78-27-3

Basic information

• Product Name: 1-Ethynyl-1-cyclohexanol
• Synonyms: 1-ETHYNYLCYCLOHEXANOL;1-ETHYNYL-1-CYCLOHEXANOL;1-ETHINYL-1-CYCLOHEXANOL;TIMTEC-BB SBB008829;(1-Hydroxycyclohexyl)ethyne;1-ethvnvl-1-cvclohexanol;1-Ethynyl-1-hydroxycyclohexane;1-Ethynylcyclohexan-1-ol
• CAS NO: 78-27-3
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18
• EINECS: 201-100-9
• Product Categories: Biphenyl & Diphenyl ether;Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 78-27-3.mol
• Article Data: 58

Chemical Properties

• Melting Point: 30-33 °C(lit.)
• Boiling Point: 180 °C(lit.)
• Flash Point: 163 °F
• Appearance: Clear colorless to light yellow/Liquid After Melting
• Density: 0.967 g/mL at 25 °C(lit.)
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Refractive Index: 1.481-1.484
• Storage Temp.: 2-8°C
• Solubility: 10 g/L (20°C)
• PKA: 13.34±0.20(Predicted)
• Explosive Limit: 1.3-8.7%(V)
• Water Solubility: 10 g/L (20 ºC)
• BRN: 471404
• CAS DataBase Reference: 1-Ethynyl-1-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethynyl-1-cyclohexanol(78-27-3)
• EPA Substance Registry System: 1-Ethynyl-1-cyclohexanol(78-27-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 21/22-36-36/37/38-20/21/22-36/38
• Safety Statements: 36/37-36/37/39-26-36-22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 1
• RTECS: GV9100000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 78-27-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 78-27-3 differently. You can refer to the following data:
1. Stabilization of chlorinated organic compounds, intermediate, corrosion inhibitor for mineral acids, medicine (sedative).
2. 1-Ethynyl-1-cyclohexanol (ECHO) can undergo acetylation in the presence of a catalytic amount of ruthenium chloride at room temperature. It can be used to synthesize novel organotellurium(IV) compounds with potent inhibitory activity towards Cathepsin B. The polymerization of ECHO by transition metal catalysts leads to the formation of poly(ECHO). It can also react with transition metal hydride complexes to form vinyl derivatives by inserting into the M-H bonds.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 416, 1955Synthetic Communications, 18, p. 131, 1988 DOI: 10.1080/00397918808077336

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H12O/c1-2-8(9)6-4-3-5-7-8/h1,9H,3-7H2

Synthetic route

cyclohexanone (108-94-1) + acetylene (74-86-2) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
Stage #1: acetylene With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; Stage #2: cyclohexanone In tetrahydrofuran at 0 - 20℃;	99.3%
With potassium hydroxide In dimethyl sulfoxide at 15 - 17℃; for 2h;	98%
Stage #1: acetylene With ammonia; sodium at -78℃; Stage #2: cyclohexanone In diethyl ether at -78℃; for 12h;	97%

1-acetoxy-1-ethynyl cyclohexane (5240-32-4) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With methanol; oxo[hexa(trifluoroacetato)]tetrazinc for 48h; Reflux; Inert atmosphere;	96%
[t-Bu2SnOH(Cl)]2 In methanol for 24h; Heating;	86 % Chromat.

1-((trimethylsilyl)ethynyl)cyclohexanol (17962-22-0) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 12h; Inert atmosphere;	95%
With tetrabutyl ammonium fluoride In tetrahydrofuran
With methanol; potassium carbonate at 20℃; for 12h; Inert atmosphere;
With potassium carbonate In tetrahydrofuran; methanol
With potassium carbonate In methanol under 760.051 Torr; for 1h;

cyclohexanone (108-94-1) + calcium carbide (75-20-7) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With tetrabutyl ammonium fluoride; water In dimethyl sulfoxide at 20℃; for 2h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;	94%
With caesium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; Inert atmosphere; Green chemistry;	61%
With caesium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; Sonogashira Cross-Coupling;
With water; caesium carbonate In dimethyl sulfoxide at 60℃; for 8h; Inert atmosphere;

