• Name

  p-Menthene-8-thiol

• EINECS 275-223-1
• CAS No. 71159-90-5
• Article Data10
• CAS DataBase
• Density 0.938 g/cm³
• Solubility
• Melting Point
• Formula C₁₀H₁₈S
• Boiling Point 229.4 °C at 760 mmHg
• Molecular Weight 170.319
• Flash Point 90.7 °C
• Transport Information
• Appearance Colourless liquid with aroma and taste of grapefruit in dilute solution Visual appearance of the given substance.
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 1-p-Menthene-8-thiol;2-(4-Methylcyclohex-3-enyl)propane-2-thiol;Grapefruit mercaptan;
• PSA 38.80000
• LogP 3.44120

Synthetic route

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Reduction;	90%

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Solvent; Inert atmosphere;	85%

98-55-5

terpineol

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

Conditions

Conditions	Yield
With Lawessons reagent In toluene for 0.5h; Heating;	20%
With tetraphosphorus decasulfide In tetrahydrofuran at 50℃; for 1h; Solvent; Reagent/catalyst; Temperature; Large scale;	500 g

127-91-3

(1R,5R)-(+)-β-pinene

A

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

B

88600-02-6

trans-Pinane-2-thiol

C

88600-04-8

4-Methyl-2,4-di(4-methyl-3-cyclohexenyl)pentane-2-thiol

Conditions

Conditions	Yield
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Yields of byproduct given;	A n/a B n/a C 13%
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Product distribution; EtAlClBr as reagent.;

...Expand

7785-26-4

(-)-α-pinene

A

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

B

88600-02-6

trans-Pinane-2-thiol

C

88600-04-8

4-Methyl-2,4-di(4-methyl-3-cyclohexenyl)pentane-2-thiol

Conditions

Conditions	Yield
With aluminum tri-bromide; hydrogen sulfide In chloroform at 20℃; for 0.5h; Product distribution; EtAlClBr as reagent.;
With aluminum tri-bromide; hydrogen sulfide In chloroform

...Expand

83108-08-1

8,9-epthio-1-p-menthene

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; 2-neopentoxyphenol; water 1.) THF, reflux, 1 h; 2.) 10 min; Yield given. Multistep reaction;

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

1,8-epithio-p-menthane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 70℃; for 1h;	97%

71159-90-5

2-(4-methylcyclohex-3-enyl)propane-2-thiol

2,8-epithio-cis-p-menthene

Conditions

Conditions	Yield
With azobisisobutyronitrile In hexane at 70℃; for 2h;	65%

p-Menthene-8-thiol Chemical Properties