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
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
264.540 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Exact Mass
262.971 Da
Monoisotopic Mass
262.971 Da
Topological Polar Surface Area
33.100 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
153.000
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
2
Calculadoras de soluciones
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Reseñas
Reseñas de cliente
Application Protocols
No assay or bioanalytical application protocols are specified for this item. As a general synthetic reagent:
Weigh and transfer under dry conditions (brief glovebox/glovebag handling or rapid bench transfer recommended).
For amidination: Dissolve in dry MeCN or EtOH, add base (Et3N/DIPEA), then introduce the amine nucleophile at 0–25 °C; monitor by LC-MS.
Quench with dilute base, extract, and purify by standard techniques (flash chromatography on neutral/alumina or reverse phase for polar amidines).
These steps are generalized literature practices and are not validated methods for this specific lot. Optimize for your substrates and consult the CoA/SDS for constraints.
Biological Roles
This product is a synthetic organic reagent used in chemical synthesis. It does not have a recognized intrinsic biological role or metabolic function.
No endogenous role: Aryl imidate hydrochlorides are not metabolites or cofactors in known biological pathways.
Research relevance: They serve as precursors to amidines, amides, and heterocycles that may be evaluated as probes or materials in chemical biology campaigns; however, any biological activity would pertain to downstream molecules, not the imidate salt itself.
For biological testing or cellular work, ensure removal of residual HCl and confirm purity of final products. This item is supplied strictly for research use only (per Product Data).
Buffer Applications
Not typically applicable. Ethyl 4-bromobenzimidate hydrochloride is not a buffering agent and is not used to prepare biochemical buffers or electrophoresis systems. For practical handling in aqueous media, see Reaction & Applications and Solvent Selection for guidance on solvent systems and moisture sensitivity.
Green Alternatives
While this product is a reagent (not a solvent), greener practice focuses on solvent choice, atom economy, and process safety during its use.
Prefer ethanol (bio-based) or 2-MeTHF over chlorinated solvents (DCM, DCE) when feasible; MeCN can be a reasonable compromise with good performance and lower volatility than DCM.
Comparison (general):
Ethanol: Renewable, low toxicity, good solubility for salts; may participate in transesterification under harsh conditions.
2-MeTHF: Greener ether, immiscible with water aiding workups; solubility of salts may be limited—co-solvent often required.
MeCN: Effective polar aprotic; petrochemical origin and toxicity require controls but often enables lower temperatures and shorter times.
DCM/DCE: Effective but higher environmental and health burdens; reserve for cases requiring their unique performance.
Reagent/route alternatives:
Direct amidination of nitriles via catalytic systems can bypass isolated imidates, reducing steps (literature strategy).
Use of polymer-supported bases for HCl scavenging minimizes neutralization waste.
Telescoping amidine formation with subsequent cross-coupling reduces solvent and handling steps.
Operational tips:
Right-first-time stoichiometry reduces quench salt waste.
Recover and recycle MeCN or EtOH via distillation when scale permits.
Implement in-process water control to prevent premature hydrolysis and rework.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. As a reactive intermediate, ethyl 4-bromobenzimidate hydrochloride may be used in research-scale synthesis of candidate molecules (e.g., introducing amidine motifs or enabling heterocycle formation), but it is not intended for drug product formulation or clinical use.
Regulatory note: Not GMP-qualified; for research use only (per Product Data).
Process chemistry context (general): When used upstream in API intermediate synthesis, ensure thorough purge of inorganic chloride and residual imidate by validated workups and controls.
Typical documentation: Rely on CoA/SDS for quality and safety information; develop internal specifications (purity, residual solvents, water) as needed for process development.
Physical Properties
Item-specific physical specifications are not provided in the Product Data. The following are general/literature expectations for aryl imidate hydrochlorides and are NOT specifications for this lot.
Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Many imidate HCl salts are crystalline solids; literature comment.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Aryl imidate HCl salts often melt/decompose over a range; literature.)
