2-(2-Bromophenyl)ethanethioamide: Properties & Lab Use Guide

2-(2-Bromophenyl)ethanethioamide is a thioamide-functionalized aryl building block bearing an ortho-bromo substituent, making it a versatile intermediate for palladium-catalyzed cross-coupling reactions and the synthesis of sulfur-containing heterocyclic scaffolds.

Chemical Name

2-(2-Bromophenyl)ethanethioamide

SKU

B178901

Molecular Formula

C8H8BrNS

Molecular Weight

230.12 g/mol

Functional Groups

Thioamide (–C(=S)NH2) and aryl bromide

Key Application

Heterocyclic synthesis; cross-coupling chemistry

Chemical Identity and Structure

2-(2-Bromophenyl)ethanethioamide (CAS not specified in source material; SKU B178901) consists of a phenethyl backbone substituted with a bromine atom at the ortho position of the aromatic ring and a thioamide group (–C(=S)NH₂) at the terminal carbon. Its molecular formula is C₈H₈BrNS, giving a molecular weight of approximately 230.12 g/mol.

The molecule presents two synthetically valuable functional handles: the electrophilic aryl C–Br bond, which is amenable to metal-catalyzed coupling reactions, and the thioamide moiety, which can participate in condensation and cyclization reactions with a variety of dinucleophiles and electrophiles. The proximity of the bromo substituent to the ethylthioamide side chain (ortho relationship) is geometrically favorable for intramolecular cyclization strategies.

Research Applications and Synthetic Utility

The dual functionality of 2-(2-Bromophenyl)ethanethioamide positions it as a key building block in medicinal chemistry and heterocyclic chemistry programs. The thioamide group is a well-established precursor for the construction of a diverse range of sulfur-containing heterocycles, including thiazoles, thiazolines, benzothiazines, and related scaffolds, via condensation with alpha-halo carbonyl compounds, acid anhydrides, or active methylene species.

The ortho-aryl bromide provides an orthogonal handle for Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira coupling reactions, enabling rapid diversification of the molecular framework after initial heterocycle formation. This sequential functionalization strategy is particularly valuable in fragment-based drug discovery and the preparation of compound libraries for biological screening.

Thioamide-containing compounds are also of interest as pharmacophores in their own right, exhibiting reported biological activities across a variety of target classes; however, researchers should validate any specific activity claims with primary literature before drawing conclusions.

Handling, Storage, and Safety Guidelines

As with all thioamide-containing organic compounds bearing a halogen substituent, 2-(2-Bromophenyl)ethanethioamide should be handled with appropriate laboratory precautions. Work in a well-ventilated fume hood, wear nitrile gloves, safety glasses, and a laboratory coat. Avoid inhalation of dust or vapors and contact with skin or mucous membranes.

Store the compound in a cool, dry, well-ventilated area, tightly sealed and protected from light, moisture, and incompatible materials such as strong oxidizers and strong bases. Recommended storage temperature is typically 2–8 °C or as indicated on the product label; consult the current Safety Data Sheet (SDS) supplied by Aladdin Scientific for authoritative hazard classification, first-aid measures, and disposal requirements.

Waste disposal must comply with local, national, and institutional regulations governing halogenated organic compounds. Do not dispose of via drain or general waste streams.

Quality, Purity, and Analytical Characterization

Aladdin Scientific supplies 2-(2-Bromophenyl)ethanethioamide (SKU B178901) as a research-grade reagent. Purity specifications and lot-specific analytical data, including HPLC purity, NMR spectra, and melting point where applicable, are available on the product detail page or upon request from technical support.

Researchers requiring high-purity material for sensitive assays (e.g., IC50 determinations, crystallography) should request the Certificate of Analysis (CoA) for their specific lot prior to use. Typical analytical techniques used to characterize this compound class include ¹H and ¹³C NMR spectroscopy, mass spectrometry (ESI or EI), FT-IR (characteristic C=S stretch ~1050–1200 cm^-1 region), and HPLC with UV detection.

If re-characterization is required after long-term storage, dissolution in deuterated DMSO (DMSO-d₆) is generally suitable for NMR analysis. Confirm solubility in the intended reaction solvent before use.

Frequently asked questions

What is 2-(2-Bromophenyl)ethanethioamide used for in organic synthesis?

It serves primarily as a bifunctional building block: the thioamide group participates in condensation and cyclization reactions to form sulfur-containing heterocycles such as thiazoles and thiazolines, while the ortho-aryl bromide enables palladium-catalyzed cross-coupling reactions for further structural diversification.

How should 2-(2-Bromophenyl)ethanethioamide be stored to maintain stability?

Store the compound in a tightly sealed container at 2–8 °C, protected from light, moisture, and strong oxidizing agents. Always consult the current Aladdin Scientific SDS and lot-specific CoA for authoritative storage conditions.

What solvents are suitable for dissolving 2-(2-Bromophenyl)ethanethioamide?

Thioamide compounds of this type are generally soluble in polar aprotic solvents such as DMSO and DMF, and moderately soluble in common organic solvents including dichloromethane and ethyl acetate. Solubility should be experimentally verified for each specific application, as solubility data for this exact compound are not confirmed in the source material.

How can I confirm the purity and identity of the received batch?

Request the Certificate of Analysis (CoA) for your specific lot from Aladdin Scientific. Identity can be confirmed by 1H NMR, 13C NMR, and mass spectrometry; purity is typically assessed by HPLC. FT-IR can be used to verify the characteristic C=S thioamide absorption band.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for thioamide chemistry and cross-coupling reactions.)
2. Larock, R. C. Comprehensive Organic Transformations. Wiley-VCH. (Reference for synthetic transformations of aryl halides and thioamides.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.