This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine 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.
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
155.280 g/mol
XLogP3
3.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
3
Exact Mass
155.167 Da
Monoisotopic Mass
155.167 Da
Topological Polar Surface Area
26.000 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
95.000
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 immunoassay or bioanalytical application protocols (WB, IHC, IF, FC, etc.) are associated with this small-molecule reagent. For synthetic usage, consult the Reaction Conditions and Synthetic Utility sections.
Biological Roles
This product is supplied strictly for research use. No biological/clinical activity is claimed. The following notes provide general biochemical context for aliphatic primary amines.
General biochemical relevance (literature)
Primary amines are ubiquitous in biology (e.g., amino acids, polyamines). They participate in Schiff base formation with aldehydes and can be protonated at physiological pH, influencing membrane interactions.
Hydrophobic amines with cycloalkyl groups often display enhanced membrane affinity; protonated forms may accumulate in acidic compartments (lysosomotropic behavior), though such behavior is highly structure- and context-dependent.
Use in chemical biology (general)
As a building block, hydrophobic primary amines are used to append cationic, lipophilic handles to probes or to modulate permeability and basicity in tool compounds.
Caution
Any inference of biological role or activity must be empirically established for the final compound. This catalog item is not intended for diagnostic, therapeutic, or in vivo use.
Buffer Applications
4-Cyclohexylbutan-2-amine is not a standard buffering reagent. While a primary amine’s conjugate acid has a pKa typically around 10–11 (literature), this compound is not commonly used to prepare defined buffer systems.
Practical note
If temporary pH control in the alkaline range is needed during a reaction or workup, forming the ammonium salt (e.g., with HCl or AcOH) can provide local pH moderation; however, for biochemical buffers use established systems (e.g., Tris, CAPS, CHES) with known pKa and compatibility profiles.
Recommendation
For analytical or biological buffer preparation, select dedicated buffering agents. Use this amine primarily as a synthetic building block.
Green Alternatives
While 4-cyclohexylbutan-2-amine is a reagent/building block (not a solvent), greener choices can be made around its use in synthesis and processing.
Greener solvent choices (literature/general)
Prefer 2-MeTHF, EtOAc, CPME, and alcohols (EtOH, i-PrOH) over chlorinated solvents (DCM, DCE) where reaction compatibility allows (e.g., amide couplings, reductive aminations).
For extractions, use EtOAc or MTBE instead of DCM when phase behavior permits; convert the amine to a salt to enable aqueous processing.
Greener coupling strategies
Employ catalytic coupling methodologies (e.g., catalytic DMAP with activated esters) or use less hazardous reagents such as CDI or T3P in greener solvents.
Consider water-assisted or solvent-minimized reductive amination using NaBH(OAc)3 or hydrogenation over Pd/C in EtOH.
Waste and odor minimization
Amines can be malodorous; choose low-volatility setups (closed systems) and adsorb acid scrubbing for off-gases.
Use salt formation (e.g., HCl, p-TsOH) to crystallize/purify and reduce volatile emissions during storage and shipping.
Comparative note (general)
Compared with smaller alkyl amines (e.g., ethyl- or propylamine), this substrate’s higher boiling point can reduce evaporative losses, improving EHS profile during handling, but downstream E-factor still depends on solvent and reagent selection.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item. It is supplied for research use only.
Typical roles in pharmaceutical R&D (general)
Building block for discovery chemistry: incorporation into amides, ureas, sulfonamides, and secondary amines to modulate lipophilicity (cLogP), basicity (pKa), and steric bulk in SAR campaigns.
Salt screening: The free base can form a variety of salts (HCl, HBr, mesylate, fumarate, maleate), enabling studies of solubility, stability, and solid-state properties of candidate molecules.
Manufacturing/formulation notes
As an intermediate, the amine may be isolated and carried forward as a crystalline salt to improve handling and reduce odor/volatility.
Item-specific regulatory/compendial info
Not specified for this item; refer to CoA/Spec Sheet. No therapeutic claims are made for this product.
Physical Properties
Item-specific specifications are not provided in the Product Data. Where useful, typical literature values and expectations for closely related aliphatic primary amines are given for context only (not item specifications).
