This compound belongs to the class of organic compounds known as secondary carboxylic acid amides. These are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
103.120 g/mol
XLogP3
-0.800
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Exact Mass
103.063 Da
Monoisotopic Mass
103.063 Da
Topological Polar Surface Area
49.300 Ų
Heavy Atom Count
7
Formal Charge
0
Complexity
47.000
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 manufacturer-tested application protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule reagent.
For synthetic applications, consider the general protocols outlined under “Reaction Conditions.”
For analytical handling:
LC analysis: Reverse-phase HPLC with water/MeCN + 0.1% formic acid or ammonium formate can resolve this polar analyte; consider HILIC for improved retention.
NMR: Record in D2O, CD3OD, or DMSO-d6; hydrogen bonding may broaden signals—gentle heating or dilute solutions improve resolution.
Item-specific tested protocols and recommended dilutions are not provided; refer to your method development best practices.
Biological Roles
Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.
General context (no therapeutic claims)
N-(3-hydroxypropyl)formamide is a small, synthetic amide–alcohol. It is not known as a native metabolite in central biochemical pathways.
As a formamide derivative, it may participate in hydrogen-bond networks and can serve as a model compound for studying amide solvation, hydrogen bonding, and conformational preferences in aqueous and mixed solvents.
Upon N-deformylation, it yields 3-aminopropanol, a simple amino alcohol that frequently appears as a fragment in biomaterials, zwitterionic surfactants, and linker motifs for bioconjugation.
Its dual functionality (amide + alcohol) makes it a convenient probe for enzyme catalysis studies (e.g., amidases, esterases) and for assessing chemoselectivity in aqueous media.
Laboratory implications
High water miscibility and polarity facilitate its use in bioconjugation method development, where solvating ability and reduced volatility are advantageous.
In protein/oligonucleotide chemistry development, the compound can act as a test substrate for evaluating coupling efficiencies, hydrolysis kinetics, or protective group strategies under benign, water-rich conditions.
All biological notes above are general literature context; this product is supplied strictly for research use only.
Buffer Applications
This compound is not a conventional buffer component and does not provide a useful acid/base conjugate pair for buffering in typical laboratory pH ranges.
Applicability
Not typically used to formulate buffers or as a buffering agent in electrophoresis or cell culture.
Practical guidance
For aqueous reactions involving N-(3-hydroxypropyl)formamide, choose established buffering systems (e.g., phosphate, HEPES, acetate) appropriate to your pH needs and compatible with amide stability.
Monitor pH if conducting hydrolysis or coupling reactions; the substrate does not meaningfully buffer the medium.
If a buffer-like role is desired, consult standard buffering agents; use this compound as a substrate or co-solute rather than as a buffer.
Green Alternatives
Because N-(3-hydroxypropyl)formamide is typically used as a reagent/building block rather than a process solvent, “green alternatives” considerations focus on the choice of media and reagents employed with it.
Greener solvents for common operations (general guidance)
Alcohol modifications (esterification/activation): Prefer EtOAc, MeTHF, or 2-MeTHF over DCM/THF when feasible; aqueous ethanol can support enzyme-catalyzed esterifications.
Oxidations of the primary alcohol: Employ TEMPO/NaClO in biphasic water/EtOAc or water/MeCN at ambient temperature, minimizing chlorinated solvents and heavy metals.
Hydrolysis (N-deformylation): Conduct in water or water/alcohol mixtures; avoid excess organic cosolvents; recover and neutralize formate streams.
Reagent choices with lower hazard (general)
Use catalytic, chemoselective activations (e.g., EDCI/DMAP) instead of acid chlorides and pyridine when compatible.
Favor solid-supported reagents and recyclable catalysts to simplify workup and reduce waste.
Greener options: EtOAc or MeTHF (medium polarity), Cyrene or propylene carbonate (for polar aprotic needs), aqueous buffers with organocatalysts or biocatalysts.
Trade-offs: Highly polar substrates like this often dissolve best in dipolar aprotics (DMF/DMSO), which have disposal concerns. Mixed-solvent systems (EtOH/MeCN/water) can mitigate this while maintaining reactivity and enabling easier solvent recovery.
Pharmaceutical Uses
Item-specific regulatory/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
General context (no therapeutic claims)
N-(3-hydroxypropyl)formamide can serve as a synthetic intermediate toward amino alcohol–containing APIs, linkers for conjugates, or polymerizable monomers after appropriate derivatization.
