L-Leucinol - Moligand™, ≥96% , CAS No.7533-40-6

CAS: 7533-40-6 Cat. No.: L117136 Fórmula: C₆H₁₅NO Peso molecular: 117.19 Beilstein Registry Number: 1719240 Número CE: 231-400-5

GRAU & PUREZA Moligand™, ≥96%

Synonyms

(L)-leucinol|(+)-Leucinol|(1S)-1-(Hydroxymethyl)-3-methyl butylamine|2-Amino-4-methyl-pentan-1-ol|1-Pentanol, 2-amino-4-methyl-, (S)-|H-Leu-ol|(S)-(+)-Leucinol|H-Leucinol|L-Leucinol|(s)-(+) leucinol|2-Amino-4-methyl-1-pentanol #|1-Pentanol, 2-amino-4-methyl-, (2S)-|(2S)-2-amino-4-methyl-1-pentanol|N,N-dimethyl-2,6-di-t-butyl-4-aminomethylphenol|(2S)-2-amino-4-methylpentanol|(S)-2-Amino-4-methyl-1-pentanol|(S)-leucinol|(S)-2-Amino-4-methyl-1-pentanol, 2-Amino-4-methyl-1-pentanol|(S)-2-Amino-4-methyl-pentan-1-ol|(S)-2-Amino-4-methylpentan-1-ol|L-(+)-Leucinol|L(+)-Leucinol|rac-leucinol|(1S)-1-(hydroxymethyl)-3methylbutylamine|(1S)-1-(hydroxymethyl)-3-methylbutylamine|Leucinol|(S)-(+)-2-Amino-4-methyl-1-pentanol

Storage

Room temperature,Argon charged

Shipped In

Normal

Visão geral

Starting material for the synthesis of aminopeptidase N and phospholipase A2 inhibitors.

Especificações

Sinónimos

(L)-leucinol | (+)-Leucinol | (1S)-1-(Hydroxymethyl)-3-methyl butylamine | 2-Amino-4-methyl-pentan-1-ol | 1-Pentanol, 2-amino-4-methyl-, (S)- | H-Leu-ol | (S)-(+)-Leucinol | H-Leucinol | L-Leucinol | (s)-(+) leucinol | 2-Amino-4-methyl-1-pentanol # | 1-Pentanol, 2-amino-4-methyl-, (2S)- | (2S)-2-amino-4-methyl-1-pentanol | N,N-dimethyl-2, Show more

Especificações e pureza

Moligand™, ≥96%

Condições de armazenamento de armazenamento

Room temperature,Argon charged

Enviado em

Normal

Grau

Moligand™

Tipo de ação

INHIBITOR

Pureza

≥96%

Nomes e identificadores

Pubchem Sid

488187468

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488187468

Sorrisos canónicos

CC(C)CC(CO)N

IUPAC Name

(2S)-2-amino-4-methylpentan-1-ol

InChIKey

VPSSPAXIFBTOHY-LURJTMIESA-N

INCHI

1S/C6H15NO/c1-5(2)3-6(7)4-8/h5-6,8H,3-4,7H2,1-2H3/t6-/m0/s1

SMILES isoméricas

CC(C)C[C@@H](CO)N

WGK Alemanha

3

CAS alternativo

7533-40-6

Termos de entrada MeSH

leucinol

Peso molecular

117.19

Beilstein

1719240

Reaxy-Rn

1719239

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1719239&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Amines
        • Level5 Alkanolamines
          • Level6 1,2-aminoalcohols

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Alkanolamines
• Direct Parent: 1,2-aminoalcohols
• Alternative Parents: Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1,2-aminoalcohol - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary alcohol - Organooxygen compound - Primary aliphatic amine - Alcohol - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
• 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

Alvos associados (humanos)

LARS1 Tchem Leucyl-tRNA synthetase (173 Activities)

Discover Target: LARS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de ação

Propriedades químicas e físicas

• Sensibilidade: Air sensitive
• Índice de refração: 1.4496-1.4516
• Rotação específica [α]: 4 ° (neat)
• Ponto de inflamação (°F): 195.8 °F
• Ponto de inflamação (°C): 90℃
• Ponto de ebulição (°C): 208-210°C
• Peso molecular: 117.190 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 117.115 Da
• Monoisotopic Mass: 117.115 Da
• Topological Polar Surface Area: 46.300 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 54.500
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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 validated bioassay, immunoassay, or analytical protocols are provided for this item. For synthetic applications, refer to the Reaction & Applications and Reaction Conditions sections for general guidance and adapt to your system.

