), surface tension of pure liquid compounds Compiled value
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is γ in N/m, T in K
Coefficient A			5.37722e-02
Coefficient B			-9.34000e-05
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Temperature range, min.			212.15
Temperature range, max.			439.15
γ	0.03	N/m	212.15	Calculated Property
γ	0.03	N/m	237.37	Calculated Property
γ	0.03	N/m	262.59	Calculated Property
γ	0.03	N/m	287.82	Calculated Property
γ	0.02	N/m	313.04	Calculated Property
γ	0.02	N/m	338.26	Calculated Property
γ	0.02	N/m	363.48	Calculated Property
γ	0.02	N/m	388.71	Calculated Property
γ	0.02	N/m	413.93	Calculated Property
γ	0.01	N/m	439.15	Calculated Property

Similar Compounds

Find more compounds similar to (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene.

Mixtures

• (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene + «beta»-Pinene
• Ethanol + Water + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Water + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Methyl Alcohol + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Methyl Alcohol + Water + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• D-Limonene + Water + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• D-Limonene + Methyl Alcohol + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• D-Limonene + (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene

Sources

• IUPAC Vapor-Liquid Critical Properties of Elements and Compounds, part 6 ChEDL chemicals 1.5.2, from Tsonopoulos, C.; Ambrose, D. Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons. J. Chem. Eng. Data 1996, 41, 645-656.
• Jasper (1972), surface tension of pure liquid compounds ChEDL chemicals 1.5.2, from Jasper, J. J. The Surface Tension of Pure Liquid Compounds. J. Phys. Chem. Ref. Data 1972, 1, 841-1010 (as transcribed in Lange's Handbook).
• Cheméo Relay (1.0)
• Cheméo Relay (1.0, beta) Beta: served but experimental, data-limited and below our cross-validation release bar; the Joback value is recommended where available.
• Crippen Method
• Crippen Method
• Ternary and quaternary (liquid + liquid) equilibria for (water + ethanol + a-pinene, +b-pinene, or +limonene) and (water + ethanol + a-pinene + limonene) at the temperature 298.15 K
• P,[rho], T and heat capacity measurements of ([alpha]-pinene + [beta]-pinene) mixtures over the temperature range 283.15 K to 358.15 K and pressures up to 40 MPa: Experiments and modelling
• Thermodynamic study of selected monoterpenes
• Mutual Solubilities of Terpene in Methanol and Water and Their Multicomponent Liquid-Liquid Equilibria
• P, rho, and T Measurements of the Limonene + alpha-Pinene Mixtures
• Joback Method
• McGowan Method
• NIST Webbook

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