2-(4-Bromophenyl)-2-hydroxyacetonitrile - ≥95% , CAS No.58289-69-3

CAS: 58289-69-3 Cat. No.: B1012227 Formule: C₈H₆BrNO Poids moléculaire: 212.040

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: C1=CC(=CC=C1C(C#N)O)Br
• IUPAC Name: 2-(4-bromophenyl)-2-hydroxyacetonitrile
• InChIKey: AYTVNJIUMVFUCJ-UHFFFAOYSA-N
• INCHI: 1S/C8H6BrNO/c9-7-3-1-6(2-4-7)8(11)5-10/h1-4,8,11H
• Poids moléculaire: 212.040

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Bromobenzenes
• Alternative Parents: Aryl bromides Secondary alcohols Cyanohydrins Alpha-hydroxynitriles Organobromides Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Bromobenzene - Aryl bromide - Aryl halide - Alpha-hydroxynitrile - Cyanohydrin - Secondary alcohol - Carbonitrile - Nitrile - Alcohol - Organonitrogen compound - Organobromide - Organohalogen compound - Organooxygen compound - Aromatic alcohol - Hydrocarbon derivative - Cyanide - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as bromobenzenes. These are organic compounds containing a bromine atom attached to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Poids moléculaire: 212.040 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 210.963 Da
• Monoisotopic Mass: 210.963 Da
• Topological Polar Surface Area: 44.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 166.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable. This listing is a small-molecule reagent, not an antibody or assay kit. No WB/IHC/IF/FC protocols or dilutions apply. For synthetic procedures, refer to the Reaction Conditions and Synthetic Utility sections.

Biological Roles

• Item-specific: None specified; this product is for research use only.

• General context (literature):

  • Cyanohydrins are biosynthetically related to cyanogenic glycosides in plants, which store stabilized cyanohydrin motifs as glucose conjugates. Hydrolysis releases HCN as a defense mechanism. However, 2-(4-bromophenyl)-2-hydroxyacetonitrile is a synthetic aryl cyanohydrin and is not known as a natural metabolite.
  • The functional group combination (benzylic OH and nitrile) makes it a useful probe substrate for enzymes such as nitrilases, nitrile hydratases, and alcohol dehydrogenases in biocatalysis research, though specific biological targets or roles for this compound are not established.

No specific biochemical signaling or metabolic role is reported for this exact molecule; applications are primarily synthetic/chemical biology as a building block.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare biological buffers or electrophoresis media. If it is included in biochemical experiments, it is generally as a substrate or small-molecule building block dissolved in an appropriate organic co-solvent. For pH control, use standard buffer systems (e.g., phosphate, HEPES) separate from this reagent.

Green Alternatives

While the compound itself is a target/intermediate rather than a solvent, greener strategies focus on how it is made and used.

• Greener synthesis considerations (literature):

  • Biocatalytic routes: Hydroxynitrile lyase (HNL)-catalyzed addition of a cyanide donor to p-bromobenzaldehyde can deliver enantioenriched product under mild, aqueous or biphasic conditions, reducing energy input and waste. Immobilized enzymes facilitate reuse.
  • Safer cyanation reagents: Consider reagent forms that mitigate free HCN exposure (e.g., acetone cyanohydrin with base under controlled conditions, or cyanation in flow). All cyanide sources are hazardous; engineer controls remain essential.
  • Solvent selection: Prefer bio-based or lower-toxicity solvents (2-MeTHF, CPME, EtOAc, propylene carbonate) over chlorinated solvents, where compatible with kinetics and selectivity.
  • Process intensification: Continuous-flow for cyanohydrin formation or nitrile hydrolysis can improve containment of volatile HCN and enhance heat/mass transfer.

• Comparison snapshot (general):

  • Conventional: THF/DCM batch processes; stoichiometric mineral acids/bases; cryogenic control for stereoselectivity.
  • Greener alternative: 2-MeTHF or EtOAc media; catalytic, aqueous-biphasic biocatalysis; flow addition with in-line pH and temperature control; minimized halogenated waste.

Trade-offs: Some green solvents may alter coupling or reduction rates; biocatalysts can have substrate scope limits. Conduct DoE screening to balance EHS benefits with performance.

Pharmaceutical Uses

• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.