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature for the neutral free base suggests C10H21N.)
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature estimate ~155.29 g/mol for free base.)
Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Literature expectation for C10 primary amines/cyclohexylalkyl amines: typically high-boiling liquids, often >200 °C at 1 atm.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Literature: many comparable amines are low-melting liquids.)
Density: Not specified for this item; refer to CoA/Spec Sheet. (Literature for related aliphatic amines: ~0.80–0.90 g/mL at 20–25 °C.)
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
pKa (conjugate acid): Not specified for this item; refer to CoA/Spec Sheet. (Literature: primary aliphatic amines typically pKaH ≈ 10–11.)
LogP (neutral base): Not specified for this item; refer to CoA/Spec Sheet. (Literature expectation: increased hydrophobicity due to cyclohexyl; logP often in the ~2–3+ range.)
Solubility: Not specified for this item; refer to CoA/Spec Sheet. (General: free base miscible with many organic solvents; limited water solubility as free base; protonated salts are water soluble.)
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grade terminology (general guidance)
Research grade: Suitable for most synthetic and discovery work; typical impurity controls include GC/HPLC area %, water content, and residual solvents.
Purified/Distilled amines: Reduced water and low-boiling impurities; beneficial for moisture-sensitive couplings (e.g., acid chloride, isocyanate reactions) and for reproducible salt formation.
Chiral quality: Because 4-cyclohexylbutan-2-amine has a stereogenic center at C-2, specifications may indicate racemic (DL) or enantiomerically enriched material; optical rotation and enantiopurity (ee/er) are relevant when provided.
Stabilizers/antioxidants
Not specified for this item; refer to CoA/Spec Sheet. In general, aliphatic amines are rarely stabilized, but suppliers may purge with inert gas to limit CO2 uptake.
Quality considerations for applications
For medicinal chemistry building-block use, low residual water and low UV-active impurities aid in parallel synthesis and analytics.
For salt screening, knowledge of residual base strength and impurity amines is important, as they can co-crystallize or alter polymorph outcomes.
Reaction and Applications
As a hydrophobic, chiral primary amine, 4-cyclohexylbutan-2-amine is a versatile nucleophile and base in synthesis, particularly valuable as a medicinal chemistry building block.
Amide formation with acid chlorides, activated esters, or coupling reagents (EDC·HCl/HOBt, HATU, T3P, CDI) to access secondary amides bearing a bulky cyclohexylbutyl side chain.
Sulfonamide synthesis via reaction with sulfonyl chlorides (e.g., TsCl, MsCl) under basic conditions.
Carbamate/urea formation with chloroformates or isocyanates; phosgene equivalents (triphosgene, CDI) can deliver ureas.
Reductive amination with aldehydes/ketones (NaBH3CN or NaBH(OAc)3) to generate secondary amines while retaining the cyclohexylbutyl motif.
N-alkylation (SN2) with primary alkyl halides/tosylates; phase-transfer or polar aprotic media can enhance rates.
Stereochemical considerations
The amine carbon (C-2) is stereogenic. If enantioselectivity matters, begin from enantioenriched starting material or resolve later (e.g., diastereomeric salt formation with chiral acids or chiral HPLC). Not specified for this item whether racemic or enantioenriched.
Practical tips
Drying: If needed, dry the free base over K2CO3 or molecular sieves; avoid strong dehydrating agents that may cause side reactions.
Workups: Protonate during extraction (e.g., 1 M HCl) to move into aqueous; basify to liberate the free base for re-extraction into organics.
Odor control and volatility: Larger hydrophobic amines have reduced volatility vs lower amines, aiding bench handling but still require fume hood use.
Use cases
Installation of a cyclohexyl-butyl, sec-alkylamino pharmacophore in fragment-to-lead campaigns and analog libraries (general medicinal chemistry context; no clinical claims).
Reaction Conditions
General literature guidance for common transformations of aliphatic primary amines. These are typical ranges, not item-specific specifications or guarantees.
Amide coupling
Conditions: Carboxylic acid (1.0 eq), amine (1.1–1.5 eq), HATU or EDC·HCl (1.1–1.5 eq), base (DIPEA 2–3 eq) in DMF, DCM, MeCN, or 2-MeTHF.
