3-Bromophenyl acetate - ≥98% , CAS No.35065-86-2

CAS: 35065-86-2 Cat. No.: B303510 Formula: C₈H₇BrO₂ Molecular Weight: 215.04

GRADE & PURITY ≥98%

Synonyms

Phenol, 3-bromo-, acetate | (3-bromophenyl) acetate | DTXSID80188572 | AKOS016003532 | AM83209 | MFCD08063242 | A6152 | Acetic acid 3-bromophenyl ester | DS-15873 | 3-BROMO-PHENYL ACETATE | SCHEMBL498839 | SY113498 | 3-Bromophenyl acetate # | FT-0660662 |

Storage

Room temperature,Desiccated

Shipped In

Normal

Specifications

Synonyms

Phenol, 3-bromo-, acetate | (3-bromophenyl) acetate | DTXSID80188572 | AKOS016003532 | AM83209 | MFCD08063242 | A6152 | Acetic acid 3-bromophenyl ester | DS-15873 | 3-BROMO-PHENYL ACETATE | SCHEMBL498839 | SY113498 | 3-Bromophenyl acetate # | FT-0660662 |

Specifications & Purity

≥98%

Storage

Room temperature,Desiccated

Shipped In

Normal

Purity

≥98%

Names and Identifiers

Pubchem Sid

488188127

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488188127

Canonical Smiles

CC(=O)OC1=CC(=CC=C1)Br

IUPAC Name

(3-bromophenyl) acetate

InChIKey

CDLTWXBTYNNYLN-UHFFFAOYSA-N

INCHI

1S/C8H7BrO2/c1-6(10)11-8-4-2-3-7(9)5-8/h2-5H,1H3

Isomeric SMILES

CC(=O)OC1=CC(=CC=C1)Br

Molecular Weight

215.04

Reaxy-Rn

2439294

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2439294&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenol esters

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenol esters
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol esters
• Alternative Parents: Phenoxy compounds Bromobenzenes Aryl bromides Carboxylic acid esters Monocarboxylic acids and derivatives Organobromides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenol ester - Phenoxy compound - Bromobenzene - Halobenzene - Aryl bromide - Monocyclic benzene moiety - Aryl halide - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organooxygen compound - Organobromide - Organohalogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Boil Point(°C): 254.9°C
• Molecular Weight: 215.040 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 213.963 Da
• Monoisotopic Mass: 213.963 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 147.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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. No bioassay or immunoassay protocols are defined for this small-molecule reagent. For synthetic applications, see Reaction Conditions and Synthetic Utility sections for representative setups.

Biological Roles

This compound is a synthetic aromatic building block and does not have an established biological role.

• General information (contextual, not item-specific):
  • Aryl acetates can hydrolyze to phenols and acetic acid under enzymatic or chemical conditions, but 3-bromophenyl acetate is not a natural metabolite and is intended for laboratory synthesis only.
  • No known participation in metabolic pathways or signaling processes is documented for this specific structure in normal physiology.

Research Use Note: For research use only.

Buffer Applications

Not typically applicable. 3-Bromophenyl acetate is a neutral, poorly water-soluble organic building block and is not used to formulate aqueous buffers. For aqueous-phase work involving this molecule, use a biphasic system or dissolve in an appropriate organic co-solvent before introducing to water-based media.

Green Alternatives

Greenness considerations focus on solvent and process choices; the reagent itself is a specialized building block typically not replaced one-for-one.

• Preferable solvent choices (compared with common but less green options):

  Comparison (general; literature):

  • Solvent: 2-MeTHF — Pros: biorenewable, lower toxicity vs THF, good for Pd couplings; Cons: peroxide formation risk (manage), slightly different solubility profile.
  • Solvent: Ethyl acetate — Pros: relatively benign, readily biodegradable, excellent for workups and some couplings; Cons: limited high-temperature range; can participate in transesterification under strong base.
  • Solvent: CPME — Pros: low peroxide formation tendency vs Et2O/THF, broad liquid range; Cons: supply/cost; odor.
  • Solvent to minimize: DMF, NMP — Concerns: reproductive toxicity, difficult removal; use only when necessary and ensure controls.
  • Chlorinated solvents (DCM/CHCl3) — Minimize when feasible; substitute with EtOAc or 2-MeTHF for extractions and reactions.