Boiling point: Not applicable for salts (decompose before boiling at 1 atm; literature generalization).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature/general):
• Readily soluble in polar protic solvents (methanol, ethanol) due to salt character.
• Soluble to moderately soluble in polar aprotic solvents (acetonitrile, DMF, DMSO).
• Low solubility expected in nonpolar hydrocarbons.
These are general trends; verify experimentally for your system.
pKa (literature context): Protonated imidate nitrogen is strongly basic in its free base form; the HCl salt reflects protonation. Exact pKa for this specific structure is not established here.
LogP: Not established. Aromatic bromide increases lipophilicity, while salt form increases hydrophilicity; net partitioning is medium-dependent (literature rationale).
Refractive index: Not applicable (solid); not specified.
Always verify key properties (mp, solubility in intended solvent system) on small scale before process use.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. Without a declared grade (e.g., AR, technical, 95%, 98%), users should confirm suitability for purpose via incoming QC.
Guidance for interpreting typical grades (general):
Research grade: Suitable for most synthetic applications. Impurity profile may include residual alcohol, chloride, or starting nitrile. Verify by NMR/LC-MS.
≥98% (if specified on CoA): Suitable for structure–activity or library synthesis where impurity carryover must be minimized.
HPLC grade (solvents) is not applicable; this is a solid reagent.
Stabilizers/additives:
Not specified for this item; refer to CoA/Spec Sheet. Imidate HCl salts are usually supplied neat without stabilizers.
Release testing recommendations (user QC):
Identity: 1H/13C NMR in d6-DMSO or CD3OD (look for imidate NH2+ resonances and ethoxy signals), HRMS (M+ for free base; isotope pattern for Br), ATR-IR (C=N stretch).
Purity: HPLC or UPLC with ELSD/UV at multiple wavelengths; assess for residual nitrile or amide byproducts.
Water/volatiles: Karl Fischer and TGA if process sensitivity to moisture exists (not specified for this item).
Always rely on the item’s CoA/Spec Sheet for definitive quality attributes.
Reaction and Applications
Ethyl 4-bromobenzimidate hydrochloride is a versatile electrophile for constructing nitrogen-containing motifs from a para-brominated aryl platform. Key application families (literature/general):
Amidines via Pinner sequence: Reaction with primary or secondary amines (often in MeOH/EtOH or MeCN) in the presence of a base (Et3N, DIPEA) affords aryl amidines. The HCl counterion is neutralized in situ. Electron-withdrawing p-bromo can modestly influence rates and facilitate downstream cross-coupling.
Amides and esters by hydrolysis/alcoholysis: Controlled aqueous workup can deliver the corresponding amide; alcoholysis under acidic conditions can generate esters (interconversion routes known for imidates). Avoid excess water when the imidate must be preserved.
Heterocycle synthesis: Amidines from this imidate can cyclize to benzimidazoles, imidazolines, or dihydroimidazoles with appropriate linkers (literature precedents). The p-bromo handle supports later diversification.
Cross-coupling after functionalization: The aryl bromide tolerates many imidate/amine couplings under mild conditions; subsequent Suzuki, Buchwald–Hartwig, or Sonogashira chemistry can elaborate the aryl core.
Practical tips:
Use dry conditions and a slight excess of amine to drive amidine formation; include a base to bind HCl for cleaner profiles.
Monitor by LC-MS; the bromine isotope pattern (M/M+2 ~1:1) aids tracking.
If base-sensitive substrates are present, premix with hindered base before adding the imidate salt to moderate acidity.
For telescoped sequences, perform the amidine formation in MeCN and switch to coupling solvent without isolation, if compatible.
All conditions above are literature-type guidance; optimize for your substrate set.
Reaction Conditions
The following conditions are general literature guidance for imidate hydrochlorides and should be optimized for each substrate.
Amidination (amine coupling):
• Reagents: Amine (1.2–2.0 equiv), Et3N or DIPEA (1.5–2.5 equiv) as HCl scavenger.
• Solvent: MeCN, MeOH, or EtOH (0.05–0.2 M).
