6-Heptyn-2-ol - ≥95% , CAS No.24395-03-7

CAS: 24395-03-7 Cat. No.: H992099 Formula: C₇H₁₂O Peso molecolare: 112.170 Numero EC: 192-646-6

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CC(CCCC#C)O

IUPAC Name

hept-6-yn-2-ol

InChIKey

UUVYQHRAOICJTA-UHFFFAOYSA-N

INCHI

1S/C7H12O/c1-3-4-5-6-7(2)8/h1,7-8H,4-6H2,2H3

Peso molecolare

112.170

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty alcohols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty alcohols
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty alcohols
• Alternative Parents: Secondary alcohols Acetylides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty alcohol - Secondary alcohol - Acetylide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 112.170 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 112.089 Da
• Monoisotopic Mass: 112.089 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 87.800
• 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

Application Protocols

Not applicable.

• No immunoassay or bioanalytical “application protocols” (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.
• For synthetic protocols using 6-heptyn-2-ol (e.g., CuAAC, Sonogashira, oxidations), see the Reaction Conditions section for general literature guidance.

Biological Roles

Applicability note

• 6-Heptyn-2-ol is supplied as a research chemical building block. It is not intended for biological administration.

General biochemistry context (literature; not product-specific)

• Small aliphatic alkynyl alcohols do not have established endogenous biological roles. However, terminal alkynes are widely used as bioorthogonal handles for post-labeling of biomolecules via CuAAC after metabolic or covalent installation.
• The secondary alcohol may be derivatized to esters, carbonates, or carbamates to modulate physicochemical properties in probe synthesis.

Caveats

• No biological activity, targets, or pathways are assigned to this item. Any use in biochemical systems should be confined to in vitro research with appropriate controls and safety review.

Buffer Applications

Not typically applicable.

• 6-Heptyn-2-ol is a hydrophobic organic building block, not a buffering agent. It does not define a useful conjugate acid–base pair in the physiological pH range.
• For work involving this compound in aqueous media, select an appropriate external buffer (e.g., phosphate, HEPES) compatible with your transformation or assay.

Green Alternatives

Context

• 6-Heptyn-2-ol is a small-molecule building block rather than a large-volume solvent. “Green alternatives” therefore focus on reaction media and reagents employed with this substrate.

Greener media choices (literature considerations)

• Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or dimethyl carbonate where compatible.
• For Pd-catalyzed couplings, consider aqueous micellar systems (TPGS-750-M), bio-derived 2-MeTHF, or EtOH/H2O mixtures under ligand-enabled conditions.
• For oxidations, Dess–Martin can be substituted by catalytic TEMPO/bleach or O2 with nitroxyl catalysts when selectivity permits.

Illustrative comparison (general)

• DCM vs. 2-MeTHF
  • Hazard: DCM (toxic, CH2Cl2) vs. 2-MeTHF (bio-derived, lower toxicity)
  • Performance: 2-MeTHF often maintains solubility for C7 alcohols and supports organometallic steps; water-partitioning facilitates workup.
• DMF/NMP vs. MeCN/EtOAc
  • Hazard: DMF/NMP (reprotoxic) vs. MeCN/EtOAc (lower chronic toxicity)
  • Performance: MeCN often sufficient for oxidations/couplings; EtOAc suitable for protection/esterification steps.

Notes

• Validate greener substitutions at small scale; catalyst/ligand solubility and selectivity can vary. No item-specific environmental certifications are provided for this product.

Pharmaceutical Uses

Scope note

• No pharmacopeial monograph or excipient status is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.

General formulation context (literature; not product-specific)

• Alkynyl alcohols can serve as synthetic intermediates when assembling small-molecule leads or conjugates. The terminal alkyne offers a handle for late-stage diversification (e.g., triazole formation) in medicinal chemistry workflows.

Compliance

• This product is supplied for research use only and is not intended for human or animal therapeutic, diagnostic, or clinical use.

Physical Properties

Item-specific (from Product Data)

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

Literature/Typical values (for reference only; not product specifications)

• Physical state: Liquid at ambient conditions (typical for C7 alkynyl alcohols)
• Boiling point: ~155–165 °C at 1 atm (literature, analogous 7-carbon alkyne alcohols)
• Melting point: Often below 0 °C (literature, secondary C7 alcohols typically remain liquid at RT)
• Density (20–25 °C): ~0.84–0.87 g/mL (literature range for C7 secondary alcohols)
• Refractive index nD20: ~1.430–1.440 (literature)
• LogP (octanol/water): ~1.5–2.0 (fragment estimate; literature)
• pKa: secondary alcohol OH ~16–17 (water, literature); terminal alkyne C–H ~25 (DMSO, literature)
• Solubility: Miscible with common organic solvents (Et2O, THF, DCM, toluene, alcohols); low-to-moderate solubility in water expected for C7 alcohols (literature)

Notes

• Do not treat literature data as specifications. For assay-relevant parameters (water, peroxides, metal content, UV cutoff, etc.), consult the CoA/Spec Sheet; not specified for this item.