1-(((1-ethynylcyclohexyl)oxy)methyl)-4-methoxybenzene (1020186-15-5) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane; water at 20 - 30℃; for 3h; Irradiation; Green chemistry;	88%
With sodium hydrogen sulfate; eosin; dihydrogen peroxide In water; acetonitrile for 25h; Irradiation;	56%

2-(1-ethynyl-cyclohexyloxy)-tetrahydro-pyran (42969-66-4) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In methanol; N,N-dimethyl-formamide at 110℃; for 19h;	84%
With iron(III) p-toluenesulfonate hexahydrate In methanol at 20℃; for 2h;	77%

triethyl((1-ethynylcyclohexyl)oxy)silane (53201-16-4) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With potassium fluoride; Tetraethylene glycol at 20℃; for 24h;	82%

trimethylaluminum (75-24-1) + sodium acetylide (1066-26-8) + cyclohexanone (108-94-1) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
In tetrahydrofuran; toluene; xylene for 3h; Ambient temperature;	81%

O-(p-nitrobenzoyl)-1-ethynylcyclohexanol (36144-39-5) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With sodium azide In methanol at 40℃; for 6h;	79%

cyclohexanone (108-94-1) + acetylenemagnesium bromide (4301-14-8) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
Stage #1: acetylenemagnesium bromide In tetrahydrofuran; tetradecyl(trihexyl)phosphonium decanoate at -78 - 20℃; Stage #2: cyclohexanone In tetradecyl(trihexyl)phosphonium decanoate; toluene for 16h; Stage #3: With water In tetradecyl(trihexyl)phosphonium decanoate; toluene	78%
In tetrahydrofuran at -10 - 20℃; for 2.16667h;	70%
In tetrahydrofuran Heating;	61%

cyclohexanone (108-94-1) + acetylene (74-86-2) → 1-ethynyl-1-(vinyloxy)cyclohexane (1356339-86-0) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With potassium hydroxide semihydrate In dimethyl sulfoxide at 90℃; under 15201 - 19001.3 Torr; for 1h;	A 40% B n/a
With potassium hydroxide semihydrate In dimethyl sulfoxide at 80℃; for 0.5h; High pressure;	A 11% B 40%
With potassium hydroxide semihydrate In dimethyl sulfoxide at 90℃; for 1h; High pressure;	A 40% B 12%

tetrachloromethane (56-23-5) + sodium acetylide (1066-26-8) + cyclohexanone (108-94-1) → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
at 130℃;

diethyl ether (60-29-7) + sodium acetylide (1066-26-8) + cyclohexanone (108-94-1) → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

sodium acetylide (1066-26-8) + cyclohexanone (108-94-1) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With diethyl ether
With ammonia
With ammonia

tetrachloromethane (56-23-5) + cyclohexanone (108-94-1) + acetylene (74-86-2) → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
at 85℃; under 14710.2 Torr;

cyclohexanone (108-94-1) + acetylene (74-86-2) → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With sodium hydroxide at 85℃; under 14710.2 Torr;
With potassium hydroxide at 85℃; under 14710.2 Torr;

cyclohexanone (108-94-1) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With diethyl ether; sodium amide nachfolgend Einleiten von Acetylen unter Druck;

cyclohexanone (108-94-1) → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With potassium hydroxide; diethyl ether Einleiten von Acetylen;
With diethyl ether; sodium amide nachfolgend Einleiten von Acetylen unter Druck;

Natrium-Verbindung des Cyclohexanons (34434-35-0) + acetylene (74-86-2) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With diethyl ether
With diethyl ether

