≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Room temperature,Argon charged Ships Normal Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 28 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Visão geral
4-Chlorobenzaldehyde reacts with 3-tert-butyl-N-4-chlorobenzyl-1-phenyl-1H-pyrazol-5-amine to form (E)-3-tert-Butyl-4-(4-chlorobenzyl)-N-(4-chlorobenzylidene)-1-phenyl-1H-pyrazol-5-amine by a microwave-mediated reaction.
This compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
External Descriptors
monochlorobenzenes - benzaldehydes
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.
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Application Protocols
No antibody or bioassay application data are associated with this chemical building block. Typical laboratory uses involve standard organic synthesis protocols (see Reaction Conditions and Synthetic Utility). For analytical use, follow general GC/HPLC sample prep: dissolve in suitable solvent (e.g., acetonitrile, methanol, or dichloromethane), filter if needed, and analyze under carbonyl-appropriate methods (derivatization with DNPH optional). Item-specific tested applications/dilutions: Not specified for this item; refer to CoA/Spec Sheet.
Biological Roles
This product is supplied for research use only. No medical or clinical claims are made.
General biochemical considerations for aromatic aldehydes (literature):
Reactivity with biomolecules: Aldehydes can form reversible Schiff bases with primary amines (e.g., lysine side chains) and react with thiols under some conditions, potentially perturbing enzyme function in vitro.
Metabolic fate: Aromatic aldehydes are typically oxidized by aldehyde dehydrogenases to the corresponding aromatic acids (e.g., p-chlorobenzoic acid) or reduced to alcohols by aldo-keto reductases in biological systems.
Toxicological note: Protein/amine reactivity underlies irritancy and cytotoxicity observed for some aldehydes; handle with care to avoid biological exposure.
Applications in bio-related research (non-clinical):
As a carbonyl probe in model reactions for Schiff-base bioconjugation studies (e.g., imine formation kinetics, reductive amination optimization) using small-molecule amines.
As a hydrophobic aryl aldehyde standard for chromatographic method development assessing carbonyl-selective derivatization (e.g., DNPH assays).
Buffer Applications
Not typically applicable. p-Chlorobenzaldehyde is a non-ionic organic building block and is not used to prepare aqueous buffer systems. For laboratory use involving this compound, select buffer systems only for downstream aqueous workups or analytics unrelated to the compound’s buffering capacity. Refer instead to sections on Reaction & Applications and Solvent Selection for relevant guidance.
Green Alternatives
While p-chlorobenzaldehyde is the required substrate in many syntheses, the environmental footprint of the process can be improved by solvent and reagent choices (general, literature-based guidance).
Replace chlorinated solvents (DCM, CHCl3) with greener aprotics where feasible: 2-MeTHF, CPME, EtOAc, or propylene carbonate, considering solubility and reaction needs.
Use toluene or ethanol in place of benzene when Dean–Stark water removal is needed for imine formation.
Reagents and conditions
Reductive amination: Prefer NaBH(OAc)3 in acetic acid/EtOAc or catalytic hydrogenation over cyanoborohydride when possible.
Oxidations: TEMPO/NaOCl (bleach) in biphasic water/EtOAc or Oxone®/NaCl systems can replace chromium(VI) reagents.
Reductions: Catalytic hydrogenation (H2/Pd-C) or transfer hydrogenation (isopropanol/Ru or Mn catalysts) as alternatives to stoichiometric LAH.
Comparison snapshot (general):
DCM vs EtOAc/2-MeTHF
Safety/Env: DCM is volatile and problematic; EtOAc/2-MeTHF are more benign and biosourced.
Performance: EtOAc often provides similar solubility and easy workups; 2-MeTHF tolerates moisture and enables biphasic separations.
Cr(VI) oxidants vs TEMPO/NaOCl
Waste: Cr(VI) hazardous waste vs aqueous salt byproducts.
Selectivity: TEMPO systems are selective for aldehyde→acid/aldehyde→carboxyl transformations under mild conditions.
Note: These are process-development suggestions; confirm compatibility with the aryl chloride and protect the aldehyde if necessary.
Pharmaceutical Uses
No excipient or pharmacopeial grade information is provided for this item; Not specified for this item; refer to CoA/Spec Sheet.
General, non-clinical context (literature/process development):
Role as an intermediate: p-Chlorobenzaldehyde is a common starting material/intermediate in the synthesis of para-chloro–substituted benzoic acids, benzyl alcohols, benzylamines, and styrenes, which can be incorporated into agrochemical and pharmaceutical development pipelines.
