This compound belongs to the class of organic compounds known as carboxylic acid hydrazides. These are carboxylic acid derivatives containing a carbonyl group in which the carbon is directly linked to a hydrazide group (N-N).
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.
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Application Protocols
Not applicable
No validated immunoassay or cell-based application protocols are associated with this small-molecule reagent in the Product Data.
General use notes (literature/practice)
For hydrazone formation: Dissolve substrates in EtOH or aqueous acetate buffer (pH 4.5–6), add catalytic AcOH or aniline, and stir at RT to 50 °C until completion by TLC/LC.
For nitrosation to acyl azide: Cool to 0–5 °C, add NaNO2 solution to the acidic hydrazide solution slowly with stirring, maintain cold, and proceed in situ to the next step. Follow strict safety protocols.
Biological Roles
Applicability
Propanoic acid hydrazide is a synthetic small molecule; it is not a known endogenous metabolite or cofactor.
General notes (literature)
Reactivity toward carbonyls: Hydrazides form hydrazones with aldehyde/ketone groups present on biomolecules (e.g., reducing ends of glycans, aldehyde-tagged proteins). This chemistry underpins labeling, immobilization, and capture strategies in biochemistry.
pH dependence: Hydrazone formation is typically favored under mildly acidic conditions (pH ~4.5–6). Catalysts such as aniline can accelerate ligation at near-neutral pH, compatible with many biomolecules.
Stability considerations: Hydrazones can hydrolyze; stabilization by reduction to secondary amines (reductive amination) is commonly employed for durable conjugates.
Limits
No intrinsic biological activity or receptor specificity is ascribed to propanoic acid hydrazide itself in standard biochemical texts. Any observed biological effects are generally attributable to derivatization chemistry rather than a direct mode of action.
Buffer Applications
Not typically applicable
Propanoic acid hydrazide is not a buffering agent and is not used to control pH in biochemical systems.
Related practical note (literature)
Hydrazone ligations involving this functional group are often carried out in acetate or citrate buffers (pH 4.5–6) or phosphate buffers with aniline catalysis. In such cases, the buffer is chosen for the reaction, not provided by the hydrazide itself.
Green Alternatives
Context
Propanoic acid hydrazide is a small acyl hydrazide used primarily as a carbonyl-capturing reagent and as a precursor to acyl azides. Greener practice focuses on solvent and catalyst choices and on safer alternatives to hazardous intermediates.
Greener choices (literature/practice)
Solvents for hydrazone formation: Use water or aqueous ethanol (EtOH from bio-based sources) with catalytic acetic acid instead of neat aprotic solvents. Avoid chlorinated solvents.
Catalysis: Aniline or anilinium salts can catalyze hydrazone formation at near-neutral pH in water, reducing need for organic solvent and heat.
Avoid nitrosating mineral acids when possible: For acyl transfer, alternatives to NaNO2/HCl include DPPA-free, imidazolide- or CDI-mediated routes where compatible, reducing formation of energetic acyl azides. If acyl azides are essential, maintain cold, dilute, and in situ conditions.
Energy minimization: Many hydrazone ligations proceed efficiently at room temperature; water-compatible conditions lower energy input and waste.
Comparison (general)
Conventional approach: DMF/AcOH or neat alcohols; nitrosation with NaNO2/HCl to acyl azide.
Greener approach: Aqueous buffers or aqueous EtOH, aniline catalysis, solid-supported scavengers to reduce solvent volume; alternative coupling chemistries (CDI, EDC) where the acyl azide/Curtius path is not mandatory.
Trade-offs
Aqueous media can slow kinetics for some hydrophobic partners; phase-transfer or surfactants may help.
Avoiding acyl azides may limit access to Curtius products; ensure route redesign meets target specifications.
Pharmaceutical Uses
Scope
No pharmacopeial monograph or excipient role is specified for this item. Not specified for this item; refer to CoA/Spec Sheet.
General context (literature; no therapeutic claims)
Process/intermediate chemistry: Acyl hydrazides are frequently used as synthetic intermediates en route to APIs (e.g., via Curtius rearrangement to primary amines or for constructing hydrazone-linked intermediates). Propanoic acid hydrazide can serve as a simple model reagent in route scouting and impurity derivatization.
Conjugation chemistry in analytics: Hydrazides are used to derivatize carbonyl-containing impurities for improved detection; such uses are analytical/process-support rather than formulation roles.
Compliance note
This product is for research use only and is not intended for human or veterinary applications.
Physical Properties
Item-specific specs
Grade/purity, appearance, and detailed specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for reference only; not product specifications)
Physical state: Typically a crystalline solid (literature)
Melting point: Reported in the ~90–100 °C range (literature; values vary by source and purity)
Boiling point: Not commonly distilled; hydrazides generally decompose before boiling at 1 atm (literature)
Solubility: Readily soluble in water; miscible with polar protic solvents (methanol, ethanol) and polar aprotic solvents (DMSO, DMF) (literature)
Acid/base behavior: Weakly basic at the terminal –NH2; can be protonated under acidic conditions; the amide nitrogen is much less basic (literature)
Partitioning: Expected low logP (high polarity) and high hydrogen-bonding capacity (literature qualitative assessment)
Refractive index, density, UV cutoff, metal/peroxide/water limits: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific details
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general)
Research use only: Supplied for laboratory research and development; not for human or veterinary use.
