4-(2,6-Dichlorophenyl)-1-butene - ≥95% , CAS No.117269-67-7

CAS: 117269-67-7 Cat. No.: D1298927 Summenformel: C₁₀H₁₀Cl₂ Molekulargewicht: 201.09 PubChem CID: 14224113

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C=CCCC1=C(C=CC=C1Cl)Cl

IUPAC Name

2-but-3-enyl-1,3-dichlorobenzene

InChIKey

ZRBPFCPGZWEQLV-UHFFFAOYSA-N

INCHI

1S/C10H10Cl2/c1-2-3-5-8-9(11)6-4-7-10(8)12/h2,4,6-7H,1,3,5H2

Isomere SMILES

C=CCCC1=C(C=CC=C1Cl)Cl

PubChem CID

14224113

Molekulargewicht

201.09

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Halobenzenes
        • Ebene5 Chlorobenzenes
          • Ebene6 Dichlorobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Chlorobenzenes
• Direct Parent: Dichlorobenzenes
• Alternative Parents: Aryl chlorides Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 1,3-dichlorobenzene - Aryl halide - Aryl chloride - Hydrocarbon derivative - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 201.090 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 200.016 Da
• Monoisotopic Mass: 200.016 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 135.000
• 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

Application Protocols

Not applicable as a standalone protocolized reagent (e.g., no WB/IHC/IF/FC usage). For synthetic applications, see the Reaction Conditions and Application notes. Typical laboratory use involves dissolving the compound in an appropriate organic solvent and applying the reaction-specific protocol (catalyst, base, temperature) as outlined under Reaction Conditions.

Biological Roles

This product is a small-molecule aryl–alkene designed for chemical synthesis. It is not a biological buffer, metabolite, or biochemical reagent with a defined role in cellular pathways.

General context (literature):

• Aryl–alkenes of this type are hydrophobic and typically partition into organic phases; they have no established physiological function.
• Any interactions with biological systems (e.g., membrane partitioning, P450 oxidation of alkenes/benzylic positions) are context-dependent and beyond the scope of research-use chemicals. No specific biomolecular targets or endogenous pathways are associated with 4-(2,6-dichlorophenyl)-1-butene.

Note: Use strictly for research and laboratory synthesis. No clinical, diagnostic, or in vivo use is intended or implied.

Buffer Applications

Not applicable. 4-(2,6-Dichlorophenyl)-1-butene is a nonpolar organic substrate and does not serve as an acid/base buffer or pH control agent. For relevant information, see the Solvent Selection, Reaction & Applications, and Synthetic Utility sections for guidance on using this compound in organic synthesis.

Green Alternatives

Although this product is a substrate rather than a process solvent, greener choices can be made in the solvents and reagents used with it.

Greener solvent swaps (literature/practice):

• Replace THF with 2-MeTHF or CPME for hydroboration, organometallic additions, and extractions (better renewability and lower peroxide propensity for 2-MeTHF vs THF).
• Use toluene, ethyl acetate, or CPME instead of dichloromethane where feasible (e.g., in Pd couplings or epoxidations using urea–hydrogen peroxide systems instead of mCPBA in DCM).
• For cross-couplings, consider aqueous micellar media (e.g., TPGS-750-M) enabling room-temperature reactions and simplified workups.

Illustrative comparison (general):

• THF vs 2-MeTHF: similar polarity and performance; 2-MeTHF derived from biomass, higher bp, easier phase separation; may improve hydroboration selectivity.
• DCM vs EtOAc/CPME: DCM offers faster epoxidations but higher environmental and health concerns; EtOAc/CPME reduce halogenated solvent usage with modest rate trade-offs.
• DMF/DMAc vs Cyrene/propylene carbonate: for polar aprotic needs, greener dipolar aprotics can substitute with attention to catalyst compatibility.

Reagent choices:

• Prefer H2O2-based epoxidations (e.g., aqueous H2O2 with methyltrioxorhenium or tungsten catalysts) over peracids to minimize chlorinated waste.
• Employ heterogeneous Pd catalysts recoverable/reusable, and ppm-level Pd catalysis in micelles to reduce precious-metal loadings.

Pharmaceutical Uses

No pharmacopeial/excipient status is indicated for this item. It may be used as a synthetic intermediate in medicinal chemistry discovery or process development due to its bifunctional handles (terminal alkene and aryl chlorides), but it is not intended for human or veterinary use.

General formulation/manufacturing context (literature/practice):

• Role: intermediate for generating substituted anilines/biaryls via aryl–Cl activation, followed by olefin elaboration to alcohols, aldehydes, or other functionalities in lead optimization campaigns.
• Handling in pharma R&D labs: typically stored as a neat liquid or concentrated solution in hydrocarbon/ether solvents; monitored by GC/LC–MS.

Note: For any use in regulated manufacturing, full impurity profiles, residual solvent limits, and elemental impurity assessments would be required; this listing is for research use only and provides no GMP or pharmacopeial compliance claims.

Physical Properties

Item-specific specifications (this lot):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed physical data (general guidance, not product specifications):

• Molecular formula (computed from structure): C10H10Cl2
• Molecular weight (computed): ~201.09 g/mol
• Physical state: typically a colorless to pale liquid for analogs of this size and functionality.
• Solubility (qualitative, literature): insoluble in water; soluble in nonpolar/medium-polar organic solvents (e.g., hexanes, toluene, ether, dichloromethane, THF).
• Volatility: moderate; expected to distill under reduced pressure; specific bp/mp not readily available in standard compilations for this exact CAS.
• LogP (qualitative): expected high (hydrophobic) due to aryl dichloro and alkyl chain; measured value not located in common databases.

