2-Bromo-1-indanol: Properties, Uses & Handling FAQ

2-Bromo-1-indanol is a halogenated bicyclic alcohol serving as a versatile electrophilic building block in organic synthesis, valued for its reactive bromo and hydroxyl functional groups on the indane scaffold.

CAS / SKU

SKU B152972 (CAS to be confirmed with supplier datasheet)

Molecular Formula

C9H9BrO

Molecular Weight

213.07 g/mol

Key Functional Groups

Allylic/benzylic C–Br and secondary C–OH on an indane ring system

Stereochemistry

Contains two stereocenters at C-1 and C-2; available as racemate or enantiopure form (verify with lot COA)

Recommended Storage

Cool, dry, dark conditions; sealed under inert atmosphere to prevent dehydrobromination or oxidation

Primary Applications

Epoxide synthesis via intramolecular SN2, nucleophilic substitution, chiral ligand precursor preparation

What Is 2-Bromo-1-indanol and What Are Its Key Chemical Properties?

2-Bromo-1-indanol is a bifunctional organic compound belonging to the indanol family. It consists of the bicyclic indane (2,3-dihydro-1H-indene) scaffold bearing a bromine substituent at the 2-position and a hydroxyl group at the 1-position. Its molecular formula is C₉H₉BrO with a molecular weight of approximately 213.07 g/mol.

The compound is classified as an α-bromohydrin on a benzylic/allylic system. The proximity of the electron-withdrawing bromine and the hydroxyl group creates significant reactivity: the C–Br bond is activated toward nucleophilic substitution (S_N2 and, under certain conditions, S_N1), and the β-relationship of the two groups facilitates intramolecular cyclization to form cis- or trans-1,2-indene oxide (indane epoxide) upon base treatment.

The compound is typically a white to off-white solid or low-melting solid at room temperature. Exact melting point data should be verified against the supplier's Certificate of Analysis (COA) for each lot.

What Are the Main Synthetic Applications of 2-Bromo-1-indanol?

2-Bromo-1-indanol is a valuable electrophilic building block in preparative organic chemistry. Its principal synthetic uses include:

• Epoxide formation: Treatment with base (e.g., K₂CO₃ or NaOH) promotes intramolecular S_N2 displacement of bromide by the alkoxide, yielding 1,2-indene oxide. The stereochemical outcome depends on the configuration of the starting material and reaction conditions.
• Nucleophilic substitution at C-2: The activated C–Br bond undergoes S_N2 reactions with a range of nucleophiles (amines, thiols, azides, organocuprates) to introduce diverse functional groups while retaining the C-1 hydroxyl.
• Chiral building block applications: Enantiopure forms of 2-bromo-1-indanol are precursors to chiral indanol derivatives widely used in asymmetric synthesis, including chiral ligand and auxiliary preparation.
• Further elaboration of the indane scaffold: The compound can serve as an entry point to substituted indanols, aminoindanols, and related pharmacophores relevant to medicinal chemistry research.

Researchers should verify stereochemical requirements before selecting the racemic or enantiopure form appropriate for their application.

How Should 2-Bromo-1-indanol Be Stored and Handled Safely?

Storage: Store 2-bromo-1-indanol in a tightly sealed container under an inert atmosphere (nitrogen or argon) in a cool (2–8 °C recommended; confirm with COA), dry location away from light and moisture. Prolonged exposure to moisture, heat, or base can promote elimination of HBr or hydrolysis of the C–Br bond.

Handling precautions: Although specific GHS hazard classifications for this compound should be confirmed from the supplier's Safety Data Sheet (SDS), general precautions for organobromine compounds apply: wear appropriate personal protective equipment (nitrile gloves, safety goggles, lab coat); work in a well-ventilated fume hood; avoid contact with skin, eyes, and mucous membranes.

Incompatibilities: Avoid strong bases, strong oxidizing agents, and prolonged exposure to protic solvents. Strong bases will convert the compound to the corresponding epoxide, which may not be desired.

Waste disposal: Dispose of in accordance with local, national, and institutional regulations for halogenated organic waste.

Researchers must consult the Aladdin SDS for B152972 for authoritative hazard and first-aid information before use.

What Solvents and Reaction Conditions Are Recommended for Use with 2-Bromo-1-indanol?

2-Bromo-1-indanol is generally soluble in common polar aprotic and chlorinated solvents such as dichloromethane (DCM), tetrahydrofuran (THF), ethyl acetate, acetonitrile, and dimethylformamide (DMF). Solubility in water is expected to be low due to the hydrophobic indane core and the lipophilic C–Br bond.

Recommended conditions by transformation:

• Epoxide synthesis: Use mild inorganic bases (K₂CO₃, Cs₂CO₃) in polar aprotic solvents (acetone, DMF) at or below room temperature to minimize side reactions.
• S_N2 substitution: Polar aprotic solvents (DMF, DMSO, MeCN) at room temperature to mild heating favor S_N2 over elimination. Use freshly dried solvents to avoid hydrolysis.
• Chiral resolution or asymmetric reactions: Select conditions compatible with the enantiopure form; consult relevant asymmetric synthesis literature for specific ligand or auxiliary protocols.

