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
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
167.210 g/mol
XLogP3
-0.600
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
167.106 Da
Monoisotopic Mass
167.106 Da
Topological Polar Surface Area
39.100 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
142.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic use, refer to the Reaction Conditions and Application notes in other sections.
Biological Roles
This compound is provided for research use as a synthetic building block and does not have assigned biological function in isolation.
General context (literature):
Morpholine is a common motif in small-molecule libraries and can modulate basicity, solubility, and H‑bonding patterns. Protonated morpholine can enhance aqueous solubility of derivatives used in biochemical assays.
Pyrazole is a privileged heteroaromatic scaffold; its ring nitrogen can act as a weak base and ligand to metals, and it features in many bioactive chemotypes. Here, N1 is alkylated, leaving the second nitrogen as the primary coordination/basic site.
Potential research relevance (non-clinical, general):
As a fragment or intermediate, 2-(1H-pyrazol-1-ylmethyl)morpholine can be incorporated into probe molecules for target engagement studies or as a polarity handle in SAR campaigns.
The dual heteroatoms support metal-binding hypotheses in enzymology models or for assembling coordination complexes as biochemical tools.
No medical, diagnostic, or therapeutic claims are made or implied. For any biological testing, confirm purity, counterions, and residual solvent content via the CoA and perform appropriate controls.
Buffer Applications
This product is not a dedicated buffer reagent. While morpholine-derived sulfonic acids (e.g., MOPS, MES) are widely used as biological buffers, 2-(1H-pyrazol-1-ylmethyl)morpholine lacks the sulfonic acid functionality required for classical Good’s buffers.
Practical note:
If an aqueous stock is required (e.g., for assay setup), prepare the hydrochloride or another suitable acid salt to improve water solubility, then adjust to the desired pH with compatible buffers (HEPES, phosphate, acetate).
For pH-sensitive experiments, avoid relying on the compound’s intrinsic basicity for buffering; instead, use an established buffer system and dissolve this compound as a solute within that buffer.
Refer to standardized buffer systems (phosphate pH 6–8, HEPES pH 6.8–8.2, acetate pH 4–5.5) for solution preparation; this compound serves only as an analyte or reagent therein.
Green Alternatives
While this product is a heterocyclic building block (not a solvent), greener choices can be made in its synthesis and use, particularly in solvent selection and reagent choice.
Greener solvent choices (general guidance):
Prefer EtOAc, MeCN, CPME, or 2‑MeTHF over chlorinated solvents (e.g., DCM) when feasible for acylations and alkylations.
For high-solubility needs, consider propylene carbonate or water/EtOH mixtures (salt form) instead of DMF/NMP where reaction compatibility allows.
Greener coupling/activation strategies:
Use carbonyldiimidazole (CDI) or DMTMM as alternatives to HATU/HBTU to reduce HF-containing waste; employ solventless or microwave conditions when appropriate.
Explore biocatalytic amidation or organocatalytic variants for late-stage functionalization if substrate scope permits.
Workup/waste minimization:
Employ telescoped sequences (e.g., in situ reductive amination without isolation of the imine).
Replace stoichiometric inorganic bases (Cs2CO3) with polymer-supported or recyclable bases when possible; recover and reuse metal catalysts if coordination chemistry is pursued.
Comparison (general; qualitative):
DCM vs EtOAc: EtOAc is less toxic and derived partly from bio-ethanol; similar polarity; EtOAc may require temperature tuning for reactivity.
DMF/NMP vs MeCN/2‑MeTHF: MeCN/2‑MeTHF have better environmental profiles and easier removal; DMF/NMP offer higher solvation but incur higher EHS burdens.
These recommendations are general; confirm reaction compatibility experimentally.
Pharmaceutical Uses
Status and scope: This listing is for research use only. The compound is a synthetic intermediate/building block and is not an approved excipient or active ingredient.
The morpholine moiety is often introduced into lead molecules to tune solubility and basicity. 2-(1H-pyrazol-1-ylmethyl)morpholine can serve as a precursor to salts (e.g., HCl) that facilitate in vitro screening and ADME studies of derivatives.
As a tertiary amide or urea/sulfonamide derivative, frameworks derived from this building block may display improved metabolic stability; however, any performance claims require case-specific data and are beyond the scope here.
