4-(4-Morpholinyl)butanohydrazide - ≥95% , CAS No.1087616-69-0

CAS: 1087616-69-0 Cat. No.: M1301291 Formula: C₈H₁₇N₃O₂ Molecular Weight: 187.243 PubChem CID: 30031527

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1COCCN1CCCC(=O)NN

IUPAC Name

4-morpholin-4-ylbutanehydrazide

InChIKey

ITWLSNLSUGHDKA-UHFFFAOYSA-N

INCHI

1S/C8H17N3O2/c9-10-8(12)2-1-3-11-4-6-13-7-5-11/h1-7,9H2,(H,10,12)

Isomeric SMILES

C1COCCN1CCCC(=O)NN

PubChem CID

30031527

Molecular Weight

187.243

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Oxazinanes
      • Subclass Morpholines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Oxazinanes
• Subclass: Morpholines
• Intermediate Tree Nodes: Not available
• Direct Parent: Morpholines
• Alternative Parents: Trialkylamines Carboxylic acid hydrazides Amino acids and derivatives Oxacyclic compounds Dialkyl ethers Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Morpholine - Amino acid or derivatives - Carboxylic acid hydrazide - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Azacycle - Organic oxide - Organic nitrogen compound - Amine - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
• 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

Chemical and Physical Properties

• Molecular Weight: 187.240 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 187.132 Da
• Monoisotopic Mass: 187.132 Da
• Topological Polar Surface Area: 67.600 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 157.000
• 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

No tested biological assay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent, and none are provided in the Product Data.

General workflow examples (literature/general, for synthesis/bioconjugation):

• Carbonyl ligation: Dissolve reagent in acetate buffer (pH 5.0) with 10–20% DMSO; combine with aldehyde-containing substrate (1.2–2.0 equiv hydrazide). Add 10 mol% aniline. Stir at rt 2–6 h; analyze by LC–MS; purify by HPLC if needed.
• Reductive stabilization: Without isolating the hydrazone, add NaBH3CN (2–3 equiv) and AcOH (0.5–1.0 equiv) at rt; monitor to completion; quench and purify.

These are illustrative only; for item-specific instructions, consult the CoA/Spec Sheet and adapt conditions to your substrate and analytical controls.

Biological Roles

Item-specific biological functions are not provided in the Product Data and should not be inferred. The compound is intended for research use only.

General context (literature/general):

• 4-(4-Morpholinyl)butanohydrazide is a synthetic small molecule combining a hydrazide coupling handle with a morpholine ring often used in medicinal chemistry for solubility modulation. It is not known as a natural metabolite.
• Hydrazide functionality is widely used to ligate with carbonyls present in biomolecules after selective oxidation (e.g., periodate-oxidized glycans on glycoproteins), enabling bioconjugation, immobilization, or capture-and-release workflows.
• Morpholine-containing motifs are frequently protonated near physiological pH, enhancing aqueous compatibility of conjugation reagents and reducing aggregation in protein or nanoparticle formulations.

No claims are made for biological activity, targets, or pharmacology of this specific item. Any use in biological systems should be limited to analytical or synthetic transformations under controlled research protocols.

Buffer Applications

This compound is not a classical buffering agent, and no buffer-use specifications are provided in the Product Data.

General note (literature/general):

• Hydrazone-forming reactions typically proceed well in mildly acidic buffers such as acetate or citrate (pH ~4.5–6.0). In such workflows, this reagent is a reactant rather than the buffer component.
• If using in aqueous media, adjust ionic strength and pH with a compatible buffer (e.g., 50–200 mM sodium acetate, pH 5.0) and consider adding an aniline catalyst to accelerate carbonyl condensations.

For applications requiring buffering capacity, refer to dedicated Good’s buffers (e.g., MOPS, MES). Do not rely on this reagent for pH control.

Green Alternatives

Greener practice focuses on solvent and catalyst choices rather than replacing the functional motif, since hydrazide–carbonyl chemistry is uniquely effective. Consider the following (literature/general):

• Solvent optimization:
  • Prefer water-rich media for hydrazone formation (acetate or citrate buffer, pH 4.5–5.5) with minimal DMSO cosolvent.
  • Replace DMF/NMP with safer polar aprotics like Cyrene (dihydrolevoglucosenone) or propylene carbonate when compatible.
  • Use ethanol or isopropanol instead of dichloromethane/THF where solubility allows.
• Catalysis and energy:
  • Use organocatalysts such as aniline or p-anisidine at low loadings to accelerate at ambient temperature, reducing heating.
  • For reductions, employ transfer hydrogenation (e.g., aqueous ammonium formate/Pd-C) or catalytic hydrogenation instead of stoichiometric borohydrides when feasible.
• Workup/waste:
  • Minimize excess hydrazide and use atom-efficient coupling strategies; trap residuals via reversible carbonyl adducts for safer disposal.

