cis-3-methoxycyclobutanamine - ≥95% , CAS No.1268521-35-2

CAS: 1268521-35-2 Cat. No.: M1369375 Fórmula: C₅H₁₁NO Peso molecular: 101.15

GRADE & PURITY ≥95%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Store at 2-8°C,Protected from light

Enviado em

Wet ice

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

COC1CC(C1)N

IUPAC Name

3-methoxycyclobutan-1-amine

InChIKey

CTZHBPUHGUPFSN-UHFFFAOYSA-N

INCHI

1S/C5H11NO/c1-7-5-2-4(6)3-5/h4-5H,2-3,6H2,1H3

SMILES isoméricas

COC1CC(C1)N

Peso molecular

101.15

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Dialkyl ethers
• Alternative Parents: Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Dialkyl ether - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Primary aliphatic amine - Amine - Aliphatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
• 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

Propriedades químicas e físicas

• Peso molecular: 101.150 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 101.084 Da
• Monoisotopic Mass: 101.084 Da
• Topological Polar Surface Area: 35.300 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 59.100
• 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

Not applicable. No immunoassay or bioassay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, see the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections for general guidance.

Biological Roles

This compound is a synthetic, non-natural small molecule. No endogenous biological role is known.

• Class context: aliphatic primary amines can interact with biological macromolecules via ionic and hydrogen-bonding interactions when protonated, but cis-3-methoxycyclobutanamine itself is best regarded as a research intermediate.
• Metabolic considerations (general literature): primary aliphatic amines are commonly metabolized by oxidative deamination (MAO/DAO in vivo) and by phase II conjugation (e.g., acetylation, glucuronidation) when part of larger molecules; the methoxy group is typically O-dealkylated by P450 enzymes in drug-like structures. These are general principles for similar functionalities and not specific to this item.
• Use in chemical biology: the amine enables conjugation to reporter tags or linkers (e.g., NHS esters) to create small, conformationally constrained probes; any bioactivity would arise from the conjugate, not from the amine itself.

Note: For research use only. No medical, diagnostic, or therapeutic uses are intended or implied.

Buffer Applications

cis-3-Methoxycyclobutanamine is not a dedicated buffering agent and is not typically used to prepare defined buffer systems. As a primary amine, it will accept a proton around physiological pH, but its buffering capacity, solubility, and volatility are not characterized for this purpose.

• If aqueous handling is required, prepare water-soluble salts (e.g., HCl) and adjust pH with standardized acid/base. For actual buffering needs, select established buffers (e.g., phosphate, HEPES, MOPS) with known pKa and capacity profiles.

For precise buffer formulations and pH stability, refer to well-characterized buffer systems rather than this reagent.

Green Alternatives

Greener chemistry with amine building blocks focuses on solvent choice, coupling reagents, and energy efficiency rather than changing the core reagent. For processes involving cis-3-methoxycyclobutanamine:

• Solvent optimization (general, with tradeoffs):
  • Replace DCM with EtOAc or 2-MeTHF where feasible for extractions and acylations (lower toxicity; similar performance). 2-MeTHF offers higher boiling point and partial water miscibility, aiding phase separations.
  • Use ethanol or isopropanol for reductive aminations (with catalytic hydrogenation or transfer hydrogenation) instead of MeCN/THF where compatible.
  • Aqueous micellar catalysis (e.g., TPGS-750-M) can enable amide couplings and alkylations under mild, water-rich conditions—evaluate amine salt solubility.
• Reagent selection:
  • Favor carbodiimide couplings with catalytic Oxyma or green peptide-coupling platforms over uronium reagents to reduce toxic byproducts, or use enzymatic amidation where applicable.
  • For reductive amination, choose hydrogen gas with Pd/C or Raney Ni (in ethanol) instead of sodium cyanoborohydride to avoid cyanide waste, balancing selectivity needs.
• Energy/processing:
  • Room-temperature or flow processes can reduce energy use and improve safety with volatile amines; in-line scavengers (acidic resins) capture excess amine.

Brief comparison (general):

• DCM: excellent performance, poor EHS profile.
• EtOAc/2-MeTHF: greener, broadly compatible; may slightly reduce rates in some acylations.
• Alcohols (EtOH/iPrOH): renewable sources available; may participate in side reactions—monitor.

Pharmaceutical Uses

No pharmacopeial monograph or excipient status is indicated for this item. It is supplied for research use only.