Compendial status: No pharmacopeial monograph is indicated. Any use in process development should include full characterization (identity, purity, residual solvents, elemental impurities) per ICH guidelines if progressing toward regulated environments.
No clinical or therapeutic claims are made. For GMP or preclinical development, source control, impurity profiles, and stability studies must be established separately.
Physical Properties
Item-specific physical property values are not provided for this catalog entry; consult the CoA/SDS for authoritative specifications. The following are general, literature/computed considerations based on the named structure and should be used as guidance only.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling point (literature/analogy): Not specified for this item; small, polar heterocycles of MW ~167 g/mol are often low-melting solids or high-boiling oils; exact values not established here.
Density/refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general expectations):
Likely highly soluble in polar organic solvents (DMSO, DMF, MeOH, EtOH) due to the morpholine and pyrazole heteroatoms (general/literature expectation).
Expected to be miscible with water to a useful extent as a free base; water solubility increases markedly upon protonation to the hydrochloride or other salts (general/literature expectation).
Acid–base properties (literature):
Morpholine conjugate acid pKa ~8.3–8.6 (literature for morpholine); secondary ring nitrogen here is expected to show similar basicity, modulated slightly by the 2‑substituent.
Pyrazole ring (with N1 alkylated) retains one pyridine-like N (weak base; conjugate acid pKa typically ~2–3 for unsubstituted pyrazole; literature).
Partitioning (literature/computed expectation): logP expected to be low to moderate (<1) in neutral form; cationic salt forms are strongly hydrophilic. Specific logP for this item: Not specified.
Always verify exact physical constants from the item’s CoA/Spec Sheet before process design.
Quality and Grades
Grade/purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
What grade means (general guidance):
For small-molecule building blocks, typical offerings include research grade (>95% or >97% by HPLC/GC), assay with NMR/LC–MS identity confirmation, and residual solvent/volatile limits consistent with research use. When stated, HPLC grade refers to solvents rather than reagents; for reagents, “>98%” etc. indicates assay purity. Absent explicit numbers here, rely on the supplied CoA.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Given the structure, stabilizers are generally unnecessary; however, salt forms (e.g., HCl) may be used in other contexts to enhance handling—this listing pertains to the free base unless otherwise noted.
Analytical characterization typically expected (general):
Identity by 1H/13C NMR and MS; purity by HPLC/GC; water by Karl Fischer (if relevant); residual solvents by GC; elemental analysis as applicable. Item-specific acceptance criteria are defined on the CoA.
Implications for use:
For air/moisture-stable amine heterocycles such as this, routine lab handling is appropriate; for sensitive transformations (e.g., metal-catalyzed couplings), consider pre-drying or using freshly opened material, and verify purity by quick 1H NMR to rule out amine salts or adventitious water if yields are critical.
Reaction and Applications
As a heterobifunctional building block, 2-(1H-pyrazol-1-ylmethyl)morpholine combines a nucleophilic secondary amine with a weakly basic, metal-binding pyrazole. This makes it valuable in heterocycle elaboration, ligand design, and fragment-based synthesis.
Amide formation: acylate the morpholine N with acid chlorides or activated esters (HATU, EDCI, CDI) to give tertiary amide motifs prevalent in medicinal chemistry.
Reductive amination: convert to tertiary amines by condensing aldehydes/ketones (NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation) under mildly acidic conditions.
N‑alkylation: SN2 alkylation (alkyl halides, sulfonates) to form tertiary morpholine derivatives; use non-nucleophilic base (K2CO3, Cs2CO3) in polar aprotic solvent.
Sulfonylation/carbamoylation: install sulfonamides (RSO2Cl) or carbamates (chloroformates) on the secondary amine to modulate pKa and physicochemical properties.
Metal coordination and chelation: the pyrazole nitrogen can bind to transition metals (Cu, Zn, Fe) enabling formation of mono- or polynuclear complexes; useful for catalyst-ligand scouting.
Practical tips:
The morpholine N (pKaH ~8.5, literature) is protonated near neutral pH; for nucleophilic reactions, maintain mildly basic conditions or pre-generate the free base.
Avoid nitrosating conditions; secondary amines can form N‑nitrosamines.
2‑Substitution on morpholine can subtly reduce basicity vs unsubstituted morpholine; consider slightly stronger base or higher temperature for sluggish acylations.