• General, non-clinical context:

  • Role: Synthetic intermediate for medicinal chemistry. The aryl bromide enables rapid SAR diversification via cross-coupling; the nitrile/benzylic alcohol provides orthogonal points for further functionalization (e.g., amide/acid/amine, ester/silyl protection).
  • Formulation/excipient: Not used as an excipient to our knowledge; no pharmacopeial monograph known for this specific compound.
  • Process chemistry: Can be a branch point intermediate en route to para-substituted mandelic acids, phenylglycinols, and related scaffolds employed in API discovery programs. Handling controls are required due to cyanohydrin hydrolysis potential (HCN risk).

All uses are confined to research and process development contexts; no therapeutic or clinical claims are made.

Physical Properties

• Item-specific (from Product Data):
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general (for context; not item-specific specifications):
  • Approx. molecular formula: C8H6BrNO (see Structure & Identity)
  • Approx. formula mass: ~212.04 g/mol (calculated)
  • Physical state: typically a crystalline solid or viscous oil for aryl cyanohydrins depending on purity and temperature; para-bromo derivatives are commonly solids.
  • Solubility profile: low in water; soluble in common organic solvents (EtOAc, DCM, THF, MeCN, toluene, alcohols). Hydrolyzes slowly in aqueous media, especially under acidic or basic conditions.
  • Partitioning: expected to be moderately lipophilic due to the aryl bromide and nitrile with a polar OH; exact logP not widely reported.
  • Boiling/Melting points, density, refractive index: not broadly standardized in the literature for this exact derivative; consult primary references or CoA if required.

Practical note (general): As an alpha-hydroxynitrile, it may equilibrate with the corresponding aldehyde and HCN under certain conditions. Avoid prolonged heating or exposure to strong acid/base in aqueous media to minimize decomposition.

Quality and Grades

• Item-specific (from Product Data):

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizer/Additives: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance for this compound class (general):

  • Research grade material is commonly supplied for synthetic use. For stereosensitive applications, suppliers may offer racemic material or enantioenriched samples prepared via biocatalytic hydroxynitrile lyase (HNL) routes. If enantiopurity matters in your workflow, verify enantiomeric excess and absolute configuration on the CoA.
  • Typical quality attributes to review on receipt:
    • Identity confirmation (1H/13C NMR, IR – strong CN stretch ~2220–2260 cm−1; OH stretch; aromatic signals). HRMS for exact mass confirmation.
    • Purity by HPLC/GC and residual solvent profile.
    • Water content (Karl Fischer) and hydrolysis byproducts (p-bromobenzaldehyde/mandelic acid) where applicable.
  • Aryl bromides are sensitive to metal impurities in cross-coupling. If planning Pd-catalyzed coupling, low ppm of Pd/Cu/Fe in the starting material may be preferred; consult the CoA if metal content is reported.

Contact us for custom specifications (e.g., enantiopure material, metal content limits, or tailored solvent residuals).

Reaction and Applications

• Functional handles:

  • Aryl bromide suitable for cross-coupling diversification (Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig after conversion to an amine nucleophile elsewhere in the molecule, etc.).
  • Alpha-hydroxynitrile motif enabling conversion to carboxylic acids, amides, or primary amines while retaining/transforming the benzylic stereocenter.

• Typical applications (literature/good practice):

  • Hydrolysis: Conversion to p-bromomandelic acid (via nitrile hydration then hydrolysis) under acidic or basic conditions. Control conditions to avoid racemization if enantioenriched.
  • Reduction: Nitrile → primary amine to give 2-amino-2-(4-bromophenyl)ethanol using catalytic hydrogenation (Pd/C, Raney Ni) or metal hydrides (e.g., LAH). This delivers beta-amino alcohol building blocks.
  • Protection/derivatization: Convert the benzylic OH to an ester or silyl ether (e.g., TBS) to improve stability under basic cross-coupling conditions.
  • Cross-coupling at Ar–Br: Install aryl/alkenyl/alkynyl groups to access diversified alpha-hydroxynitriles; the nitrile and protected OH typically tolerate Pd catalysis with appropriate base and ligands.
  • Dehydrative or acylative modifications: Formation of cyanohydrin esters (e.g., acetate) for enhanced leaving group ability in subsequent substitutions.

• Use-case examples:

  • Route to substituted phenylglycinols via nitrile reduction followed by protecting group manipulations.
  • Synthesis of para-functionalized mandelic acid derivatives through coupling first, then nitrile hydrolysis.

Note: Due to cyanohydrin equilibrium, minimize exposure to strong acid/base and elevated temperature unless conversion is intended; conduct operations in a fume hood.