1-ethynyl-1-(trimethylsiloxy)cyclohexane (62785-90-4) → 1-Ethynyl-1-cyclohexanol (78-27-3)

cyclohexanone (108-94-1) + trimethylsilylacetylene (1066-54-2) → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With sodium hydroxide; n-butyllithium 1.) THF, -78 deg C; 2.) MeOH; Yield given. Multistep reaction;
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: cyclohexanone at -78 - 20℃; Stage #3: With potassium carbonate In methanol

cyclohexanone (108-94-1) + sodium amide + acetylene (74-86-2) → 1-Ethynyl-1-cyclohexanol (78-27-3)

cyclohexanone (108-94-1) + acetylene (74-86-2) + KOH → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
at 85℃; under 14710.2 Torr;

diethyl ether (60-29-7) + cyclohexanone (108-94-1) + acetylene (74-86-2) + KOH → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
unter Kuehlung;

acetylene (74-86-2) + etheric cyclohexanone → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
With potassium hydroxide
With potassium 2-methylbutan-2-olate

3-(1-hydroxycyclohexyl)propiolic acid (25294-58-0) + copper-powder → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
at 200℃; under 20 Torr;

1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6) + K2CO3 → cyclohexanone (108-94-1) + 1-Ethynyl-1-cyclohexanol (78-27-3) + acetylene (74-86-2)

cyclohexanone (108-94-1) + lithium acetylide (70277-75-7) → 1-Ethynyl-1-cyclohexanol (78-27-3)

cyclohexanone (108-94-1) + ethynylmagnesium halide → 1-Ethynyl-1-cyclohexanol (78-27-3)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;

cyclohexanone (108-94-1) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1,2-di(1-hydroxycyclohexyl)acetylene (78-54-6)

Conditions	Yield
Stage #1: 1-Ethynylcyclohexan-1-ol With ethylmagnesium bromide In tetrahydrofuran at 23 - 80℃; Stage #2: cyclohexanone In tetrahydrofuran at 23 - 25℃; Stage #3: With ammonium chloride In tetrahydrofuran; water	100%
With sodium hydroxide; tetrabutylammomium bromide In toluene at 70℃; for 2h;	89%
Stage #1: 1-Ethynylcyclohexan-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: cyclohexanone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -78 - 20℃; for 14h;	74%

acetic anhydride (108-24-7) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-acetoxy-1-ethynyl cyclohexane (5240-32-4)

Conditions	Yield
indium(III) chloride In acetonitrile at 20℃; for 0.5h;	100%
With magnesium(II) perchlorate at 20℃; for 0.5h;	100%
tetrafluoroboric acid; silica gel at 20℃; for 6h;	96%

1-Ethynyl-1-cyclohexanol (78-27-3) → 1-cyclohexenyl methyl ketone (932-66-1)

Conditions	Yield
With NH4NO3-exchanged zeolite HSZ-320 In chlorobenzene at 130℃; for 4h;	100%
With aliquat 366; water; PtCl4-CO In various solvent(s) at 110℃; under 1034.3 Torr; for 4.5h;	97%
With Dowex-50; acetic acid Rupe rearrangement; Heating;	95%

phenyl isocyanate (103-71-9) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-ethynylcyclohexyl phenylcarbamate (73623-16-2)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 90h;	100%
In 1,2-dichloro-ethane at 20℃; for 16h;	82%
With 1-methyl-pyrrolidin-2-one

1-heptyl vinyl ether (764-95-4) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-ethynyl-1-(1-heptyloxy-ethoxy)-cyclohexane

Conditions	Yield
With trifluoroacetic acid at 20 - 40℃; Addition;	100%

diethylene glycol divinyl ether (764-99-8) + 1-Ethynyl-1-cyclohexanol (78-27-3) → C24H38O5

Conditions	Yield
With trifluoroacetic acid at 30 - 35℃; for 12h; Addition;	100%

1-Ethynyl-1-cyclohexanol (78-27-3) + bis adduct of diethylene glycol divinyl ether and diethylene glycol (273406-64-7) → C36H62O11