Quality and Grades

Item-specific (from Product Data)

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

General guidance (literature; for context only)

• Research grade vs. higher analytical grades: Research-grade 6-heptyn-2-ol is commonly suitable for synthetic applications (e.g., coupling, oxidation, protection chemistry). If low UV background or trace metal limits are critical (e.g., photochemistry or catalysis screening), an analytical or HPLC-grade specification may be preferred.
• Water and volatile impurities: For air-/moisture-sensitive transformations (e.g., strong-base alkynylations, organolithium), drying over activated 3 Å molecular sieves and/or distillation under reduced pressure may be beneficial. Verify acceptance criteria on the CoA.
• Metals/halides: Trace copper can promote undesired Glaser coupling; consider metal-scavenging or chelation if needed in process. Specific metal limits are Not specified for this item; refer to CoA/Spec Sheet.

Documentation

• For exact assay, GC purity, residual solvents, metals, water, and other release criteria, refer to the item-specific CoA/Specification Sheet.

Reaction and Applications

Use profile (literature; general guidance)

• Dual functionality: A terminal alkyne and a secondary alcohol enable orthogonal transformations.

Representative applications

• Terminal alkyne chemistry
  • CuAAC “click” reaction with organic azides to give 1,4-disubstituted 1,2,3-triazoles (Cu(I) catalysis). The proximal secondary OH can be left unprotected or protected depending on compatibility.
  • Sonogashira cross-coupling (Pd/Cu) after halogenation at the terminal position (or via coupling of the terminal alkyne with aryl/vinyl halides under standard Sonogashira conditions).
  • Glaser–Hay oxidative coupling to form diynes (typically undesired during storage, but synthetically useful under controlled conditions with Cu and O2).
• Alcohol-site chemistry
  • Oxidation to 6-heptyn-2-one (e.g., PCC, Dess–Martin, Swern).
  • Esterification (Steglich, Fischer) to tune polarity or introduce handles for further coupling.
  • Mitsunobu reaction for substitution/inversion at C2 with suitable nucleophiles.
  • Protection as silyl ethers (TBDMS, TIPS) or carbonates to mask the OH during alkyne transformations.
• Hydrofunctionalization of the alkyne
  • Hydroboration–oxidation (catecholborane or disiamylborane) to aldehydes from terminal alkynes; hydration (Hg- or Au-catalyzed) to methyl ketones under Markovnikov control.

Practical tips

• Terminal alkyne pKa ~25 (DMSO); use strong bases (NaNH2, LDA, n-BuLi) for clean deprotonation. Alcohol pKa ~16–17—protect if strongly basic conditions would lead to alkoxide formation and side reactions.
• Avoid copper and oxygen during reactions where diyne formation is detrimental.

Reaction Conditions

General conditions (literature; illustrative, not item-specific specifications)

• Deprotonation/alkynylation
  • Base: n-BuLi (1.0–1.2 equiv) or NaNH2 (1.5–2.0 equiv)
  • Solvent: anhydrous THF or toluene; –78 to 0 °C (n-BuLi) or 0 to 25 °C (NaNH2)
  • Followed by electrophile addition (e.g., alkyl halides, carbonyls). Protect or account for concurrent alkoxide formation from the OH.
• CuAAC (click)
  • Catalyst: CuSO4 (1–5 mol%) + sodium ascorbate (reducing agent) or premade Cu(I) sources; solvent H2O/tBuOH or MeOH/H2O; RT to 50 °C; typical reactions complete in 0.5–12 h.
• Oxidation of secondary alcohol
  • Dess–Martin periodinane (1.3 equiv), DCM, 0 °C to RT, 1–2 h; or Swern (DMSO, (COCl)2, Et3N), –78 to 0 °C.
• Partial hydrogenation of alkyne
  • Lindlar catalyst, H2 (1 atm), EtOAc or MeOH, 0–25 °C to obtain cis-alkene; monitor to avoid over-reduction.
• Sonogashira coupling (of terminal alkyne)
  • Pd(PPh3)2Cl2 (1–3 mol%), CuI (2–5 mol%), amine base (Et3N, iPr2NH), DMF/Et3N or iPr2NH as solvent, RT–80 °C; inert atmosphere; 2–24 h.

Yields

• Reported isolated yields for these transformations typically range from 60–95% depending on substrate and conditions (literature). Optimize stoichiometry, temperature, and protection strategy for the OH to maximize selectivity.

Safety and Handling

Item-specific (from Product Data)

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• Storage: Room temperature (per product data).

General safety guidance for alkynyl secondary alcohols (literature; not product-specific)

• Likely hazards: Flammable liquid and vapor; may cause skin/eye irritation. Terminal alkynes can undergo copper-catalyzed oxidative coupling (Glaser-type) in air; avoid unnecessary copper contamination during storage/handling.
• PPE: Use chemical-resistant gloves, safety goggles/face shield, lab coat. Handle in a fume hood to avoid inhalation of vapors.
• Incompatibilities: Strong oxidizers; strong bases may deprotonate the terminal alkyne; avoid copper salts and oxygen if dimerization is undesirable in process streams.
• First aid overview: Eye/skin contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical advice. Always follow your institutional SOPs.
• Fire-fighting: Use CO2, dry chemical, or alcohol-resistant foam. Vapors may form explosive mixtures with air; ground/bond during transfer.

