1687-29-2

Basic information

• Product Name: Dimethyl cyclohexane-1,2-dicarboxylate
• Synonyms: TIMTEC-BB SBB008381;DIMETHYL CIS-1,2-CYCLOHEXANEDICARBOXYLATE;DIMETHYL CYCLOHEXANE-1,2-DICARBOXYLATE;DIMETHYL CIS-HEXAHYDROPHTHALATE;Dimethyl Hexahydrophthalate;DIMETHYL 1,2-CYCLOHEXANEDICARBOXYLATE;cis-1,2-Cyclohexanedicarboxylic Acid Dimethyl Ester;(1α,2α)-1,2-Cyclohexanedicarboxylic acid dimethyl ester
• CAS NO: 1687-29-2
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23
• Mol File: 1687-29-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 111 °C / 5mmHg
• Flash Point: 121.3 °C
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.4570-1.4610
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Dimethyl cyclohexane-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl cyclohexane-1,2-dicarboxylate(1687-29-2)
• EPA Substance Registry System: Dimethyl cyclohexane-1,2-dicarboxylate(1687-29-2)

Safety Data

• Hazardous Substances Data: 1687-29-2(Hazardous Substances Data)

Usage

General Description

Dimethyl cyclohexane-1,2-dicarboxylate is a type of organic compound that belongs to the class of organic compounds known as carbonyl compounds. It is primarily characterized by a carboxylic acid ester functional group, which includes two methyl ester groups and a cyclohexane ring in its structure. This chemical is often used in various industrial applications and scientific research due to its ability to act as a reagent or intermediate compound. Its properties such as solubility, boiling point, and melting point among other factors may vary based on conditions like pressure, temperature, and presence of other substances. It is crucial to handle this chemical with care as it may elicit negative health and environmental effects when improperly used or disposed of.

InChI:InChI=1/C10H16O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h7-8H,3-6H2,1-2H3/t7-,8+

Upstream product

• 67-56-1 methanol 
• 610-09-3 (1R,2S)-cyclohexane-1,2-dicarboxylic acid 
• 131-11-3 phthalic acid dimethyl ester 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 149-73-5 trimethyl orthoformate 
• 201230-82-2 carbon monoxide 
• 110-83-8 cyclohexene 
• 74-88-4 methyl iodide 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 868-74-6 2,7-dibromooctanedioic acid dimethyl ester 
• 186581-53-3 diazomethane 

Downstream Products

• 13990-96-0 dimethyl (1S,2R)-4-oxocyclohexane-1,2-dicarboxylate 
• 98516-00-8 cis-1,2-cyclohexanedimethanol diacetate 
• 96894-63-2 (1S,2R)-2-Hydroxymethyl-cyclohexanecarboxylic acid methyl ester 
• 496811-06-4 (1S,2R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclohexanecarboxylic acid 
• 18886-70-9 (+/-)-trans-cyclohexane-1,2-dicarboxylic acid dihydrazide 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 118685-70-4 cis-cyclohexane-1,2-bis-carbohydroxamic acid 
• 18886-70-9 cis-cyclohexane-1,2-dicarboxylic acid dihydrazide 
• 46022-05-3 (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 
• 610-10-6 (1S,2S)-cyclohexane-1,2-dicarboxylic acid 
• 186204-35-3 (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 
• 65376-05-8 (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane 
• 13990-96-0 (1RS,2SR)-dimethyl 4-oxocyclohexane-1,2-dicarboxylate 
• 88335-91-5 cyclohexane-1,2-dicarboxylic acid monomethyl ester 

Relevant articles and documents

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Synthesis of Dimethyl 1,2-Cycloalkanedicarboxylates by Electrochemical Cyclization of Dimethyl α,α-Dibromoalkanedioates Using a Copper Anode

The electrochemical cyclization of dimethyl α,α'-dibromoalkanedioates by making use of a platinum cathode and a copper anode in the presence of sodium iodide gave three- to six-membered dimethyl 1,2-cycloalkanedicarboxylates in good yields.

Highly-efficient Ru/Al-SBA-15 catalysts with strong Lewis acid sites for the water-assisted hydrogenation of: P -phthalic acid

Ruthenium nanoparticles supported onto aluminum-doped mesoporous silica catalysts (Ru/Al-SBA-15) are fabricated using hydrothermal and impregnation methods for catalysis application. The Ru/Al-SBA-15-3 catalyst at a Si/Al molar ratio of 3 exhibited excellent catalytic performance for the hydrogenation of p-phthalic acid with high conversion efficiency (100.0%) and cis-isomer selectivity (84.0%) in water. Moreover, this system displays exceptional stability and recyclability through preserving the conversion efficiency, as well as a cis-isomer selectivity of 90.2 and 83.3%, respectively, after reusing it fourteen times. Such an exceptional system can also be ideal for the hydrogenation of aromatic dicarboxylic acids and their ester derivatives in water. Strong Lewis acid sites due to doped Al species play significant roles in the hydrogenation reaction. Moreover, isotope labeling studies indicated that water molecules effectively participated in the hydrogenation reaction. Hydrogen and water contributed half of the hydrogen atoms for this hydrogenation reaction. In the end, a plausible mechanistic pathway for the hydrogenation of p-phthalic acid using the Ru/Al-SBA-15-3 catalyst in water is proposed.

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.

Scalable, Electrochemical Oxidation of Unactivated C-H Bonds

A practical electrochemical oxidation of unactivated C-H bonds is presented. This reaction utilizes a simple redox mediator, quinuclidine, with inexpensive carbon and nickel electrodes to selectively functionalize "deep-seated" methylene and methine moieties. The process exhibits a broad scope and good functional group compatibility. The scalability, as illustrated by a 50 g scale oxidation of sclareolide, bodes well for immediate and widespread adoption.