Conditions	Yield
With trifluoroacetic acid at 30 - 35℃; for 10h; Addition;	100%

1-Ethynyl-1-cyclohexanol (78-27-3) + (E)-4-Ethoxy-5,5,6,6,6-pentafluoro-1-phenyl-3-(phenylsulfonyl)hex-3-en-1-yne → (2R*,3R*)-2-Ethoxy-4-methylene-2-pentafluoroethyl-3-phenylethynyl-3-phenylsulfonyl-1-oxaspiro[4.5]decane

Conditions	Yield
Stage #1: 1-Ethynylcyclohexan-1-ol With sodium hydride In N,N-dimethyl-formamide Stage #2: (E)-4-Ethoxy-5,5,6,6,6-pentafluoro-1-phenyl-3-(phenylsulfonyl)hex-3-en-1-yne In N,N-dimethyl-formamide at 0℃; for 0.166667h; Further stages.;	100%

1-Ethynyl-1-cyclohexanol (78-27-3) + 1-methyl-3-iodo-1H-indole-2-carbaldehyde (372954-67-1) → 3-(1-hydroxycyclohexylethynyl)-1-methylindole-2-carboxaldehyde (474267-09-9)

Conditions	Yield
With triethylamine; 2percent PdCl2(PPh3)2 at 60℃; for 18h; Sonogashira coupling;	100%

trimethylsilylazide (4648-54-8) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-(2H-1,2,3-triazol-4-yl)cyclohexan-1-ol

Conditions	Yield
With copper(l) iodide In methanol; N,N-dimethyl-formamide at 100℃; Inert atmosphere;	100%

1-Ethynyl-1-cyclohexanol (78-27-3) + benzyl azide (622-79-7) → (1-benzyl-1H-[1,2,3]triazol-4-yl)-cyclohexylmethanol (83027-66-1)

Conditions	Yield
With bis[1-(4-sodiumsulfonatepropyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-3-ylidine]copper(I) hexafluorophosphate In neat (no solvent) at 20℃; for 0.0833333h;	99%
With (2,4-dimesityl-4,5-dihydro-1H-naphtho[1,8-ef][1,3]diazocin-3(2H)-ylidene)copper(I) bromide at 25℃; Inert atmosphere; Schlenk technique;	99%
With copper-supported ionic liquid catalyst In ethanol; water at 20℃; for 1.5h; Huisgen cycloaddition;	98%

1-Ethynyl-1-cyclohexanol (78-27-3) → 1,4-bis(1-hydroxycyclohexyl)buta-1,3-diyne (5768-10-5)

Conditions	Yield
With copper(l) iodide; ethyl bromoacetate; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃;	99%
With N,N,N,N,-tetramethylethylenediamine; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride In acetonitrile at 24℃; for 24h;	99%
With 1-n-butyl-3-methylimidazolim bromide; copper(II) trifluoroacetate hydrate name... In water at 50℃; for 24h; Solvent; Green chemistry;	99%

Phenylselenyl chloride (5707-04-0) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-(E-2'-phenylseleno-1'-chloroethenyl)cyclohexanol (77955-98-7)

Conditions	Yield
In dichloromethane Ambient temperature;	99%

iodobenzene (591-50-4) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-(phenylethynyl)-1-cyclohexanol (20109-09-5)

Conditions	Yield
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride at 80℃; Sonogashira coupling;	99%
With piperidine; copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium(0) In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere;	97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 20℃; Inert atmosphere;	97%

carbon dioxide (124-38-9) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 4-methylidene-1,3-dioxaspiro[4.5]decan-2-one (92474-80-1)