Process considerations: The aldehyde can be protected (acetal) for compatibility with strong bases and Pd-catalyzed couplings, enabling late-stage diversification while maintaining the para-chloro handle for cross-coupling.
Quality attributes for GMP/process adoption (general): Control of oxidation impurity (p-chlorobenzoic acid), residual solvents, and formation of acetals/hydrates is important. Elemental impurities and Pd residuals (if couplings are used) may be governed by ICH Q3D in API manufacturing contexts.
All uses are for research and manufacturing development only; no therapeutic claims are made.
Physical Properties
Note: Values below are general literature data for p-chlorobenzaldehyde and are NOT item-specific specifications for SKU C104155.
Phase/appearance: Typically a crystalline solid at ambient temperature (literature). Item-specific appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: ~46–49 °C (literature)
Boiling point: ~214–216 °C at 1 atm (literature)
Density: ~1.30–1.32 g/cm³ at 20–25 °C (literature)
Vapor pressure: Low at room temperature (literature qualitative)
Solubility: Low in water; freely soluble in common organic solvents (e.g., ethanol, ether, dichloromethane, toluene) (literature)
LogP (octanol/water): ~2.7–3.0 (literature)
Refractive index: Not typically reported for solids; molten/liquid nD not commonly tabulated (literature)
UV absorption: Aromatic π→π* band near 250–280 nm; carbonyl n→π* weak band near ~320–330 nm (literature, qualitative)
pKa: Not applicable for the aldehyde; conjugate acid of the carbonyl is very strong acid (pKa << 0) (literature concept)
Item-specific physicochemical specifications (water content, residual solvents, metals, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/Purity for this item: Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance):
Research-grade aromatic aldehydes are commonly specified for purity by GC/HPLC and may include limits on related benzoic acid impurity (from oxidation) and aldehyde hydrates/acetals. Low water content is desirable to minimize hydrate/imine side equilibria in moisture-sensitive syntheses.
If “ACS/AR grade” is offered in other contexts, it typically indicates compliance with analytical reagent criteria for assay and specified maximum levels of common inorganic contaminants; for synthetic organics, the emphasis is on organic purity (GC) rather than metals.
Stabilizers: Not indicated for this item. Some aldehydes are supplied under inert gas to slow oxidation; accordingly, this SKU is argon charged (from Product Data).
Documentation: For assay method, impurity profile, residual solvents, and trace metals, consult the item-specific CoA/Spec Sheet. Avoid assuming UV cutoff or trace-metal specifications unless explicitly reported.
Reaction and Applications
General synthetic roles for p-chlorobenzaldehyde (literature):
Carbonyl electrophile:
Imine/Schiff base formation with primary amines; downstream reduction to p-chlorobenzylamines (reductive amination, NaBH3CN/NaBH(OAc)3).
Nucleophilic additions: Grignard/organolithium to furnish secondary alcohols; cyanohydrin formation (KCN/TMSCN) as a handle to α-hydroxynitriles.
Reductions: To p-chlorobenzyl alcohol (NaBH4, LiAlH4, catalytic hydrogenation) or to p-chlorotoluenes (Wolff–Kishner, Clemmensen) when deoxygenation is required.
Oxidations: To p-chlorobenzoic acid (KMnO4, Jones, TEMPO/bleach), or to the corresponding acyl chlorides via Oxalyl chloride/SOCl2 after acid formation.
Olefination: Wittig, Horner–Wadsworth–Emmons, or Julia–Kocienski to install alkenes; para-chloro often tolerated under these conditions.
Aromatic chloride handle:
Cross-coupling (Buchwald–Hartwig amination, Suzuki–Miyaura, Stille, Negishi) on the aryl chloride of derivatives where the aldehyde is protected (e.g., as acetal/oxime) or chemoselectively tolerated using modern ligands (e.g., BrettPhos, XPhos) and mild bases.
Nucleophilic aromatic substitution is generally disfavored without additional ring activation; however, directed metalation or lithium–halogen exchange (at low temperature) enables further functionalization.
Heterocycle synthesis: As a C1 electrophile in Knoevenagel condensations (with active methylenes such as malononitrile, ethyl cyanoacetate) to access para-chloro–substituted styryls and heteroaromatic precursors.
Materials/ligands: Aldehyde-to-imine condensations with diamines for Schiff-base ligands and polymer precursors where the p-chloro serves as a later diversification point.
