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4-Methylcyclohexanol is an organic compound with the molecular formula C7H14O. It is a colorless liquid with a distinctive odor and is commonly found as a mixture of cis and trans isomers. 4-Methylcyclohexanol is used in various applications across different industries due to its unique properties.

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  • 589-91-3 Structure
  • Basic information

    1. Product Name: 4-Methylcyclohexanol
    2. Synonyms: 4-methyl-cyclohexano;4-Methylcyclohexanol cis+trans;4-Methylcyclohexanol,c&t;4-methylcyclohexanol,mixtureofcisandtrans;Cyclohexanol, 4-methyl-;HEXAHYDRO-P-CRESOL;4-METHYLCYCLOHEXANOL;4-METHYLHEXALIN
    3. CAS NO:589-91-3
    4. Molecular Formula: C7H14O
    5. Molecular Weight: 114.19
    6. EINECS: 209-664-8
    7. Product Categories: N/A
    8. Mol File: 589-91-3.mol
  • Chemical Properties

    1. Melting Point: -41 °C
    2. Boiling Point: 171-173 °C(lit.)
    3. Flash Point: 158 °F
    4. Appearance: Clear colorless to yellow/Viscous Liquid
    5. Density: 0.914 g/mL at 25 °C(lit.)
    6. Vapor Density: 3.94 (vs air)
    7. Vapor Pressure: 1.5 mm Hg ( 30 °C)
    8. Refractive Index: n20/D 1.458(lit.)
    9. Storage Temp.: N/A
    10. Solubility: N/A
    11. PKA: 15.32±0.40(Predicted)
    12. Water Solubility: slightly soluble
    13. BRN: 1445998
    14. CAS DataBase Reference: 4-Methylcyclohexanol(CAS DataBase Reference)
    15. NIST Chemistry Reference: 4-Methylcyclohexanol(589-91-3)
    16. EPA Substance Registry System: 4-Methylcyclohexanol(589-91-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 20
    3. Safety Statements: 24/25
    4. RIDADR: 2617
    5. WGK Germany: 1
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 589-91-3(Hazardous Substances Data)

589-91-3 Usage

Uses

Used in Research and Development:
4-Methylcyclohexanol is used as a research compound for studying its effects on various biological processes. For instance, it has been used to investigate the effects of 4-Methylcyclohexanol on oviposition, which is the process of egg-laying in certain organisms.
Used in Chemical Synthesis:
4-Methylcyclohexanol serves as a valuable intermediate in the synthesis of various chemicals and pharmaceuticals. Its unique structure allows for further chemical modifications, making it a versatile building block in the development of new compounds with potential applications in various fields.
Used in Flavor and Fragrance Industry:
Due to its distinctive odor, 4-Methylcyclohexanol is used as a component in the creation of various fragrances and flavors. It can be found in the formulation of perfumes, colognes, and other scented products, as well as in the flavor industry for enhancing the taste and aroma of food and beverages.
Used in Solvent Applications:
4-Methylcyclohexanol's solubility properties make it suitable for use as a solvent in various chemical processes. It can be employed in the purification and separation of different compounds, as well as in the production of coatings, adhesives, and other industrial products.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 525, 1988 DOI: 10.1016/S0040-4039(00)80139-2

Check Digit Verification of cas no

The CAS Registry Mumber 589-91-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 589-91:
(5*5)+(4*8)+(3*9)+(2*9)+(1*1)=103
103 % 10 = 3
So 589-91-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H14O/c1-6-2-4-7(8)5-3-6/h6-8H,2-5H2,1H3/t6-,7-

589-91-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A16734)  4-Methylcyclohexanol, cis + trans, 98%   

  • 589-91-3

  • 50ml

  • 309.0CNY

  • Detail
  • Alfa Aesar

  • (A16734)  4-Methylcyclohexanol, cis + trans, 98%   

  • 589-91-3

  • 250ml

  • 522.0CNY

  • Detail
  • Alfa Aesar

  • (A16734)  4-Methylcyclohexanol, cis + trans, 98%   

  • 589-91-3

  • 1000ml

  • 2025.0CNY

  • Detail

589-91-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methylcyclohexanol

1.2 Other means of identification

Product number -
Other names HEXAHYDRO-P-CRESOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:589-91-3 SDS