Biological Roles

• General biochemical context (literature; not item-specific)
  • L-Leucinol is the reduced alcohol analog of the essential amino acid L-leucine. While L-leucine is central to protein biosynthesis and branched-chain amino acid (BCAA) metabolism, L-leucinol itself is not a canonical metabolite.
  • As a primary amino alcohol, it can form salts and hydrogen-bonded complexes and has been employed as a chiral probe or derivatization agent in some biochemical analyses. Any observed biological interactions typically arise from its amine/basic character and hydrophobic isobutyl side chain.
• Laboratory relevance
  • Useful for preparing chiral tagging reagents or ligands that can interrogate enzymes or transport processes in vitro; however, such uses are exploratory and system-dependent.
• Important note
  • This product is for research use only (per Product Data). No clinical or diagnostic use is implied. Any biological effects should be characterized in the specific experimental system before drawing conclusions.

Buffer Applications

• Not a dedicated buffering reagent.
  • L-Leucinol is a primary amine/alcohol and lacks a well-defined conjugate acid/base pair with a narrow pH range suitable for standardized buffering. While the protonated amine can contribute to solution basicity near pH ~9–10 (literature range for aliphatic amines), it is not used as a conventional buffer.
• Practical note
  • If present in aqueous systems, expect pH drift upon CO2 uptake (carbamate formation) or acid/base additions. For controlled pH, use established buffers (e.g., phosphate, HEPES) and consider potential interactions (ion pairing, hydrogen bonding) with L-leucinol.

Green Alternatives

• Intrinsic green aspects
  • Chiral-pool origin: Readily derived from the natural amino acid L-leucine via reduction, leveraging renewable bio-based feedstocks.
  • Atom economy in ligand generation: Formation of oxazaborolidines from amino alcohols occurs with minimal byproducts (H2), improving process mass intensity in asymmetric reductions.
• Greener processing choices (literature guidance)
  • Solvent selection: Prefer water/EtOH/i-PrOH where feasible for salt formations, acylations, and simple condensations; for moisture-sensitive steps, 2-MeTHF or CPME can partially replace THF/Et2O in extractions and borane-mediated steps when compatible.
  • Protecting-group strategy: Boc protection via Boc2O in aqueous-organic biphasic media reduces reliance on chlorinated solvents and acid chlorides.
  • Workup optimization: Utilize CO2-free bases and aqueous crystallizations to minimize solvent volumes and amine loss.
• Comparison snapshot (general)
  • THF vs 2-MeTHF: Similar polarity; 2-MeTHF often allows reduced peroxide formation and improved phase separation, but may alter enantioselectivity in catalyst formation—pilot trials advised.
  • DCM vs EtOAc/MTBE: EtOAc/MTBE provide lower toxicity; amine extractability is good under basic conditions.
• Trade-offs
  • Aqueous ethanol may increase salt formation and complicate phase separation; balance green metrics with isolation efficiency and desired form (free base vs salt).

Pharmaceutical Uses

• Formulation/excipient status
  • No pharmacopeial monograph is known for L-leucinol; it is not a standard excipient. It is primarily a research chemical and chiral building block.
• Process chemistry context (literature; not item-specific)
  • Can serve as an intermediate toward chiral auxiliaries/ligands used in API synthesis (e.g., oxazaborolidines), or be transformed into urethanes/amides as chiral synthons.
  • Salt formation (e.g., hydrochloride, p-toluenesulfonate) can improve handling and crystallinity during process development.
• Compliance note
  • For any cGMP or clinical manufacturing, full specification, impurity profiling, and residual solvent/metal controls are required. This catalog item is designated For research use only and is not supplied with clinical-use documentation.