Conditions	Yield
With potassium acetate; silver(I) iodide In N,N-dimethyl-formamide at 45℃; under 750.075 Torr; for 24h;	99%
With (dimethylamino)methyl-polystyrene supported copper(I) iodide at 40℃; under 105011 Torr; for 24h; Autoclave;	96%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 30℃; under 7500.75 Torr; for 12h; Catalytic behavior; Autoclave; Green chemistry;	96%

para-iodoanisole (696-62-8) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-[2-(4-methoxyphenyl)ethynyl]cyclohexanol (104581-29-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride at 55℃; for 3h; Sonogashira Cross-Coupling; Ionic liquid; Green chemistry;	99%
With piperidine; copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate In N,N-dimethyl-formamide at 60℃; for 2h;	98%
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride at 80℃; Sonogashira coupling;	91%

triethylsilane (617-86-7) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-((E)-2-(Triethylsilyl)ethenyl)-1-cyclohexanol

Conditions	Yield
With sodium iodide In tetrahydrofuran at 20℃; for 1h; stereoselective reaction;	99%
With platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane; tri-tert-butyl phosphine In tetrahydrofuran at 20℃; Inert atmosphere; stereoselective reaction;	93%
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; triphenylphosphine In acetone at 50℃; for 16h;	92%

Isopropenyl acetate (108-22-5) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-acetoxy-1-ethynyl cyclohexane (5240-32-4)

Conditions	Yield
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene at 25℃; for 15h;	99%

p-nitrobenzene iodide (636-98-6) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-[2-(4-nitrophenyl)ethynyl]cyclohexanol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride at 55℃; for 3h; Sonogashira Cross-Coupling; Ionic liquid; Green chemistry;	99%
With piperidine In water; acetonitrile at 40℃; for 4h; Sonogashira coupling;	95%
With sodium hydroxide; palladium diacetate In water; acetone at 60℃; for 1h; Sonogashira reaction;	94%
With [bbim]BF4; triethylamine; palladium dichloride at 30℃; for 2.5h; Sonogashira reaction; sonication;	72%

1-Azidoadamantane (24886-73-5) + 1-Ethynyl-1-cyclohexanol (78-27-3) → C18H27N3O

Conditions	Yield
With triethylamine; copper carbide In 1,4-dioxane at 60℃; for 2h;	99%

1-Fluoro-2-iodobenzene (348-52-7) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-(2-fluorophenylethynyl)cyclohexanol (1007120-34-4)

Conditions	Yield
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride at 80℃; Sonogashira coupling;	99%

1-Ethynyl-1-cyclohexanol (78-27-3) + carbonic acid dimethyl ester (616-38-6) → methyl 1,1-pentamethyleneprop-2-ynyl carbonate (61699-43-2)

Conditions	Yield
Stage #1: carbonic acid dimethyl ester With lanthanum (III) nitrate * water; TOP at 20℃; Stage #2: 1-Ethynylcyclohexan-1-ol for 10h; Molecular sieve; Reflux;	99%
Stage #1: carbonic acid dimethyl ester With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 20℃; Stage #2: 1-Ethynylcyclohexan-1-ol for 12h; Reflux; chemoselective reaction;	97%
With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 110℃; for 12h; Reagent/catalyst; Molecular sieve;	97%

Vinyl bromide (593-60-2) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-vinylethynyl-1-cyclohexanol (2696-22-2)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 0 - 20℃; for 6.5h;	98%

1-Ethynyl-1-cyclohexanol (78-27-3) + benzyl azide (622-79-7) → C15H19N3O (1354827-06-7)

Conditions	Yield
With (η5-C5Me5)Ru(P(i-Pr)3)Cl In dichloromethane at 20℃; for 0.0166667h;	99%

phenethyl azide (6926-44-9) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 1-(1-phenethyl-1H-1,2,3-triazol-4-yl)cyclohexanol (1370006-18-0)

Conditions	Yield
With bis[1-(4-sodiumsulfonatepropyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-3-ylidine]copper(I) hexafluorophosphate In neat (no solvent) at 20℃; for 1.3h;	99%
With copper(ll) sulfate pentahydrate; betaine; sodium L-ascorbate In water at 30℃; for 24h;	96%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; β‐cyclodextrin In water at 20℃; for 0.2h;	95%