Tertiary amine formation by reductive amination often proceeds in good yields (60–90%) in MeOH/AcOH with NaBH3CN at rt–40 °C.
Amide couplings with acid chlorides typically quantitative at 0–25 °C with triethylamine in DCM.
Reaction Conditions
General, literature-style guidance for common transformations of this scaffold. Always optimize for your substrate set.
Amide formation (acylation of morpholine N):
Typical: acid chloride (1.1–1.5 eq), Et3N (2.0 eq), DCM or EtOAc, 0–25 °C, 0.5–4 h; workup with aqueous bicarbonate then brine. Alternative: HATU (1.1 eq), DIPEA (2.0 eq), DMF/MeCN, rt, 1–2 h.
Expected outcomes: good to excellent yields; minimize overacylation by temperature control.
Reductive amination (to tertiary amines):
Form imine with aldehyde/ketone (0.5–2 h, MeOH or MeCN, 0.5–1.0 eq AcOH), then reduce with NaBH3CN (1.2–2.0 eq) at rt–40 °C for 2–8 h. Alternatively, NaBH(OAc)3 in DCE/MeCN with 3 Å MS for water removal.
N‑alkylation (SN2):
Alkyl halide (1.1–1.5 eq), K2CO3 or Cs2CO3 (2–3 eq), MeCN/acetone, 40–70 °C, 4–16 h. For more challenging electrophiles, use KI or TBAI as halide scavenger/catalyst.
Sulfonylation/carbamoylation:
RSO2Cl or ClCOOR′ (1.1–1.3 eq), base (2.0 eq; DIPEA or pyridine), DCM/EtOAc, 0–25 °C, 1–3 h.
Metal coordination/complex assembly (pyrazole):
Combine with metal salts (e.g., Cu(II), Zn(II)) in MeOH/MeCN at rt; adjust stoichiometry for mono- vs polydentate complexes; characterize by UV–Vis/ESI–MS.
Notes:
Maintain mildly basic conditions to keep the morpholine nitrogen nucleophilic; in protic media at neutral pH, significant protonation can reduce rates.
If salt formation occurs inadvertently (e.g., HCl uptake), free-base regeneration by basification and extraction may be necessary before further transformations.
Safety and Handling
GHS classification, signal word, pictograms, and H-statements (item-specific): Not specified for this item; refer to the SDS for authoritative safety information.
General hazards (general chemistry guidance):
Contains a secondary amine (morpholine), which can be irritating to skin, eyes, and respiratory tract. Amines may cause sensitization in susceptible individuals.
Basic organic amines may react exothermically with strong acids, acylating agents, anhydrides, acid chlorides, isocyanates, and strong oxidizers. Avoid contact with nitrosating agents (e.g., nitrite in acidic media) to prevent formation of N‑nitrosamines.
Recommended PPE and controls:
Wear lab coat, safety glasses or splash goggles, and nitrile gloves; handle in a fume hood to minimize inhalation.
Use secondary containment for larger volumes; keep eyewash and safety shower accessible.
First-aid overview (general):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with copious water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
Ingestion: rinse mouth; do not induce vomiting; obtain medical advice.
Fire-fighting (general):
Likely combustible organic; use dry chemical, CO2, or alcohol-resistant foam. Combustion may produce NOx and COx.
Spill/leak response (general):
Absorb with inert material (vermiculite, sand), collect for disposal; wash area with water/detergent, avoiding incompatible reagents.
Always consult the product’s SDS and your institutional EHS procedures before use.
Solvent Selection
This item is a polar, basic heterocycle used as a building block rather than a solvent. Nevertheless, solvent choice strongly impacts its reactivity and handling.
Highly soluble in polar aprotic media: DMSO, DMF, NMP, acetonitrile.
Good solubility in alcohols (MeOH, EtOH) and partially in water as the free base; excellent in water when converted to a mineral-acid salt (e.g., HCl) for bioconjugation or assay prep.
Limited solubility expected in nonpolar hydrocarbons (hexanes, toluene) unless co-solvent is used.
Selection by application:
Amide couplings / acylations: DMF, DCM, or MeCN with base (DIPEA) are typical; for greener choices, 2‑MeTHF or EtOAc often suffice with modern coupling agents.
