16187-15-8

Basic information

• Product Name: 1,2,4-Trioxolane,3,5-dimethyl-, trans- (8CI,9CI)
• Synonyms: trans-2-Buteneozonide; trans-3,5-Dimethyl-1,2,4-trioxolane
• CAS NO: 16187-15-8
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.11
• Mol File: 16187-15-8.mol

Chemical Properties

• CAS DataBase Reference: 1,2,4-Trioxolane,3,5-dimethyl-, trans- (8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Trioxolane,3,5-dimethyl-, trans- (8CI,9CI)(16187-15-8)
• EPA Substance Registry System: 1,2,4-Trioxolane,3,5-dimethyl-, trans- (8CI,9CI)(16187-15-8)

Safety Data

• Hazard Codes: 3:
• Safety Statements: OZONE." target="_blank">May explode when heated. When heated to decomposition it emits acrid smoke and fumes. See also OZONE.:
• Hazardous Substances Data: 16187-15-8(Hazardous Substances Data)

Usage

Family

Trioxolane family

Type

Cyclic peroxides

Potential Activity

Antimalarial

Target Parasite

Plasmodium falciparum (malaria parasite)

Potency

Exhibits potent activity against Plasmodium falciparum

Research Focus

Studying the compound for its potential use in treating malaria

Purpose

Developing new and effective antimalarial treatments

Ongoing Research

Research on 1,2,4-Trioxolane,3,5-dimethyl-, trans- (8CI,9CI) and other trioxolanes continues in the pursuit of better antimalarial options.

Upstream product

• 590-18-1 (Z)-2-Butene 
• 187737-37-7 propene 
• 624-64-6 trans-2-Butene 
• 646-04-8 (E)-pent-2-ene 
• 15981-73-4 cis-4,5-Dimethyl-1,2,3-trioxolane 
• 4696-26-8 (E)-1-ethoxyprop-1-ene 
• 75-07-0 acetaldehyde 
• 4696-25-7 (Z)-1-ethoxyprop-1-ene 

Relevant articles and documents

MECHANISM OF THE OZONOLYSIS OF PROPENE IN THE LIQUID PHASE.

Propylene was ozonized in isobutane, hlorodifluoromethane, and methyl chloride solvents. Propylene ozonide, ethylene ozonide, and 2-butene ozonide (cis and trans isomers) were obtained in ratios of about 82:16:2. The amount of butene ozonide increased while that of ethylene ozonide usually decreased for reactions in the presence of added acetaldehyde. The cis-trans stereochemistry of the butene cross ozonide from propylene was studied at various conditions. Usually the cis isomer was preferentially formed, but addition of acetaldehyde could alter this. The cis-(trans-butene ozonide ratio was 67/33 when formed from cis- or trans-2-butene in CHClF//2 and 50/50 as a cross ozonide from trans-2-pentene. The kinetic secondary isotope effects upon ozonolysis of propene-2-d//1 (k//H/k//D equals 0. 88 (6) and propene-1-d//1 (0. 88 (8) were evaluated. These results are discussed with reference to the Criege mechanism of ozonolysis. 37 refs.

Stereochemical Effects in the Ozonolysis of (E)- and (Z)-1-Ethoxypropene

The ozonolysis of (E)-1-ethoxypropene (or (Z)-1-ethoxypropene) gave cis and trans pairs of 1,2-dioxolanes, 1,2,4-trioxolanes (ozonides), and 1,2,4,5-tetroxanes.Ozonolysis of mixtures of the E and Z alkenes led to variation in the dioxolane stereoisomer ratios but not in the trioxolane ratios.Ozonolysis in the presence of added alcohol or aldehydes produced hydroperoxides or ozonides, respectively, from the methyl-substituted carbonyl oxide.The results are consistent with a Criegee ozonolysis mechanism if the two alkenes produce different relative amounts of the syn and anti carbonyl oxide (CH3HCOO), which recombine at different rates with dipolarophiles.

High-Field Rapid Injection NMR: Observation of Unstable Primary Ozonide Intermediates

A "rapid injection" NMR system is described for use on a 360-MHz superconducting spectrometer.The major advantages of the high-field sytem over our original system are increased sensitivity, resolution, and rapidity.The technique was used to study the ozonolysis of tetramethylethylene and (briefly) cis-but-2-ene, particularly the decomposition of the corresponding primary ozonides 2 and 4, with half-lives of 0.74 and 0.06 s, respectively, at -92 deg C.It was found that the decomposition of 2 in CD2Cl2 (a) had Δ H(excit) = 39 kJ/mol and Δ S(excit) = 28 J/(molK), (b) was unaffected by the presence of TCNE, but (c) was acid-catalyzed.The effects of substituents, solvent, and acid catalysts on the decomposition of primary ozonides are discussed.