• Likely role (general): a synthetic intermediate/building block for discovery chemistry to introduce a cis-3-methoxycyclobutyl motif into candidate molecules via amide, urea, sulfonamide, or secondary amine linkages.
• Advantages of the motif: the strained cyclobutane ring provides conformational constraint and can modulate pKa/logD; the vicinal methoxy offers a handle for further derivatization or polarity tuning.
• Process considerations: for scale-up, the amine is often handled as a crystalline salt (e.g., hydrochloride, p-toluenesulfonate) to improve stability and facilitate purification. Salt selection studies (HCl, mesylate, fumarate) can optimize solid-state properties of downstream intermediates.

No therapeutic claims are made. This product is not intended for human or veterinary use.

Physical Properties

Item-specific physico-chemical specifications are not provided for this catalog entry.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (No robust literature value located for this exact cis isomer.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• UV/Vis cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Water content/peroxides/metals: Not specified for this item; refer to CoA/Spec Sheet.

General/literature-based properties for the class (aliphatic primary amines, small-ring):

• pKa (conjugate acid, literature/class): primary aliphatic amines typically have pKaH ~10–11; ring strain and α-alkoxy substitution can moderately modulate basicity.
• LogP (estimated/class): small aliphatic amino ethers tend to be moderately polar (cLogP often ~0 to 1.5 depending on isomer); expect good water miscibility in the protonated form.
• Solubility (general): free base typically miscible with many organic solvents (alcohols, ethers, chlorinated, polar aprotics); as the HCl salt, freely water-soluble.

Note: For exact material specifications and release criteria (e.g., assay, residual solvents, isomer ratio, enantiopurity if applicable), consult the product’s CoA/Spec Sheet.

Quality and Grades

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

Guidance on interpreting grades for amine building blocks (general):

• Research-grade/analytical-grade materials typically specify assay (GC/LC, qNMR), residual solvents, and impurity profiles (including regio-/stereoisomers). For stereodefined “cis” products, the diastereomeric ratio (cis:trans) is an important quality attribute.
• Chromatography grade (if applicable) emphasizes low non-volatile residue and low UV background; less relevant for amines unless used as mobile phase additives or derivatization agents.
• Stabilization: Aliphatic amines are generally supplied neat without stabilizers; if offered as an acid salt (e.g., HCl), it improves shelf-life and handling but alters solubility. No stabilizer is specified for this item; refer to CoA/Spec Sheet.
• Identity confirmation: Typical methods include 1H/13C NMR (diagnostic upfield cyclobutane signals; methoxy singlet), IR (N–H stretches ~3300 cm−1, C–O–C ~1050 cm−1), MS (M+H+ ~102.2), and chiral/achiral HPLC/GC as relevant.

What is specific here: Only storage/shipping conditions are defined (2–8°C, protect from light; wet ice). All other release specifications (purity, water, inorganic ions, stereochemical ratio) are Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As a stereodefined, small-ring, primary amine with an α-alkoxy substituent, cis-3-methoxycyclobutanamine serves as a versatile building block in medicinal and synthetic chemistry.

Applications (general/literature):

• Amide/urea/thiourea formation: coupling to carboxylic acids (EDC/HOBt, HATU, CDI) or isocyanates to install constrained cyclobutyl motifs in SAR libraries.
• Reductive amination partner: reaction with aldehydes/ketones (NaBH3CN, BH3·THF, or catalytic hydrogenation) to access secondary amines featuring the cis-3-methoxycyclobutyl fragment.
• N-alkylation: via alkyl halides (careful to minimize overalkylation); phase-transfer or polar aprotic media often helpful.
• Sulfonamide/carbamate synthesis: reaction with sulfonyl chlorides or chloroformates to give protecting groups or stable linkages.
• Cyclobutane chemistry: ring strain can bias neighboring group reactivity; the vicinal methoxy substituent offers orthogonal functionalization via O-deprotection or substitution after activation.
• Stereochemical relay: the cis relationship can influence conformations and receptor interactions in discovery chemistry; retention of relative stereochemistry through downstream transformations is often desirable.

Practical tips:

• Use anhydrous conditions for acylations and reductive aminations; dry solvents and molecular sieves help suppress imine hydrolysis.
• Control base strength and temperature to avoid undesired elimination or rearrangement; primary aliphatic amines are nucleophilic and can induce solvolysis in sensitive electrophiles.
• Consider salt formation (e.g., HCl) for isolation and purification—improves crystallinity and handling, followed by basification when needed.