Alkylation to tertiary amines: MeCN, acetone, or isopropanol with carbonate bases; polar aprotic solvents favor SN2.
Metal coordination/complexation studies: MeOH, MeCN, or aqueous buffers (salt form) wherein the pyrazole N can participate in binding.
Quick comparison (general):
DMSO/DMF: maximal solubility, high boiling; harder workup.
MeCN/EtOAc: balanced polarity, easier removal; may need higher equivalents/base.
Aqueous media (salt form): ideal for bioconjugation-like workflows; adjust pH 7.5–9 for free-base availability.
Storage and Reconstitution
Storage (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from incompatible reagents (strong acids, acylating agents, and strong oxidizers). Protect from prolonged exposure to air if forming hygroscopic salts.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Stability (general guidance): Secondary amine heterocycles like morpholine derivatives are typically air- and moisture-stable. Avoid nitrosating conditions. For long-term storage, keep in amber glass if light sensitivity of downstream impurities is a concern.
Prepare concentrated stocks in DMSO, DMF, MeOH, or MeCN (e.g., 10–100 mg/mL) for synthetic or screening workflows. Filter (0.22 µm PTFE) if needed.
For aqueous work, form an acid salt (e.g., HCl) to enhance solubility, then dilute into buffer. Adjust pH to maintain desired protonation state.
Freeze–thaw: Typically not required. If preparing aqueous stocks, aliquot and freeze at −20 °C to avoid repeated freeze–thaw.
Always consult the product’s CoA and SDS for definitive storage and handling guidance. Research use only.
Structure and Identity
A bifunctional heterocycle combining a morpholine ring and an N1‑substituted pyrazole via a methylene linker at the 2‑position of morpholine. Useful as a polar heteroaromatic building block for synthesis and coordination studies.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/derived from the name; not item-specific specs):
Heterocycles: one morpholine ring (O- and N-heteroatoms) and one pyrazole ring (1,2‑diazole).
Connectivity: morpholine is substituted at C-2 with a –CH2–N(pyrazol-1-yl) group (i.e., pyrazole N1 is alkylated by the methylene).
Functional groups: secondary amine (morpholine NH), ether (ring O), aromatic azole (pyrazole) with one pyridine-like N (weak base) and one N bound through the linker (non-basic when N1-alkylated).
Stereochemistry: none specified; the described structure is achiral.
Empirical formula and formula mass (literature/structure-derived calculation):
Molecular formula (calculated from name): C8H13N3O (literature/computed)
Formula weight (calculated): ~167.21 g/mol (literature/computed)
2D structure in words: a six-membered morpholine ring (–O–CH2–CH2–NH–CH2–CH2–) bearing at the carbon alpha to oxygen a methylene substituent that terminates at N1 of a five-membered aromatic pyrazole ring.
Synthetic Utility
Key reactivity arises from the secondary amine (morpholine) and the pyrazole ring.
Functional group handles:
Secondary amine (morpholine N): nucleophilic; engages in acylation, sulfonylation, carbamoylation, alkylation, reductive amination. Salt formation enables phase-switch manipulations.
Pyrazole ring: weak base and ligand; participates in electrophilic aromatic substitution (at C4/C5 under activating conditions), N2-metal coordination, and N‑oxide formation (with peracids) on suitably substituted analogs.
Benzylic-type linker (–CH2–N–pyrazolyl): can be leveraged for further diversification (e.g., oxidation to iminium followed by nucleophile capture) under specialized conditions.
Retrosynthetic value:
Serves as a convergent junction: late-stage installation onto morpholine (via N-alkylation/acylation) or onto pyrazole (via N‑alkylation with a 2‑chloromethylmorpholine synthon) to rapidly access analog series.
Orthogonality:
The pyrazole nitrogen remains mostly unreactive toward acylation under standard conditions, allowing chemo-selective modification at the morpholine N.
Under strongly basic conditions, N–H acidity at pyrazole (not present here due to N1-alkylation) is not a concern, simplifying reaction planning compared with N‑H pyrazoles.
Library expansion:
Rapid access to tertiary amines (alkylate or reductively aminate), amides (acylate), ureas (with CDI-activated amines), and sulfonamides (with sulfonyl chlorides), enabling matrix libraries for SAR.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity is defined for this item.
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