3,3,5-Trimethylcyclohexanol

Base Information

• Chemical Name: 3,3,5-Trimethylcyclohexanol
• CAS No.: 116-02-9
• Deprecated CAS: 64840-01-3
• Molecular Formula: C9H18O
• Molecular Weight: 142.241
• Hs Code.: 2906 19 00
• European Community (EC) Number: 213-268-0,212-183-6,204-122-7
• NSC Number: 4008
• UNII: 08CL3G94GH
• DSSTox Substance ID: DTXSID9041815
• Nikkaji Number: J46.555K
• Wikipedia: 3,3,5-Trimethylcyclohexanol
• Wikidata: Q27126431
• Metabolomics Workbench ID: 43902
• ChEMBL ID: CHEMBL3186608
• Mol file: 116-02-9.mol

Synonyms:3,3,5-trimethylcyclohexanol;3,3,5-trimethylcyclohexanol, (cis)-isomer;3,3,5-trimethylcyclohexanol, (trans)-isomer;cis-3,3,5-trimethylcyclohexanol

Chemical Property of 3,3,5-Trimethylcyclohexanol

Chemical Property:

• Appearance/Colour: White crystalline mass
• Vapor Pressure: 0.173mmHg at 25°C
• Melting Point: 30-32 °C
• Refractive Index: 1.447
• Boiling Point: 187.655 °C at 760 mmHg
• PKA: 15.35±0.60(Predicted)
• Flash Point: 73.201 °C
• PSA: 20.23000
• Density: 0.879 g/cm³
• LogP: 2.19350
• Storage Temp.: Store below +30°C.
• Water Solubility.: 1.8 g/L (20 ºC)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 142.135765193
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

3,3,5-Trimethylcyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC1CC(CC(C1)(C)C)O
• Uses: Menthol and camphor substitute, antifoaming agent, hydraulic fluids and textile soaps, odor masking, esterification agent, pharmaceuticals,wax additive, printing inks.

Technology Process of 3,3,5-Trimethylcyclohexanol

There total 24 articles about 3,3,5-Trimethylcyclohexanol 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: 100.0%

dihydroisophorone (873-94-9) → 3,3,5-trimethylcyclohexanol (116-02-9)

Guidance literature:

With zinc hydride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0022-328X(00)93381-3

Reference yield: 88.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,3,5-trimethylcyclohexanol (116-02-9) + dihydroisophorone (873-94-9)

Guidance literature:

With NiCRASi; In tetrahydrofuran; at 45 ℃; for 0.75h;

DOI:10.1016/S0040-4039(00)85244-2

Reference yield: 51.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,3,5-trimethylcyclohexanol (116-02-9) + (R)-3,3,5-trimethylcyclohexanone (33496-82-1)

Guidance literature:

With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; bis(triphenylphosphane)copper(I) nitrate; hydrogen; sodium t-butanolate; In isopropyl alcohol; at 30 ℃; for 18h; under 37503.8 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1055/s-0029-1218347

upstream raw materials:

3,5,5-Trimethylcyclohex-2-en-1-one

dihydroisophorone

4,6-dimethylbicyclo<4.1.0>heptan-2-one

isopropyl alcohol

Downstream raw materials:

2,2,4-trimethyl hexanedioic acid

2,4,4-trimethyl-adipic acid

3-bromo-1,1,5-trimethyl-cyclohexane

3,5,5-trimethyl-cyclohexene

Refernces

• 1、 Ashby et al.. "". . p. 3133. Retrieved 1977.
• 2、 B?rner, Armin,Gandelman, Mark,Holz, Jens,Spannenberg, Anke,Wenzel, Gudrun. "New P-chirogenic tert.-butyl-xantphos ligands and their application in asymmetric hydrogenation and alkylation". . . Retrieved 2020.
• 3、 Koning, A. J. De,Boersma, J.,Kerk, G. J. M. Van Der. "SYNTHESIS, CHARACTERIZATION AND PROPERTIES OF SOME ORGANOZINC HYDRIDE COMPLEXES". . p. 1 - 12. Retrieved 1980.
• 4、 Cossy, Janine,Furet, Nathalie. "Photochemical ring opening of cyclopropyl ketones induced by electron transfer". . p. 8107 - 8110. Retrieved 1993.
• 5、 Chaudhuri, Haribandhu,Dash, Subhajit,Sarkar, Ashis. "Preparation and application of surface activated Si-MCM-41 and SBA-16 as reusable supports for reduction of cyclic ketones with preferential stereoselectivity". . p. 99444 - 99454. Retrieved 2016.
• 6、 Xu, Lei,Sun, Shaoyin,Zhang, Xing,Gao, Haofei,Wang, Wei. "Study on the selective hydrogenation of isophorone". . p. 4465 - 4471. Retrieved 2021/02/03.
• 7、 -. "P-CHIRAL PHOSPHINE LIGANDS AND USE THEREOF FOR ASYMMETRIC SYNTHESIS". Paragraph 0920-0923. . Retrieved 2019/07/23.