Reaction Conditions

General literature guidance (optimize per substrate and scale; observe cyanide safety):

• Suzuki–Miyaura coupling at Ar–Br:

  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3/XPhos (0.5–2 mol%).
  • Base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
  • Solvent: toluene/H2O, 1,4-dioxane/H2O, or 2-MeTHF/H2O; 70–100 °C, 2–12 h.
  • Note: Protect benzylic OH as TBS or acetate for strongly basic conditions to prevent side reactions.

• Sonogashira coupling:

  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%).
  • Base: Et3N, iPr2NH, or K2CO3.
  • Solvent: THF, MeCN, or 2-MeTHF; 25–70 °C.

• Nitrile reduction to primary amine:

  • Catalytic hydrogenation: H2 (10–50 bar), Pd/C or Raney Ni, EtOH or iPrOH, 25–60 °C, 4–24 h. Benzylic OH typically retained.
  • Hydride route: LiAlH4 (1.5–3 equiv) in THF/Et2O, 0–25 °C to reflux; careful quench.

• Hydrolysis to acid/amides:

  • Acidic: H2SO4 or HCl (aq), organic co-solvent (dioxane/MeCN), 0–50 °C for amide; higher T/reflux for acid. Control pH and venting to manage HCN.
  • Basic: NaOH or KOH in aqueous alcohols; lower temperatures preferred to preserve stereochemistry.

• Protection of OH:

  • TBSCl, imidazole, DMF, 0–25 °C; or Ac2O/pyridine, 0–25 °C.

Caution: Cyanohydrin cleavage can occur under strong acid/base or heat, releasing HCN. Use a fume hood, cyanide antidote kit availability per institutional policy, and appropriate gas scrubbing on scale.

Safety and Handling

• Item-specific hazard data (from Product Data):

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification/Pictograms: Not specified for this item; refer to SDS.

• General safety considerations for aryl cyanohydrins (literature/good practice):

  • Cyanohydrin functionality can liberate hydrogen cyanide (HCN) upon hydrolysis, especially in acidic or strongly basic aqueous environments and upon heating. Handle under well-ventilated conditions; avoid inhalation and skin contact.
  • Incompatibilities: strong acids, strong bases, aqueous media (accelerates decomposition), strong oxidizers, and reactive metals. Avoid contact with nitrile-hydrolyzing catalysts in the presence of water.
  • PPE: laboratory coat, nitrile gloves (change regularly), splash goggles. Use a fume hood for all operations, particularly when heating or when acid/base is present.
  • First aid (general):
    • Inhalation: move to fresh air; seek medical attention. If exposure to HCN is suspected, follow emergency response protocols.
    • Skin/eye contact: rinse with water for 15+ minutes; remove contaminated clothing; seek medical attention.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention immediately.
  • Fire safety: Combustible organic; use CO2, dry chemical, or foam. Thermal decomposition can produce toxic fumes including HBr, NOx, and HCN.

Always consult the product SDS for authoritative hazard classification and response measures for this specific item.

Solvent Selection

This is a solid/reactive intermediate rather than a solvent; selection here refers to solvents for dissolution and reactions.

• General polarity/compatibility (literature):

  • Miscibility: insoluble to sparingly soluble in water; readily soluble in polar aprotic and moderately polar organic solvents (MeCN, THF, DCM, EtOAc). Soluble in alcohols and aromatics (toluene) to varying extents.
  • Dielectric considerations: choose polar aprotics (MeCN, DMF, DMSO) for nucleophilic transformations (e.g., nitrile reduction or substitution after activation). Use less polar solvents (toluene, 2-MeTHF) for Pd-catalyzed cross-couplings on the aryl bromide.

• Practical choices by task:

  • Cross-coupling (Suzuki/Sonogashira): toluene, dioxane, or 2-MeTHF with aqueous base; or MeCN/EtOH/water mixtures. Ensure the benzylic OH is protected if base-sensitive.
  • Nitrile reduction (hydrogenation): EtOH, iPrOH, or MeOH under H2 with Pd/C or Raney Ni; or Et2O/THF for LiAlH4 reductions.
  • Hydrolysis to acid/amides: acetonitrile/water or dioxane/water with mineral acid or base; strictly control pH and temperature to minimize HCN release.

• Comparison note:

  • 2-MeTHF or CPME often substitute for THF/DCM with improved sustainability and phase behavior, while MeCN offers superior stability toward base and low viscosity for coupling workups.