589-91-3Relevant articles and documents

CATALYTIC PROPERTIES OF THE PLATINUM AND PALLADIUM BLACKS OBTAINED FROM VAPORIZED METALS AS REVEALED IN THE HYDROGENATION OF 4-METHYLCYCLOHEXANONE IN ETHANOL

Nishimura, Shigeo,Iwafune, Sei-ichiro,Nagura, Toshikazu,Akimoto, Yoshinori,Uda, Masahiro

, p. 1275 - 1278 (1985)

The platinum and palladium blacks obtained from vaporized metals have been found to catalyze the acetal formation efficiently in the hydrogenation of 4-methylcyclohexanone in ethanol.The catalytic properties of these blacks are compared with those of various blacks prepared by chemical procedures.

A novel and efficient N-doping carbon supported cobalt catalyst derived from the fermentation broth solid waste for the hydrogenation of ketones via Meerwein–Ponndorf–Verley reaction

Chen, Yuxin,He, Runxia,Liu, Quansheng,Yao, Xuefeng,Zhou, Huacong

, (2021/12/10)

Most of the non-noble metal catalysts used for the Meerwein–Ponndorf–Verley (MPV) reaction of carbonyl compounds rely on the additional alkaline additives during preparation to achieve high efficiency. To solve this problem, in this work, we prepared a novel N-doped carbon supported cobalt catalyst (Co@CN), in which the carriers were derived from the nitrogen-rich organic waste, i.e., oxytetracycline fermentation residue (OFR, obtained from oxytetracycline refining workshop). No additional nitrogen sources were used during preparation. The results showed that inherent nitrogen in OFR could provide N-containing basic sites, and formed Co-N structures via coordinating with cobalt. The Co-N sites together with the coexisting Co(0) cooperated to catalyze the conversion of ethyl levulinate (EL) to γ-valerolactone (GVL) by MPV reaction. Co(0) dominated the activation of H in isopropanol, while Co-N dominated the formation of the six-membered ring transition state.

Catalytic role of metals supported on SBA-16 in hydrodeoxygenation of chemical compounds derived from biomass processing

Szczyglewska, Paulina,Feliczak-Guzik, Agnieszka,Jaroniec, Mietek,Nowak, Izabela

, p. 9505 - 9517 (2021/03/16)

Hydrodeoxygenation (HDO) carried out at high temperatures and high hydrogen pressures is one of the alternative methods of upgrading pyrolytic oils from biomass, leading to high quality biofuels. To save energy, it is important to carry out catalytic proc

CATALYTIC PROCESS

-

Paragraph 0224; 0244; 0248, (2021/12/03)

A catalytic process for the deoxygenation of an organic substrate, such as a biomass or bio-oil, is described. The catalytic process is conducted in the presence of a gaseous mixture containing both hydrogen and nitrogen. The presence of nitrogen in the gaseous mixture gives rise inter-aliato increased catalytic activity and/or increased selectivity for aromatic reaction products.

Synthesis method of 4-substituent cyclohexanone liquid crystal intermediate

-

Paragraph 0044-0045, (2021/05/19)

The invention discloses a synthesis method of a 4-substituent cyclohexanone liquid crystal intermediate, which comprises the following step: carrying out oxidation catalytic reaction on 4-substituent cyclohexanol under the action of trichloroisocyanide urea to obtain the 4-substituent cyclohexanone liquid crystal intermediate. The method is high in reaction selectivity, high in yield, environment-friendly, simple in post-treatment and suitable for industrial production.

Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof

-

Paragraph 0094-0097; 0100-0104, (2021/05/29)

The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.

