2607-03-6

Basic information

• Product Name: CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER
• Synonyms: CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER;CIS-DIMETHYL CYCLOBUTANE-1,2-DICARBOXYLATE;1β,2α-Cyclobutanedicarboxylic acid dimethyl ester;(1R)-Cyclobutane-1β,2β-dicarboxylic acid dimethyl ester;(1β,2β)-1,2-Cyclobutanedicarboxylic acid dimethyl ester;cyclobutane-1,2-dicarboxylic acid dimethyl ester;Cis-diMethyl-1, 2-cyclobutane dicarboxylate (CBDE);(1R,2S)-rel-1,2-cyclobutanedicarboxylic acid dimethyl ester
• CAS NO: 2607-03-6
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.17848
• Mol File: 2607-03-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 225℃
• Flash Point: 106℃
• Appearance: /
• Density: 1.177
• Refractive Index: 1.4455 (estimate)
• CAS DataBase Reference: CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER(2607-03-6)
• EPA Substance Registry System: CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER(2607-03-6)

Safety Data

• Hazardous Substances Data: 2607-03-6(Hazardous Substances Data)

Usage

General Description

CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER is a chemical compound with the molecular formula C8H12O4. It is a colorless liquid with a fruity odor, often used as a flavoring agent or fragrance in various products. CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER is commonly used in the production of perfumes, soaps, and other personal care products. It is also used as a solvent in organic synthesis and as a plasticizer in polymer production. However, it is important to handle this chemical with care as it may be harmful if inhaled or swallowed, and can cause irritation to the skin and eyes.

InChI:InChI=1/C8H12O4/c1-11-7(9)5-3-4-6(5)8(10)12-2/h5-6H,3-4H2,1-2H3/t5-,6-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 4462-96-8 3-oxabicyclo[3.2.0]heptane-2,4-dione 

Downstream Products

• 874799-59-4 (1R,2S)-2-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclobutanecarboxylic acid methyl ester 
• 221158-94-7 methyl 2-amino-(1R,2S)-cyclobutane-1-carboxylate 
• 517913-98-3 methyl (1S,2R)-2-(((benzyloxy)carbonyl)amino)cyclobutane-1-carboxylate 
• 221158-91-4 methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate 
• 809-43-8 (1S,2S)-α,α,α',α'-tetraphenylcyclobutane-1,2-dimethanol 
• 7371-64-4 trans-(cyclobutane-1,2-diyl)dimethanol 
• 35630-06-9 trans-1,2-cyclobutanedimethanol, bis(toluenesulfonate) 

Relevant articles and documents

Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination

Optically pure trans-cyclobutane analogues of glutamic acid are prepared by highly selective enzymatic transamination of a single racemic trans-cyclobutane α-ketoglutaric acid derivative 5, which is synthesized in five steps from maleic anhydride. (2S,1′R,2′R)- and (2S,1′S,2′S)-2- (2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I are obtained using aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT), respectively.

Stereoselective synthesis of (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acid, a conformationally constrained β-amino acid

The title compound as well as some derivatives have been synthesized for the first time in optically active form by means of a chemoenzymatic transformation used to induce asymmetry in achiral precursors. The enantio- and diastereomeric purity has been determined by HPLC and NMR techniques.

A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase

Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates.The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10percent to 100percent.Some of these optically active monoesters are valuable synthons in natural products synthesis.An additivity pattern of α- and β-substituents with the glutaric esters on the stereoselectivity of enzymatic hydrolysis was observed.Analysis of the experimental results leads to a model of enzyme stereoselectivity of diester hydrolysis in which the substitution pattern at α- and β-C-atoms is found to determine the absolute configuration of the resulting monoester.