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Dicyclohexylmethanol, also known as DCHM, is an organic compound with the chemical formula C13H24O. It is a colorless to pale yellow liquid with a mild odor and is commonly used as a reagent in the chemical industry. Its molecular structure consists of two cyclohexyl groups attached to a central methanol group, which provides it with unique properties and makes it suitable for various applications.

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  • 4453-82-1 Structure
  • Basic information

    1. Product Name: DICYCLOHEXYLMETHANOL
    2. Synonyms: Cyclohexanemethanol, alpha-cyclohexyl-;DICYCLOHEXYLMETHANOL;DICYCLOHEXYLCARBINOL;alpha-cyclohexylcyclohexanemethanol;Dicyclohexylmethanol,98%;α-Cyclohexylcyclohexanemethanol;Dicyclhexylmethanol
    3. CAS NO:4453-82-1
    4. Molecular Formula: C13H24O
    5. Molecular Weight: 196.33
    6. EINECS: 224-695-7
    7. Product Categories: N/A
    8. Mol File: 4453-82-1.mol
  • Chemical Properties

    1. Melting Point: 58-64 °C(lit.)
    2. Boiling Point: 154 °C12 mm Hg(lit.)
    3. Flash Point: 153-155°C/12mm
    4. Appearance: /
    5. Density: 0.8924 (rough estimate)
    6. Vapor Pressure: 0.000894mmHg at 25°C
    7. Refractive Index: 1.4790 (estimate)
    8. Storage Temp.: -20°C Freezer, Under inert atmosphere
    9. Solubility: methanol: 0.1 g/mL, clear
    10. PKA: 15.17±0.20(Predicted)
    11. BRN: 1926669
    12. CAS DataBase Reference: DICYCLOHEXYLMETHANOL(CAS DataBase Reference)
    13. NIST Chemistry Reference: DICYCLOHEXYLMETHANOL(4453-82-1)
    14. EPA Substance Registry System: DICYCLOHEXYLMETHANOL(4453-82-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4453-82-1(Hazardous Substances Data)

4453-82-1 Usage

Uses

Used in Chemical Synthesis:
Dicyclohexylmethanol is used as a reagent for the synthetic preparation of cyclohexane derivatives. Its unique molecular structure allows it to act as an intermediate in the synthesis of various organic compounds, particularly those with cyclohexane rings. This makes it a valuable component in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, dicyclohexylmethanol is used as a building block for the synthesis of various drug molecules. Its ability to form cyclohexane derivatives makes it a key component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Dicyclohexylmethanol is also utilized in the agrochemical industry for the synthesis of compounds with pesticidal, herbicidal, or fungicidal properties. Its role in creating cyclohexane derivatives contributes to the development of more effective and targeted agrochemicals.
Used in Specialty Chemicals:
In the specialty chemicals sector, dicyclohexylmethanol is employed in the production of various compounds with specific applications, such as additives, coatings, and adhesives. Its versatility as a reagent allows for the creation of tailored products with desired properties for specific industries.

Check Digit Verification of cas no

The CAS Registry Mumber 4453-82-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,5 and 3 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 4453-82:
(6*4)+(5*4)+(4*5)+(3*3)+(2*8)+(1*2)=91
91 % 10 = 1
So 4453-82-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H24O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-14H,1-10H2

4453-82-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B20099)  Dicyclohexylmethanol, 98%   

  • 4453-82-1

  • 1g

  • 258.0CNY

  • Detail
  • Alfa Aesar

  • (B20099)  Dicyclohexylmethanol, 98%   

  • 4453-82-1

  • 5g

  • 864.0CNY

  • Detail
  • Alfa Aesar

  • (B20099)  Dicyclohexylmethanol, 98%   

  • 4453-82-1

  • 25g

  • 3782.0CNY

  • Detail

4453-82-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Dicyclohexylmethanol

1.2 Other means of identification

Product number -
Other names DICYCLOHEXYLMETHANOL

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:4453-82-1 SDS

4453-82-1Relevant articles and documents

COMPOUNDS HAVING A FUNGICIDAL ACTIVITY, THEIR AGRONOMIC COMPOSITIONS AND USE THEREOF FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI

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Page/Page column 45, (2021/01/29)

Compounds having general formula (I) with a high fungicidal activity are described, and their use for the control of phytopathogenic fungi of important agricultural crops.