Catalytic transfer hydrogenation of 4-O-5 models in lignin-derived compounds to cycloalkanes over Ni-based catalysts

Chen, Changzhou,Liu, Peng,Xia, Haihong,Zhou, Minghao,Jiang, Jianchun

, p. 582 - 591 (2020/12/01)

There is an urgent need to develop a selective hydrogenolysis of Caryl-O bonds in lignin to produce valued-added chemicals and fuels. Recently, hydrogen has been used in the hydrogenation reaction, which hides inevitable danger and is not economical. Therefore, isopropanol, as a hydrogen-donor solvent, is employed for aryl ether hydrogenolysis in lignin models over nickel supported on a carbon nanotube (CNT). Except for aromatic ether (4-O-5), the Ni/CNT catalyst is also found to be suitable for alkyl-aryl ether (α-O-4 and β-O-4) cleavage in control experiments. The physicochemical characterizations were carried out by means of H2-temperature-programmed reduction, X-ray diffraction, transmission electron microscopy, and X-ray photoelectron spectroscopy analyses. The catalyst can be magnetically recovered and efficiently reused for five consecutive recycling tests in the transfer hydrogenation of aromatic ethers. A mechanism study indicated that the hydrogenolysis cleavage of the ether bond is the first step in the reaction process, and hydrogenation of aromatic rings is only a successive step in which phenol and benzene are intermediate states and are then further hydrogenated. Furthermore, it has been demonstrated that aryl groups play an important role in the hydrogenation of phenol in the competitive catalytic hydrogenation reaction of phenol.

Aliphatic C–H hydroxylation activity and durability of a nickel complex catalyst according to the molecular structure of the bis(oxazoline) ligands

Hikichi, Shiro,Izumi, Takashi,Matsuba, Naki,Nakazawa, Jun

, (2021/07/13)

Applicability of the oxazoline-based compounds, bis(2-oxazolynyl)methane (BOX) and 2,6-bis(2-oxazolynyl)pyridine (PyBOX), as supporting ligands of nickel(II) complexes for the catalysis of aliphatic C–H hydroxylation with m-CPBA (meta-chloroperoxybenzoic acid) was explored. Substituent groups at the fourth and fifth positions of oxazoline rings and the bridgehead carbon atom of the BOX derivatives affected the catalytic performances toward cyclohexane hydroxylation. Presence of dioxygen led to a reduced catalytic performance of the nickel complexes, except in the case of a fully substituted BOX ligand complex.

Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier

Garg, Nidhi,Paira, Soumen,Sundararaju, Basker

, p. 3472 - 3476 (2020/05/29)

Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.

Efficient alkane hydroxylation catalysis of nickel(ii) complexes with oxazoline donor containing tripodal tetradentate ligands

Hikichi, Shiro,Horii, Sena,Nakazawa, Jun,Okamura, Masaya,Terao, Ikumi

, p. 6108 - 6118 (2020/05/25)

Tris(oxazolynylmethyl)amine TOAR(where R denotes the substituent groups on the fourth position of the oxazoline rings) complexes of nickel(ii) have been synthesized as catalyst precursors for alkane oxidation withmeta-chloroperoxybenzoic acid (m-CPBA). The molecular structures of acetato, nitrato,meta-chlorobenzoato and chlorido complexes with TOAMe2have been determined using X-ray crystallography. The bulkiness of the substituent groups R affects the coordination environment of the nickel(ii) centers, as has been demonstrated by comparison of the molecular structures of chlorido complexes with TOAMe2and TOAtBu. The nickel(ii)-acetato complex with TOAMe2is an efficient catalyst precursor compared with the tris(pyridylmethyl)amine (TPA) analogue. Oxazolynyl donors’ strong s-electron donating ability will enhance the catalytic activity. Catalytic reaction rates and substrate oxidizing position selectivity are controlled by the structural properties of the R of TOAR. Reaction of the acetato complex with TOAMe2andm-CPBA yields the corresponding acylperoxido species, which can be detected using spectroscopy. Kinetic studies of the decay process of the acylperoxido species suggest that the acylperoxido species is a precursor of an active species for alkane oxidation.

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