Illustrative comparison (general):

• Conventional: Hydrazone in DMF with 10 equiv reagent, overnight at 50 C.
• Greener: Hydrazone in 100 mM acetate buffer (pH 5.0) with 10–20% EtOH, 10 mol% aniline, rt, shorter time; simplified aqueous workup.

Tradeoffs: Water-rich media may slow reactions with sterically hindered ketones; some greener solvents can reduce substrate solubility—co-solvent tuning is often necessary.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or GMP grade is provided in the Product Data. This product is supplied for research use only.

General R&D context (literature/general):

• As a hydrazide-functional linker with a solubilizing morpholine motif, it may be explored in discovery chemistry for preparing hydrazone-linked conjugates, attaching to oxidized carbohydrate handles on biomolecules, or as an intermediate toward ureas/carbamates via acyl azide or isocyanate pathways.
• Morpholine units are common solubility-enhancing elements in medicinal chemistry; however, suitability for clinical development requires dedicated impurity control, residual solvent limits, and comprehensive safety profiling not covered by this listing.

Process notes:

• For early development, confirm stability in formulation-relevant media and establish analytical methods (HPLC with ELSD/UV, LC–MS) to monitor hydrazide integrity and hydrazone formation.
• Any scale-up or use in regulated contexts should follow internal quality systems and separate qualified sourcing; consult the CoA/Spec Sheet for available quality attributes.

Physical Properties

Item-specific physico-chemical specifications are not provided in the Product Data for this catalog entry. Do not treat any literature values as specifications; consult the CoA/Spec Sheet for release criteria.

Item-specific (Product Data):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for morpholine-bearing aliphatic hydrazides (informational only):

• State: typically low-melting solids or viscous oils; hydrazides often crystalline where hydrogen bonding is strong.
• Polarity: high (multiple heteroatoms and an amide), enabling solubility in polar aprotic media (DMSO, DMF) and frequently in alcohols; water solubility varies with chain length and protonation state.
• Acid–base behavior: hydrazide NHs are weakly basic/nucleophilic; morpholine nitrogen is a moderate base (conjugate acid pKa for morpholine ~8.3; literature, for morpholine itself). Overall protonation increases aqueous solubility in mildly acidic media.
• Partitioning: logP expected to be low-to-moderate due to multiple heteroatoms (qualitative, literature-level trend for analogous scaffolds).
• Thermal behavior: hydrazides generally show elevated decomposition on strong heating; avoid prolonged exposure to >150–180 C unless characterized (general guidance).

For authoritative values (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal limits), refer to the item’s CoA/Spec Sheet.

Quality & Grades

Item-specific grade/purity and stabilizer information are not provided in the Product Data.

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/general):

• Research grade hydrazide linkers are typically supplied at high purity to support conjugation chemistry, where trace carbonyl or amine impurities can consume reagent. When grade is unspecified, verify suitability by reviewing chromatographic purity, residual solvents, water content, and assay on the CoA.
• If low UV background is critical (e.g., analytical conjugation tracking), consider lots screened for low non-volatile residue and clean baseline in common eluents.
• For bioconjugation workflows, confirm levels of free hydrazine or hydrolysis byproducts are controlled; such species can cause over-reaction or side products.

Recommendations:

• Perform a small pilot conjugation with the received lot to benchmark conversion and background.
• If required, polish by recrystallization or preparative chromatography using anhydrous polar aprotic solvents. Verify identity by NMR and HRMS.

Reaction & Applications

This reagent is best viewed as a hydrazide-bearing linker with a solubilizing morpholine headgroup. Its primary utility lies in selective capture and ligation of carbonyl compounds and in downstream transformations of acyl hydrazides.

Key application families (literature/general):

• Hydrazone formation: Reacts with aldehydes/ketones to give hydrazones. Useful for tagging oxidized glycans on proteins/biomaterials, immobilizing carbonyl-bearing analytes, or forming reversible linkages for dynamic combinatorial chemistry. Rates increase at pH ~4.5–6.0 and with aniline catalysis; oxo-aldehydes react faster than ketones.
• Reductive stabilization: Hydrazones can be reduced (e.g., NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation) to stable alkylated hydrazides/hydrazines, forming permanent C–N linkages.
• Acyl hydrazide transformations: Conversion to acyl azides (e.g., nitrosylation followed by rearrangement) enabling Curtius rearrangements to isocyanates, or to activate carboxyl groups for urea/carbamate formation.
• Conjugation spacer: The butylene chain provides spacing between the hydrazide linkage and the morpholine ring, which can improve aqueous solubility and reduce steric hindrance near the reactive site.
• Solid support/surface coupling: Hydrazide-functional surfaces capture carbonyl-functional ligands; morpholine functionality can modulate charge and wetting in coatings.

