This compound belongs to the class of organic compounds known as fatty acid methyl esters. These are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
161.160 g/mol
XLogP3
0.700
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
5
Exact Mass
161.069 Da
Monoisotopic Mass
161.069 Da
Topological Polar Surface Area
72.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
140.000
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
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Application Protocols
No assay protocols or biological testing applications (e.g., WB, IHC, IF, FC) are specified for this small-molecule reagent.
General laboratory usage examples (non-validated, for synthetic context):
Hydrogenation setup: Charge substrate in EtOH (0.05–0.2 M), add 5 wt% Pd/C (5–10% w/w vs substrate), purge with N2 then H2, stir under 1–3 bar H2 at rt until uptake ceases. Filter through celite, concentrate, and analyze by GC/LC.
Basic hydrolysis: Dissolve in THF/H2O (4:1), cool to 0–5 °C, add 1 M NaOH (1.2 equiv), warm to rt for 1–2 h. After completion, acidify to pH ~2, extract with EtOAc, dry, and concentrate.
These are illustrative only; adapt to your equipment and safety protocols. For validated, application-specific methods, consult the primary literature.
Biological Roles
Item-specific biological roles are not defined for this catalog product; it is intended for research use only.
General context (biochemistry/chemical biology relevance without medical claims):
Functional surrogate/precursor: Reduction of the nitro group affords methyl 5‑aminopentanoate, which upon hydrolysis gives 5‑aminopentanoic acid (δ‑aminovaleric acid). Such ω‑amino acids are useful as spacers in bioconjugation, peptide modification, and as model compounds for studying chain length effects in enzyme specificity and membrane interactions.
Lipophilicity and permeability: As a small aliphatic ester, the parent compound exhibits modest hydrophobicity and can permeate organic phases; however, it lacks specific biological targeting motifs and is not designed as a probe.
Reactivity in bio-orthogonal contexts: The nitro group itself is generally inert toward most biomolecules, allowing the compound to act as a masked amine precursor in multistep syntheses conducted off-protein/off-cell, followed by downstream coupling of the amine-containing derivative.
Metabolic considerations (general): Esters may be susceptible to hydrolysis by esterases under biological conditions; nitro groups can be reduced enzymatically in certain microbial systems. These notes are provided as general chemical biology background only and do not imply suitability for in vivo use.
For any application intersecting biology, confirm purity, residual solvents, and endotoxin/bioburden requirements separately; this listing does not specify such controls.
Buffer Applications
This compound is a small, neutral organic ester and is not a buffering agent. It lacks acid/base pairs in the physiological pH range and is not typically used to prepare buffering systems.
Practical note:
If employing this molecule in aqueous workups or bioconjugation after conversion to the amine/acid, select conventional buffers (e.g., phosphate, HEPES, acetate) appropriate to the downstream chemistry. The parent ester should be handled predominantly in organic media to avoid hydrolysis.
Green Alternatives
Greener choices can be made in solvents and methods rather than in replacing the substrate itself.
Solvent alternatives (compared to legacy choices):
Replace DCM/CHCl3 with ethyl acetate or 2‑methyltetrahydrofuran (2‑MeTHF) for workups, extractions, and some reactions; both offer improved environmental profiles and can often replicate solvation for aliphatic esters.
Use ethanol or isopropanol as hydrogenation media instead of THF/DMF when compatible with chemoselectivity.
Reductive methods:
Favor catalytic hydrogenation (H2/Pd, H2/Raney Ni) over stoichiometric metal reductions (Fe/Zn/Sn salts) to minimize waste; employ reusable heterogeneous catalysts and continuous-flow where appropriate.
If transfer-hydrogenation is required, consider safer reductants (e.g., formate salts with Pd/C) and aqueous/alcoholic solvent systems.
Workup/processing:
Employ aqueous EtOAc biphasic systems for extractions to avoid halogenated waste; optimize crystallization or solvent swaps to minimize energy-intensive distillations.
Utilize solvent recovery for EtOAc/MeTHF/IPA.
Energy and safety:
Conduct reductions at ambient temperature/pressure when feasible; use flow hydrogenation to enhance mass transfer and lower solvent volumes.
Illustrative comparison (general):
DCM vs EtOAc: Similar dissolving power for small esters; EtOAc is biodegradable and has lower toxicity. Tradeoff: Slightly higher boiling point and flammability management required.
Fe/HCl vs H2/Pd: Fe/HCl generates significant iron sludge and salts; H2/Pd minimizes waste but requires hydrogen handling and careful control to avoid ester hydrogenolysis.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; it is supplied for research use only.