Authoritative information

• For definitive hazard classification and exposure controls, consult the product’s SDS. The above is general guidance only.

Solvent Selection

Applicability note

• 6-Heptyn-2-ol is a substrate/reagent rather than a process solvent. The following guidance concerns solvents suitable for dissolving and reacting this compound.

Solubility and polarity (literature)

• Expected to be highly soluble in ethers (THF, MTBE), chlorinated solvents (DCM, CHCl3), esters (EtOAc), aromatics (toluene), and alcohols (MeOH, EtOH); limited water solubility typical of C7 alcohols.
• Polarity: Moderately polar due to the secondary OH, but overall hydrophobic C7 chain with a terminal alkyne. Suitable for both polar aprotic and moderately nonpolar media.

Selection tips by transformation

• Base-mediated alkynylation/deprotonation: Dry, aprotic solvents (THF, Et2O, toluene) under inert atmosphere.
• Pd-catalyzed couplings (Sonogashira): Polar aprotic solvents (DMF, DMAc, NMP) or mixed amine solvents (Et3N, iPr2NH) frequently used; oxygen exclusion recommended.
• Oxidation of the alcohol (to ketone): DCM, MeCN, or DMSO-based protocols (e.g., Swern) depending on reagent.
• Protection of the OH (silylation, acylation): DCM, DMF, or pyridine as bases/solvents.

Practical notes

• Where phase-transfer or aqueous workups are critical, biphasic systems with MTBE/EtOAc or DCM often aid separations. Avoid protic solvents when a strong base is present to prevent side reactions at the terminal alkyne.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature; not product-specific)

• Keep container tightly closed in a cool, well-ventilated place. Protect from ignition sources.
• For long-term integrity, store under inert gas (nitrogen/argon) and dry conditions to minimize oxidative dimerization of terminal alkynes in the presence of adventitious copper and air.
• If solid residues or crystallization occur at low ambient temperatures, gently warm to room temperature and mix to homogenize before use.
• No reconstitution is required; use as supplied. If required for water-sensitive transformations, dry over activated 3 Å molecular sieves or distill under reduced pressure immediately prior to use.

Documentation

• For any special stabilizers, allowable storage temperature excursions, and container materials, consult the product’s CoA/Spec Sheet and SDS.

Structure and Identity

Item-specific (from Product Data)

• Product name: 6-Heptyn-2-ol (SKU: H992099)
• CAS: 24395-03-7
• PubChem CID: 13337173
• InChIKey: 369841 (as provided)
• Storage condition: Room temperature

Literature/Computed (general identifiers and structural description; not item-specific specifications)

• Preferred IUPAC name (literature): Hept-6-yn-2-ol
• Molecular formula (literature): C7H12O
• Molecular weight (literature): ~112.17 g/mol
• SMILES (literature): CC(O)CCCC#C
• Key functional groups: secondary alcohol (at C2), terminal alkyne (C6≡C7–H)
• Structural features (2D verbal): A linear seven-carbon chain. C2 bears a hydroxyl substituent (secondary alcohol). The C6–C7 bond is a carbon–carbon triple bond with a terminal acetylenic hydrogen at C7. No stereochemistry is specified at C2 (racemic if not resolved).

Notes

• Where literature identifiers are shown, they are provided for general reference only and are not guaranteed item-specific identifiers. Refer to the product’s CoA/Spec Sheet for definitive identification data.

Synthetic Utility

Functional group leverage (literature)

• Terminal alkyne (C≡CH)
  • Nucleophilicity after deprotonation enables C–C bond formation with electrophiles (alkylation, carbonyl addition as lithium acetylides).
  • Cycloaddition platform (CuAAC) to access 1,2,3-triazoles—robust, modular linkages useful in tagging and conjugation chemistries.
  • Hydrometalation pathways (hydroboration, hydrosilylation) providing vinylboranes/silanes for subsequent cross-coupling.
• Secondary alcohol (R2CHOH)
  • Oxidation to ketone; reduction/inversion (Mitsunobu) to diversify substitution at C2.
  • Protection options (silyl ethers, carbonates) allowing orthogonal manipulation of the alkyne.

Retrosynthetic value

• 6-Heptyn-2-ol sits at the homopropargylic level relative to carbonyl precursors. It can arise from addition of an ethynyl anion equivalent to 2-hexanone, or by reduction of 6-heptyn-2-one. Alternatively, asymmetric reduction can access enantioenriched material from the ketone.

Select downstream elaborations

• Formation of 6-heptyn-2-one (oxidation), 6-hepten-2-ol (partial hydrogenation/Lindlar), or diynes (Glaser–Hay) provides entry to diverse motifs in materials and synthesis.

Target Specificity

Not applicable.

• This product is a small-molecule chemical reagent (alkynyl alcohol) and does not possess antigen/epitope specificity, clone information, or species reactivity attributes.
• No target binding data are provided for this item.