Practical tips:

• Dry solvents and exclude extraneous carbonyls to minimize side reactions.
• Use slight excess of hydrazide to drive condensations; remove water (molecular sieves or azeotrope) for challenging ketones.
• Monitor by LC–MS; hydrazones show characteristic mass shifts and sometimes E/Z isomerism.

Reaction Conditions

Typical conditions below are general literature guidance for hydrazide chemistry and should be optimized per substrate. They are not item-specific specifications.

• Hydrazone formation (carbonyl ligation):
  • Solvent: 50–200 mM acetate buffer (pH 4.5–5.5), often with 10–30% DMSO or EtOH for solubility.
  • Catalyst: 5–20 mol% aniline or p-anisidine to accelerate.
  • Temperature/time: rt to 37 C; 1–16 h depending on carbonyl sterics.
  • Workup: buffer exchange or quench with base; isolate by preparative HPLC or extraction if in organic media.
• Reductive stabilization of hydrazones:
  • Reagents: NaBH3CN or NaBH(OAc)3 in MeOH/AcOH or MeCN/AcOH; or H2/Pd-C in EtOH/AcOH.
  • Conditions: rt to 40 C; 1–6 h; monitor by LC–MS.
• Acyl azide/Curtius from acyl hydrazide:
  • Activation: nitrosylation (e.g., NaNO2/HCl at 0–5 C) to acyl azide, then thermal rearrangement to isocyanate.
  • Trapping: amines (ureas) or alcohols (carbamates) under anhydrous conditions.
  • Caution: manage exotherm and potential gas evolution; perform behind blast shield.
• N-Acylation/amide coupling:
  • Reagents: EDC·HCl/HOBt or HATU/DIPEA in DMF or NMP.
  • Stoichiometry: 1.0–1.5 equiv activated acid per hydrazide nitrogen; control mono- vs di-acylation by base and temperature.

Monitoring and analytics:

• LC–MS for conversion/selectivity; 1H NMR for hydrazone E/Z ratio; IR for C=O and N–N stretches.
• Avoid excess strong base or high temperatures that can promote hydrazide hydrolysis or rearrangement.

Safety & Handling

Always review the SDS before use. The following points provide general good-practice guidance for hydrazides and morpholine-containing organics.

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 (Product Data)
• Shipped In: Normal (Product Data)

General safety considerations (literature/general):

• Likely hazards: Many hydrazides are irritants or harmful if swallowed/inhaled; morpholine derivatives may cause skin/eye irritation. Treat as harmful/irritant in absence of specific data.
• PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dusts/vapors/aerosols.
• Incompatibilities: strong oxidizers, strong acids/bases (can lead to degradation or salt formation), acylating agents (uncontrolled reaction), and carbonyl electrophiles (can form hydrazones/acetals unintentionally). Avoid nitrosating conditions.
• First aid (overview):
  • Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical evaluation.
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: rinse mouth; do not induce vomiting; obtain medical help.
• Spill/cleanup: Absorb with inert material, avoid dust generation, collect for disposal in accordance with local regulations.
• Fire: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2/NOx; firefighters wear SCBA.

Defer to the SDS for definitive hazard classification and response measures.

Solvent Selection

This compound is a polar, multifunctional organic featuring a hydrazide and a morpholine ring. Solubility and handling benefit from polar media.

Item-specific solubility is not provided; the following are literature/general considerations for analogous morpholine–hydrazide scaffolds:

• Highly recommended (for stock solutions and reactions):
  • DMSO, DMF, NMP: excellent solvating power for amides/hydrazides; compatible with hydrazone formation and amide couplings.
  • Alcohols (MeOH, EtOH, i-PrOH): often good solubility; useful for carbonyl condensations with water removal.
• Conditional:
  • Water: solubility may be moderate and pH-dependent (enhanced under mildly acidic conditions via morpholinium formation). Buffer pH 4.5–6.0 is typical for hydrazone formation.
  • Acetonitrile/acetone: variable; may require co-solvent.
• Generally poor: non-polar solvents (hexanes, toluene) unless used as anti-solvents for crystallization.