• Process intensification:

  • Micellar catalysis (aqueous surfactant media) has enabled some Suzuki couplings of aryl bromides at room temperature, reducing organic solvent use; assess compatibility with the ester functionality.
  • Use ligand/catalyst systems active at lower loadings and milder temperatures (reduces energy and waste).

• Waste minimization:

  • Plan orthogonal sequence: perform cross-coupling first, then a single global deprotection step to minimize protection/deprotection cycles.

Pharmaceutical Uses

No excipient role is established for this compound. It is best viewed as a synthetic intermediate for discovery chemistry.

• Context (general):
  • Aryl bromides with masked phenols are common in medicinal chemistry routes to enable cross-coupling diversification followed by phenol unveiling for SAR exploration.
  • If used in GMP settings, specifications would need to define identity, purity, residual solvents, and stability indicative of ester integrity; for this catalog item, such specifications are not provided here (refer to CoA/Spec Sheet).

No therapeutic claims are made; for research and manufacturing development use only.

Physical Properties

• Item-specific physical properties from Product Data:

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Physical constants (bp, mp, density, refractive index, solubility, UV cutoff, water/peroxide/metal limits): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed reference (not item specifications):

  • Formula: C8H7BrO2 (literature)
  • Molecular weight: ~214.94 g/mol (literature)
  • Expected phase/solubility: Neutral aryl ester; typically low polarity; generally miscible with common organic solvents (e.g., dichloromethane, ethyl acetate, THF, toluene) and poorly soluble in water (general chemical knowledge for aryl acetates).
  • Acidity/basicity: Non-basic, non-acidic; hydrolyzable ester functionality (general).

• Practical implications (general):

  • Moisture can promote slow hydrolysis to 3-bromophenol and acetic acid; keep dry to maintain purity.
  • Avoid prolonged heating in the presence of base or acid if ester integrity must be preserved.

For authoritative values for this specific lot, consult the CoA/SDS.

Quality & Grades

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

• General notes on quality for aryl ester building blocks (informational):

  • Purity considerations: For cross-coupling workflows, low halide impurities and minimal hydrolysis (phenol) content help ensure reproducible reactivity. Monitor by GC/GC–MS or HPLC.
  • Water content: Low moisture is preferred to minimize ester hydrolysis during storage; Karl Fischer values are typically reported on the CoA when relevant. For this item: Not specified; refer to CoA/Spec Sheet.
  • Stabilizers: Aryl acetates generally do not require stabilizers; avoid basic contaminants that could catalyze transesterification/hydrolysis.
  • Chromatographic suitability: If using in purity-critical applications, consider a specification with defined assay by GC/HPLC and UV profile. For this item: Not specified; refer to CoA/Spec Sheet.

Interpret any certificate designations (AR, HPLC, etc.) on your specific lot’s documentation; absent such, treat as a general research-grade building block.

Reaction & Applications

3-Bromophenyl acetate serves as a bifunctional building block combining an aryl bromide (cross-coupling handle) with a masked phenol (acetate protecting group).

• Cross-coupling via the aryl bromide (literature):

  • Suzuki–Miyaura: couples with boronic acids/esters to form biaryls; catalysts such as Pd(PPh3)4 or Buchwald-type ligated systems; bases like K2CO3, K3PO4, Cs2CO3 in aqueous/organic mixtures (e.g., dioxane/H2O).
  • Sonogashira: coupling with terminal alkynes using Pd/Cu co-catalysis; amine or carbonate bases; solvent such as THF, Et3N, or DMF.
  • Buchwald–Hartwig amination: aryl–N bond formation using Pd precatalysts and appropriate ligands; base (NaOtBu, Cs2CO3) and elevated temperature.
  • Heck arylation: vinylation of alkenes under Pd catalysis.

• Orthogonal manipulation of the acetate (literature):

  • Deprotection to 3-bromophenol under basic hydrolysis (e.g., K2CO3/MeOH, NaOH/H2O–THF) or acid (HCl/MeOH) to reveal the phenolic OH for subsequent etherification, carbonate formation, or further acylations.
  • Transesterification to alternative esters (ROH, catalytic acid/base).

