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TCI

CAS 491-35-0

Lepidine TCI L0024

Lepidine TCI L0024

Chemical Identity

CAS No.
491-35-0
PubChem
CID 10285·SID 87571993
Formula
C10H9N
Molecular weight
143.18 g/mol
Purity
>97.0%(GC)(T)
Reference databases
ChEBI·ChemSpider·ECHA·Wikipedia
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
4-methylquinoline
SMILES
CC1=CC=NC2=CC=CC=C12
InChIKey
MUDSDYNRBDKLGK-UHFFFAOYSA-N
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Lepidine, also known as 4-methylquinoline, is a nitrogen-containing aromatic heterocyclic compound that serves as an important building block in organic synthesis. Its quinoline framework is a core structure frequently encountered in medicinally active compounds, dyes, and coordination ligands, while the methyl group at the four position provides a reactive site for further transformation. In the laboratory, this compound is used as a precursor for preparing quinoline derivatives, as a ligand in coordination chemistry, and as a model substrate in studies of the reactivity of nitrogen-containing heteroaromatic rings.

The properties that make lepidine a widely preferred choice are the combination of a pyridinic nitrogen base capable of binding metals or protons, and a methyl group that is sufficiently acidic to be deprotonated and then reacted with aldehydes or other electrophiles. This capability opens condensation routes that yield styryl derivatives and extended conjugated systems useful as chromophores. As a liquid at room temperature, lepidine is easily measured volumetrically and dissolves well in common organic solvents. Reagent-grade quality from TCI maintains consistency of results in reactions that are sensitive to impurities.

In Indonesian laboratories, lepidine is typically encountered in synthetic organic chemistry work where quinoline derivatives are the target, in coordination chemistry groups preparing metal complexes, and in method-development studies that use nitrogen heteroaromatics as model substrates. Because it is a liquid, it fits routines where reagents are dispensed by volume, and its solubility in common organic solvents means it can be introduced into standard reaction setups without special solvent systems being required.

TCI brochures (PDF)

  • Synthesis of quinoline derivatives: lepidine provides a ready-made quinoline core, so chemists build outward from an established heterocyclic framework rather than constructing the ring system from scratch.
  • Ligand in coordination chemistry: the pyridinic nitrogen acts as a donor atom able to bind metal centres, making lepidine directly usable in the preparation of metal complexes.
  • Condensation reactions with aldehydes: the four-position methyl group is acidic enough to be deprotonated and then reacted with aldehydes, giving access to styryl derivatives.
  • Preparation of chromophores and conjugated systems: condensation routes from lepidine yield extended conjugated systems, which are of interest where light-absorbing or dye-related properties are needed.
  • Model substrate in reactivity studies: lepidine serves as a representative nitrogen-containing heteroaromatic ring for investigating how such systems behave under various reaction conditions.

From the TCI brochure

  • Reagent in scheme step (d) with Mn(OAc)3, TFA, AcOH, H2O

Brand TCI
CAS number 491-35-0
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes available in the pack sizes listed for this catalogue item
Physical form liquid at room temperature; soluble in common organic solvents
Storage store according to the manufacturer's stated conditions on the product label
  • Chemical name: Lepidine (4-methylquinoline)

Store lepidine in its original tightly closed container, kept in a cool, dry, well-ventilated area away from direct sunlight and sources of ignition. Containers of glass or other solvent-compatible material are suitable for dispensing and short-term working use; keep them properly labelled and closed when not in use. Handle the material in a fume hood, wearing safety glasses, gloves, and a laboratory coat, and avoid contact with skin and eyes as well as inhalation of vapours. As a liquid reagent that can be sensitive to impurities, avoid introducing contamination during transfer and use clean, dry glassware and syringes. Refer to the manufacturer's safety data sheet for full handling, incompatibility, and disposal guidance.

References cited in the TCI brochure

  1. Taeho Kang. Multifaceted Substrate–Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds ACS Catalysis, 2020. doi:10.1021/acscatal.0c03622