1-Ethynyl-1-cyclohexanol (78-27-3) + benzyl azide (622-79-7) → 1-(1-phenethyl-1H-1,2,3-triazol-4-yl)cyclohexanol (1370006-18-0)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol	99%

1-Ethynyl-1-cyclohexanol (78-27-3) → 1-[(Z)-2-iodoethenyl]cyclohexanol (1447908-97-5)

Conditions	Yield
Stage #1: 1-Ethynylcyclohexan-1-ol With triethyl borane; dichloroindium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	99%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-Ethynyl-1-cyclohexanol (78-27-3) → C16H22O2*C6H12N2

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 12h;	99%

Upstream product

• 1066-26-8 sodium acetylide 
• 108-94-1 cyclohexanone 
• 34434-35-0 Natrium-Verbindung des Cyclohexanons 
• 74-86-2 acetylene 
• 62785-90-4 1-ethynyl-1-(trimethylsiloxy)cyclohexane 
• 1066-54-2 trimethylsilylacetylene 
• 5240-32-4 1-acetoxy-1-ethynyl cyclohexane 
• 5463-75-2 tris(1-ethinylclohexyloxy)borane 
• 7732-18-5 water 
• 1020186-15-5 1-(((1-ethynylcyclohexyl)oxy)methyl)-4-methoxybenzene 
• 75-20-7 calcium carbide 
• 53201-16-4 triethyl((1-ethynylcyclohexyl)oxy)silane 
• 54655-07-1 lithium trimethylsilylacetylenide 
• 17962-22-0 1-((trimethylsilyl)ethynyl)cyclohexanol 

Downstream Products

• 42969-66-4 2-(1-ethynyl-cyclohexyloxy)-tetrahydro-pyran 
• 873375-35-0 4-(1-hydroxy-cyclohexylethynyl)-1,2,5-trimethyl-piperidin-4-ol 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 
• 127623-92-1 4-<(cyclohexylideneethenyl)sulfinyl>morpholine 
• 130721-59-4 4-methylene-3-(toluene-4-sulfonyl)-1-oxa-3-azaspiro[4.5]decan-2-one 
• 5609-22-3 1-Ethynyl-1-isobutoxymethoxy-cyclohexane 
• 5549-46-2 1-Ethynyl-1-(3-methyl-butoxymethoxy)-cyclohexane 
• 5990-43-2 1-Cyclohexyloxymethoxy-1-ethynyl-cyclohexane 
• 6023-72-9 1-Methoxymethoxy-1-(3-methoxy-prop-1-ynyl)-cyclohexane 
• 5288-72-2 1-Ethinyl-1-butyloxymethoxy-cyclohexan 
• 5240-33-5 1-Ethinyl-1-ethoxymethoxy-cyclohexan 
• 5240-35-7 1-Ethinyl-1-isopropyloxymethoxy-cyclohexan 
• 5240-34-6 1-Ethinyl-1-propyloxymethoxy-cyclohexan 
• 5288-73-3 1-Ethynyl-1-hexyloxymethoxy-cyclohexane 

Relevant articles and documents

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Fluorocyclization of Allyl Alcohols and Amines to Access 3-Functionalized Oxetanes and Azetidines

An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N3 or -OR) plays a crucial role in polarizing the C= C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.

ETHERS AND ESTERS OF 1-SUBSTITUTED CYCLOALKANOLS FOR USE AS AROMA CHEMICALS

The present invention relates to the use of an ether or an ester of a 1 -substituted cycloalkanol or of mixtures of two or more ethers or esters of 1 -substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ether or an ester of a 1 -substituted cycloalkanol or of mixtures of two or more ethers or esters of 1 -substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific ethers or esters of 1 -substituted cycloalkanols.