• Strategy notes:

  • The acetate can suppress phenol coordination during metal-catalyzed couplings, often improving catalyst performance and selectivity; deprotect after coupling.
  • Meta-bromo substitution offers access to m-functionalized phenol derivatives difficult to obtain otherwise.

• Practical tips:

  • Maintain dry conditions to prevent unintended hydrolysis during storage/reaction setup.
  • For couplings, degas solvents, and consider using modern air-stable Pd precatalysts to improve reproducibility.

Reaction Conditions

General literature guidance (not item specifications):

• Suzuki–Miyaura coupling on aryl bromide:

  • Catalyst: 1–5 mol% Pd(PPh3)4 or Pd2(dba)3 with SPhos/XPhos.
  • Base: K3PO4, K2CO3, or Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (3:1) or 2-MeTHF/H2O; 60–100 °C; 2–16 h.
  • Notes: Maintain some water for boron activation; acetate group typically survives.

• Buchwald–Hartwig amination:

  • Catalyst: 1–3 mol% Pd-precatalyst (e.g., Pd-PEPPSI, Pd2(dba)3 + BrettPhos).
  • Base: NaOtBu or Cs2CO3; Solvent: toluene, t-AmylOH, or dioxane; 80–120 °C.
  • Watch for ester stability with strong alkoxides; milder bases (K3PO4) can work with more active ligands.

• Sonogashira coupling:

  • Catalyst: Pd(PPh3)2Cl2 (1–3 mol%) + CuI (2–5 mol%).
  • Base/solvent: Et3N or i-Pr2NH in THF/MeCN; 25–80 °C.
  • Copper-free protocols available to minimize Glaser byproducts.

• Ester deprotection (to 3-bromophenol):

  • Basic: K2CO3 or Na2CO3 in MeOH/THF/H2O at rt–50 °C, 1–6 h.
  • Acidic: HCl/MeOH or catalytic TsOH in MeOH, rt–reflux.
  • Workup: neutralize, extract with EtOAc, dry, and concentrate; monitor by TLC/LC–MS.

• Transesterification:

  • ROH (3–10 equiv), catalytic acid (p-TsOH) or base (NaOMe), 0–60 °C; remove byproduct MeOH/AcOH as needed to drive equilibrium.

Optimize conditions per substrate and scale; monitor ester integrity when using strong bases/heating.

Safety & 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 guidance for aryl bromide esters (literature/general):

  • Likely to cause irritation to skin/eyes/respiratory tract upon contact; handle in a fume hood.
  • PPE: lab coat, safety glasses or splash goggles, appropriate chemical-resistant gloves (e.g., nitrile). Avoid inhalation and skin contact.
  • First aid (overview): Remove to fresh air if inhaled; rinse eyes cautiously with water for several minutes if contacted; wash skin with soap and water; seek medical attention if symptoms persist. Refer to SDS for detailed instructions.
  • Incompatibilities: Strong bases and strong acids accelerate ester cleavage; strong oxidizers may react with the aromatic moiety; avoid moisture to prevent hydrolysis.
  • Fire safety: Organic combustible; use CO2, dry chemical, or foam extinguishers. Combustion may release HBr and other irritating fumes; self-contained breathing apparatus recommended for large fires.

Always consult the product-specific SDS for definitive hazard, exposure limits, and spill/cleanup procedures.

Solvent Selection

Applicability: As a neutral, hydrophobic aryl ester, 3-bromophenyl acetate is soluble in many organic media and poorly soluble in water.

• Polarity/miscibility (general):

  • Expected to dissolve well in moderately polar aprotic solvents (THF, acetone, acetonitrile, DMF, DMSO) and nonpolar/aromatic solvents (toluene, chlorobenzenes) as well as chlorinated solvents (DCM, chloroform). Limited aqueous solubility.

• Typical use scenarios:

  • Cross-coupling on the aryl bromide: Often toluene/THF/dioxane/MeCN with water or alcohol co-solvents depending on boron/organometallic partner.
  • Ester manipulations (hydrolysis/transesterification): Alcoholic solvents (MeOH/EtOH/i-PrOH) with acid/base catalysts; or biphasic aqueous base with an organic phase (THF, DCM, MTBE) for extraction.

