4-Bromoindoline: Properties, Uses & Handling FAQs

4-Bromoindoline is a brominated, partially saturated bicyclic heterocyclic compound widely used as a versatile building block in medicinal chemistry and organic synthesis.

Chemical Name

4-Bromoindoline

CAS Number

Not specified in source material — see product datasheet

Molecular Formula

C₈H₈BrN

Core Scaffold

Indoline (2,3-dihydro-1H-indole) with bromine at position 4

Primary Application

Synthetic building block and coupling partner in medicinal chemistry

SKU

B590407

What Is 4-Bromoindoline and What Is Its Chemical Structure?

4-Bromoindoline belongs to the indoline family of compounds. Indoline itself is the 2,3-dihydro form of indole, meaning the 2- and 3-positions of the five-membered ring are saturated, while the benzene ring remains aromatic. In 4-Bromoindoline, a bromine substituent is located at the 4-position of the benzene ring, adjacent to the nitrogen-bearing ring junction.

This substitution pattern confers the molecule with two chemically distinct reactive sites: the secondary amine (N–H) of the dihydropyrrole ring and the aryl C–Br bond on the benzene ring. The combination makes 4-Bromoindoline a bifunctional intermediate suitable for sequential or orthogonal functionalization strategies.

What Are the Key Physicochemical Properties of 4-Bromoindoline?

4-Bromoindoline (molecular formula C₈H₈BrN) is a nitrogen-containing heterocyclic compound with a moderate molecular weight contributed by the bromine atom. The secondary amine in the indoline ring renders the molecule a weak base and a hydrogen-bond donor, influencing both its solubility profile and its reactivity toward electrophiles and acylating agents.

For precise values of melting point, boiling point, density, and solubility, researchers should consult the official Aladdin product datasheet for SKU B590407, as authoritative numerical data were not included in the source material provided and should not be assumed.

How Is 4-Bromoindoline Used in Organic and Medicinal Chemistry?

The aryl bromide functionality of 4-Bromoindoline is well suited for transition-metal-catalysed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Heck couplings. These reactions allow the introduction of aryl, heteroaryl, vinyl, or amino groups at the 4-position, generating structurally diverse indoline derivatives for structure–activity relationship (SAR) studies.

The indoline N–H can be independently protected or acylated, alkylated, or sulfonylated, enabling orthogonal two-step diversification. The indoline scaffold itself is found in several pharmacologically active compounds, making 4-Bromoindoline a valuable entry point for the synthesis of drug candidates and bioactive natural product analogues.

How Should 4-Bromoindoline Be Stored and Handled Safely?

As with most secondary arylamines and organobromine compounds, 4-Bromoindoline should be handled with appropriate personal protective equipment, including laboratory coat, nitrile gloves, and safety glasses. Work should be conducted in a well-ventilated fume hood to minimise inhalation exposure.

Storage conditions (temperature, inert atmosphere requirements, and light sensitivity) should be confirmed from the Safety Data Sheet (SDS) and product label supplied by Aladdin for SKU B590407. General best practice for amine-containing heterocycles is to store under cool, dry, and dark conditions, ideally under an inert gas blanket if long-term stability is required. Disposal must comply with local regulations governing organohalogen waste.

How Can I Order 4-Bromoindoline from Aladdin Scientific?

4-Bromoindoline is available from Aladdin Scientific under SKU B590407. Researchers and procurement teams can place orders through the Aladdin online store or by contacting the Aladdin sales team directly. Bulk quantities, custom pack sizes, and institutional pricing may be available upon request.

For Certificate of Analysis (CoA), SDS, or additional technical specifications, please visit the product page for B590407 on the Aladdin website or reach out to technical support.

Frequently asked questions

What is the difference between 4-Bromoindoline and 4-Bromoindole?

4-Bromoindoline is the 2,3-dihydro (partially saturated) analogue of indole, meaning its five-membered ring lacks the C2–C3 double bond present in indole. This saturation makes the nitrogen a secondary amine rather than a vinylogous amide, significantly altering reactivity: the N–H is more nucleophilic and the ring is non-aromatic. 4-Bromoindole retains full aromaticity across both rings, making it a different class of reagent with distinct chemical behaviour.

Can 4-Bromoindoline participate in palladium-catalysed cross-coupling reactions?

Yes. The aryl C–Br bond in 4-Bromoindoline is a competent electrophilic partner in palladium-catalysed cross-coupling reactions such as Suzuki–Miyaura (with boronic acids), Buchwald–Hartwig (with amines), and related protocols. Standard palladium precatalysts and phosphine ligands used for aryl bromide couplings are applicable. Reaction conditions should be optimised with reference to published literature on analogous indoline substrates, and the N–H may require protection depending on the coupling protocol employed.

What solvents are typically used to dissolve 4-Bromoindoline for reaction purposes?

Indoline derivatives are generally soluble in common organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate, dimethylformamide, and dimethyl sulfoxide. Solubility in aqueous systems is limited due to the lipophilic bromine and aromatic ring. Researchers should verify solubility experimentally for their specific conditions, as precise solubility data for 4-Bromoindoline were not available in the source material.

Is 4-Bromoindoline available with a Certificate of Analysis?

Yes. Aladdin Scientific provides a Certificate of Analysis (CoA) for SKU B590407 (4-Bromoindoline), confirming purity and lot-specific quality data. The CoA can be requested through the Aladdin website product page or by contacting customer support with the lot number.

What purity grade of 4-Bromoindoline does Aladdin Scientific supply?

Specific purity grade information for B590407 should be confirmed on the current Aladdin product listing or the Certificate of Analysis, as this detail was not explicitly stated in the source material provided. Aladdin Scientific typically supplies research-grade reagents with purity data verified by analytical methods such as HPLC or GC.

References

1. Aladdin Scientific product page for 4-Bromoindoline, SKU B590407.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley. (General reference for indoline chemistry and cross-coupling reactions.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. (General reference for heterocyclic chemistry and palladium-catalysed couplings.)

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