10224-72-3

Basic information

• Product Name: DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE
• Synonyms: DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE;1,1-cyclobutanedicarboxylic acid dimethyl ester;Dimethyl cyclobutane-1,1-dicarboxylate;1,1-Bis(methoxycarbonyl)cyclobutane
• CAS NO: 10224-72-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: -0
• Product Categories: blocks;Carboxes
• Mol File: 10224-72-3.mol

Chemical Properties

• Boiling Point: 122°C 55mm
• Flash Point: 122°C/55mm
• Appearance: /
• Density: 1,118 g/cm3
• Vapor Pressure: 0.806mmHg at 25°C
• Refractive Index: 1.4420
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible in water.
• BRN: 2364241
• CAS DataBase Reference: DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE(10224-72-3)
• EPA Substance Registry System: DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE(10224-72-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• Hazardous Substances Data: 10224-72-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE is used as a flavoring agent and fragrance ingredient for its ability to impart specific scents and tastes to consumer products, enhancing their sensory appeal.
Used in Pharmaceutical Synthesis:
DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE is utilized as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of various medicinal compounds.
Used in Agrochemical Synthesis:
DIMETHYL 1,1-CYCLOBUTANEDICARBOXYLATE is employed in the production of agrochemicals, playing a part in the creation of substances that help protect and enhance crop yields and manage pests.

InChI:InChI=1/C8H12O4/c1-11-6(9)8(4-3-5-8)7(10)12-2/h3-5H2,1-2H3

Upstream product

• 5445-51-2 cyclobutane-1,1'-dicarboxylic acid 
• 109-64-8 1,3-dibromo-propane 
• 108-59-8 malonic acid dimethyl ester 
• 102127-54-8 Bicyclo<1.1.0>butan-2,2-dicarbonsaeuredimethylester 
• 67-56-1 methanol 
• 29554-48-1 (3-Brompropyl)-malonsaeuredimethylester 
• 865-34-9 lithium methanolate 

Downstream Products

• 1571067-20-3 methyl 1-(quinolin-8-ylcarbamoyl)-2,4-bis(1-tosyl-1H-indol-3-yl)cyclobutane-1-carboxylate 
• 1398047-71-6 C₁₄H₁₅NO₄ 
• 22308-09-4 [1-(p-tolylsulfonyloxymethyl)cyclobutyl]methyl-4-methylbenzenesulfonate 
• 155380-49-7 1-Formyl-1-methylcyclobutanecarboxylate 

Relevant articles and documents

Tetramethyl 1,1,4,4-Cyclohexanetetracarboxylate: Preparation and Conversion to Key Precursors of Fluorinated, Stereochemically Defined Cyclohexanes

Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the litle tetraester 3 affords trans-1,4-dialdehyde 4a as the major product.Fluorination of 4a,b, followed by additional elaboration leads to novel, 1,1,4,4-tetrasubstituted cyclohexanes bearing trans-1,4-difluoromethyl and fluoromethyl groups.The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of dimethyl 1,1-cycloalkyl diesters 7a-c with excess DIBALH results in reduction of only one ester group.An entry into trans-1,4-trifluoromethylated tetrasubstituted cyclohexanes has been gained through stereoselective SF4 fluorination of 1,1,4,4-cyclohexanetetracarboxylic acid 17.Stereochemical assignments are supported by X-ray crystallographic data.

Perkin-Markovnikov Type Reaction Initiated with Electrogenerated Superoxide Ion

The cyclic condensation of α,ω-dihaloalkanes with acticvated methylene of malonic acid and acetoacetic acid esters is studied using an electrogenerated superoxide ion.Two possible mechanisms for this reaction are postulated.

Hydrogenolysis of Small Cycloalkanes, XVII. - Catalytic Hydrogenation of Dimethyl Bicyclobutane-2,2-dicarboxylate

Catalytic hydrogenation of the title compound 1 yields 92-95percent of ethyl methyl malonate (2), 3-5percent of n-propyl malonate (3), 2-3percent of dimethyl 2-methyl-1,1-cyclopropanedicarboxylate (4), and no 1,1-cyclobutanedicarboxylate 5, the formation of which, however, can be induced with a poisoned catalyst.