(-)-Menthyl chloride supplier

Name
(-)-Menthyl chloride
EINECS 240-200-7
CAS No. 16052-42-9
Article Data33
CAS DataBase
Density 0.92 g/cm³
Solubility
Melting Point -20-16.5 °C
Formula C₁₀H₁₉Cl
Boiling Point 216.1 °C at 760 mmHg
Molecular Weight 174.714
Flash Point 78.9 °C
Transport Information
Appearance colorless liquid
Safety 23-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Cyclohexane,2-chloro-4-methyl-1-(1-methylethyl)-, [1S-(1a,2b,4b)]-;p-Menthane, 3-chloro-,(1R,3R,4S)-(-)- (8CI);(-)-Menthyl chloride;(1R,2S,5R)-Menthyl chloride;Menthyl chloride;NSC 55430;l-Menthyl chloride;
PSA 0.00000
LogP 3.68600

Synthetic route

: 2216-51-5
(-)-menthol

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With hydrogenchloride; zinc(II) chloride In water at 0 - 20℃; for 48h; Schlenk technique;	99%
With hydrogenchloride; zinc(II) chloride Substitution;	92%
With hydrogenchloride; zinc(II) chloride at 60℃; for 12h;	91%

: 61548-81-0
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With chloro-trimethyl-silane; iron(III)-acetylacetonate In dichloromethane at 20℃; for 3h; Inert atmosphere;	99%

: 15356-60-2
(1S,2R,5S)-(+)-menthol

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With Lucas' reagent	91%

: 1082742-74-2
C22H34O7S

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; Inert atmosphere;	90%

: 2230-82-2
menthyl tosylate

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; Inert atmosphere;	90%
With chloro-trimethyl-silane; iron(III)-acetylacetonate In dichloromethane at 20℃; for 20h; Inert atmosphere;	75%

: 117800-93-8
l-menthyl 8-quinolinesulfonate

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; Inert atmosphere;	90%

: 2216-51-5
(-)-menthol

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 13371-12-5
neomenthyl chloride

Conditions

Conditions	Yield
With phosphorus pentachloride In pentane at -20℃; for 2.5h; Product distribution;	A 50% B 30%
With phosphorus pentachloride In pentane at -20℃; for 2.5h;	A 50% B 30%
With phosphorus pentachloride; iron(III) chloride In hexane at 0℃; for 1.5h; Title compound not separated from byproducts.;
With N-chloro-succinimide; para-thiocresol In dichloromethane Overall yield = 80 %Spectr.;	A n/a B n/a
Multi-step reaction with 3 steps 1.1: diethyl ether / 1.5 h / 0 - 23 °C / Inert atmosphere 1.2: 0 - 23 °C / Inert atmosphere 2.1: caesium carbonate / tetrahydrofuran; water / 0.17 h / 23 °C / Inert atmosphere 3.1: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; Ethyl trichloroacetate / dichloromethane / 24 h / 27 °C / Inert atmosphere; Sealed tube; Irradiation View Scheme

: 72020-06-5, 80924-03-4, 97526-56-2, 123121-06-2, 128946-28-1, 128946-29-2, 128946-30-5, 128946-31-6, 134052-28-1
2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)tetrahydro-2H-pyran

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 13371-12-5
neomenthyl chloride

C: 5113-93-9
(1R)-trans-p-menth-2-ene

Conditions

Conditions	Yield
With dichloromethylenedimethyliminium chloride In acetonitrile at 0℃;	A 50 % Spectr. B 45 % Spectr. C 5 % Spectr.
With dichloromethylenedimethyliminium chloride In dichloromethane at 0℃;	A 18 % Spectr. B 42 % Spectr. C 40 % Spectr.