The parent molecule itself is not a common excipient. However, its deformylation product (3-aminopropanol) is frequently used to build zwitterionic and cationic excipient frameworks (e.g., betaines, quaternary ammonium derivatives) and hydrophilic linkers.
High polarity and water miscibility ease handling in aqueous process streams, but residual solvent removal and drying steps should be validated due to hydrogen bonding and potential hygroscopicity.
If incorporated as a process intermediate, ensure thorough purge of formate/byproducts per ICH Q3A/B when hydrolysis or reductive steps are used.
No pharmacopeial monograph or excipient designation is claimed for this product listing. Use is limited to research and development in non-clinical settings.
Physical Properties
Item-specific physico-chemical data
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Density, refractive index, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Phase at ambient: typically a low-melting, polar liquid or low-melting solid for small amide–alcohols of this size; strongly hydrogen bonding.
Solubility: expected to be completely miscible with water and polar protic solvents (MeOH, EtOH); high solubility in polar aprotic media (DMSO, DMF) due to dual H-bonding character.
Boiling/melting points: small N-formylated amino alcohols commonly have elevated b.p. due to association; specific values for this compound should be taken from primary literature or the CoA.
LogP: anticipated very low (strongly hydrophilic) for a C4 amide-alcohol; consult measured data if partitioning is critical.
Practical notes (general)
The presence of both –OH and –CONH– leads to strong intermolecular hydrogen bonding; viscosity and melting behavior may be sensitive to water content.
If precise values (bp, mp, nD, density) are required for process design or chromatography, obtain the lot-specific CoA/Spec Sheet or measure under controlled conditions.
Authoritative values for this catalog item are not specified above; defer to CoA/SDS for exact numbers.
Quality and Grades
Item-specific quality
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 (general guidance for small-molecule reagents)
Research grade: adequate for most synthetic/biochemical workflows; typical focus on assay purity by GC/HPLC and major residual solvents.
Analytical/HPLC grade (if offered): tighter control on UV absorbance and trace impurities; supports analytical workflows and photometric detection.
Bio/Cell culture suitability (if claimed): requires low endotoxin/bioburden; absence of animal-derived components is sometimes specified. No such claims are made for this listing.
Practical QC considerations for N-(3-hydroxypropyl)formamide (general)
Key assays often include water content (Karl Fischer), residual solvents, and identity purity by NMR/GC/HPLC.
Because the material is highly polar and hydrogen-bonding, GC methods may require derivatization; LC or qNMR can be preferable for purity assessment.
Trace metal specifications are typically irrelevant unless the reagent will be used in metal-catalyzed transformations at ppm-sensitive loadings.
Documentation
For this SKU, consult the lot-specific Certificate of Analysis for: assay/purity method, water content, residual solvent profile, and any stabilizers.
If you require application-specific quality (e.g., low UV background, bioburden limits), contact Aladdin Scientific for availability of tailored grades or additional QC.
Reaction and Applications
N-(3-hydroxypropyl)formamide is a bifunctional handle that provides orthogonal reactivity at the alcohol and at the N-formyl moiety, enabling versatile synthetic elaboration.
Transformations at the alcohol (general literature)
Activation and substitution: Convert the –CH2OH to a leaving group (tosylate/mesylate) under standard conditions, then perform SN2 displacement to introduce halides, azides, thiols, or other nucleophiles; intramolecular cyclizations to morpholine/oxazoline motifs are accessible with appropriate partners.
Esterification and carbonate formation: Use Steglich or acid chloride methods to append acyl groups; carbonate/urethane linkages enable prodrug-like or polymer conjugation strategies.
Oxidation: Primary alcohol oxidation to aldehyde (e.g., Swern, Dess–Martin) or acid (TEMPO/bleach variants), furnishing an amide-bearing aldehyde/acid for further coupling.
Transformations at the N-formyl group (general literature)
Hydrolysis (N-deformylation): Acidic or basic aqueous conditions liberate 3-aminopropanol, a valuable intermediate for zwitterions, betaines, or further N-acylation/alkylation.
Reductive pathways: Borane or catalytic hydrogenation conditions can deoxygenate formamides to amines. Alternatively, formyl groups participate in N-methylation chemistry under Eschweiler–Clarke-type contexts with formic acid (method-dependent outcome; consult primary literature to avoid overalkylation).