Reaction progress can typically be monitored by TLC or HPLC; consult the COA for purity and characterization data as a reference standard.

How Do I Assess Purity and Quality of 2-Bromo-1-indanol Upon Receipt?

Upon receipt, inspect the sample for physical appearance (typically a white to pale solid) and any signs of discoloration, which may indicate decomposition or oxidation. Key analytical methods for quality assessment include:

• GC or HPLC purity: The Certificate of Analysis (COA) provided by Aladdin Scientific for each lot will state the purity by chromatographic method. Cross-check your in-house analysis against this reference.
• NMR spectroscopy: ¹H and ¹³C NMR in CDCl₃ or DMSO-d₆ are definitive for structural confirmation. The C-1 CH (bearing OH) and C-2 CH (bearing Br) protons appear as characteristic diastereotopic signals; coupling constants report relative stereochemistry.
• Optical rotation: For enantiopure material, measure [α]_D and compare with the value cited in the COA or literature to confirm enantiomeric identity and integrity.
• Mass spectrometry: ESI-MS or EI-MS will confirm the molecular ion with the characteristic bromine isotope pattern (M and M+2 in approximately 1:1 ratio).

Store the compound immediately under recommended conditions after opening. Contact Aladdin Scientific technical support (SKU B152972) if quality concerns arise.

Frequently asked questions

What is the difference between the cis and trans isomers of 2-bromo-1-indanol, and which should I order?

2-Bromo-1-indanol has two stereocenters (C-1 and C-2), giving rise to cis (1R,2S / 1S,2R) and trans (1R,2R / 1S,2S) diastereomeric pairs, each available as a racemate or in enantiopure form. The cis isomer typically undergoes faster intramolecular cyclization to the epoxide due to the anti-periplanar geometry required for S₂ attack, while the trans isomer may behave differently in substitution reactions. Select the isomer based on the stereochemical requirements of your downstream synthesis; consult the COA to confirm the specific stereochemistry supplied under SKU B152972.

Can 2-bromo-1-indanol be used directly in asymmetric synthesis without further resolution?

If the material supplied is racemic, it cannot be used directly in enantioselective applications without a chiral resolution step or an asymmetric reaction that differentiates the enantiomers. Enantiopure 2-bromo-1-indanol, if available, can serve directly as a chiral building block or auxiliary precursor. Always confirm the enantiomeric excess (ee) from the COA before proceeding with asymmetric synthesis workflows, and verify the available stereoisomeric form with Aladdin Scientific for SKU B152972.

How stable is 2-bromo-1-indanol on the bench, and what decomposition pathways should I be aware of?

2-Bromo-1-indanol is moderately stable under ambient conditions but is susceptible to several degradation pathways: (1) elimination of HBr under basic or thermally forcing conditions to yield an indenol or related alkene; (2) hydrolysis of the C–Br bond by moisture over prolonged periods; and (3) oxidation of the secondary alcohol to the corresponding ketone. To maximize shelf life, always reseal the container under inert gas immediately after use, store at low temperature, and minimize exposure to air and moisture. If discoloration or a change in physical state is observed, re-analyze by NMR or GC before use in sensitive applications.

What analytical data should I expect in the Certificate of Analysis for SKU B152972?

A typical COA for 2-Bromo-1-indanol (B152972) from Aladdin Scientific should include: product name, lot number, CAS number, molecular formula and weight, appearance description, purity (% by GC or HPLC), and where applicable, NMR confirmation and optical rotation for enantiopure lots. Some COAs also include melting point, water content (Karl Fischer), and heavy metals data depending on the grade. Contact Aladdin Scientific customer service or technical support to request the specific COA for your lot prior to purchase if detailed characterization data is critical for your application.

Is 2-bromo-1-indanol compatible with organometallic reagents such as Grignard or organolithium species?

2-Bromo-1-indanol is generally not directly compatible with strongly basic organometallic reagents such as Grignard reagents or organolithiums without protection of the hydroxyl group, because the free OH proton will protodehalogenate or deprotonate the reagent before productive C–C bond formation occurs. Protect the alcohol as a silyl ether (e.g., TMS or TBS) or other suitable protecting group prior to introduction of such reagents. After protection, the activated C–Br bond may then be used for metal-halogen exchange or cross-coupling reactions depending on the specific synthetic target.

References

1. March, J.; Smith, M. B. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed.; Wiley: Hoboken, NJ, 2013. (General reference for bromohydrin chemistry and S₂ reactions.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Reference for epoxide formation from halohydrins and stereochemical principles.)
3. Aladdin Scientific Product Page and Certificate of Analysis for 2-Bromo-1-indanol, SKU B152972. (Primary source for lot-specific purity, physical data, and hazard information.)

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