Half-Sandwich Nickel(II) NHC-Picolyl Complexes as Catalysts for the Hydrosilylation of Carbonyl Compounds: Evidence for NHC-Nickel Nanoparticles under Harsh Reaction Conditions

Ulm, Franck,Shahane, Saurabh,Truong-Phuoc, Lai,Romero, Thierry,Papaefthimiou, Vasiliki,Chessé, Matthieu,Chetcuti, Michael J.,Pham-Huu, Cuong,Michon, Christophe,Ritleng, Vincent

supporting information, p. 3074 - 3082 (2021/08/03)

The cationic [NiCp(Mes-NHC-CH2py]Br complex 2 a was prepared directly by the reaction of nickelocene with 1-(2-picolyl)-3-mesityl-imidazolium bromide (1), and its PF6? derivative 2 b, by subsequent salt metathesis. X-ray diffraction studies and Variable Temperature 1H NMR experiments run with 2 a and 2 b strongly suggest the bidentate coordination of the picolyl-functionalized carbene to the nickel both in the solid state and in solution in both cases. These data suggest the absence of hemilabile behavior of the latter, even in the presence of a coordinating anion. Both complexes show similar activity in aldehyde hydrosilylation, further implying the absence of hemilability of the picolyl-functionalized carbene, and effectively reduce a broad scope of aldehydes in the absence of additive under mild conditions. In the case of ketones, effective hydrosilylation is only observed in the presence of a catalytic amount of potassium t-butoxide at 100 °C. Dynamic light scattering, scanning transmission electron microscopy and X-ray photoelectron spectroscopy show evidence for the involvement of NHC-picolyl-Ni nanoparticles under these conditions.

Kinetic resolution of racemic allylic alcoholsviairidium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity

Wu, Haibo,Margarita, Cristiana,Jongcharoenkamol, Jira,Nolan, Mark D.,Singh, Thishana,Andersson, Pher G.

, p. 1937 - 1943 (2021/02/22)

Asymmetric hydrogenation is one of the most commonly used tools in organic synthesis, whereas, kinetic resolutionviaasymmetric hydrogenation is less developed. Herein, we describe the first iridium catalyzed kinetic resolution of a wide range of trisubstituted secondary and tertiary allylic alcohols. Large selectivity factors were observed in most cases (sup to 211), providing the unreacted starting materials in good yield with high levels of enantiopurity (ee up to >99%). The utility of this method is highlighted in the enantioselective formal synthesis of some bioactive natural products including pumiliotoxin A, inthomycin A and B. DFT studies and a selectivity model concerning the origin of selectivity are presented.

Method for preparing alcohol compounds through hydrogenation reduction of ketone and aldehyde

-

Paragraph 0060-0064; 0095-0098, (2020/02/14)

The invention belongs to the technical field of medical and natural compound chemical intermediates and related chemistry, and provides a method for preparing alcohol compounds through a hydrogenationreduction of ketone and aldehyde. Ketone, aldehyde and derivatives thereof, which are used as raw materials, are subjected to hydrogenation reduction with nano-porous palladium as a catalyst and hydrogen as a hydrogen source, wherein the pressure of hydrogen is 0.1-0.5 MPa, the molar concentration of the ketone, aldehyde and derivatives thereof in the solvent is 0.01-2 mmol/m, the pore skeleton size of the adopted catalyst is 1-50 nm, and the molar ratio of ketone, aldehyde and derivatives thereof to the catalyst is 1:0.01 to 1:0.5. The method has the advantages of high product yield, very mild reaction conditions, simplicity in operation and post-treatment, good repeatability of the catalyst, no obvious reduction of the catalytic effect after the catalyst is used for many times, and provision of the possibility for industrialization.

Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh&at;SILP Catalyst

Bordet, Alexis,Emondts, Meike,Leitner, Walter,Moos, Gilles

supporting information, p. 11977 - 11983 (2020/06/02)

Rhodium nanoparticles immobilized on an acid-free triphenylphosphonium-based supported ionic liquid phase (Rh&at;SILP(Ph3-P-NTf2)) enabled the selective hydrogenation and hydrodeoxygenation of aromatic ketones. The flexible molecular approach used to assemble the individual catalyst components (SiO2, ionic liquid, nanoparticles) led to outstanding catalytic properties. In particular, intimate contact between the nanoparticles and the phosphonium ionic liquid is required for the deoxygenation reactivity. The Rh&at;SILP(Ph3-P-NTf2) catalyst was active for the hydrodeoxygenation of benzylic ketones under mild conditions, and the product distribution for non-benzylic ketones was controlled with high selectivity between the hydrogenated (alcohol) and hydrodeoxygenated (alkane) products by adjusting the reaction temperature. The versatile Rh&at;SILP(Ph3-P-NTf2) catalyst opens the way to the production of a wide range of high-value cyclohexane derivatives by the hydrogenation and/or hydrodeoxygenation of Friedel–Crafts acylation products and lignin-derived aromatic ketones.

COMPOUNDS HAVING A FUNGICIDAL ACTIVITY, THEIR AGRONOMIC COMPOSITIONS AND USE THEREOF FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI

-

Page/Page column 62, (2020/11/22)

Compounds having general formula (I) with a high fungicidal activity and their use for the control of phytopathogenic fungi of important agricultural crops, are described.