Practical tips:
Protect aldehyde (acetal, 1,3-dioxolane) before strong basic or Pd-catalyzed couplings to suppress side reactions/over-reduction.
Store and handle under inert gas (as provided) to minimize oxidation to p-chlorobenzoic acid.
Reaction Conditions
Typical literature conditions involving p-chlorobenzaldehyde (general guidance; verify experimentally):
Imine formation / Reductive amination
Solvent: Toluene (Dean–Stark), MeCN, or CH2Cl2; add 3Å molecular sieves.
Conditions: Room temp to reflux; catalytic acid (p-TsOH, AcOH). For reduction: NaBH(OAc)3 (AcOH, rt) or H2/Pd-C (EtOH, rt–40 °C).
Notes: Remove water to drive equilibrium. Para-chloro is stable under these conditions.
Wittig/Horner–Wadsworth–Emmons olefination
Solvent: THF, toluene, or DCM.
Base: n-BuLi or NaHMDS for unstabilized ylides; K2CO3/NaH for stabilized phosphonates.
Temp: −78 °C to reflux depending on reagent. Often E-selective with HWE (electron-withdrawing phosphonates).
Reduction to alcohol
NaBH4: MeOH/EtOH, 0 °C to rt, 0.5–2 h; typically high conversion.
LAH/DIBAL: THF/Et2O under inert atmosphere, 0 °C to rt.
Oxidation to acid
TEMPO/NaOCl: CH2Cl2/H2O, NaHCO3 buffer, 0–25 °C, 1–4 h.
Jones (CrO3/H2SO4): Acetone, 0–25 °C (use greener alternatives where possible).
Cross-coupling on aryl chloride (with protected aldehyde)
Suzuki–Miyaura: Pd2(dba)3/XPhos, K3PO4, toluene/H2O or 1,4-dioxane, 80–110 °C; aldehyde as acetal.
Buchwald–Hartwig amination: Pd(OAc)2/BrettPhos, NaOtBu, toluene, 80–100 °C.
These are representative literature conditions; optimize for scale, ligand, and base compatibility. Protect the aldehyde if strong base or prolonged heating is required.
Safety and Handling
GHS/SDS status for this specific item: Not specified for this item; refer to SDS.
General hazards for aromatic aldehydes (literature/general):
Irritating to skin, eyes, and respiratory tract; may cause sensitization in susceptible individuals due to aldehyde reactivity with amines/proteins.
Harmful if swallowed or inhaled; use engineering controls to minimize vapors and dust.
Special chemical risks (general):
Aldehydes can auto-oxidize to the corresponding benzoic acids upon exposure to air/oxygen and light; inert-atmosphere storage helps maintain purity.
Can undergo self-condensation (e.g., base-catalyzed aldol-type side reactions) if exposed to strong base.
Use in a fume hood. Wear safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin contact and inhalation of dust/vapor.
First-aid overview (general guidance; defer to SDS):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: Rinse with copious water for at least 15 minutes; remove contaminated clothing; obtain medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical help.
Fire safety: Combustible organic; use CO2, dry chemical, or foam. Thermal decomposition may release HCl and other irritants.
Storage note specific to this item (from Product Data): Store at room temperature under argon (argon charged).
Solvent Selection
This product is a solid building block, not a solvent. Solvent choice pertains to its use in reactions, purifications, and analyses.
Polarity/miscibility considerations (general):
Moderately nonpolar aromatic with a polar aldehyde; dissolves well in nonpolar/aprotic media (toluene, DCM, chloroform, EtOAc, THF, MeCN). Limited solubility in alcohols increases with temperature; poor in water.
Choosing solvents by transformation (literature guidance):
Nucleophilic additions/Reductions (e.g., NaBH4, hydride reagents): Protic (MeOH/EtOH) for NaBH4; aprotic (THF/Et2O/toluene) for strong hydrides (LiAlH4, DIBAL-H).
Imine formation/Reductive amination: Toluene, benzene, or Dean–Stark azeotrope to remove water; MeCN or CH2Cl2 with molecular sieves for milder conditions.
Wittig/Still–Gennari/HWE olefinations: THF, toluene, or DCM depending on base/ylide stability.
Oxidations to p-chlorobenzoic acid: Acetonitrile, acetone, or biphasic systems; avoid overexposure to strong oxidants if other functionalities present.
Electrophilic aromatic substitution (nitration, sulfonylation): Mixed acid or chlorosulfonic-based systems; note deactivation from –Cl/–CHO.