• Temperature/time: 0–25 °C, 1–16 h; warming to 40–60 °C can accelerate stubborn cases.
• Monitoring: LC-MS; look for loss of ethoxy imidate resonances and formation of amidine (characteristic downfield N–H signals).
• Typical outcome: Clean conversion with minimal hydrolysis under dry conditions; isolate as free base or acid salt as needed.
Hydrolysis to amide (if desired):
• Reagents: Aqueous buffer or dilute acid/base; carefully controlled water equivalents.
• Solvent: MeCN/H2O or alcohol/H2O mixtures.
• Temperature: 20–60 °C; avoid strong base if aryl bromide is to be retained intact.
Post-functionalization (Suzuki on aryl bromide):
• Catalyst: Pd(PPh3)4 (1–3 mol%) or modern Buchwald precatalysts.
• Base: K2CO3 or K3PO4 (2–3 equiv).
• Solvent: 1,4-dioxane/H2O, EtOH/H2O, or toluene/H2O; 60–90 °C.
• Note: If the amidine remains cationic, choose conditions tolerant of salts or convert to a neutral derivative first.
Workup tips: Salt-rich mixtures benefit from biphasic quenches (sat. NaHCO3 or NaCl). For MeOH/EtOH systems, evaporate solvent under reduced pressure, then partition between water and EtOAc.
All numerical ranges are literature-type guidance only.
Safety and Handling
Hazard classifications are not specified in the Product Data for this item. The following are general safety considerations for aryl imidate hydrochlorides; consult the product SDS for authoritative information.
GHS classification, pictograms, signal word, and H-statements: Not specified for this item; refer to SDS.
Likely hazards (general): Irritation to skin, eyes, and respiratory tract; hydrochloride salts may liberate HCl upon contact with strong bases or moisture. Avoid inhalation of dusts.
PPE: Use lab coat, safety glasses or face shield, and appropriate gloves (e.g., nitrile). Handle in a chemical fume hood to avoid inhalation exposure.
Handling notes:
• Hygroscopicity: Imidate HCl salts can be moisture sensitive; minimize atmospheric exposure.
• Avoid strong bases and nucleophiles during storage; these can deprotonate and/or react with the imidate.
• Avoid strong oxidizers as with most organic salts.
First aid (overview; follow institutional SOPs):
• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: Rinse with water for 15 minutes; remove contaminated clothing; seek medical attention if irritation develops.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill/cleanup: Avoid dust generation; collect with inert absorbent and place in suitable container for disposal. Neutralize/clean with compatible solvent while controlling for moisture.
Fire: Use CO2, dry chemical, or foam. Combustion may release HCl, NOx, HBr, and aromatic bromide fragments (general expectation).
Always defer to the vendor SDS and institutional risk assessments.
Solvent Selection
This product is a solid electrophilic reagent rather than a process solvent. Solvent selection refers to dissolving it for reactions or handling.
General solubility/miscibility expectations (literature):
Moderate: dichloromethane, ethyl acetate (variable, watch for alcoholysis/basic impurities).
Poor: alkanes and other nonpolar media.
Selection guidance:
Nucleophilic substitution to form amidines: Use alcohol solvents (MeOH, EtOH) or polar aprotics (MeCN) with a base scavenger (e.g., Et3N) to neutralize HCl and solubilize amine partners.
Base-sensitive substrates: Prefer milder bases (DIPEA) and polar aprotics (MeCN, DCE) to limit competitive hydrolysis.
Moisture control: Dry solvents to suppress hydrolysis to amides or esters.
Workup-friendly choices: EtOH/MeOH often simplify handling; MeCN can improve rate and selectivity with less transesterification than ROH in some systems.
Small comparison (literature-based):
EtOH vs MeCN: EtOH offers higher solubility but can engage in exchange (ethoxy group) under strongly acidic/basic conditions; MeCN lowers nucleophilicity of medium, often improving chemoselectivity.
DMF/DMSO: Excellent solubilizers for polar partners; consider difficult removal and potential side reactions at higher temperatures.