General formulation/manufacturing context (non-therapeutic, no clinical claims):
Intermediate: Methyl 5‑nitropentanoate serves as a convenient intermediate en route to 5‑aminopentanoate derivatives after nitro reduction. The resulting ω‑amino esters/acids are common linkers in small-molecule conjugates and polymer–drug attachment chemistries.
Protecting-group strategy: The methyl ester masks the carboxylic acid, facilitating chemoselective nitro reduction and amine derivatization prior to hydrolysis to the free acid when needed.
Process considerations: For scale-up, catalytic hydrogenation in alcohol/ester solvents is attractive due to benign solvent profiles and facile catalyst separation. Careful control prevents over-reduction (e.g., hydrogenolysis of C–O) and preserves the methyl ester.
Analytical controls: Identity/purity confirmation via GC–MS or LC–MS; monitoring residual catalysts and inorganic salts is advisable if the material is advanced to further synthetic steps that feed into GMP routes.
Note: No pharmacopoeial monograph is indicated for this compound. Any use in regulated manufacture would require establishing in-house specifications and validation.
Physical Properties
Item-specific specifications (this catalog item):
Boiling point, melting point, density, refractive index, water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values and qualitative behavior (for professional planning only; verify with primary sources for your application):
Physical state: Typically a colorless to pale liquid for low‑molecular‑weight aliphatic nitro esters (literature, analogous compounds)
Polarity: Moderately polar aprotic; dielectric lower than short-chain nitriles and higher than hydrocarbons (qualitative)
Solubility profile: Expected to be miscible with many organic solvents (EtOAc, DCM, THF, MeOH) and only sparingly soluble in water due to the hydrophobic chain despite polar functions (qualitative, literature expectation for aliphatic methyl esters with nitro)
Volatility: Moderate; handle under adequate ventilation to control vapor exposure (general practice)
Partition behavior: Nitroalkyl esters often show modest logP (ca. 0.5–1.5 range for C6 esters; literature on related structures). Use this only as a heuristic and measure if critical.
Practical notes:
The ester can undergo hydrolysis in strong aqueous acid/base; minimize prolonged exposure to high pH or strong acid if neat material integrity is needed.
The nitro group is thermally stable under normal laboratory conditions; avoid high-temperature distillation without assessment, and consider short-path techniques if purification is required.
For analytical methods, GC and HPLC (RP, C18) are commonly suitable for small aliphatic esters; UV detection may be weak above 230 nm due to limited chromophore.
Quality and Grades
Item-specific grade/purity and stabilizers:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades for this compound class (general guidance):
Research/Bulk grade aliphatic esters are commonly suitable for synthesis and process development; HPLC or GC assays typically indicate purity while residual solvents, water, and acidity may be limited. For moisture/acid-sensitive uses (e.g., base-catalyzed transformations), request detailed specifications.
Low-UV/HPLC grade (if offered) focuses on minimal background absorbance and low particulate, useful if employing UV detection at short wavelengths.
Trace metal content is generally low for small molecules synthesized by organic routes; if using in catalysis where metal poisons are critical, obtain ICP data.
Batch-specific documentation:
Certificate of Analysis (CoA) typically includes assay, related substances profile, water (Karl Fischer), and GC/HPLC chromatogram. For this item, any such values are Not specified for this item; refer to CoA/Spec Sheet.
Practical QA tips:
For amine synthesis via nitro reduction, monitor for residual acid/base or metal catalysts from prior steps that can affect hydrogenation.
Verify identity by GC–MS or LC–MS; the nitro group provides a strong NO2 fragment (m/z 46/30) in EI spectra of related compounds; confirm with exact mass when necessary.
Reaction and Applications
This nitro-functionalized methyl ester is a versatile bifunctional building block. Common research applications include:
Nitro-to-amine conversions (literature):
Catalytic hydrogenation (H2, Pd/C or Raney Ni) in EtOH/EtOAc gives methyl 5‑aminopentanoate. The primary amine can be further coupled (amide/urea/carbamate formation) or cyclized to lactams (e.g., δ-lactam formation after deprotection/hydrolysis under appropriate conditions).
Transfer hydrogenation (e.g., Fe/AcOH, Zn/HCl, SnCl2/HCl) affords the amine salt; neutralization/isolation under mild conditions helps preserve the ester.
Ester transformations:
Hydrolysis to 5‑nitropentanoic acid (aq. base or acid); the acid is amenable to further activation (acid chlorides, anhydrides) for coupling.
