TRANS-2-METHYLCYCLOHEXANOL

Base Information

• Chemical Name: TRANS-2-METHYLCYCLOHEXANOL
• CAS No.: 7443-52-9
• Molecular Formula: C7H14 O
• Molecular Weight: 114.188
• Hs Code.: 2906120010
• European Community (EC) Number: 231-186-3
• DSSTox Substance ID: DTXSID301032693
• Nikkaji Number: J231.800H
• Mol file: 7443-52-9.mol

Synonyms:Cyclohexanol,2-methyl-, trans- (8CI); (?à)-trans-2-Methylcyclohexanol; NSC 244887; NSC 245854;rel-(1S,2S)-2-Methylcyclohexanol; trans-1-Hydroxy-2-methylcyclohexane;trans-2-Methyl-1-cyclohexanol; trans-2-Methylcyclohexanol

Chemical Property of TRANS-2-METHYLCYCLOHEXANOL

Chemical Property:

• Melting Point: −21 °C(lit.)
• Refractive Index: n20/D 1.461(lit.)
• Boiling Point: 167.2-167.6 °C(lit.)
• PKA: 15.33±0.40(Predicted)
• Flash Point: 138 °F
• PSA: 20.23000
• Density: 0.924 g/mL at 25 °C(lit.)
• LogP: 1.55740
• Water Solubility.: Slightly soluble in water
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 114.104465066
• Heavy Atom Count: 8
• Complexity: 70.8

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-2-Methylcyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-20
• Safety Statements: 26-36/37/39-38-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCCCC1O
• Isomeric SMILES: C[C@@H]1CCCC[C@H]1O
• Uses: 2-Methylcyclohexanol was used in the fragment-based crystallographic screening against HIV protease.

Technology Process of TRANS-2-METHYLCYCLOHEXANOL

There total 141 articles about TRANS-2-METHYLCYCLOHEXANOL 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: 38.0%

2-Methylcyclohexanol (583-59-5) → (+/-)-trans-2-methylcyclohexanol (7443-52-9) + 2-Methylcyclohexanone (583-60-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; dimethylsulfide; oxygen; copper(I) bromide dimethylsulfide complex; 6,6'-bis(C₈F₁₇(CH₂)4)-2,2'-bipyridine; In chlorobenzene; at 90 ℃; for 9.5h;

DOI:10.1016/S0040-4020(02)00250-8

Reference yield:

methyl cyclohexane (82166-21-0) → 1-Methylcyclohexanol (590-67-0) + trans-4-methylcyclohexan-1-ol (7731-29-5) + cis-4-methylcyclohexanol (7731-28-4) + (+/-)-trans-2-methylcyclohexanol (7443-52-9) + cis-2-methylcyclohexanol (7443-70-1) + rac-trans-3-methylcyclohexanol (7443-55-2) + cis-3-methylcyclohexanol (5454-79-5) + 1-methylcyclohexan-4-one (589-92-4) + 2-Methylcyclohexanone (583-60-8) + cyclohexylmethyl alcohol (100-49-2) + cyclohexanecarbaldehyde (2043-61-0) + 3-Methylcyclohexanone (591-24-2,625-96-7)

Guidance literature:

With C₂₂H₁₇BClF₉N₆NiO₃; at 70 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja4020277

Reference yield:

1-methylcyclohex-1-ene (591-49-1) → m-methylcyclohexanol (591-23-1) + (+/-)-trans-2-methylcyclohexanol (7443-52-9) + cyclohexylmethyl alcohol (100-49-2)

Guidance literature:

With alkaline hydrogen peroxide; borane; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, reflux, 10 h;

DOI:10.1246/cl.1980.461

upstream raw materials:

2-Methylcyclohexanone

ortho-cresol

(+/-)-cis-2-methylcyclohexanol acetate

Octanoic acid (1R,2S)-2-methyl-cyclohexyl ester

Downstream raw materials:

1-iodo-2-methylcyclohexane

1-methyl-1-cyclohexanecarboxylic acid

1-chloro-1-methylcyclohexane

(1R,2R)-(-)-trans-2-methylcyclohexanol

Refernces

• 1、 Yoon, Nung Min,Kim, Kwan Eung,Kang, Jahyo. "Potassium Triphenylborohydride. A New Reducting Agent for the Reduction of Carbonyl Compounds with an Exceptional Stereo- and Chemoselectivity". . p. 226 - 229. Retrieved 1986.
• 2、 Davies, Stephen G.,Wollowitz, Susan. "Epoxide opening with organocuprates and grignard reagents in the presence of chiral ligands". . p. 4175 - 4178. Retrieved 1980.
• 3、 Brown, Herbert C.,Park, Won Suh,Cha, Jin Soon,Cho, Byung Tae,Brown, Charles A.. "Addition Compounds of Alkali Metal Hydrides. 28. Preparation of Potassium Dialkoxymonoalkylborohydrides from Cyclic Boronic Esters. A New Class of Reducing Agents". . p. 337 - 342. Retrieved 1986.
• 4、 Bilyachenko, Alexey N.,Khrustalev, Victor N.,Zubavichus, Yan V.,Shul'Pina, Lidia S.,Kulakova, Alena N.,Bantreil, Xavier,Lamaty, Frédéric,Levitsky, Mikhail M.,Gutsul, Evgeniy I.,Shubina, Elena S.,Shul'Pin, Georgiy B.. "Heptanuclear Fe5Cu2-Phenylgermsesquioxane containing 2,2′-Bipyridine: Synthesis, Structure, and Catalytic Activity in Oxidation of C-H Compounds". . p. 528 - 534. Retrieved 2018/01/11.
• 5、 Gordon, Jonathan,Hildebrandt, Sven,Dewese, Kendra R.,Klare, Sven,Gans?uer, Andreas,Rajanbabu,Nugent, William A.. "Demystifying Cp2Ti(H)Cl and Its Enigmatic Role in the Reactions of Epoxides with Cp2TiCl". supporting information. p. 4801 - 4809. Retrieved 2019/01/08.