Physical Properties

• Item-specific specs
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Measured MP/BP/density/refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general information (for reference; not item-specific)
  • Molecular formula: C6H15NO
  • Molecular weight: 117.19 g/mol
  • Physical state: Typically a low-melting solid or viscous liquid depending on salt form and hydration; forms hygroscopic salts with acids (literature, amino alcohols of this class)
  • Solubility: High in water and polar protic solvents (MeOH, EtOH); moderate in polar aprotic solvents (DMF, DMSO); low in nonpolar hydrocarbons (literature trends for aliphatic amino alcohols)
  • Acid–base behavior: Primary amine readily protonated; pKaH of analogous aliphatic primary amines typically ~9–10 (literature range). Exact pKa for L-leucinol should be confirmed experimentally.
  • Hydrogen bonding: Bifunctional H-bond donor/acceptor; tends to form intra/intermolecular H-bonds, impacting crystallinity and melting behavior.
• Practical notes
  • Hygroscopicity and strong hydrogen bonding can complicate accurate Karl Fischer moisture and RI measurements; equilibrate samples under controlled humidity for analytical consistency.
  • Enantiomeric purity (ee) and salt form can significantly shift observed MP and solubility; consult the item’s CoA for definitive values.

Quality and Grades

• Item-specific grade
  • Moligand™: Aladdin’s designation for materials suitable for ligand and catalyst development, chiral pool syntheses, and coordination/organometallic applications where functional group integrity and stereochemical fidelity are important.
• What this typically implies (general; not item-specific guarantees)
  • Emphasis on defined stereochemistry and low levels of inorganic/organic residues that interfere with metal-catalyzed transformations.
  • Suitability for derivatization to chiral ligands (e.g., oxazaborolidines, oxazolines) and auxiliaries.
• Not provided for this item (consult CoA/Spec Sheet)
  • Enantiomeric excess/optical rotation
  • Residual solvents and water content
  • Trace metals profile
  • UV–Vis background/LC baseline characteristics
• Practical QA recommendations
  • Verify enantiopurity by chiral HPLC or derivatization (e.g., Marfey’s/mandelic esters) as required by your application.
  • For catalytic use, pre-screen with a metal-scavenging test or ICP-MS if metal sensitivity is critical.
  • Record optical rotation in your solvent system to establish an internal acceptance range for future lots.

Reaction and Applications

• Representative uses (literature; not item-specific)
  • Chiral ligand/precatalyst precursor: Formation of oxazaborolidines (CBS-type) from amino alcohols for asymmetric carbonyl reductions and Diels–Alder reactions; leucinol-derived variants have been reported to induce asymmetry via the α-stereocenter.
  • Building block for chiral auxiliaries: Conversion to oxazolines/oxazolidines with carboxylic acids/aldehydes; application in enantioselective additions and resolutions.
  • Derivatization chemistry: Carbamate protection (Boc, Cbz), sulfonylation (Ts, Ms) of the alcohol, and subsequent SN2 displacement for chain elaboration with retention of α-stereochemistry when appropriately protected.
  • Amide/urethane formation: Coupling of the amine with activated acids (EDC/HATU) to furnish leucinol-derived amides; alcohol left as handle for further functionalization.
  • Immobilization/linkers: The primary alcohol enables attachment to solid supports (carbonate/ether linkages) for chiral phase preparation.
• Practical notes
  • Protect amine (e.g., Boc) before selective alcohol transformations to avoid overacylation; alternatively, protect alcohol (TBS/TBDPS) for amide-first routes.
  • For oxazaborolidine formation, use borane sources (BH3·THF) under inert atmosphere at 0–25 °C; remove hydrogen safely.
  • Control stereointegrity: Avoid strong base at elevated temperatures that may induce racemization at the α-carbon; mild conditions (≤25–40 °C) preferred for enolizable intermediates.
  • Salt switches (HCl, p-toluenesulfonate) can aid isolation and ee maintenance by crystallization.