Reaction Conditions

General literature guidance for common transformations involving aliphatic primary amines like cis-3-methoxycyclobutanamine (optimize per substrate):

• Amide coupling:
  • Solvent: DMF, MeCN, DCM, or 2-MeTHF.
  • Reagents: HATU (1.1–1.5 equiv) + DIPEA (2–3 equiv) or EDC·HCl (1.2–1.5 equiv) + Oxyma (1.2–1.5 equiv).
  • Temperature: 0–25°C; time: 0.5–4 h. Typical isolated yields: 70–95% (literature, substrate-dependent).
• Reductive amination:
  • Solvent: MeOH, iPrOH, or EtOH with 3Å molecular sieves.
  • Conditions: carbonyl (1.0 equiv), amine (1.2–2.0 equiv); NaBH3CN (1.5 equiv) at pH 5–6 (AcOH/AcONa buffer) or H2 (1–3 bar) with 5–10% Pd/C.
  • Temperature: 20–40°C; time: 2–16 h. Typical yields: 60–90% (literature).
• N-Boc protection:
  • Solvent: THF/MeCN; Boc2O (1.1–1.5 equiv); base: NaHCO3 or Et3N (2–3 equiv).
  • Temperature: 0–25°C; time: 1–3 h. Yields commonly >80%.
• Sulfonylation (TsCl):
  • Solvent: DCM or MeCN; base: pyridine or Et3N (2–3 equiv).
  • Temperature: 0–25°C; time: 1–4 h.

Notes:

• Maintain anhydrous conditions to suppress imine hydrolysis in reductive aminations and to improve coupling efficiency.
• For stereodefined substrates, avoid strong bases and elevated temperatures that may induce epimerization or ring-opening.
• Monitor by TLC/LC–MS; amines often streak—derivatize spots (e.g., ninhydrin) for visualization if needed.

Safety and Handling

GHS hazard classifications and statements are not specified for this item; refer to the SDS for authoritative safety information.

General safety guidance for aliphatic primary amines and small cyclic amines:

• Likely hazards (general): skin/eye irritation, respiratory irritation, sensitization potential; may be harmful if swallowed; can be corrosive to some materials when concentrated. Amines are basic and can react exothermically with strong acids.
• Personal protective equipment: lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles; handle in a fume hood to avoid inhalation of vapors or aerosols.
• Incompatibilities: strong oxidizers; acid chlorides/anhydrides/isocyanates (acylation); nitrosating agents; strong mineral acids (violent neutralization); copper alloys that may catalyze oxidative processes. Avoid carbonyl-containing reagents without control if unintentional imine formation is a concern.
• Special risks: primary amines can absorb CO2/H2O to form ammonium carbamates on prolonged air exposure; keep containers tightly closed. Small-ring amines can have noticeable odor—minimize headspace and use secondary containment.
• First aid (overview): eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; do not induce vomiting; seek medical attention. Always follow SDS instructions.
• Spill response: absorb with inert material, avoid neutralization with strong acids in open containers due to heat evolution; ventilate area.

Storage per Product Data: Store at 2–8°C, protected from light. Shipments are on wet ice.

Solvent Selection

cis-3-Methoxycyclobutanamine is a small, basic, polar organic compound. Solvent choice depends on whether it is used as a free base or as a protonated salt.

• Polarity/acid–base profile (general): primary amine (pKaH ~10–11, literature/class). As free base, soluble in many organics; as ammonium salt, highly water-soluble.
• Preferred solvents for free base handling: ethanol, methanol, dichloromethane (DCM), ethyl acetate, THF, acetonitrile, DMF/DMSO (for high polarity applications). Hydrocarbon solubility may be limited unless co-solvent is used.
• Aqueous work: convert to HCl (or other acid) salt to increase water solubility and enable pH-controlled extractions and crystallizations.
• Moisture/CO2 considerations: for precise stoichiometry, pre-dry solvents and minimize exposure to air to avoid formation of carbamates/salts on the container walls.
• When to choose protic vs aprotic: protic alcohols facilitate salt formation and may participate in H-bonding; aprotic polar solvents (MeCN, DMF) favor nucleophilic reactivity of the amine and can suppress side reactions like imine formation with traces of aldehydes.