...Expand

: 87161-57-7
(1S,2S,4R)-2-bromo-1-isopropyl-4-methylcyclohexane

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 13371-12-5
neomenthyl chloride

Conditions

Conditions	Yield
With bismuth(III) chloride In 1,2-dichloro-ethane for 2h; Heating;

(-)-menthol: (-)-menthol

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With phosphorus pentachloride; iron(III) chloride; Petroleum ether Kuehlung;

: 2216-51-5
(-)-menthol

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: (1S,2R,4R)-2-bromo-1-isopropyl-4-methylcyclohexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C / Inert atmosphere 2: ferric(III) bromide; chloro-trimethyl-silane / dichloromethane / 0.17 h / 20 °C / Inert atmosphere View Scheme

: 61548-81-0
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: (1S,2R,4R)-2-bromo-1-isopropyl-4-methylcyclohexane

Conditions

Conditions	Yield
With ferric(III) bromide; chloro-trimethyl-silane In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;

: 1170718-78-1
L-menthol chlorosulfite ester

: 100-47-0
benzonitrile

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 1147723-25-8
(-)-N-((1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl)benzamide

Conditions

Conditions	Yield
With titanium(IV) fluoride In dichloromethane at 0℃; for 2h; Inert atmosphere;

...Expand

: 2216-51-5
(-)-menthol

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 1147723-25-8
(-)-N-((1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl)benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / Inert atmosphere; Cooling with ice 2: titanium(IV) fluoride / dichloromethane / 2 h / 0 °C / Inert atmosphere View Scheme

: 1170718-78-1
L-menthol chlorosulfite ester

: 16052-42-9
(1R,2S,5R)-menthyl chloride

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
With titanium tetrachloride at -78 - 0℃; for 1.25h; Catalytic behavior; Reagent/catalyst;

: 2216-51-5
(-)-menthol

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 13371-12-5
neomenthyl chloride

C: (1S,3R)-1-(1-chloro-2-methylpropyl)-3-methylcyclopentane

D: (1S,3R)-1-(2-chloro-2-methylpropyl)-3-methylcyclopentane

E: 26510-92-9
dimenthyl sulfite

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane at 45℃; for 18h;

...Expand

: 70894-19-8
2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoacetic acid

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 13371-12-5
neomenthyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / tetrahydrofuran; water / 0.17 h / 23 °C / Inert atmosphere 2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; Ethyl trichloroacetate / dichloromethane / 24 h / 27 °C / Inert atmosphere; Sealed tube; Irradiation View Scheme

: cesium 2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoacetate

A: 16052-42-9
(1R,2S,5R)-menthyl chloride

B: 13371-12-5
neomenthyl chloride

Conditions

Conditions	Yield
With Ethyl trichloroacetate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In dichloromethane at 27℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 50 %; Overall yield = 25.3 mg; stereoselective reaction;	A n/a B n/a

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 63474-24-8
(1R,2S,5R)-(-)menthylmagnesium chloride

Conditions

Conditions	Yield
With ethyl bromide; magnesium In tetrahydrofuran 1.) 4 h, 50 degC, 2.) 1 h, 70 deg C;	95%

: 124-38-9
carbon dioxide

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 16052-40-7
(-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With iodine; magnesium; ethylene dibromide at 70 - 75℃; for 4h; Inert atmosphere; Autoclave; Stage #2: carbon dioxide at 85 - 90℃; for 7.5h; Stage #3: With hydrogenchloride In water Temperature;	93%
With manganese; 2,9-dibutyl-3,4,7,8-tetramethyl-1,10-phenanthroline; NiBr2(monoglyme)2; lithium chloride In N,N-dimethyl-formamide under 760.051 Torr; Schlenk technique; Heating;	57%
Stage #1: carbon dioxide; (1R,2S,5R)-menthyl chloride With magnesium; iodine In tetrahydrofuran Stage #2: With hydrogenchloride In tetrahydrofuran; water Ice; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;	40%

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 73183-34-3
bis(pinacol)diborane

: 1357000-40-8
2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 20℃; for 92h; Inert atmosphere; Schlenk technique;	93%
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	91%
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride In tetrahydrofuran at 20℃; for 31h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	85%

: 83095-83-4, 14647-25-7
[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)]

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 7439-95-4
magnesium

: 106-93-4
ethylene dibromide

: Pt(menthyl)(1,2-bis(diphenylphosphino)ethane)(bromide)

Conditions

Conditions	Yield
In tetrahydrofuran (N2), Schlenk techniques; addn. of 1,2-dibromoethane to Mg in THF at 50°C, after 10 min addn. of menthyl chloride, heating under reflux for 5 h at 65°C, addn. to soln. of Au complex in THF, stirring for1 h at 50°C; cooling to room temp., addn. of satd. aq. NH4Cl, opening to air, extn. (CH2Cl2), drying (MgSO4), filtration (Celite), evapn. in vacuo, washing with petroleum ether, drying in vacuo, elem. anal.;	82%

