Carbonochloridic acid,5-methyl-2-(1-methylethyl)cyclohexyl ester, (1S,2R,5S)- supplier

Name
(+)-MENTHYL CHLOROFORMATE
EINECS
CAS No. 7635-54-3
Article Data6
CAS DataBase
Density 1.04 g/cm³
Solubility
Melting Point
Formula C₁₁H₁₉ClO₂
Boiling Point 233.9 °C at 760 mmHg
Molecular Weight 218.724
Flash Point 70 °C
Transport Information UN 3277 6.1/PG 2
Appearance Colorless to light yellow liquid
Safety 26-36/37/39-45-25
Risk Codes 23-34-20/21/22
Molecular Structure
Hazard Symbols T,C
Synonyms Carbonochloridicacid, 5-methyl-2-(1-methylethyl)cyclohexyl ester, [1S-(1a,2b,5a)]-;Formic acid, chloro-, p-menth-3-yl ester, (+)- (8CI);(+)-Menthylchloroformate;
PSA 26.30000
LogP 3.82260

Synthetic route

bis(trichloromethyl) carbonate: bis(trichloromethyl) carbonate

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

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

Conditions

Conditions	Yield
With pyridine In dichloromethane at -5 - 25℃; for 13h; Reagent/catalyst; Temperature; Solvent;	99%
Carbonylation;

: 75-44-5
phosgene

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

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.75h;	95%
In toluene

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 494-52-0
Anabasine

: (2'S)-[(1S,2R,5S)-menthoxycarbonyl]anabasine

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃; for 2h;	100%

: 1-((4R,5R)-4,5-dihydro-2-(6-((4R,5R)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-yl)-4,5-diphenylimidazol-1-yl)(mesityl)methanone

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 2-(1-(2,4,6-trimethyl-benzoyl)-[4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-6-(1-((1S,2R,5S)-2-iso-propyl-5-methylcyclohexyl-3-oxycarbonyl)-[4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)pyridine

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 6h;	99%

: 5950-36-7
aziridine-2-carboxylic acid ethyl ester

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 0 - 20℃;	99%

: 102555-71-5, 124414-36-4, 124414-37-5
1,1'-binaphthalene-2,2'-dithiol

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: Thiocarbonic acid O-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester S-[2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylsulfanyl)-[1,1']binaphthalenyl-2-yl] ester

: Thiocarbonic acid O-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester S-[2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylsulfanyl)-[1,1']binaphthalenyl-2-yl] ester

Conditions

Conditions	Yield
With triethylamine In benzene for 1h; Ambient temperature; Yields of byproduct given;	A 98% B n/a
With triethylamine In benzene for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 199923-84-7
5-monoamino-25,26,27,28-tetrakis(propyloxy)-calix[4]arene

: 5-menthyl carbamate-25,26,27,28-tetrapropoxycalix[4]arene

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	98%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: C12H17O4P

: C23H35O6P

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 22℃; for 2.5h; Inert atmosphere;	97%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 602-09-5
1,1'-bi-2-naphthol

: Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-[1,1']binaphthalenyl-2-yl ester

: Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-[1,1']binaphthalenyl-2-yl ester

Conditions

Conditions	Yield
With triethylamine In benzene for 1h; Ambient temperature; Yields of byproduct given;	A 95% B n/a
With triethylamine In benzene for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 156286-12-3
1,2-(2,3-dihydro-1H-azirino)-<60>fullerene

: C71H19NO2

Conditions

Conditions	Yield
With pyridine In various solvent(s) at 70℃; for 1h;	95%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 170850-75-6
BOC-Hyp-OtBu

: 865303-09-9
(2S,4R)-di-tert-butyl 4-{[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]carbonyloxy}pyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
Stage #1: BOC-Hyp-OtBu With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: (+)-(1S,2R,5S)-menthylchloroformate In tetrahydrofuran at 20℃; for 22h;	95%

: 952060-29-6
(3S)-3-(propan-2-yl)-3,4-dihydroquinoxalin-2(1H)-one

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1261061-28-2
C22H32N2O3

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃;	94%

: 1046789-84-7
4-(2-ethynyl-5-methoxyphenyl)-2-methylenebutan-1-ol

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1046789-85-8
4-(2-ethynyl-5-methoxyphenyl)-2-methylenebutyl (1R,2R,5S)-2-isopropyl-5-methylcyclohexyl carbonate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;	93%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: t-butylphosphine-borane