Always verify solubility and stability of the imidate under your selected conditions on small scale.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Best practices (general for imidate HCl salts):
Keep tightly closed in original container with desiccant; limit exposure to ambient humidity to prevent hydrolysis.
Store away from strong bases and nucleophiles.
If long-term storage is anticipated, consider secondary containment and low-humidity cabinet; avoid freeze–thaw cycling of any prepared solutions.
Reconstitution/solution preparation:
Solvents: Dry MeCN, EtOH, MeOH, DMF, or DMSO are commonly suitable (literature). Begin with 10–50 mg/mL test concentrations to confirm solubility.
Procedure: Allow container to equilibrate to room temperature before opening; quickly weigh required amount; dissolve in pre-dried solvent under inert atmosphere if feasible.
Filtration: For reaction solutions, a brief PTFE syringe filtration (0.2–0.45 µm) can remove particulates.
Solution stability: Imidate solutions are moisture sensitive; prepare fresh or store short-term at 2–8 °C in sealed vials with desiccant. Validate stability empirically for your solvent system.
Disposal: Collect waste containing residual HCl and organic bromides according to institutional and regulatory requirements.
Research Use Note: For research use only (per Product Data).
Structure and Identity
Ethyl 4-bromobenzimidate hydrochloride is an aryl imidate salt derived from p-bromobenzonitrile (Pinner-type imidate). The cation contains an imidate functionality Ar–C(=NH2+)–OEt paired with chloride.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Note: A typical literature formula for the salt is often reported as C9H11BrClNO (literature, for reference only).
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Note: A typical calculated FW for C9H11BrClNO is ~264.5 g/mol (literature/computed, non-specification).
Structural features (descriptive):
Aromatic ring: monosubstituted benzene bearing a para-bromine.
Functional group: imidate (imidic ester) cation, ethoxy-substituted; protonation on the imidate nitrogen in the HCl salt.
Connectivity (2D): p-bromophenyl–C(=NH2+)–O–CH2–CH3 with Cl− counterion; no stereocenters.
Notes:
The imidate salt is typically generated via Pinner reaction of the corresponding nitrile with gaseous HCl in ethanol (literature context). This item is supplied as the isolated hydrochloride salt for use as a bench-stable electrophilic imidate reagent.
Item-specific identifiers beyond those listed above are not specified; consult the CoA/SDS for definitive structural identifiers and testing data.
Synthetic Utility
Key reactivity stems from two orthogonal features: (1) the electrophilic imidate carbon and (2) the para-bromo handle on the aryl ring.
Electrophilic imidate carbon:
• Amidination: Nucleophilic amines add to give amidines (Pinner-type amidine synthesis).
• Hydrolysis/alcoholysis: Controlled conversion to amides or esters; potential for interchange of the alkoxy group under acidic conditions.
• N- vs O-acylation selectivity: Reaction conditions (solvent, base, temperature) influence chemoselectivity toward desired amidines versus side hydrolysis.
Aryl bromide as a synthetic linchpin:
• Cross-coupling: Suzuki–Miyaura (aryl–B(OH)2), Buchwald–Hartwig (amines), and Sonogashira (alkynes) on the p-bromo site enable rapid scaffold diversification post-amidination.
• Metalation pathways: Directed lithium–halogen exchange is generally incompatible with the imidate salt; perform after conversion to a more robust functionality or protect as needed.
Retrosynthetic value: The imidate encodes the benzonitrile oxidation state but in a form primed for N-nucleophile installation. Compared to acyl chlorides, imidates often give higher selectivity for amidines and offer milder conditions with fewer over-acylation issues.
Practical notes:
Use non-nucleophilic bases (Et3N, DIPEA) to neutralize HCl without competing reactions.
Sequence planning: Construct the amidine or heterocycle first, then engage the aryl bromide in Pd-catalyzed couplings to minimize catalyst poisoning by salts.
Target Specificity
Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme, or biological ligand with defined target specificity. No antigen/epitope, species reactivity, clone, or isotype information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