Yield

In tetrahydrofuran (N2), Schlenk techniques; addn. of 1,2-dibromoethane to Mg in THF at 50°C, after 10 min addn. of menthyl chloride, heating under reflux for 5 h at 65°C, addn. to soln. of Au complex in THF, stirring for1 h at 50°C; cooling to room temp., addn. of satd. aq. NH4Cl, opening to air, extn. (CH2Cl2), drying (MgSO4), filtration (Celite), evapn. in vacuo, washing with petroleum ether, drying in vacuo, elem. anal.;

82%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 7439-95-4
magnesium

: 639-58-7
triphenyltin chloride

: (1R,2S,5R)-menthyltriphenyltin

Conditions

Conditions	Yield
With HCl; PPh3; tert-butylhydroperoxide In tetrahydrofuran byproducts: Ph3PO; stirring (room temp., 1.5 h), refluxing (30 min), HCl addn., extg. (CH2Cl2), drying (MgSO4), evapn. (vac.), hexane and CH2Cl2 addn., fitering Ph3P off, tBuOOH addn., stirring (15 min), H2O addn.; chromy. (SiO2, hexane / CH2Cl2 = 80 : 20); elem. anal.;	73%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 29289-13-2
2-iodo-4-methylaniline

: C17H27N*ClH

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With magnesium In tetrahydrofuran; ethylene dibromide at 60℃; for 1h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; Negishi Coupling; Schlenk technique; Inert atmosphere; Stage #3: 2-iodo-4-methylaniline diastereoselective reaction;	73%

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 64662-57-3
2,6-diiodo-4-methylaniline

: 2,6-bis[(1R,2S,5R)-menthyl]-4-methylaniline

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With magnesium In tetrahydrofuran at 60℃; for 1h; Negishi Coupling; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; Negishi Coupling; Inert atmosphere; Schlenk technique; Stage #3: 2,6-diiodo-4-methylaniline With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Schlenk technique;	73%

Yield

Stage #1: (1R,2S,5R)-menthyl chloride With magnesium In tetrahydrofuran at 60℃; for 1h; Negishi Coupling; Schlenk technique; Inert atmosphere; Reflux;
Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; Negishi Coupling; Inert atmosphere; Schlenk technique;
Stage #3: 2,6-diiodo-4-methylaniline With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Schlenk technique;

73%

: 14243-64-2
(triphenylphosphine)gold(I) chloride

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 7439-95-4
magnesium

: Au(menthyl)(triphenylphosphine)

Conditions

Conditions	Yield
With 1,2-dibromoethane In tetrahydrofuran (N2), Schlenk techniques; addn. of 1,2-dibromoethane to Mg in THF at 50°C, after 20 min addn. of menthyl chloride, heating under reflux for 5 h at 65°C, addn. to soln. of Au complex in THF, stirring for2 h; addn. of dilute H2SO4, opening to air, extn. (CH2Cl2), drying (MgSO4), treatment with charcoal, filtration (Celite), evapn. in vacuo, washing with petroleum ether, drying in vacuo, elem. anal.;	67%

Yield

With 1,2-dibromoethane In tetrahydrofuran (N2), Schlenk techniques; addn. of 1,2-dibromoethane to Mg in THF at 50°C, after 20 min addn. of menthyl chloride, heating under reflux for 5 h at 65°C, addn. to soln. of Au complex in THF, stirring for2 h; addn. of dilute H2SO4, opening to air, extn. (CH2Cl2), drying (MgSO4), treatment with charcoal, filtration (Celite), evapn. in vacuo, washing with petroleum ether, drying in vacuo, elem. anal.;

67%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 4376-01-6
sodium diphenylphosphide

A: 43077-29-8
((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-diphenyl-phosphane

B: 43077-30-1
neomenthyldiphenylphosphine oxide

C: 829-85-6
diphenylphosphane

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 25 - 67℃; for 16h;	A 66% B 24% C 5%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 4102-54-9
2-iodo-4,6-dimethylaniline

: 2-[(1R,2S,5R)-menthyl]-4,6-dimethylaniline

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With magnesium In tetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; Negishi Coupling; Inert atmosphere; Schlenk technique; Stage #3: 2-iodo-4,6-dimethylaniline With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; Schlenk technique; diastereoselective reaction;	64%