Temperature/time: 0 °C to rt, 1–16 h. Typical isolated yields: 70–95% depending on substrate.
Reductive amination
Conditions: Carbonyl (1.0 eq), amine (1.2–2.0 eq), NaBH(OAc)3 (1.5–3.0 eq) in DCE/MeOH, MeCN/AcOH, or toluene/MeOH; catalytic AcOH to promote imine formation.
Temperature/time: rt to 40 °C, 2–24 h. Alternative: H2 (1–5 bar) with Pd/C in EtOH for 2–8 h.
Sulfonylation/carbamoylation
Conditions: RSO2Cl or ROCOCl (1.05–1.2 eq), base (Et3N or DIPEA, 2–3 eq) in DCM or THF, 0 °C to rt, 1–4 h.
N-alkylation (SN2)
Conditions: Alkyl halide (1.05–1.5 eq), base (K2CO3, Cs2CO3), KI catalyst (0–20 mol%) in DMF/DMSO or acetonitrile.
Temperature/time: 25–80 °C, 4–24 h; monitor to limit over-alkylation.
Protection/deprotection
Boc protection: (Boc)2O (1.1–1.5 eq), base (NaHCO3/Et3N) in DCM/THF, 0 °C to rt, 1–3 h; deprotect with TFA in DCM at 0 °C to rt.
Workup tips
Protonate amine for aqueous extraction (dil. HCl), then basify to recover free base into organic solvents. Add 1–2% Et3N to silica eluents for clean chromatography.
Safety and Handling
Safety classifications are not provided in the Product Data; consult the SDS for authoritative guidance. The following are general considerations for aliphatic primary amines.
GHS/CLP status (item-specific): Not specified for this item; refer to SDS.
Common hazards (general for primary amines)
Corrosive/irritant to skin, eyes, and respiratory tract; may cause burns on prolonged contact.
Flammable liquid/combustible vapors possible; vapors may form explosive mixtures with air.
Amines can be harmful by inhalation/ingestion; strong, fishy odor typical.
Incompatibilities
Strong oxidizers, acid chlorides, acylating/sulfonylating agents (vigorous reactions), isocyanates, epoxides, and carbonyls (can form imines/Schiff bases).
CO2 and moisture may lead to gradual salt formation; keep containers tightly closed.
PPE and handling
Use chemical-resistant gloves (e.g., nitrile), splash goggles/face protection, lab coat; handle in a fume hood.
Ground/bond when transferring flammable liquids; eliminate ignition sources.
First aid (general)
Skin/eye contact: Immediate decontamination with water for ≥15 minutes; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; monitor breathing; medical evaluation advised.
Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
Storage (per Product Data): Store at room temperature. Keep tightly sealed, away from acids/oxidants. Consult SDS for precise conditions and any transport classifications. {
"signal_word": "Not specified for this item; refer to SDS",
"pictograms": "Not specified for this item; refer to SDS",
"h_statements": "Not specified for this item; refer to SDS",
"ghs_classification": "Not specified for this item; refer to SDS"
}
Solvent Selection
This product is a reactive amine building block rather than a solvent. The following guidance addresses solvents commonly chosen when using aliphatic primary amines.
Polarity/miscibility profile (general for the free base)
Expected to be miscible with many organic solvents (EtOH, MeOH, acetone, CH2Cl2, THF, toluene); limited solubility in water as the free base but high solubility as protonated salts.
Dielectric constant/logP: Not specified for this item; refer to CoA/Spec Sheet. (Literature: hydrophobic due to cyclohexyl group; favors less polar organic media.)
Solvent choices by reaction class
Amide coupling: DMF, NMP, DCM, MeCN, or greener 2-MeTHF/EtOAc when using carbodiimides or uronium reagents.
Reductive amination: Toluene/MeOH, DCE/MeOH, or EtOH; water-tolerant protocols exist with NaBH(OAc)3.
Sulfonylation/carbamoylation: DCM, THF, or acetonitrile with a base (e.g., DIPEA).
N-alkylation: Polar aprotic solvents (DMF, DMSO) to enhance SN2 rates; control over-alkylation by stoichiometry and temperature.