Carbonyl and ester C-O bond hydrosilylation using κ4-diimine nickel catalysts

Rock, Christopher L.,Groy, Thomas L.,Trovitch, Ryan J.

supporting information, p. 8807 - 8816 (2018/07/13)

The synthesis of alkylphosphine-substituted α-diimine (DI) ligands and their subsequent addition to Ni(COD)2 allowed for the preparation of (iPr2PPrDI)Ni and (tBu2PPrDI)Ni. The solid state structures of both compounds were found to feature a distorted tetrahedral geometry that is largely consistent with the reported structure of the diphenylphosphine-substituted variant, (Ph2PPr DI)Ni. To explore and optimize the synthetic utility of this catalyst class, all three compounds were screened for benzaldehyde hydrosilylation activity at 1.0 mol% loading over 3 h at 25 °C. Notably, (Ph2PPr DI)Ni was found to be the most efficient catalyst while phenyl silane was the most effective reductant. A broad scope of aldehydes and ketones were then hydrosilylated, and the silyl ether products were hydrolyzed to afford alcohols in good yield. When attempts were made to explore ester reduction, inefficient dihydrosilylation was noted for ethyl acetate and no reaction was observed for several additional substrates. However, when an equimolar solution of allyl acetate and phenyl silane was added to 1.0 mol% (Ph2PPr DI)Ni, complete ester C-O bond hydrosilylation was observed within 30 min at 25 °C to generate propylene and PhSi(OAc)3. The scope of this reaction was expanded to include six additional allyl esters, and under neat conditions, turnover frequencies of up to 990 h-1 were achieved. This activity is believed to be the highest reported for transition metal-catalyzed ester C-O bond hydrosilylation. Proposed mechanisms for (Ph2PPr DI)Ni-mediated carbonyl and allyl ester C-O bond hydrosilylation are also discussed.

Cobalt-Catalyzed Hydroboration of Alkenes, Aldehydes, and Ketones

Tamang, Sem Raj,Bedi, Deepika,Shafiei-Haghighi, Sara,Smith, Cecilia R.,Crawford, Christian,Findlater, Michael

, p. 6695 - 6700 (2018/11/21)

An operationally convenient and general method for hydroboration of alkenes, aldehydes, and ketones employing Co(acac)3 as a precatalyst is reported. The hydroboration of alkenes in the presence of HBpin, PPh3, and NaOtBu affords good to excellent yields with high Markovnikov selectivity with up to 97:3 branched/linear selectivity. Moreover, Co(acac)3 could be used effectively to hydroborate aldehydes and ketones in the absence of additives under mild reaction conditions. Inter- and intramolecular chemoselective reduction of the aldehyde group took place over the ketone functional group.

Neutral Dinuclear Copper(I)-NHC Complexes: Synthesis and Application in the Hydrosilylation of Ketones

Trose, Michael,Lazreg, Fa?ma,Chang, Tao,Nahra, Fady,Cordes, David B.,Slawin, Alexandra M. Z.,Cazin, Catherine S. J.

, p. 238 - 242 (2017/06/07)

The synthesis of a class of highly stable neutral dinuclear Cu(I)-NHC complexes using 1,2,4-triazole as a bridging ligand is described. Various NHCs were used to generate a library of [Cu(μ-trz)(NHC)]2 complexes. Interestingly, [Cu(μ-trz)(IPr)]2 was found to be highly active in the hydrosilylation of ketones, without the need for an external base or any other additive. A wide range of aryl and alkyl ketones, as well as sterically hindered ketones, was successfully reduced to alcohols using the lowest catalyst loading reported to date.

Ferrous complexes supported by sterically encumbered asymmetric bis(arylimino)acenaphthene (BIAN) ligands: synthesis, characterization and screening for catalytic hydrosilylation of carbonyl compounds

Yu, Xun,Zhu, Feifeng,Bu, Donglei,Lei, Hao

, p. 15321 - 15329 (2017/03/17)

Six ferrous chloride complexes ((Ar-BIANX)FeCl2: Ar = 2,6-diisopropylphenyl (Dipp), X = F (1), Cl (2), Me (3); Ar = mesityl (Mes), X = F (4), Cl (5), Me (6)) supported by sterically bulky asymmetric bis(arylimino)acenaphthene (BIAN) ligands were prepared through the treatment of anhydrous FeCl2 with the corresponding ligands in a molar ratio of 1:1. The compounds were characterized by X-ray crystallography, IR, NMR and electrochemical methods. This series of complexes represents rare examples of structurally characterized iron compounds bearing asymmetric bidentate BIAN ligands. The complexes were tested for catalytic hydrosilylation of aldehydes and ketones at room temperature, and moderate to good yields of alcohol derivatives were obtained after hydrolysis workup.

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