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TCI

CAS 4437-51-8

3,4-Hexanedione TCI H0573

3,4-Hexanedione TCI H0573

Chemical Identity

Other names
Dipropionyl
CAS No.
4437-51-8
PubChem
CID 62539·SID 87570959
Formula
C6H10O2
Molecular weight
114.14 g/mol
Purity
>96.0%(GC)
Storage
<0°C
Reference databases
ChEBI·ChemSpider·ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
hexane-3,4-dione
SMILES
CCC(=O)C(=O)CC
InChIKey
KVFQMAZOBTXCAZ-UHFFFAOYSA-N
MDL
MDL00010237
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TCI H0573 3,4-Hexanedione is a symmetrical vicinal diketone carrying two adjacent carbonyl groups at the centre of a six-carbon chain. This arrangement makes it a highly useful non-heterocyclic building block, because the two neighbouring carbonyls provide a distinctive reactivity pattern that ordinary ketones simply do not offer. In the laboratory the compound serves as a starting material for constructing heterocyclic rings, as a chelating ligand once converted into its dioxime derivative, and as a reference compound in studies of volatile compounds with buttery aroma character.

The property that makes it a preferred choice is the high electrophilicity of both carbonyl groups, which arises from their mutual electron-withdrawing effect. As a result, the compound reacts rapidly with nitrogen nucleophiles such as diamines, hydrazines, and hydroxylamine. The reaction with ortho-phenylenediamine, for example, proceeds smoothly to form the quinoxaline framework in a single step. The molecular symmetry removes any question of regioselectivity, since the two carbonyl groups are equivalent, so a single product is formed and purification remains straightforward.

As a yellowish, readily volatile liquid, the compound is also easy to separate from reaction mixtures by evaporation or distillation. In Indonesian laboratories this makes it a practical choice for synthetic chemistry groups in universities and research institutes, where heterocycle construction, ligand preparation, and flavour or aroma compound studies are routine activities and where simple workup procedures using standard rotary evaporation or distillation equipment are preferred.

  • Heterocyclic ring synthesis: the adjacent carbonyl pair condenses directly with ortho-phenylenediamine to build the quinoxaline framework in a single step without additional activation.
  • Chelating ligand preparation: conversion into the corresponding dioxime derivative with hydroxylamine yields a bidentate nitrogen donor suitable for coordination chemistry and metal complex studies.
  • Condensation with hydrazines: the strongly electrophilic carbonyls react rapidly with hydrazine reagents, giving clean access to nitrogen-containing ring systems from a simple starting material.
  • Aroma and flavour research: the compound serves as a reference standard in studies of volatile substances that carry a characteristic buttery aroma profile.
  • General non-heterocyclic building block work: molecular symmetry eliminates regioselectivity problems, so reactions give a single product that is straightforward to isolate and purify.

Brand TCI
CAS number 4437-51-8
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes available in standard TCI catalogue pack sizes; please confirm the required size when ordering
Physical form yellowish, readily volatile liquid
Storage keep in a tightly closed container in a cool, well-ventilated place away from ignition sources

Store the material in a tightly closed container in a cool, well-ventilated area, away from heat, open flames, and other ignition sources. Because the compound is a volatile liquid, containers should be closed immediately after use to limit vapour loss and odour spread in the laboratory. Amber glass bottles with chemically resistant closures are suitable. Handle inside a fume hood and wear safety goggles, gloves, and a laboratory coat. Keep the compound separated from strong oxidising agents and from reactive nitrogen nucleophiles such as amines and hydrazines, since condensation may occur on contact. Transfer with clean, dry glassware to avoid contamination, and consult the supplier safety data sheet before use.

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