Quick comparison (general guidance):

• MeOH/EtOH: excellent solubility; easy removal; may form H-bonded complexes.
• DCM/EtOAc: good for extractions and rapid workups; limited base stability toward acid chlorides present.
• THF/2-MeTHF: good balance of polarity/volatility; consider peroxide testing for ethers on storage (solvent-specific precaution).

Storage and Reconstitution

• Storage conditions (from Product Data): Store at 2–8°C, protected from light. Shipments on wet ice.
• Container: tightly seal to minimize CO2/H2O uptake by the basic amine; use amber vials to limit light exposure.
• Atmosphere: inert gas backfill (N2/Ar) recommended for long-term storage of the free base; avoid prolonged headspace exposure.
• Form: supplied form (free base vs salt) and appearance are Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/handling:
  • If solid or viscous: dissolve in a suitable dry solvent (e.g., DCM, MeOH, MeCN, THF, or DMSO) to prepare a stock solution at a convenient concentration (e.g., 0.1–1.0 M) for immediate use.
  • If provided as a salt and aqueous work is desired: dissolve in deionized water or buffer; adjust pH as needed. For free base in water, consider in situ acidification to form a soluble ammonium salt.
• Freeze–thaw: not typically required at 2–8°C; if frozen stocks are prepared, aliquot to avoid repeated freeze–thaw cycles that can concentrate moisture or cause container seal breathing.

Always consult the product’s CoA/Spec Sheet and SDS for item-specific guidance on stability, appearance, and compatibility.

Structure and Identity

cis-3-Methoxycyclobutanamine is a small, saturated, bicyclic-classified building block bearing a primary amine and an alkyl methyl ether arranged cis on a cyclobutane ring.

• SKU: M1369375
• Product name: cis-3-methoxycyclobutanamine
• CAS: 1268521-35-2
• PubChem CID: 53302285
• InChIKey (as provided): 53607 (format atypical as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (computed/literature): C5H11NO
• Molecular weight (computed/literature): ~101.15 g/mol

Structural features (general description):

• Core ring: four-membered cyclobutane (strained, sp3 carbons) with two substituents at positions 1 and 3.
• Functional groups: primary aliphatic amine (–CH–NH2) and methyl ether (–CH–O–CH3).
• Stereochemistry: “cis” indicates the amine-bearing carbon and the methoxy-bearing carbon are on the same face of the cyclobutane ring, giving a defined relative configuration (diastereomeric to the trans isomer). Absolute configuration at the substituted centers is not specified.
• Polarity: amphiphilic; basic nitrogen (protonatable) and weakly lipophilic methoxy substituent.

2D structure in words (general): a cyclobutane square with substituents at C1 (–NH2) and C3 (–OCH3) projecting on the same side (cis), the remaining ring positions bearing hydrogens.

Synthetic Utility

Key functional elements and reactivity:

• Primary amine (nucleophile/base): readily forms amides (acid activation), imines/oximes (with carbonyls), and participates in reductive amination and alkylation.
• Ether (–OMe): typically inert under many conditions; can direct stereochemical outcomes and be transformed after activation (e.g., demethylation under strong Lewis/Brønsted acids is generally harsh—consider alternative routes if O-functionalization is desired).
• Strained cyclobutane: confers rigidity; C–C activation is uncommon but ring-retentive transformations are robust.

Representative transformations (general/literature):

• Amide coupling: HATU/DIPEA in DMF or EDC·HCl/Oxyma in MeCN/DMF at 0–25°C; rapid conversion to the corresponding amide with minimal epimerization at adjacent stereocenters when mild bases are used.
• Reductive amination: condensation with aryl/alkyl aldehydes in MeOH or iPrOH (3Å MS), followed by NaBH3CN (pH 5–6 acetate buffer) or catalytic H2 (Pd/C, 1–3 bar) to secondary amines.
• Sulfonylation/carbamylation: reaction with TsCl (pyridine or Et3N, 0–25°C) or chloroformates (phosgene equivalents avoided for EHS) to install protecting/functional groups.
• N-Boc protection: Boc2O, base (NaHCO3/Et3N), 0–25°C in THF/MeCN, yielding Boc-protected amine suitable for further O-/C-functionalization.

Retrosynthetic value: introduces a cis-1,3-disubstituted cyclobutane unit; amenable to diversification at nitrogen while preserving ring substitution pattern and relative stereochemistry.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.