If offered in multiple grades (general guidance):
Synthetic/technical grade: Suitable for routine transformations (e.g., hydrazone formation) where ultra-low impurities are not critical.
High-purity grade: Preferred for sensitive applications such as bioconjugation, peptide hydrazide chemistry, or analytical derivatization where trace impurities, UV background, or metal content matter.
Argon-charged packaging: Helps minimize oxidative degradation and moisture uptake, preserving reactivity of the hydrazide functionality. After first opening, re-purge headspace with inert gas if possible.
Documentation: For batch-specific attributes (assay, residual solvents, water content, identity confirmation), consult the CoA/Spec Sheet supplied with the lot.
Reaction and Applications
Key application families (literature/practice)
Carbonyl capture: Formation of hydrazones with aldehydes/ketones under mild acid catalysis. Useful for carbonyl protection, purification, and analytical derivatization of reducing sugars or aldehydic impurities.
Acyl transfer chemistry: Conversion of acyl hydrazides to acyl azides via nitrosation (NaNO2/HCl or similar). The acyl azide can undergo Curtius rearrangement to isocyanates, enabling access to primary amines, ureas, and carbamates after trapping.
Peptide hydrazide chemistry: Propionyl hydrazide itself is a simple hydrazide; in analogous systems, peptide C-terminal hydrazides are precursors to acyl azides and thioesters used in native chemical ligation workflows. The propionyl system serves as a model substrate in method development.
Ligation/bioconjugation: Hydrazone ligation to aldehyde-functionalized biomolecules or polymers. Hydrazone exchange and stabilization (via aniline catalysis, pH 4.5–6, or reduction to secondary amines with NaBH3CN/NaBH(OAc)3) are common strategies.
Directing group chemistry: Acyl hydrazide motifs can serve as transient directing groups in some C–H functionalizations (substrate- and metal-dependent), though this is more often explored with aryl/heteroaryl systems.
Practical tips
Driving hydrazone formation: Remove water (Dean–Stark in refluxing toluene for higher-boiling systems) or use molecular sieves in lower-boiling alcohols; maintain mild acidity (AcOH) to balance rate and stability.
Handling acyl azides: Generate in situ at low temperature; avoid concentration to dryness; use appropriate blast shields and scale-down protocols.
Purification: Hydrazones often crystallize and can be isolated by filtration; otherwise, use reverse-phase or normal-phase chromatography mindful of strong H-bonding.
Reaction Conditions
General conditions (literature; illustrative, not specifications)
Hydrazone formation with aldehydes/ketones:
Solvent: EtOH, MeOH, or 1:1 EtOH/H2O; for bioconjugation, 50–100 mM acetate or citrate buffer (pH 4.5–6). Aniline (10–100 mM) can catalyze at pH 5–7.
Temperature/time: 20–60 °C, 1–24 h depending on substrate; water removal or sieves accelerates.
Workup: Filtration if crystalline; otherwise evaporate solvent and purify by chromatography.
Reduction of hydrazones (to stable secondary amines):
Reagents: NaBH3CN or NaBH(OAc)3; solvent: MeOH, EtOH, or DCE/AcOH mixtures; temp: 0–25 °C; monitor to avoid over-reduction.
Conversion to acyl azide (for Curtius):
Generate in situ at 0–5 °C by treating the hydrazide with NaNO2 in 2–6 M HCl (or similar nitrosating system). Keep dilute; do not concentrate acyl azides. Trap subsequent isocyanate with ROH (carbamate) or R2NH (urea) upon warming to 40–80 °C.
Alternative activations:
CDI (1.1–1.5 equiv) in anhydrous DMF or THF at 0–25 °C to form reactive intermediates for downstream coupling (substrate-dependent).
Expected outcomes
Hydrazone equilibria generally favor product for aldehydes; ketones may require longer times or catalysts. Yields vary widely (50–95%) depending on substrate electronics and conditions.
Safety and Handling
Item-specific hazard information
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to the SDS.
Storage per Product Data: Store at room temperature under argon (argon charged). Ship normal.
General safety considerations for acyl hydrazides (literature/good practice)
Hazards: May cause skin/eye irritation and respiratory irritation; avoid inhalation of dust and contact with skin/eyes. Some hydrazide derivatives can be harmful if swallowed. Handle as a potentially hazardous organic nitrogen compound.
Peroxide formation: Not applicable (no ether functionality), but hydrazide groups can slowly oxidize; inert gas blanket (as provided) helps preserve quality.
Incompatibilities: Strong oxidizers, strong reducing agents, nitrosating agents (can form acyl azides/other reactive species), strong acids/bases (may cause decomposition or uncontrolled reactions). Avoid isocyanate-forming reagents unless intended.