Transesterification to alternate alkyl esters (MeOH/acid or other ROH with catalytic acid/base). Control conditions to avoid nitro reduction.
Amidation via standard coupling reagents (EDC/HOBt, HATU, T3P) after converting to the acid or using direct ester aminolysis at elevated temperature with excess amine.
Chain-extension/linker chemistry:
After nitro reduction, the resulting ω‑amino ester (or ω‑amino acid) serves as a 5‑carbon spacer in conjugation chemistry, polymer modification, and surface tethering.
Radical and substitution chemistry:
Aliphatic nitro groups participate in radical denitration (e.g., Bu3SnH/AIBN or modern tin-free silane systems) to access the corresponding pentyl ester.
Practical tips:
Protect the ester if using strong base during nitro chemistry; consider chemoselective reductions that spare the ester (e.g., catalytic hydrogenation over Pd/C at ambient pressure). Monitor for over-reduction or N‑alkylation side products.
Reaction Conditions
General, literature-informed conditions for common transformations of methyl 5‑nitropentanoate (verify and optimize for your system):
Nitro reduction to primary amine (chemoselective over ester):
Catalytic hydrogenation: H2 (1–5 bar), 5–10 wt% Pd/C (2–10 mol% Pd relative to substrate), solvent EtOH or EtOAc, 20–40 °C, 2–8 h. Work up by filtration of catalyst and concentration. Typically preserves methyl ester under mild conditions.
Transfer hydrogenation: Ammonium formate or cyclohexene with Pd/C; EtOH or MeOH, 25–50 °C, 3–10 h. Useful when H2 infrastructure is unavailable.
Metal/acid reductions: Fe powder (3–5 equiv) in AcOH/H2O or Zn/HCl (aq), 0–25 °C to reflux, 1–6 h; isolate as amine salt then free-base. Monitor for ester hydrolysis under aqueous acidic conditions.
Ester hydrolysis/transesterification:
Basic saponification: NaOH (1–2 equiv) in MeOH/H2O (1:1) or THF/H2O, 0–25 °C to rt, 1–4 h → 5‑nitropentanoic acid (acidify to pH ~2 to isolate). Nitro group remains intact.
Acidic methanolysis/transesterification: Catalytic H2SO4 or p‑TsOH (1–5 mol%) in ROH solvent, reflux (e.g., MeOH, EtOH), 2–12 h. Control water content to drive equilibrium.
Amidation (via acid):
EDC·HCl (1.1–1.5 equiv), HOBt or Oxyma (1.1–1.5 equiv), base (DIPEA), solvent DMF/DCM, 0 °C to rt, 2–16 h. Alternatively, T3P or HATU for more hindered amines.
Radical denitration:
AIBN (10 mol%) with tris(trimethylsilyl)silane or Bu3SnH (1.2 equiv) in toluene, 80–110 °C, 2–6 h. Provides the de-nitrated alkyl ester; tin-free protocols preferred for greener practice.
Monitoring and workup:
Track progress by GC/LC and IR (NO2 vs NH/CO signals). For hydrogenations, ensure complete gas uptake and absence of nitroso/hydroxylamine intermediates. Neutralize cautiously after metal/acid reductions to avoid emulsions and ester cleavage.
Safety and Handling
Item-specific hazard details:
GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
General safety guidance for aliphatic nitro esters (provide as context; always defer to the SDS for the specific lot):
Likely hazards: Combustible liquid; may cause skin/eye irritation; vapor may cause respiratory irritation. Nitroalkyls can be harmful if swallowed or inhaled (based on class behavior).
PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood.
Storage incompatibilities: Avoid strong bases and strong acids (hydrolysis of ester), strong reducing agents (may affect nitro group), and strong oxidizers. Keep away from ignition sources.
Handling tips:
Prevent moisture ingress to limit hydrolysis over time; keep container tightly closed.
Use inert gas blanket for long-term storage of opened containers if feasible.
When scaling reductions of nitro to amine, control exotherm and gas evolution (e.g., during catalytic hydrogenation).
First aid overview (non-exhaustive):
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; obtain medical advice if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Combustion may release NOx and CO/CO2.
Always consult the SDS for authoritative, product-specific safety data and regulatory information.
Solvent Selection
Applicability: As a small, neutral, moderately polar ester with a nitro terminus, solvent choice typically aims to balance solubility of both starting materials and catalysts in subsequent transformations.
Polarity class (qualitative): Moderately polar aprotic solute; dissolves well in common organic solvents.
For reductions of the nitro group: Alcoholic solvents (EtOH, iPrOH) or ethyl acetate with H2/Pd are common; avoid strongly basic media that can hydrolyze the ester.
