Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
233.040 g/mol
XLogP3
0.400
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
231.965 Da
Monoisotopic Mass
231.965 Da
Topological Polar Surface Area
55.100 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
179.000
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
Lösungsrechner
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Application Protocols
No validated bioassay or immunoassay protocols are provided for this chemical building block.
For synthetic applications, see the “Reaction Conditions” tab for representative literature-style conditions for hydrazone formation, cross-coupling at the aryl bromide, and Curtius rearrangement sequences.
For bioconjugation-style hydrazone formation (general guidance):
Prepare a 100–500 mM DMSO stock of 2-bromo-4-fluorobenzohydrazide.
Dilute into acetate buffer (100 mM, pH 5.0) to achieve 0.5–5 mM final concentration with ≤5% DMSO.
Add aldehyde-bearing partner (1–2 eq), incubate at room temperature to 37 °C for 1–4 h; optional aniline catalysis (10–50 mM) can accelerate hydrazone formation (literature practice).
Purify by spin filtration or preparative chromatography as needed.
These are generic, literature-style suggestions and are not item-specific validated protocols. Optimize for your substrates and analytical endpoints.
Biological Roles
From Product Data: Research Use Note: For research use only.
Applicability:
This compound is a synthetic small-molecule building block without an established endogenous biological role.
General biochemical context (literature/general):
Hydrazide functionality is widely used to conjugate to biomolecules bearing aldehydes (e.g., oxidized glycans on glycoproteins) forming hydrazone linkages. Such reactions are commonly performed near neutral to mildly acidic pH and can be leveraged for bioconjugation, immobilization, or labeling strategies.
The aryl bromide/fluoride substituents are not biological motifs but can modulate physicochemical properties (lipophilicity, electron density) in medicinal chemistry campaigns when this building block is elaborated into larger molecules.
Cautions:
No claims are made for biological activity, pharmacology, or clinical utility of this item. Any use with biological samples should be performed strictly in vitro and under appropriate biosafety and chemical safety protocols.
Practical note:
For bioconjugation-style experiments, solubilize in DMSO to create a stock, then dilute into buffered media (pH 4.5–6 for efficient hydrazone formation) while keeping the final DMSO content low to maintain biomolecule integrity.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare buffer systems.
When relevant to hydrazone formation with biomolecules, acetate or citrate buffers in the pH 4.5–6.0 range are commonly employed (literature/general). For such applications, the choice of buffer, ionic strength, and cosolvent (e.g., ≤10% DMSO or 10–30% EtOH) can significantly influence reaction rate and selectivity.
For synthetic workflows, standard inorganic bases (K2CO3, K3PO4) in aqueous/organic mixtures may be used for cross-coupling at the aryl bromide, but these are reaction media rather than true buffer applications.
If a specific buffer recipe is required for your protocol, consult methodological literature; no item-specific buffer guidance is provided for this product.
Green Alternatives
While the compound itself is a specific synthetic intermediate, greener choices can be made in the processes employing it.
Less green: DMF/DMSO (use only as cosolvents to minimize EHS footprint).
Cross-coupling:
Greener: 2-MeTHF, aqueous micellar media (e.g., TPGS-750-M), bio-derived solvents like Cyrene for some steps.
Conventional: Dioxane, toluene, DMAc.
Base and additive considerations:
Prefer K3PO4, K2CO3 over stronger or hazardous bases where feasible. Avoid excess phosphine ligands; consider precatalysts enabling low catalyst loadings.
Energy and workup:
Conduct condensations at ambient temperature when possible; use solvent-switch or direct crystallization to reduce solvent usage. Employ aqueous workups that allow phase separations with safer solvents (EtOAc over DCM where compatible).
Waste minimization:
Plan routes that exploit the differential reactivity of C–Br vs C–F to minimize protection/deprotection steps. Consider telescoping hydrazone formation and coupling without isolating intermediates when purity constraints allow.
Tradeoffs: Very green media (water, bio-based solvents) may reduce solubility or rate; a small amount of DMSO or EtOH as cosolvent often restores performance with acceptable EHS impact.
Pharmaceutical Uses
No pharmacopeial or excipient status is indicated for this item.
From Product Data: Research Use Note: For research use only.
General context (literature/general):
Aromatic acyl hydrazides often serve as intermediates in medicinal chemistry for structure–activity relationship (SAR) exploration. The hydrazide can be diversified via hydrazone formation or transformed through Curtius rearrangement chemistry to ureas/carbamates.