Storage and Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for this compound class:

  • Storage: Keep tightly closed in a dry, well-ventilated place. Minimize exposure to moisture, acids, and bases to reduce cyanohydrin cleavage. For extended storage, an inert atmosphere (N2/Ar) and desiccation are prudent but not mandatory unless specified on CoA.
  • Container: Amber glass recommended to limit photolysis; use PTFE-lined caps.
  • Stability: Alpha-hydroxynitriles can slowly equilibrate to the parent aldehyde and HCN under unfavorable conditions. Monitor by NMR/LC for prolonged projects and retest before critical use.

• Reconstitution/solubility:

  • Readily dissolves in DCM, EtOAc, THF, MeCN, and alcohols. Prepare stock solutions fresh; store solutions at 2–8 °C if needed and use within a few days. Avoid aqueous solutions except for immediate use.

Always defer to the product’s CoA/SDS for lot-specific stability and handling recommendations.

Structure and Identity

Overview: 2-(4-Bromophenyl)-2-hydroxyacetonitrile is an aryl cyanohydrin (para-brominated mandelonitrile) featuring an aryl bromide, a tertiary carbinol (alpha-hydroxy), and a nitrile.

• Item-specific (from Product Data):
  • Product Name: 2-(4-Bromophenyl)-2-hydroxyacetonitrile (SKU: B1012227)
  • CAS: 58289-69-3
  • CID: 10560461
  • InChIKey: 18432 (as provided)
  • Storage Conditions: Room temperature
  • Research Use Note: For research use only
• Literature/computed (general reference; not item-specific specs):
  • Synonym: p-Bromomandelonitrile; 4-bromophenylglycolonitrile
  • Molecular formula (literature): C8H6BrNO
  • Molecular weight (literature, calculated): ~212.04 g/mol
  • SMILES (literature): N#CC(O)c1ccc(Br)cc1
  • Structural features:
    • Aromatic ring para-substituted with bromine
    • Alpha-hydroxynitrile: –C(OH)(CN)– attached to the aryl ring
    • One stereogenic center at the carbinol carbon (commercial material is typically racemic unless otherwise specified)
  • 2D structure description: A para-bromobenzene ring bearing at the para position a benzylic tertiary carbon bearing a hydroxyl group and a nitrile (–C≡N). The hydroxyl and nitrile are geminal on the benzylic carbon.

Note: Where exact identifiers (e.g., definitive InChIKey for this lot) are required, consult the CoA/Spec Sheet.

Synthetic Utility

• Retrosynthetic value:

  • Disconnection at the benzylic center maps to p-bromobenzaldehyde + cyanide donor (chemical or biocatalytic) → target cyanohydrin. This provides a late-stage aryl diversification handle (Ar–Br) orthogonal to CN/OH chemistry.

• Transformations (literature):

  • Nitrile → acid/amide: Acidic or basic hydrolysis furnishes p-bromomandelic acid or amide derivatives; conditions can be tuned for partial hydration (amide) vs full hydrolysis (acid). Maintain low temperature for stereochemical integrity if chiral.
  • Nitrile → amine: LAH or catalytic hydrogenation affords 2-amino-2-(4-bromophenyl)ethanol (beta-amino alcohol), useful for ligand or chiral auxiliary development.
  • Benzylic OH manipulations: Protection (TBS, TBDPS, acetyl) to withstand basic cross-coupling; activation (mesylate/tosylate) to enable substitution or intramolecular cyclizations.
  • Aryl bromide cross-coupling: Suzuki–Miyaura to diversify aryl/heteroaryl; Sonogashira to introduce alkynes; Heck to append alkenes. The CN and protected OH are generally tolerated with appropriate ligands/bases.
  • Oxidation/rearrangements: Selective oxidation of the benzylic alcohol to the corresponding cyanoketone is less common but may be accessed with mild oxidants; care required to avoid cyanide loss.

• Strategy tips:

  • Sequence planning: Perform Pd-catalyzed coupling prior to nitrile hydrolysis/reduction to minimize functional group incompatibilities.
  • Protect the OH for strong-base conditions; avoid high-temperature aqueous media to suppress cyanohydrin cleavage.

Target Specificity

Not applicable. This product is a small-molecule chemical intermediate and has no antibody/biological target specificity. No antigen/epitope, clone, isotype, or species reactivity data apply.