PPE: Lab coat, safety glasses, appropriate chemically resistant gloves (e.g., nitrile), and use in a fume hood to minimize dust/vapor exposure.
First aid (overview; defer to SDS): Eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; do not induce vomiting; seek medical attention.
Fire response: Use water spray, CO2, dry chemical, or foam. Combustion may release nitrogen oxides; firefighters should wear SCBA.
Waste: Collect organic nitrogen-containing waste in properly labeled containers; follow institutional and regulatory disposal guidelines.
Solvent Selection
Applicability
As a small, polar acyl hydrazide, solvent choice is driven by the intended transformation (e.g., hydrazone formation, activation to acyl azide) rather than by use as a solvent.
Aqueous compatibility: Dissolves well in water and aqueous buffers at acidic to neutral pH; protonation of –NH2 improves aqueous solubility under mildly acidic conditions.
Organic solvents: Highly soluble in methanol/ethanol; soluble in DMSO and DMF; limited solubility in nonpolar hydrocarbons.
Typical use scenarios:
Hydrazone formation with aldehydes/ketones: Ethanol, methanol, or aqueous ethanol with catalytic acetic acid; for bioconjugation, aqueous acetate or citrate buffers (pH 4.5–6) are common.
Activation to acyl azides (for Curtius or thioester formation): Aqueous mineral acid with NaNO2 at 0–5 °C, then extraction to inert organic solvents (e.g., toluene, THF) as needed.
Peptide/acyl transfer chemistry: DMF or NMP with coupling reagents; DMSO or mixed aqueous-organic media when required by solubility.
When to choose alternatives
If water-sensitive substrates are present, favor anhydrous alcohols or aprotic polar media.
For bioconjugation at neutral pH, aminooxy reagents (oxime ligation) may proceed faster than hydrazides; solvent/buffer choice may shift accordingly.
Container: Store in a tightly sealed container under inert gas to limit oxidation and moisture uptake. Protect from prolonged exposure to air and humidity.
Stability: Acyl hydrazides are generally stable solids; avoid strong acids/bases and oxidizers. If long-term storage is anticipated, consider desiccation and limited headspace.
Reconstitution/dissolution: Readily dissolves in water, methanol, ethanol, and DMSO. For moisture-sensitive applications, use anhydrous solvents. Filter solutions (0.2 µm) for bioconjugation or analytical use.
Freeze–thaw: Not typically required for solids. If preparing stock solutions, aliquot and store at 2–8 °C or −20 °C as appropriate for the solvent; allow to warm to RT before opening to minimize condensation.
Specifications (water content, UV cutoff, stabilizers): Not specified for this item; refer to CoA/Spec Sheet.
Usage note
After each use, re-purge the container headspace with inert gas (argon or nitrogen) and reseal promptly to maintain quality.
Literature/general identifiers (for reference; not item-specific specs)
Molecular formula (literature): C3H8N2O
Molecular weight (literature): ~88.11 g/mol
Common SMILES (literature): CCC(=O)NN
IUPAC name (literature): Propanehydrazide
Structural features (general description)
Functional groups: A terminal hydrazide (–CONH–NH2) attached to a propionyl chain (–CH3CH2–). One carbonyl (amide-like) and two nitrogens capable of hydrogen bonding.
2D description: An unbranched three-carbon chain terminating in a carbonyl carbon double-bonded to oxygen; the carbonyl carbon is single-bonded to –NH–NH2. No rings or stereocenters.
Donor/acceptor profile (general): Two H-bond donors (–NH– and –NH2) and one H-bond acceptor (C=O), imparting high polarity and hydrophilicity.
Synthetic Utility
Functional group leverage (literature)
Nucleophilic nitrogen(s): The terminal –NH2 participates in condensation with aldehydes/ketones to form hydrazones; the internal –NH adjacent to C=O is far less nucleophilic.
Electrophilic handle via activation: The acyl moiety can be converted to an acyl azide under nitrosative conditions, enabling Curtius rearrangement to isocyanates/primary amines.
Hydrogen bonding: Strong donor/acceptor profile often aids crystallization of derivatives and can modulate selectivity via H-bonding networks in supramolecular assemblies.
Named and common transformations
Hydrazone formation/exchange; aniline-catalyzed hydrazone ligation; reductive amination of hydrazones to secondary amines.
CDI or EDC-mediated coupling to introduce hydrazide onto carboxylate-bearing substrates (general method development relevance).
Retrosynthetic value
As a propionyl surrogate in methodology screening, propionohydrazide provides a convenient, low-mass acyl fragment that simplifies spectral interpretation and kinetic analysis while preserving hydrazide reactivity.
Practical considerations
Keep water content controlled for reversible condensations; use mild acid catalysis. For hazardous intermediates (acyl azides), operate cold, dilute, and behind safety shields.
Target Specificity
Not applicable
This product is a small-molecule reagent, not a biological targeting reagent or antibody. No antigen/epitope specificity, isotype, or species reactivity applies.
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