• When to choose alternatives:

  • If solubility limits coupling rate, move to more polar media (DMF/DMAc/DMSO) or raise temperature in high-boiling solvents (dioxane, toluene).
  • For greener profiles, prefer EtOAc or 2-MeTHF over DCM/DMF where feasible.

• Quick comparison (general):

  • Toluene: good for Pd couplings at elevated temperature; low polarity.
  • 1,4-Dioxane/2-MeTHF: balanced polarity; good for Suzuki/Heck with aqueous base; 2-MeTHF is greener.
  • DMF/DMSO: high solvating power but more challenging workups and EHS considerations.

Storage & Reconstitution

• Storage conditions (item-specific from Product Data):

  • Store at room temperature, desiccated (dry conditions).
  • Shipped: Normal (ambient).

• Practical storage guidance (general):

  • Keep tightly sealed under inert gas if possible to minimize moisture ingress and hydrolysis of the acetate.
  • Store away from strong acids/bases and oxidants. Protect from prolonged exposure to humidity and heat.
  • For long-term storage, consider amber glass to limit light exposure, though light sensitivity is not typically severe for aryl acetates.

• Reconstitution/handling:

  • Solid/liquid state and specific solvent recommendations: Not specified for this item; refer to CoA/Spec Sheet. In general, dissolve in dry organic solvents (e.g., DCM, THF, EtOAc, toluene, MeCN) immediately before use.
  • After opening, recap promptly in a dry environment; if frequent access is needed, aliquot under dry conditions to minimize repeated moisture exposure.

• Stability: Ester moiety can hydrolyze under moist or acidic/basic conditions; monitor by TLC/GC/LC for any increase in 3-bromophenol content over time.

Structure & Identity

Brief: 3-Bromophenyl acetate is the acetate ester of 3-bromophenol; an aryl bromide bearing a phenoxy acetate protecting group.

• Item-specific identifiers from Product Data:

  • CAS: 35065-86-2
  • SKU: B303510
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: 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 identity (for reference only; not item specifications):

  • Typical molecular formula: C8H7BrO2 (literature)
  • Typical molecular weight: ~214.94 g/mol (average mass, literature)
  • Common structure description: A benzene ring substituted with bromine at the meta (3-) position relative to a phenoxy acetate group. The phenolic oxygen is acetylated (–O–C(=O)–CH3), giving an aryl ester. Functional groups: aryl bromide (C–Br), aryl ester (Ar–O–C(=O)–R). No stereocenters.

• Structural features (general):

  • Aromatic ring enabling electrophilic substitution (deactivated by –OAc meta director and –Br).
  • Aryl bromide suitable for Pd-catalyzed cross-couplings (Suzuki–Miyaura, Sonogashira, Heck, etc.).
  • Acetate is a common protecting group for phenols; removable under acidic or basic conditions.

Synthetic Utility

• Functional group handles:

  • Aryl bromide: versatile for Pd-catalyzed cross-couplings (Suzuki, Sonogashira, Heck, Stille, Negishi) and for lithium–halogen exchange under controlled low temperatures (followed by electrophile trapping), though ester sensitivity must be considered.
  • Phenol protected as acetate: enables sequences where the free phenol would otherwise poison catalysts or undergo side reactions; acetate can be exchanged or removed orthogonally.

• Strategic applications (literature/general):

  • Build meta-substituted phenol frameworks by first installing new C–C/C–N/C–O bonds via the bromide position, then deprotect to reveal the phenolic OH for further diversification (etherification, carbonate/urethane formation).
  • Late-stage diversification: The acetate increases stability and reduces polarity, improving handling and chromatographic behavior relative to the free phenol.

• Compatibility notes:

  • Avoid strong bases/nucleophiles that can attack the ester during metalations; if halogen–lithium exchange is attempted, use very low temperatures (≤ −78 °C) and quench rapidly with electrophiles to minimize ester cleavage.
  • In Pd catalysis, ligands that tolerate phenoxy acetates (e.g., dialkylbiaryl phosphines) perform well; acetate is generally compatible with Suzuki/Heck but verify for amination conditions using strong alkoxides.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent (no antigen/epitope/clone/isotype characteristics).