Yield

Stage #1: (1R,2S,5R)-menthyl chloride With magnesium In tetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere; Reflux;
Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; Negishi Coupling; Inert atmosphere; Schlenk technique;
Stage #3: 2-iodo-4,6-dimethylaniline With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; Schlenk technique; diastereoselective reaction;

64%

: 124-38-9
carbon dioxide

: 16052-42-9
(1R,2S,5R)-menthyl chloride

A: 70985-58-9
(1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid

B: 16052-40-7
(-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With magnesium In tetrahydrofuran at 50℃; for 2h; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	A 7.6% B 60.2%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 829-85-6
diphenylphosphane

: 43077-29-8
((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-diphenyl-phosphane

Conditions

Conditions	Yield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 63h;	54%

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 4376-01-6
sodium diphenylphosphide

A: 43077-29-8
((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-diphenyl-phosphane

B: 829-85-6
diphenylphosphane

Conditions

Conditions	Yield
With 15-crown-5 In tetrahydrofuran at 25 - 67℃; for 16h;	A 15% B 53%

...Expand

: (1R,2S,5R)-menthyltriphenyltin

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 7646-78-8
tin(IV) chloride

: 7439-95-4
magnesium

: ((C3H7C6H9CH3)3Sn)2

Conditions

Conditions	Yield
With HCl In tetrahydrofuran; benzene refluxing (5 h), stirring (room temp., 16 h), HCl and H2O addn., extg. (ether), drying (MgSO4), evapn. (vac.); recrystn. (EtOH); elem. anal.;	50%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 1135-99-5
diphenyltin(IV) dichloride

: 182160-38-9, 916576-67-5, 250636-43-2
di(-)menthyldiphenyltin

Conditions

Conditions	Yield
With magnesium In tetrahydrofuran Ar-atmosphere; treatment of menthyl chloride with Mg, dropwise addn. of Sn-compd. (0°C, over 1 h), stirring at room temp. for 48 h; dropwise addn. of water at 0°C, stirring for 30 min at room temp., ether addn., washing of org. layer (water), drying (MgSO4), solvent removal, distn. (150-180°C/0.01 Torr); elem. anal.;	49%

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 753-73-1
dimethyltin dichloride

: di(-)menthyldimethyltin

Conditions

Conditions	Yield
With magnesium In tetrahydrofuran Ar-atmosphere; treatment of menthyl chloride with Mg, dropwise addn. of Sn-compd. (0°C, over 1 h), stirring at room temp. for 48 h; dropwise addn. of water at 0°C, stirring for 30 min at room temp., drying (MgSO4), solvent removal, distn. (90°C/40 mbar); elem. anal.;	48.2%

: 124-38-9
carbon dioxide

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 70-11-1
α-bromoacetophenone

A: 1537179-13-7
2-oxo-2-phenylethyl (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxylate

B: 1537179-15-9
2-oxo-2-phenylethyl (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxylate

C: 1537179-16-0
2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-2-oxoethyl benzoate

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With chloro-trimethyl-silane; magnesium; ethylene dibromide In tetrahydrofuran at 70℃; for 3h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70 - 80℃; for 2h; Inert atmosphere; Stage #3: α-bromoacetophenone In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; Inert atmosphere;	A 44% B 15% C 1%
Stage #1: (1R,2S,5R)-menthyl chloride With chloro-trimethyl-silane; magnesium; ethylene dibromide In tetrahydrofuran at 70℃; for 3h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70 - 80℃; for 2h; Stage #3: α-bromoacetophenone In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃;	A 44% B 15% C 1%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 567-19-1
3-chloro-1,2-benzisothiazole 1,1-dioxide

A: 18715-95-2
3-[(1'R)-menthoxy]-1,2-benzisothiazole 1,1-dioxide

B: (-)-3-[(1'R)-1'-menthyl]-1,2-benzisothiazole 1,1-dioxide

C: (+)-3-[(1'S)-1'-menthyl]-1,2-benzisothiazole 1,1-dioxide

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl chloride With ethyl bromide; magnesium In tetrahydrofuran for 0.5h; Metallation; Heating; Stage #2: 3-chloro-1,2-benzisothiazole 1,1-dioxide In tetrahydrofuran at 0℃; Grignard reaction; Further stages.;	A 15% B 38% C 13%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