For ester hydrolysis or transesterification: Alcoholic solvents under acid catalysis (MeOH/H2SO4) or biphasic aqueous base (NaOH, K2CO3) with an organic co-solvent (THF/MeTHF) to manage phase transfer.
For amidations: Polar aprotic media (DMF, NMP, DCM, THF, 2-MeTHF) with coupling reagents; low-water content recommended to limit hydrolysis.
Comparison notes (general):
DCM offers fast dissolution and easy removal but has environmental concerns; EtOAc or 2-MeTHF are greener with similar solvation for esters.
Alcohols can assist hydrogenation rates but may participate in transesterification; monitor for methyl/alkyl exchange.
Tip: If planning aqueous workups, add a modest percentage of EtOAc to improve phase disengagement and extraction efficiency for this C6 ester.
Storage and Reconstitution
Item-specific:
Storage Conditions: Room temperature (per Product Data)
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for aliphatic nitro esters and methyl esters:
Store tightly closed in the original container at ambient temperature, away from direct sunlight and ignition sources.
Protect from moisture to limit ester hydrolysis during prolonged storage; adding a dry inert gas headspace after opening can improve shelf life.
Segregate from strong acids/bases and strong oxidizing or reducing agents.
Reconstitution/handling:
If the material is solidified or viscous at lower temperatures, warm gently to ambient and swirl to homogenize before use.
For solution preparation, use dry, oxygen-free solvents when conducting air- or moisture-sensitive downstream reactions (e.g., selective reductions or couplings). Filter through a PTFE syringe filter (0.45 µm) if particulate is observed.
Stability notes:
Under normal lab conditions at room temperature, aliphatic nitro esters are generally stable. Avoid unnecessary heating or extended exposure to aqueous media.
For long-term storage after first opening, periodic GC/HPLC check is recommended to confirm assay and absence of hydrolysis products (acid/alcohol).
Structure and Identity
Brief: Methyl 5-nitropentanoate is an aliphatic nitro-terminated methyl ester, useful as a bifunctional building block (ester + nitro) for chain-extension, reductions to amines, and subsequent derivatizations.
Item-specific (from Product Data):
SKU: M996434
CAS: 34805-47-5
PubChem CID: 543911
InChIKey: 439356 (as provided in Product Data)
Storage Conditions: Room temperature
Research Use Note: For research use only
Literature/computed identity details (general reference information for this compound):
Structural features (2D description): A linear five‑carbon chain bearing a terminal nitro group at C5; C1 is a methyl ester carbonyl (MeO–C(=O)–), followed by four methylenes (–CH2–) leading to –CH2–NO2.
Stereochemistry: None (achiral, no stereocenters)
General notes:
The ester confers typical electrophilicity at the carbonyl; the nitro group is a versatile handle for reductions to the corresponding primary amine or for radical denitration chemistry.
Synthetic Utility
Key functional motifs and their reactivity:
Ester (–CO2Me): Electrophilic carbonyl enabling hydrolysis, transesterification, aminolysis (with activation or forcing conditions), and reduction to alcohols (DIBAL-H to aldehyde at low temperature; LiAlH4/borohydrides to primary alcohols under more forcing conditions, noting potential nitro incompatibility).
Aliphatic nitro (–CH2–NO2): Precursor to primary amine via reduction (H2/Pd, Raney Ni, catalytic transfer hydrogenation, or selective metal/acid reductions). Can participate in radical denitration to give the corresponding alkyl derivative.
Strategic roles:
Bifunctional spacer: After nitro-to-amine reduction, provides a 5‑carbon ω‑amino ester or ω‑amino acid upon hydrolysis—valuable as a flexible linker in conjugation and materials.
Route B: Ester manipulation first (hydrolysis/transesterification) → nitro reduction on the acid/alternate ester → downstream couplings.
Selectivity management:
Choose conditions orthogonal to the second functionality: e.g., hydrogenation to reduce NO2 while preserving methyl ester; avoid strong base that could saponify.
Analytical: Monitor by GC or LC; nitro-to-amine conversion is readily tracked by IR (NO2 stretches ~1550/1350 cm−1 disappearing; NH bands appearing) and MS.
Target Specificity
Not applicable. This product is a small organic molecule (nitro-functionalized ester) and is not an antibody, enzyme, or biological ligand with defined target specificity.
For applications requiring molecular recognition (e.g., bioconjugation), consider derivatives obtained after nitro reduction to the primary amine, which can be coupled to target-binding scaffolds.
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