Workup/purification tips:
Benzoic acid byproduct (oxidation) can be removed by bicarbonate wash (forms water-soluble benzoate). Residual aldehyde can be tracked by TLC (UV-active) and 2,4-DNPH derivatization if needed.
Analytical solvents: For HPLC, acetonitrile/water or MeOH/water with acid modifier; for GC, nonpolar columns with split injection; ensure sample integrity (avoid acetalization in alcoholic solvents unless intended).
Storage and Reconstitution
Storage conditions (from Product Data): Store at room temperature under argon (argon charged). Shipment: Normal.
Rationale (general): Inert atmosphere minimizes air-oxidation of the aldehyde to p-chlorobenzoic acid and suppresses moisture-driven hydrate/acetal formation.
Container handling (good practice):
Keep tightly sealed under inert gas after each use. Purge headspace with argon or nitrogen. Store in a dry place away from light and oxidants.
Avoid prolonged exposure of opened containers to air or basic vapors to prevent degradation/condensation.
Stability considerations (general):
Aldehydes may slowly oxidize; monitor by TLC/GC for appearance of the acid impurity (more polar on silica; extractable into aqueous bicarbonate).
Reconstitution/dissolution:
Solid readily dissolves in common organic solvents (e.g., toluene, EtOAc, THF, MeCN, CH2Cl2). Warm gently if needed; avoid aqueous media.
For moisture-sensitive transformations, dry solvents and consider molecular sieves.
Freeze–thaw: Not applicable; store as supplied at room temperature under argon. Do not refrigerate if it promotes crystallization that complicates handling unless beneficial for your workflow.
Item-specific stability data, shelf life, and impurity limits: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Brief description: p-Chlorobenzaldehyde is a para-chloro–substituted aromatic aldehyde, a versatile electrophilic building block combining an aldehyde function with a deactivating aryl chloride.
Item identifiers (from Product Data)
SKU: C104155
Product Name: p-Chlorobenzaldehyde
CAS: 104-88-1
PubChem CID: 7726
InChIKey: 16134 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structure features (general/literature)
Molecular formula: C7H5ClO (literature)
Molecular weight: 140.57 g/mol (literature)
Preferred SMILES (literature): O=Cc1ccc(Cl)cc1
Functional groups: aromatic aldehyde (–CHO) para to chloro (–Cl) on a benzene ring.
Substitution pattern: 1,4-disubstituted benzene (para), leading to a symmetric ring environment relative to the –CHO/–Cl axis.
Electronic effects: –Cl is weakly deactivating/ortho–para directing; –CHO is strongly electron-withdrawing and meta-directing for electrophilic aromatic substitution. Aldehyde carbonyl is conjugated with the ring, enhancing electrophilicity.
2D structure in words (general)
A benzene ring bearing an aldehyde group at position 1 and a chlorine atom at position 4 (para). The aldehyde carbonyl (C=O) is planar with the ring and conjugated; the chlorine resides opposite the aldehyde across the ring.
Stereochemistry: None (achiral, planar aromatic).
Synthetic Utility
Key functional elements and reactivity (literature):
Aldehyde electrophile:
Forms imines/oximes/hydrazones readily; platform for reductive amination or Beckmann-like downstream chemistry.
Undergoes Wittig/HWE olefination to give p-chloro–substituted alkenes (E/Z control by reagent choice).
Amenable to chemoselective reductions: to alcohol (NaBH4, catalytic H2), or further to methylene (Clemmensen/Wolff–Kishner) when carbonyl removal is desired.
Oxidation to acid provides access to p-chlorobenzoic acid—an important intermediate and resolving agent precursor.
Aryl chloride as diversification site:
Pd-catalyzed couplings (Suzuki, Buchwald–Hartwig, Sonogashira) feasible with appropriate ligands/bases; aldehyde often protected to avoid side reactions.
Directed ortho-metalation strategies are limited by deactivation but can proceed adjacent to the aldehyde under strong bases at low temperature, enabling halogen–lithium exchange followed by electrophile quench.
Orthogonality:
The aldehyde can be temporarily masked (acetals, imines) while exploiting the aryl chloride for cross-coupling, then unveiled for late-stage carbonyl manipulations.
Retrosynthetic value:
Serves as a convergent node for building p-chloro–substituted motifs in heterocycles, ligands, and functional materials; easy access to acid, alcohol, and alkene manifolds from a single substrate.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, enzyme, or probe). No antigen/epitope, species reactivity, clone, or isotype information applies.
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