1-Ethynylcyclohexanol

Base Information

• Chemical Name: 1-Ethynylcyclohexanol
• CAS No.: 78-27-3
• Deprecated CAS: 1612287-66-7
• Molecular Formula: C8H12O
• Molecular Weight: 124.183
• Hs Code.: 29061900
• European Community (EC) Number: 201-100-9,249-123-3
• NSC Number: 8194
• UNII: 6RV04025EH
• DSSTox Substance ID: DTXSID0021757
• Nikkaji Number: J55.435I
• Wikipedia: 1-Ethynylcyclohexanol
• Wikidata: Q27265398
• ChEMBL ID: CHEMBL394631
• Mol file: 78-27-3.mol

Synonyms:1-Ethynyl-1-cyclohexanol;1-Ethynylcyclohexanol;78-27-3;1-Ethynylcyclohexan-1-ol;Ethynylcyclohexanol;CYCLOHEXANOL, 1-ETHYNYL-;(1-Hydroxycyclohexyl)ethyne;1-ethynyl-cyclohexanol;1-Ethynyl-1-hydroxycyclohexane;NSC 8194;EINECS 201-100-9;Cyclohexyl ethynyl carbinol;1-ethynyl-cyclohexan-1-ol;BRN 0471404;UNII-6RV04025EH;AI3-07064;1-Hydroxy-1-ethynylcyclohexane;DTXSID0021757;6RV04025EH;NSC-8194;28652-54-2;EC 201-100-9;4-06-00-00348 (Beilstein Handbook Reference);1-ethynyl cyclohexanol;Cyclohexanol, ethynyl-;Ethynylcyclohexan-1-ol;MFCD00003858;NSC8194;1-ethynylcyclohexane-1-ol;1-(1-Ethynyl)cyclohexanol;SCHEMBL36060;CHEMBL394631;DTXCID801757;WLN: L6TJ AQ A1UU1;AMY37050;BCP04342;EINECS 249-123-3;Tox21_302106;1-Ethynyl-1-cyclohexanol, >=99%;AKOS009156705;CS-W011179;CAS-78-27-3;NCGC00255158-01;LS-57165;A3540;BB 0253696;E0297;FT-0607765;EN300-152788;N11899;J-504613;Q27265398;F8883-8239

Chemical Property of 1-Ethynylcyclohexanol

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Melting Point: 30-32 °C
• Refractive Index: 1.481-1.484
• Boiling Point: 174 °C at 760 mmHg
• PKA: 13.34±0.20(Predicted)
• Flash Point: 62.8 °C
• PSA: 20.23000
• Density: 0.99 g/cm³
• LogP: 1.31480
• Storage Temp.: 2-8°C
• Solubility.: 10 g/L (20°C)
• Water Solubility.: 10 g/L (20 ºC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 124.088815002
• Heavy Atom Count: 9
• Complexity: 134

Purity/Quality:

>99% ^*data from raw suppliers

1-Ethynylcyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C#CC1(CCCCC1)O
• Uses: Stabilization of chlorinated organic compounds, intermediate, corrosion inhibitor for mineral acids, medicine (sedative). 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.

Technology Process of 1-Ethynylcyclohexanol

There total 33 articles about 1-Ethynylcyclohexanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + acetylene (74-86-2,25067-58-7) → 1-Ethynylcyclohexan-1-ol (78-27-3)

Guidance literature:

acetylene; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;

cyclohexanone; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield: 96.0%

1-acetoxy-1-ethynyl cyclohexane (5240-32-4) → 1-Ethynylcyclohexan-1-ol (78-27-3)

Guidance literature:

With methanol; oxo[hexa(trifluoroacetato)]tetrazinc; for 48h; Reflux; Inert atmosphere;

DOI:10.1002/chem.201000960

Reference yield: 95.0%

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

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/jhet.3454

upstream raw materials:

tetrachloromethane

sodium acetylide

cyclohexanone

diethyl ether

Downstream raw materials:

2-(1-ethynylcyclohexyloxy)ethanol

2-[2-(1-ethynyl-cyclohexyloxy)-ethoxy]-ethanol

2-(1-ethynyl-cyclohexyloxy)-tetrahydro-pyran

acetoacetic acid-(1-ethynyl-cyclohexyl ester)

Refernces

• 1、 Wu, Penglin,Ma, Shengming. "Halogen-Substituted Allenyl Ketones through Ring Opening of Nonstrained Cycloalkanols". supporting information. p. 2533 - 2537. Retrieved 2021/04/13.
• 2、 Huo, Xiaohong,Ma, Shengming,Xiao, Junzhe,Zhang, Jiacheng,Zhang, Wanbin,Zhao, Ling. "Enantio- And Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis". supporting information. p. 12622 - 12632. Retrieved 2021/08/31.