: C26H50BO4P

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at -20 - 0℃;	92%

: 162053-46-5
tert-butylphosphine-borane

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: tert-butyl(dimenthyloxycarbonyl)phosphine borane

Conditions

Conditions	Yield
With NaH In tetrahydrofuran (Ar); addn. slowly of (t-C4H9)PH2BH3 to mixt. of NaH (3 equiv.) and (+)menthyl chloroformate (2.2 equiv.) in THF at -20°C, warming to 0°C for 30 min, stirring for several hours; pouring of soln. onto ice/water containing HCl, sepn. of org. layer, extn. of aq. layer with ethyl acetate, washing of combined extracts with water and brine, drying (Na2SO4), concn. in vac., chromy. on SiO2 eluting with hexane/ethyl acetate, as oil;	92%

Yield

With NaH In tetrahydrofuran (Ar); addn. slowly of (t-C4H9)PH2BH3 to mixt. of NaH (3 equiv.) and (+)menthyl chloroformate (2.2 equiv.) in THF at -20°C, warming to 0°C for 30 min, stirring for several hours; pouring of soln. onto ice/water containing HCl, sepn. of org. layer, extn. of aq. layer with ethyl acetate, washing of combined extracts with water and brine, drying (Na2SO4), concn. in vac., chromy. on SiO2 eluting with hexane/ethyl acetate, as oil;

92%

: 61-54-1
tryptamine

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 945910-39-4
(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (2-(1H-Indol-3-yl)ethyl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	92%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 100-46-9
benzylamine

: 683247-05-4
Benzyl-carbamic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	91%

: 863491-46-7
2,6-bis-([4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-pyridine

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 2,6-bis-(1-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxycarbonyl)-[4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-pyridine

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	90%
With dmap In dichloromethane at 20℃; for 1h;	90%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 99553-79-4, 108509-76-8, 85380-77-4
2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole

: 1017848-52-0
(S)-menthyl 2-(4-methoxyphenyl)-4-methyloxazol-5-yl carbonate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	86%

: 61-90-5
L-leucine

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1047650-51-0
N-[menthyloxycarbonyl]-L-leucine

Conditions

Conditions	Yield
Stage #1: L-leucine; (+)-(1S,2R,5S)-menthylchloroformate With sodium hydroxide In water at 0 - 20℃; Stage #2: With hydrogenchloride In water	85%

: 245554-93-2
(S)-3-benzyl-3,4-dihydroquinoxalin-2(1H)-one

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1261061-27-1
C26H32N2O3

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃;	85%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 475273-53-1, 475588-02-4, 475588-03-5
(+/-)-9H,9'H-[4,4']bicarbazole-3,3'-diol

: Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 3'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-9H,9'H-[4,4']bicarbazolyl-3-yl ester

Conditions

Conditions	Yield
With triethylamine In acetonitrile	85%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 56-40-6
glycine

: 1380401-10-4
N-(1S,3S,4R-menthyloxycarbonyl)glycine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 15h;	83%

: 958879-25-9
1,1-dimethyl-1,3,4,9-tetrahydrospiro[carbazole-2,2'-[1,3]dioxolane]

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 1,1-dimethyl-3,4-dihydrospiro[carbazole-2,2'-[1,3]dioxolane]-9(1H)-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,1-dimethyl-1,3,4,9-tetrahydrospiro[carbazole-2,2'-[1,3]dioxolane] With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: (+)-(1S,2R,5S)-menthylchloroformate In tetrahydrofuran at -78 - 20℃; for 2h; Further stages.;	80%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 5950-39-0
aziridine-2-carboxylic acid isopropyl ester

: 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid isopropyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 0 - 20℃;	79%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1049019-27-3
4-hydroxymethylidene-2-phenyl-4,5-dihydrooxazol-5-one

: (Z)-(-)-menthyl 5-oxo-2-phenyloxazol-4-methylenecarbonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -5℃; for 3h;	78%