Reaction Conditions

• General conditions for common transformations (literature; not item-specific)
  • Boc protection: Boc2O (1.1–1.5 eq), base (NaHCO3, Na2CO3, or Et3N), 0–25 °C, aqueous dioxane/THF/MeOH; 1–4 h, typically high yields.
  • Cbz protection: CbzCl (1.1 eq), Na2CO3, biphasic H2O/EtOAc, 0–25 °C; 2–6 h.
  • Tosylation (alcohol): TsCl (1.1–1.5 eq), base (pyridine or Et3N), 0–25 °C, DCM/MeCN; monitor to minimize N-tosylation—prefer N-protection first.
  • Oxazaborolidine formation: Treat amino alcohol with BH3·THF (1–2 eq) at 0 °C to rt in dry THF/toluene under argon; remove H2 safely; subsequent activation with borane or borane–Lewis acid complexes; apply 1–10 mol% catalyst for ketone reductions at 0–25 °C.
  • Amide coupling: HATU or EDCI (1.1–1.2 eq), base (DIPEA), DMF/MeCN, 0–25 °C; 1–12 h.
• Workup and purification
  • Utilize acid/base extraction to switch between free base (organic-soluble) and ammonium salt (aqueous-soluble) forms.
  • For chiral integrity, avoid prolonged exposure to strong base and elevated temperatures; verify ee by chiral HPLC.
• Expected performance
  • Amino alcohol transformations of this class typically afford 70–95% yields under optimized conditions; actual results depend on substrate and protection strategy.

Safety and Handling

• Item-specific hazard data
  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• General safety considerations for aliphatic amino alcohols (literature/typical; not item-specific)
  • Hazards: May cause skin and eye irritation; ingestion/inhalation can be harmful. Amines can be corrosive to some metals via salt formation with acidic residues.
  • Incompatibilities: Strong oxidizers, acid chlorides/anhydrides, isocyanates (vigorous reactions); avoid mixing with nitrosating agents (risk of nitrosamine formation).
  • PPE: Safety glasses, lab coat, appropriate gloves (e.g., nitrile). Use in a fume hood to limit vapor/aerosol exposure during reactions or solvent removal.
  • First aid (overview): Eyes—rinse with water 15 min and seek medical advice; Skin—wash with soap/water; Inhalation—fresh air; Ingestion—rinse mouth, do not induce vomiting; seek medical attention.
  • Spill response: Absorb with inert material, avoid neutralizing with strong oxidants; wash area with water/detergent.
• Storage guidance (per Product Data)
  • Store at room temperature, under argon (inert atmosphere) to minimize oxidative discoloration and moisture uptake.
  • Ship conditions: Normal (ambient). Always defer to the product’s SDS for authoritative safety and regulatory information.

Solvent Selection

• Polarity and miscibility (general behavior for L-leucinol)
  • Highly polar, bifunctional (amine + alcohol); miscible with water and polar protic solvents (MeOH, EtOH, i-PrOH). Readily soluble in DMSO/DMF; limited solubility in ethers (THF) and poor in hydrocarbons (hexanes, heptane).
• Choosing solvents by task
  • Reaction medium: For nucleophilic substitutions, condensations, and protective group operations, use EtOH/MeOH (protic) or DMF/DMSO (aprotic) depending on base/coupling system.
  • Workup/extraction: Partition into aqueous phase when protonated; basify to liberate free base and extract into moderately polar organics (EtOAc, i-BuOAc). Avoid chlorinated solvents for long contacts with free amine due to potential HCl formation upon degradation traces.
  • Crystallization/salt formation: Alcohols/ketones with controlled addition of acids (HCl in i-PrOH/Et2O) can provide crystalline salts for purification.
• Comparison to alternatives (amino alcohols)
  • Versus valinol or alaninol: Leucinol is more hydrophobic (branched isobutyl), aiding extraction into organics but slightly reducing water solubility.
• Practical tips
  • CO2 absorption can form carbamates in basic alcohols; keep under inert gas (argon) as per Product Data.
  • Dry polar aprotic solvents thoroughly for moisture-sensitive derivatizations (tosylation, carbamate formation).