Linker/bioconjugation utility
The 3-carbon spacer offers flexibility between attachment points; one end can be anchored via amide chemistry while the alcohol engages in orthogonal coupling to carboxylic acids, isocyanates, or activated carbonates.
Practical tips
Drying: If anhydrous conditions are needed (e.g., for acid chloride couplings), dry over molecular sieves or by azeotrope; strong heating can induce amide hydrolysis in wet media.
Protecting groups: The alcohol can be protected (e.g., TBDMS, THP) to enable selective N-chemistry, or vice versa (Boc-protect 3-aminopropanol after deformylation) to manage chemoselectivity.
Reaction Conditions
The following representative conditions are general literature guidance for molecules of this class; they are not item-specific specifications.
Alcohol activation and substitution
Tosylation: p-TsCl (1.1–1.5 eq), pyridine or Et3N, 0–25 °C, 2–12 h; monitor by TLC/LC. Work under anhydrous conditions to avoid hydrolysis.
SN2 displacement of tosylate: NaN3, NaI, or thiols in DMF/MeCN, 25–80 °C, 2–24 h; for azide, subsequent Staudinger/hydrogenation to amine.
Oxidation of primary alcohol
TEMPO/NaClO/NaClO2 (for acid): biphasic H2O/EtOAc or MeCN, 0–25 °C; typical 70–95% yields reported for primary alcohols under optimized conditions.
Swern or Dess–Martin to aldehyde: DMSO/(COCl)2 then Et3N at −78→0 °C (Swern) or DMP in DCM at 0–25 °C; generally high selectivity for primary alcohols adjacent to non-activated chains.
N-Deformylation (hydrolysis)
Acidic: 3–6 M HCl, reflux 1–6 h, aqueous medium; affords 3-aminopropanol salts after basification.
Basic: 2–6 M NaOH, 60–100 °C; monitor to suppress competing alcohol oxidation.
Reductive manipulation of the formamide (method-dependent outcomes; consult primary literature)
Borane–THF: reduces formamides to amines under reflux; quench carefully. Can deliver 3-aminopropanol from the N-formyl precursor.
Catalytic hydrogenation in presence of formic acid can effect N-methylation (Eschweiler–Clarke-type chemistry); control conditions to avoid overalkylation.
Amine protection post-deformylation: Boc2O, NaHCO3, dioxane/H2O, 0–25 °C.
Always optimize stoichiometry, temperature, and solvent based on scale and impurity profile.
Safety and Handling
GHS and hazard statements (item-specific)
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification and pictograms: Not specified for this item; refer to SDS.
General safety profile (for similar amide–alcohols; not a substitute for the SDS)
Likely causes eye/skin irritation with prolonged contact; ingestion/inhalation may be harmful. Avoid aerosol generation.
Not an oxidizer or flammable solvent per se; however, treat as a combustible organic. Keep away from strong oxidizers and strong acids/bases that promote hydrolysis or degradation.
PPE and engineering controls
Use in a fume hood or well-ventilated area.
Wear lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles.
Have access to eyewash and safety shower.
First-aid overview (consult SDS for formal guidance)
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
Inhalation: Move to fresh air; monitor for respiratory irritation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Storage incompatibilities and stability (general)
Separate from strong oxidants, acid chlorides/anhydrides, and dehydrating agents that could acylate or cyclodehydrate the molecule.
Protect from moisture contamination if water content is critical to your application.
Always defer to the product SDS for authoritative hazard classification and emergency measures.
Solvent Selection
This compound is generally used as a polar building block rather than as a bulk solvent. The notes below are provided to guide handling and reaction medium choices when using it.
Polarity and miscibility (general/literature-based)
Strongly polar and hydrogen-bonding (both H-bond donor and acceptor).
Expected to be fully miscible with water and polar alcohols; high solubility in DMSO, DMF, and other dipolar aprotics.
Limited solubility anticipated in nonpolar hydrocarbons; co-solvents (EtOH, MeCN) can aid dissolution in mixed media.
Selecting a reaction medium (general)
For transformations at the alcohol (e.g., tosylation, Mitsunobu), use anhydrous polar aprotic solvents (DCM, THF, MeCN) with base or coupling reagents as appropriate; the amide enhances overall polarity—ensure complete dissolution.
For amide hydrolysis or N-deprotection, aqueous acidic or basic conditions (e.g., HCl, NaOH) in water/MeOH are typical; control temperature to limit side reactions.