The aryl bromide provides a handle for Pd-catalyzed diversification, allowing rapid analog generation from a single starting scaffold.
Manufacturing/formulation note:
As a reactive small-molecule intermediate, this compound is not typically formulated as a drug product or excipient. Any handling within a pharmaceutical R&D setting would be confined to synthetic steps under GMP-like or research conditions as appropriate.
No therapeutic or clinical claims are made or implied for this product.
Physical Properties
From Product Data (item-specific):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature expectations (reference only; not item specifications):
Molecular formula: C7H6BrFN2O (structure-based)
Molecular weight: ~233.04 g/mol (structure-based)
Physical state: Aromatic acyl hydrazides are typically crystalline solids with relatively high melting points due to strong intermolecular hydrogen bonding (literature trend).
Solubility profile (literature/general): Poorly soluble in nonpolar hydrocarbons; sparingly to moderately soluble in polar organics (EtOH, MeOH, acetonitrile); readily soluble in highly polar aprotic solvents (DMF, DMSO) and in basic aqueous media upon deprotonation of the hydrazide.
Acid–base behavior: The terminal –NH2 in acyl hydrazides is weakly basic and the –CONH– is weakly acidic; overall, acyl hydrazides show limited ionization near neutral pH (literature).
Partitioning: Presence of one carbonyl, two nitrogens, and two aryl halogens yields moderate polarity; logP expected to be in the low-to-moderate range for aryl hydrazides (literature trend; specific value not provided).
Spectroscopic handles: Strong amide C=O stretch ~1650–1700 cm−1, N–H stretches ~3200–3400 cm−1; characteristic 1H NMR signals for hydrazide NHs often broad and solvent-dependent (literature).
Item-specific numeric properties (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal limits): Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
From Product Data (item-specific):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance):
When purity is not specified on the catalog page, refer to the accompanying Certificate of Analysis (CoA) or Specification Sheet for batch-specific assay, related substances, and moisture/ash/metal profiles.
Typical expectations for research-grade small-molecule building blocks include: identity confirmation by 1H NMR/LC–MS/HRMS, purity by HPLC or GC where applicable, and residual solvent limits per internal specifications. However, these are not item-specific claims—verify on the CoA.
Stabilizers/inhibitors: None are listed for this item. If stabilizers are required, they will be declared on the CoA/label. In their absence, assume the neat solid is provided without intentional additives.
Chromatographic use: If employing this compound as an analytical standard or for quantitative work, confirm UV absorbance background and purity grade; for trace analysis or LC–MS applications, a high-purity lot with low nonvolatile residue is preferred (check CoA for UV cutoffs/absorptivity—Not specified for this item).
Lot-to-lot consistency: For sensitive syntheses (e.g., medicinal chemistry SAR), document lot numbers and retain aliquots for requalification if needed.
For any unlisted specification (water, peroxide, metal content, UV cutoff), status is: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
This building block combines an acyl hydrazide with an aryl bromide and aryl fluoride, enabling orthogonal transformations.
Condensation chemistry (literature/general):
Hydrazone/azomethine formation with aldehydes/ketones under acid catalysis (AcOH, pH 4–5) in MeOH/EtOH or aqueous-organic media. Useful for reversible conjugation and carbonyl capture/derivatization (e.g., analytical tagging).
Oxime-like stabilization via anilide neighbors is not applicable here; however, electron-withdrawing halogens can modestly influence acidity and condensation kinetics.
Curtius/Schmidt access via acyl azides (from hydrazides):
Nitrosylation of the hydrazide (NaNO2/HCl, 0–5 °C) affords the corresponding acyl azide, which upon heating yields an isocyanate (Curtius rearrangement). Trapping with amines/alcohols furnishes ureas/carbamates. Exercise strict temperature control and safety protocols with azides.
Cross-coupling at the aryl bromide (leaving aryl fluoride intact):
Suzuki–Miyaura (B(OH)2, Pd, K2CO3/K3PO4, dioxane/H2O), Buchwald–Hartwig amination (Pd/XPhos class ligands), or Sonogashira (Pd/Cu, amine base) can install diverse substituents. The aryl fluoride typically survives these conditions, enabling sequential diversification.
Protection/activation strategies:
Temporarily protect the hydrazide (e.g., Boc on terminal –NH2) to avoid catalyst poisoning or undesired condensation during cross-coupling.