Practical notes
If salt form is used (e.g., HCl salt), dissolve in polar protic solvents or neutralize in biphasic media.
For purification, normal-phase silica often requires pre-treatment (1–2% Et3N in eluent) to prevent streaking/tailing of amines.
Comparison (general)
Versus smaller alkyl amines, the cyclohexylbutylamine is less volatile and more hydrophobic, simplifying handling (reduced odor/evaporation) but potentially reducing aqueous miscibility.
Storage and Reconstitution
Storage conditions (Product Data)
Store at room temperature.
Additional handling guidance (general for aliphatic amines)
Keep container tightly closed to limit uptake of CO2 and moisture; store under inert gas if possible for long-term stability.
Segregate from acids, oxidizing agents, and acid chlorides/isocyanates. Avoid contact with carbonyl-containing materials in storage to prevent imine formation.
If supplied as a solid salt (e.g., HCl salt), store in a dry environment; the salt form typically offers improved stability and handling. Item-specific salt form/appearance is not specified.
Reconstitution
Not applicable; product is a neat reagent. If crystallized or received as a salt, dissolve in a suitable solvent (e.g., MeOH, EtOH, DCM, THF) or water for protonated salts. No item-specific solvent or concentration recommendations are provided; refer to CoA/Spec Sheet.
Shipping
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Shelf life
Not specified for this item; refer to CoA/Spec Sheet. As a general practice, minimize headspace, use clean/dry tools, and record open dates to track stability over time.
Research use note
For research use only. Not for human or veterinary use.
Structure and Identity
4-Cyclohexylbutan-2-amine is a saturated, aliphatic primary amine bearing a hydrophobic cyclohexyl substituent and a single stereogenic center at C-2 (racemic unless otherwise specified).
Item-specific identifiers (Product Data)
SKU: C962316
CAS: 791752-94-8
PubChem CID: 15014628
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity details (general reference; not item specifications)
Common name: 4-cyclohexyl-2-aminobutane; sec-butylamine bearing a cyclohexyl group at C-4
Molecular formula (calculated from name): C10H21N (literature)
A four-carbon chain with the amine at C-2: CH3–CH(NH2)–CH2–CH2–R. The terminal carbon (C-4) is bonded to a cyclohexyl ring (R = cyclohexyl). The amine-bearing carbon is tetrahedral and chiral; the product is typically supplied as a racemate unless an enantiomeric enrichment is stated (not specified for this item).
Synthetic Utility
Key reactive handle: a primary aliphatic amine on a chiral, hydrophobic scaffold. This combination provides strong nucleophilicity/basicity with a sterically differentiated environment.
Functional group reactivity (literature)
Nucleophilic attack on activated carboxylic acid derivatives to form amides; compatible with standard peptide-coupling reagents (EDC/HATU/T3P/CDI).
Reaction with sulfonyl chlorides and chloroformates to afford sulfonamides and carbamates, respectively.
Reductive amination with aldehydes/ketones; hydrogenation or hydride-based methods.
Alkylation/acylation under phase-transfer or polar aprotic conditions; care to avoid over-alkylation to tertiary amines if undesired.
Retrosynthetic value
Serves as a convergent fragment to install a cyclohexylbutyl, sec-alkylamino motif late in synthesis, enabling rapid diversification of head groups without perturbing core scaffolds.
Chiral center at C-2 allows access to diastereomeric series when combined with chiral partners; resolution strategies include diastereomeric salt formation (e.g., with tartaric/camphorsulfonic acids) or chiral chromatography.
Purification/handling
Salt switching (e.g., HCl ↔ free base) facilitates isolation and chromatographic behavior.
For silica chromatography, add 1–2% Et3N to eluents to reduce tailing.
Protecting group chemistry
Although a primary amine, protection is often unnecessary; when needed, Boc- or Cbz-protection proceeds under standard conditions and can be removed under acidic (Boc) or hydrogenolytic (Cbz) conditions.
Target Specificity
Not applicable. This product is a small-molecule amine building block, not a biological affinity reagent or antibody. No antigen/epitope, clone, isotype, or species reactivity applies.
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