For oxidations of the primary alcohol (e.g., to aldehyde/acid), DMF, DCM, or MeCN with standard oxidants are common; buffer H-bonding with molecular sieves when water sensitivity matters.
Comparison to alternatives (when substrate solubility is poor)
Water-miscible green solvents (MeOH, EtOH, 2-propanol) often dissolve this substrate well and are easier to remove than high-boiling dipolar aprotics.
MeCN provides a good balance of polarity and volatility when strictly aprotic media are required.
Storage and Reconstitution
Storage (item-specific)
Storage conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling
Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to atmospheric moisture if water content is critical to your process.
If prolonged storage is anticipated, consider inert headspace (e.g., nitrogen) and store away from strong acids, bases, and oxidizing agents.
Reconstitution/solubilization (general guidance)
Readily soluble in water, alcohols (MeOH, EtOH), and polar aprotic solvents (DMSO, DMF). Start with 10–100 mg/mL depending on application.
For strictly anhydrous use, dissolve in dry solvent and, if necessary, pass through activated molecular sieves (3Å/4Å) to reduce residual water.
Freeze–thaw and stability
Not typically sensitive to ambient temperature; avoid repeated freeze–thaw cycles that can introduce condensation. If storing solutions, prefer aliquots at 2–8 °C for short term, or below −20 °C for longer term, based on solvent stability.
Always consult the product’s CoA and SDS for lot-specific stability and handling recommendations.
Structure and Identity
N-(3-hydroxypropyl)formamide is a small, bifunctional organic molecule bearing both an amide and a primary alcohol, useful as a polar building block and linker.
Item-specific identifiers (from Product Data)
SKU: N970840
CAS: 49807-74-1
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (for general reference; not item-specific specs)
Structural features: one secondary amide (N–CHO, “formamide”) and one terminal primary alcohol (–CH2OH) separated by a 3‑carbon tether.
2D structural description (literature): a linear three-carbon chain bearing –OH at the terminal carbon (HO–CH2–CH2–CH2–), attached at the internal carbon to a nitrogen that is N-formylated (–NH–CHO). No rings, no stereocenters.
Functional group implications (general):
The amide confers strong hydrogen-bonding capacity (HBA and HBD) and attenuates basicity at nitrogen due to conjugation with the formyl carbonyl.
The primary alcohol enables standard alcohol transformations (oxidation, substitution after activation, esterification), while the amide can be hydrolyzed or selectively engaged under orthogonal conditions.
Note: Structure descriptors provided above under “literature” are for general chemical context only; consult the product’s CoA/Spec Sheet for item-certified identifiers.
Synthetic Utility
N-(3-hydroxypropyl)formamide is a compact, polar, bifunctional synthon enabling divergent routes from either the alcohol or the N-formylated nitrogen.
Orthogonal handles
Alcohol (primary): amenable to oxidation (aldehyde/acid), activation (tosylate/mesylate/triflate), esterification/carbonate formation, and Mitsunobu-type substitution (with inversion at C1 if chiral derivatives are used downstream).
N-Formyl amide: hydrolytically removable to reveal a primary amine (3-aminopropanol); can be selectively acylated under mild conditions; participates in reductive transformations (method-dependent) to tailored amine derivatives.
Steglich esterification to install cleavable linkers or masking groups on the alcohol.
Swern or Dess–Martin oxidation to aldehyde, followed by reductive amination or Wittig/HWE to extend carbon chains while retaining the amide.
Tosylation then intramolecular cyclization with N-nucleophiles (after N-deformylation) to furnish morpholine/oxazolidine scaffolds.
Hydrolysis (acid/base) to 3-aminopropanol, then Boc protection and subsequent N-acylation/alkylation to produce spacer-bearing ureas, amides, or quaternary ammonium salts.
Retrosynthetic value
Serves as a masked 3-aminopropanol where the amine is protected as a formamide, simplifying handling and selectivity in multistep sequences.
The formyl group provides a handle for selective N-chemistry without introducing bulky protecting groups, minimizing steric encumbrance in dense scaffolds.
Workup/handling tips
Due to high polarity, plan for aqueous workups and use of reverse-phase or ion-exchange purification when silica chromatography is challenging.
Target Specificity
This product is a small-molecule reagent and does not possess biological target specificity parameters such as antigen, epitope, clone, isotype, or species reactivity.
Item-specific immunological targeting data: Not applicable.
For biochemical use, see “Reaction & Applications” and “Synthetic Utility” for relevant workflows.
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