Activation with CDI or carbodiimides can transform the hydrazide into more reactive intermediates (acyl imidazolides or directly to ureas with amines).
Applications in discovery chemistry:
Scaffolding for hydrazone-linked libraries, PROTAC-like linker exploration (hydrazone cleavable linkers), and late-stage functionalization at C–Br for SAR while retaining C–F as a spectroscopic handle.
Reaction Conditions
General literature guidance (not item-specific specifications):
Hydrazone formation:
Typical conditions: Carbonyl partner (1.0 eq), hydrazide (1.0–1.2 eq), solvent MeOH/EtOH or 1:1 MeOH/AcOH, catalytic AcOH (0.1–0.5 eq) or buffer pH 4.5–5.5; 20–50 °C; 1–16 h. Water removal (Dean–Stark in toluene for higher-boiling systems) can drive equilibrium where applicable.
Workup: Direct crystallization or concentration and trituration; hydrazones may hydrolyze under strong acid/base—handle accordingly.
Suzuki–Miyaura at aryl C–Br:
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-precatalyst with XPhos/SPhos (0.5–2 mol%).
Base: K3PO4 (2–3 eq), K2CO3, or Cs2CO3.
Solvent: 1,4-dioxane/H2O (3:1), toluene/H2O, or DMAc/H2O.
Temperature: 60–100 °C; 2–12 h. The hydrazide may coordinate; protection or lower loadings with robust ligands can help.
Buchwald–Hartwig amination:
Catalyst/ligand: Pd2(dba)3 (1–2 mol% Pd) with DavePhos/XPhos; base NaOtBu or K3PO4; solvents toluene, dioxane, or t-BuOH; 80–110 °C.
Curtius via acyl azide (from hydrazide):
Formation: NaNO2 (1.1 eq) in HCl(aq), 0–5 °C; extract acyl azide into cold organic solvent (DCM/Et2O). Strict temperature control to minimize side reactions.
Rearrangement: Heat to 60–90 °C in inert solvent (toluene, chlorobenzene) to generate isocyanate; trap with amine/alcohol (1.5–2.0 eq) to give urea/carbamate.
Analytical monitoring:
LC–MS in MeOH/H2O with 0.1% formic acid typically detects both parent and hydrazone products; UV 220–260 nm is suitable for aryl hydrazides.
Adjust conditions empirically to accommodate substrate electronics and solubility.
Safety and Handling
From Product Data (item-specific):
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
Storage Conditions: Room temperature.
General safety guidance for acyl hydrazides and aryl halides (literature/general; not a substitute for SDS):
Likely hazards: May cause skin/eye irritation and respiratory irritation; ingestion/inhalation may be harmful. Hydrazide functionalities can be sensitizing in some cases. Avoid dust formation and inhalation of particulates.
PPE: Use lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Handle in a fume hood to minimize exposure.
Incompatibilities: Strong oxidizers; strong acids/bases may lead to decomposition or hydrolysis. Avoid prolonged exposure to moisture which may affect purity over time.
Thermal stability: Aromatic acyl hydrazides are generally thermally stable under ambient handling but can decompose at elevated temperatures; avoid heating above necessary process temperatures.
First aid (overview; follow institutional protocols):
Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect as hazardous organic waste. Aryl halide-containing residues should be disposed of according to local regulations.
Always consult the product’s SDS for authoritative hazard classification and response measures.
Solvent Selection
Solubility and solution behavior are driven by the acyl hydrazide moiety (hydrogen bonding) and the dihalogenated aryl ring (increasing lipophilicity).
General polarity/miscibility (literature/general):
Preferred solvents for dissolution: DMSO and DMF (excellent), NMP (good), and alcohols such as MeOH/EtOH (moderate to good, may require warming).
Limited solubility: Acetonitrile and acetone may dissolve modestly; ethers (THF, MTBE) and chlorinated solvents (DCM, CHCl3) vary from low to moderate.
Poor solubility: Aliphatic hydrocarbons (hexanes, heptane) are typically poor.
Practical selection by application:
Hydrazone formation with aldehydes/ketones: Alcoholic solvents (MeOH/EtOH) or aqueous/organic mixtures buffered slightly acidic (acetic acid) enhance rates; DMSO can be used for poorly soluble partners.
Cross-coupling at C–Br: Toluene, dioxane, DMAc, or mixed dioxane/water under Pd catalysis are common; ensure the hydrazide tolerates base (use milder bases like K3PO4, Cs2CO3).