Selection tips (general):

• For hydrazone formation with biomolecules: aqueous buffer (acetate, pH 4.5–5.5) with 10–30% DMSO to improve solubility; aniline or p-anisidine can catalyze.
• For amide coupling to carboxylates (to prepare or derivatize): DMF or NMP with carbodiimide additives.
• For purification: polar eluents (DCM/MeOH, EtOAc/MeOH, or MeOH with NH3 for silica) help elute polar hydrazides without tailing.

Storage & Reconstitution

Item-specific storage and handling:

• Storage Conditions: Room temperature (Product Data)
• Shipped In: Normal (Product Data)

Additional guidance (general):

• Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to moisture and strong light to limit hydrolysis or degradation.
• If preparing stock solutions, use dry, oxygen-free polar solvents (e.g., anhydrous DMSO or DMF) and store aliquots in sealed vials to minimize atmospheric moisture and adventitious carbonyl contamination.
• Reconstitution: Solubility data are not provided for this item. As a starting point, attempt dissolution at 10–100 mM in DMSO or DMF, or 1–10 mg/mL in alcohols; for aqueous work, adjust pH (slightly acidic) and use co-solvent if needed. Filter through 0.2 µm when required for bioconjugation workflows.
• Stability: Hydrazides are generally stable at ambient conditions when dry; avoid strong acids/bases and oxidants. For long-term storage, consider desiccation and inert atmosphere.

For definitive reconstitution concentrations, solution stability, and shelf-life, refer to the CoA/Spec Sheet and SDS.

Structure & Identity

A morpholine-bearing aliphatic hydrazide designed as a polar, amide-linked hydrazide handle for carbonyl-capture chemistry.

• Item name: 4-(4-Morpholinyl)butanohydrazide (SKU: M1301291)
• CAS: 1087616-69-0 (Product Data)
• PubChem CID: 30031527 (Product Data)
• InChIKey: 150417 (as provided in Product Data; note this is not a standard-length InChIKey)
• 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.

Structural features (general description from name; literature/general):

• Contains a terminal hydrazide moiety (–CONHNH2) capable of forming hydrazones with aldehydes/ketones.
• Includes a morpholine ring (six-membered heterocycle with one N and one O opposite each other). The “4-morpholinyl” substituent indicates attachment at the ring’s 4-position (a carbon), conferring tertiary-amine character when protonated and enhanced aqueous compatibility.
• A butylene spacer links the morpholine ring and the hydrazide carbonyl, providing conformational flexibility and distance from conjugation sites.
• Functional group summary: tertiary amine (in morpholine), cyclic ether (morpholine O), amide carbonyl, hydrazide N–N.

2D description (general): a morpholine ring substituted at C-4 by a butyl chain ending in an acyl hydrazide; the chain order is morpholine–(CH2)4–C(=O)–NH–NH2.

Synthetic Utility

This reagent serves as a versatile nucleophilic partner and convertible acyl equivalent.

Key transformations (literature/general):

• Carbonyl capture: Formation of hydrazones/azines with aldehydes and ketones; reversible under acidic aqueous conditions, enabling dynamic combinatorial chemistry or purification handles.
• Reductive functionalization: Hydrazones can be chemoselectively reduced to C–N single bonds (NaBH3CN, NaBH(OAc)3, catalytic hydrogenation), forming stable hydrazide or hydrazine derivatives.
• Acyl activation: Acyl hydrazides can be converted to acyl azides (e.g., via nitrosation), enabling Curtius rearrangement to isocyanates and downstream urea/carbamate formation with amines/alcohols.
• Coupling chemistry: The hydrazide can be N-acylated using activated esters (NHS, HATU/EDC couplings) to elaborate amide frameworks. Conversely, selective mono- vs di-acylation can be managed by base and protecting group strategies.
• Linker engineering: The butylene spacer and morpholine ring add hydrophilicity and distance, useful when hydrazide must access bulky carbonyl sites on macromolecules or surfaces.

Practical considerations:

• Protecting groups: Boc/CBz on the distal nitrogen can modulate selectivity. Monitor for acyl transfer and O/N-acylation under strong activating conditions.
• Analysis: LC–MS and 1H/13C NMR (DMSO-d6 or CD3OD) typically provide clear signatures; hydrazones often exhibit E/Z isomer signals.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent or antibody. No target, epitope, clone, or species reactivity information is provided in the Product Data.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1087616-69-0, the molecular formula is C8H17N3O2, and the molecular weight is 187.243 g/mol. InChIKey ITWLSNLSUGHDKA-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.