Storage and Reconstitution

• Storage (from Product Data)
  • Store at room temperature.
  • Keep under an argon atmosphere (argon charged) to limit oxidation, CO2 uptake (carbamate formation), and moisture absorption.
  • Shipped under normal ambient conditions.
• Container and handling
  • Minimize headspace and reseal promptly under inert gas after each use. Use dry, clean tools to avoid introducing acids/oxidants.
• Solution preparation (general guidance)
  • Readily dissolves in water, alcohols, and polar aprotic solvents. Prepare stock solutions in dry solvent when moisture-sensitive downstream steps are planned. Filter through 0.2 μm PTFE if particulate is observed.
  • For salt formation (e.g., HCl), gas dry HCl into anhydrous i-PrOH/Et2O at 0–5 °C and add to a cooled solution of the free base; isolate crystalline salt by filtration. Verify stoichiometry by titration or NMR.
• Stability notes
  • Amines may discolor upon air exposure due to trace oxidation; inert storage as specified helps maintain appearance and purity.
  • No reconstitution requirements are specified for this item; refer to CoA/Spec Sheet for any lot-specific instructions.

Structure and Identity

L-Leucinol is the amino alcohol obtained by reducing the carboxyl group of L-leucine to a primary alcohol, retaining the L (S) configuration at the α-carbon.

• Item-specific (from Product Data)
  • CAS: 7533-40-6
  • SKU: L117136
  • Grade: Moligand™
  • InChIKey (as provided): 385195 (note: format appears nonstandard; verify against CoA/Spec Sheet)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature identity details (for reference; not item-specific specs)
  • Common name: (S)-2-amino-4-methylpentan-1-ol (L-Leucinol)
  • Molecular formula: C6H15NO
  • Molecular weight: 117.19 g/mol
  • Canonical SMILES (literature): NC@HCC(C)C
  • Key functional groups: primary amine (–NH2), primary alcohol (–CH2OH), single stereocenter at the α-carbon (S)
• Described 2D structure
  • A chiral backbone with the α-carbon bearing –NH2, –CH2OH, an isobutyl side chain –CH2–CH(CH3)2, and hydrogen. The molecule is an aliphatic, branched amino alcohol with one stereocenter (L configuration).

Synthetic Utility

• Functional group reactivity
  • Amine: N-acylation (acid chlorides, anhydrides, coupling agents), reductive amination (as nucleophile or auxiliary), carbamate protection (Boc, Cbz, Fmoc), sulfonamide formation.
  • Alcohol: O-acylation (carbonates, esters), sulfonate activation (OTs/OMs) enabling SN2 substitution, oxidative transformations to aldehydes/acids under protected amine conditions.
• Chiral derivatization
  • Oxazaborolidines (CBS-type): Generated by cyclization with borane; catalyze enantioselective reductions of ketones and imines.
  • Oxazolines/oxazolidines: Condensation with carboxylic acids or carbonyls provides chiral auxiliaries/ligands for asymmetric catalysis and resolution.
• Retrosynthetic value
  • Serves as a branch point to access both N- and O-functionalized chiral intermediates from a single pool reagent. The isobutyl side chain confers hydrophobicity, facilitating phase manipulation and crystallization strategies.
• Practical guidance
  • Orthogonal protection: Choose N-Boc/TBS-O or N-Cbz/benzylidene acetal motifs to enable stepwise functionalization without cross-reactivity.
  • Stereochemical integrity: Maintain mild temperatures and avoid strong bases near enolizable carbonyl intermediates to prevent racemization at the α-center.

Target Specificity

Not applicable. This product is a small-molecule amino alcohol, not an antibody, enzyme, or affinity reagent. No target-binding specificity data are provided for this item.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥96% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 7533-40-6, the molecular formula is C6H15NO, and the molecular weight is 117.19 g/mol. InChIKey VPSSPAXIFBTOHY-LURJTMIESA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.