Curtius sequence via acyl azide (from hydrazide nitrosation): Typically carried out in polar aprotics (MeCN, DCM, THF) at low temperature for azide formation; subsequent rearrangement often in toluene or chlorinated solvents.
Comparison notes:
DMSO/DMF maximize solubility and reaction rates but complicate workup; MeOH/EtOH are greener and allow simpler isolation.
For bioconjugation-style hydrazone formation, aqueous buffers (pH 4.5–6) with 10–30% ethanol or DMSO co-solvent often balance rate and compatibility.
Storage and Reconstitution
From Product Data (item-specific):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance for aromatic acyl hydrazides (literature/general):
Store tightly closed in a dry, well-ventilated place, protected from moisture and direct light. Use desiccant if ambient humidity is high.
To minimize hydrolysis or gradual degradation, avoid prolonged exposure to strong acids/bases and elevated temperature.
If long-term storage is planned, consider keeping the container under inert gas after opening, especially if frequent opening/closing is expected.
Solution preparation:
Prepare concentrated stock solutions in anhydrous DMSO or DMF (e.g., 100–500 mM). Filter through a 0.2 µm PTFE syringe filter if particulate is present.
For short-term use, DMSO stocks are generally stable for days to weeks at 2–8 °C; for longer-term storage, aliquot and freeze at −20 °C to −30 °C to avoid repeated freeze–thaw. Allow to equilibrate to room temperature before opening to limit moisture condensation.
Avoid preparing aqueous stocks far in advance; hydrazones may form adventitiously with trace carbonyls in solution.
For any unlisted storage or shipping constraints (e.g., light sensitivity, stabilizers), status is: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Brief description: 2-Bromo-4-fluorobenzohydrazide is an ortho-brominated, para-fluorinated benzoyl hydrazide building block featuring one acyl hydrazide moiety attached to a dihalogenated benzene ring.
From Product Data (item-specific):
Product Name: 2-Bromo-4-fluorobenzohydrazide
CAS: 935657-73-1
PubChem CID: 16780865
InChIKey: 122634 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature identifiers and features (for reference; not item-specific specs):
2D structure (verbal): a benzene ring bearing an acyl hydrazide at C1 (benzoyl link), a bromine at C2 (ortho to the carbonyl), and a fluorine at C4 (para to the carbonyl). The carbonyl carbon is bonded to –NH–NH2.
General structural notes:
The acyl hydrazide can serve as a nucleophile at the terminal –NH2 and can condense with carbonyl compounds to form hydrazones.
The aryl bromide enables cross-coupling (e.g., Suzuki, Buchwald–Hartwig after appropriate activation), while the aryl fluoride is significantly less reactive, often surviving conditions that transform the C–Br site.
No stereocenters are present; the compound is achiral.
Synthetic Utility
Key functional elements and their use:
Acyl hydrazide (–CONH–NH2):
Nucleophilic at the terminal –NH2, enabling condensation with aldehydes/ketones to form hydrazones (reversible under acidic/aqueous conditions for cleavable linkers).
Precursor to acyl azides via nitrosation (NaNO2/HCl), enabling Curtius rearrangement to isocyanates; trapping then furnishes ureas/carbamates.
Can engage in coupling with activated carboxylic acids (e.g., via EDC/HOBt or CDI) to extend to diacyl hydrazides or ureas.
Aryl bromide (C–Br):
Amenable to Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings under conditions that typically leave the aryl fluoride intact, allowing stepwise diversification (chemoselectivity advantage: C–Br > C–F).
Aryl fluoride (C–F):
Electron-withdrawing; modulates acidity and N–H hydrogen bonding; generally inert to many cross-coupling conditions, surviving as a persistent substituent that can influence binding interactions and metabolic stability in medicinal chemistry derivatives.
Strategic tactics:
Protect hydrazide (e.g., Boc on terminal nitrogen) prior to Pd-catalyzed couplings to reduce catalyst deactivation and side reactions.
Sequence planning: First, couple at C–Br; second, perform hydrazone formation or Curtius rearrangement; third, optionally unmask or further derivatize the hydrazide.
Late-stage diversification: Use mild bases (K3PO4, Cs2CO3) and ligand systems (XPhos, SPhos) for coupling tolerance toward the hydrazide functionality.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and does not possess biological target specificity parameters (e.g., antigen, epitope, clone, isotype). No item-specific data are provided for any biochemical targeting attributes.
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