A: 619-52-3
(1R)-menth-3-ene

B: 135637-19-3
(+)-Menthyllithium

C: 3294-50-6
(2R,5S,2'S,5'R)-2,2'-Diisopropyl-5,5'-dimethyl-bicyclohexyl

Conditions

Conditions	Yield
With lithium In pentane 1) 2h, reflux, 2) 48h;	A 15.6% B 37% C n/a

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 201733-56-4
2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

: 2–((1R,2R,5R)–2–isopropyl–5–methylcyclohexyl)–5,5–dimethyl–1,3,2–dioxaborinane

Conditions

Conditions	Yield
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride In tetrahydrofuran for 24h; Inert atmosphere;	28%

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 65567-06-8, 4541-02-0
lithium diphenylphosphide

: 43077-29-8
((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-diphenyl-phosphane

Conditions

Conditions	Yield
In tetrahydrofuran at 40℃; for 40h;	24%

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 1135-99-5
diphenyltin(IV) dichloride

: 7439-95-4
magnesium

: bis((1R,2S,5R)-menthyl)diphenyltin

Conditions

Conditions	Yield
In tetrahydrofuran stirring (room temp., 44 h), H2O addn., extg. (ether), drying (MgSO4), evapn. (vac.); chromy. (SiO2, hexane / CH2Cl2 = 97 : 3), evapn.; elem. anal.;	22%

...Expand

: 16052-42-9
(1R,2S,5R)-menthyl chloride

: 4376-01-6
sodium diphenylphosphide

: 43077-29-8
((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-diphenyl-phosphane

Conditions

Conditions	Yield
With 15-crown-5 In tetrahydrofuran at 25 - 67℃; for 16h;	15%

(-)-Menthyl chloride Specification

The (-)-Menthyl chloride, with the CAS registry number 16052-42-9, is also known as [1S-(1alpha,2beta,4beta)]-2-Chloro-1-isopropyl-4-methylcyclohexane. It belongs to the product categories of Biochemistry; Monocyclic Monoterpenes and Terpenes. Its EINECS registry number is 240-200-7. This chemical's molecular formula is C₁₀H₁₉Cl and molecular weight is 174.71. What's more, its IUPAC name is 2-Chloro-4-methyl-1-propan-2-ylcyclohexane and systematic name is called 2-Chloro-4-methyl-1-(propan-2-yl)cyclohexane. It is colorless liquid. The (-)-Menthyl chloride is synthetic organic intermediates and used to synthetic family planning medicine Benzene alcohol ethers.

Physical properties about this chemical are: (1) ACD/LogP: 4.89; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): 4.89; (4) ACD/LogD (pH 7.4): 4.89; (5) ACD/BCF (pH 5.5): 3073.69; (6) ACD/BCF (pH 7.4): 3073.69; (7) ACD/KOC (pH 5.5): 10915.98; (8) ACD/KOC (pH 7.4): 10915.98; (9) #H bond acceptors: 0; (10) #H bond donors: 0; (11) #Freely Rotating Bonds: 1; (12) Polar Surface Area: 0 Å²; (13) Index of Refraction: 1.452; (14) Molar Refractivity: 51.04 cm³; (15) Molar Volume: 189.1 cm³; (16) Surface Tension: 27.1 dyne/cm; (17) Density: 0.92 g/cm³; (18) Flash Point: 78.9 °C; (19) Enthalpy of Vaporization: 43.4 kJ/mol; (20) Boiling Point: 216.1 °C at 760 mmHg; (21) Vapour Pressure: 0.209 mmHg at 25 °C; (22) Melting Point: -20-16.5 °C.

When you are dealing with this chemical, you should be very careful. You should avoid contacting with skin, eyes and do not breathe gas/fumes/vapour/spray.

You can still convert the following datas into molecular structure:
(1) SMILES: ClC1CC(CCC1C(C)C)C
(2) InChI: InChI=1/C10H19Cl/c1-7(2)9-5-4-8(3)6-10(9)11/h7-10H,4-6H2,1-3H3
(3) InChIKey: OMLOJNNKKPNVKN-UHFFFAOYAB

Product Name

(-)-Menthyl chloride

Synthetic route

(-)-Menthyl chloride Specification

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