: 273-53-0
benzoxazole

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 1158181-10-2
2-isocyanophenyl (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl carbonate

Conditions

Conditions	Yield
Stage #1: benzoxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: (+)-(1S,2R,5S)-menthylchloroformate In tetrahydrofuran; hexane at -78 - 20℃;	78%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 82912-42-3
(+/-)-aziridine-2-carboxylic acid tert-butyl ester

: 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 0 - 20℃;	78%

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

: 5950-34-5, 118396-26-2, 151526-74-8, 151526-75-9
methyl aziridine-2-carboxylate

: 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetone at 0 - 20℃;	76%

: 1429043-78-6
N-benzyl-N-cyclopent-1-enyl-isonicotinamide

: 7635-54-3
(+)-(1S,2R,5S)-menthylchloroformate

A: C29H36N2O3

B: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-benzyl-2-oxo-3,5,6,6a-tetrahydro-1’H,2H-spiro[cyclopenta[b]pyrrole-1,4’-pyridine]-1’-carboxylate

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; Inert atmosphere; Overall yield = 92 %;	A n/a B 75%

...Expand

Carbonochloridic acid,5-methyl-2-(1-methylethyl)cyclohexyl ester, (1S,2R,5S)- Specification

The CAS register number of Carbonochloridic acid,5-methyl-2-(1-methylethyl)cyclohexyl ester, (1S,2R,5S)- is 7635-54-3. It also can be called as (+)-Menthyl Chloroformate and the IUPAC name about this chemical is [(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] carbonochloridate. The molecular formula about this chemical is C₁₁H₁₉ClO₂ and the molecular weight is 218.72. It belongs to the following product categories, such as Chiral; Biochemistry; for Resolution of Alcohols & Thiols; for Resolution of Bases; Monocyclic Monoterpenes; Optical Resolution; Synthetic Organic Chemistry; Terpenes; Acid HalidesAsymmetric Synthesis; Chiral Resolving ReagentsDerivatization Reagents; Chiral Building Blocks; Chiral Resolution Reagents; Derivatization Reagents HPLC; Organic Building Blocks; UV-VIS and so on.

Physical properties about Carbonochloridic acid,5-methyl-2-(1-methylethyl)cyclohexyl ester, (1S,2R,5S)- are: (1)ACD/LogP: 4.83; (2)ACD/LogD (pH 5.5): 4.83; (3)ACD/LogD (pH 7.4): 4.83; (4)ACD/BCF (pH 5.5): 2766.25; (5)ACD/BCF (pH 7.4): 2766.25; (6)ACD/KOC (pH 5.5): 10122.82; (7)ACD/KOC (pH 7.4): 10122.82; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 26.3Å²; (11)Index of Refraction: 1.462; (12)Molar Refractivity: 57.53 cm³; (13)Molar Volume: 209 cm³; (14)Polarizability: 22.8x10^-24cm³; (15)Surface Tension: 32 dyne/cm; (16)Enthalpy of Vaporization: 47.06 kJ/mol; (17)Boiling Point: 233.9 °C at 760 mmHg; (18)Vapour Pressure: 0.0546 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed, it can cause burns. When you are using it, wear suitable protective clothing, gloves and eye/face protection, you also need avoid contact with eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice and in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Cl)O[C@@H]1[C@H](CC[C@@H](C1)C)C(C)C
(2)InChI: InChI=1/C11H19ClO2/c1-7(2)9-5-4-8(3)6-10(9)14-11(12)13/h7-10H,4-6H2,1-3H3/t8-,9+,10-/m0/s1
(3)InChIKey: KIUPCUCGVCGPPA-AEJSXWLSBD
(4)Std. InChI: InChI=1S/C11H19ClO2/c1-7(2)9-5-4-8(3)6-10(9)14-11(12)13/h7-10H,4-6H2,1-3H3/t8-,9+,10-/m0/s1
(5)Std. InChIKey: KIUPCUCGVCGPPA-AEJSXWLSSA-N

Product Name

(+)-MENTHYL CHLOROFORMATE

Synthetic route

Carbonochloridic acid,5-methyl-2-(1-methylethyl)cyclohexyl ester, (1S,2R,5S)- Specification

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