Notes:

• If exact values (bp, density, refractive index, UV cutoff) are critical, consult the item’s CoA/SDS or request a spec sheet. Avoid assuming parity with close structural analogs when designing purification or QC assays.

Quality and Grades

Item-specific grade/purity information:

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

Interpreting typical grades (general guidance):

• Research/technical grade: suitable for most synthetic applications; trace impurities may be present (e.g., residual solvents, isomeric byproducts). Verify by NMR/GC as needed for sensitive catalysis.
• High-purity or ≥98%: preferred for precision catalysis (e.g., Pd-catalyzed couplings, metathesis), kinetic studies, and analytical reference use. Lower UV background assists in HPLC/UV detection of reaction mixtures.

Stabilizers/inhibitors:

• Not specified for this item; refer to CoA/Spec Sheet. Terminal alkenes are sometimes shipped without inhibitors; if an inhibitor is present, it should be declared on the CoA, and users may need to remove it (e.g., by basic alumina) before polymerization/catalysis.

Recommended QC checks (user side, general):

• 1H/13C NMR to confirm olefinic signals and aryl substitution pattern (2,6-dichloro typically simplifies aromatic region).
• GC or GC–MS for volatile impurity profile.
• Water content by Karl Fischer if moisture-sensitive transformations are planned (not typically critical for neutral hydrocarbons but relevant to e.g., organometallic additions).

Reaction and Applications

As a bifunctional building block, 4-(2,6-dichlorophenyl)-1-butene provides an isolated terminal alkene and two aryl chlorides, enabling stepwise diversification.

Representative applications (literature/general):

• Olefin functionalization:
  • Hydroboration–oxidation (e.g., 9-BBN/catecholborane → H2O2/NaOH) to give the anti-Markovnikov primary alcohol.
  • Epoxidation (mCPBA or in situ peracids); subsequent epoxide opening affords β-aryl alcohols/amines.
  • Ozonolysis (O3, −78 °C; then Me2S or PPh3 workup) to furnish an aldehyde at the terminal position (via oxidative cleavage to 2,6-dichlorophenylbutanal after appropriate chain considerations).
  • Hydrosilylation/hydroformylation to introduce Si or CHO functionality under Pt/Rh catalysis.
  • Olefin metathesis (RCM/cross-metathesis) with Grubbs-type catalysts to build complexity.
• Aryl chloride derivatization (two ortho-Cl):
  • Pd-catalyzed cross-couplings (Buchwald–Hartwig amination, Suzuki–Miyaura, Negishi, Kumada) using robust ligand systems (e.g., BrettPhos/SPhos/XPhos) to activate aryl–Cl bonds; 2,6-disubstitution can influence oxidative addition and sterics, often beneficial for mono-functionalization selectivity.
  • Directed metal–halogen exchange (aryl–Cl is less reactive than Br/I; specialized conditions needed) followed by electrophile trapping.
• Materials/ligand precursors: the 2,6-dichloro motif can be elaborated to ortho-disubstituted anilines/phenols, valuable in ligand and material design, while the terminal alkene enables grafting to polymers or further chain extension.

Workflow strategies:

• Orthogonal sequence control: functionalize the olefin under conditions benign to aryl–Cl (e.g., hydroboration), then perform Pd-catalyzed coupling; or invert the order with appropriate protecting/compatibility planning.
• Purification: avoid strong acid on silica after epoxidations; for metal-catalyzed steps, incorporate scavengers (e.g., Si-TMT) to reduce Pd/Rh residues.

Reaction Conditions

General literature conditions for representative transformations (guidance only; optimize per substrate/catalyst):

• Hydroboration–oxidation (anti-Markovnikov alcohol):

  • Reagents: 9-BBN (1.1–1.2 equiv) or BH3·THF, then H2O2/NaOH.
  • Solvent: THF or 2-MeTHF; 0 °C to rt; 1–3 h for hydroboration, then oxidation at 0–25 °C.
  • Notes: 9-BBN minimizes over-addition; inert atmosphere recommended.

• Epoxidation of terminal alkene:

  • Reagent: mCPBA (1.1–1.5 equiv) in CH2Cl2 at 0–25 °C, 1–4 h; or H2O2 (30%) with catalytic tungstate in MeOH/H2O.
  • Workup: aqueous Na2SO3 to quench peracids; careful silica to avoid acid-catalyzed rearrangement.

• Ozonolysis (to carbonyl derivatives):

  • Conditions: O3 in O2 at −78 °C in MeOH/DCM until blue persists; reductive workup (Me2S) for aldehydes or oxidative (H2O2) to acids.

• Pd-catalyzed Suzuki–Miyaura on aryl–Cl:

  • Catalyst/ligand: Pd2(dba)3 (1–2 mol%) with SPhos/XPhos/Buchwald ligands (2–4 mol%).
  • Base: K3PO4 or Cs2CO3 (2–3 equiv).
  • Solvent/temp: toluene/dioxane/H2O (biphasic) at 80–110 °C, 4–16 h.
  • Note: 2,6-dichloro sterics may enable selective mono-coupling; increase catalyst loading for the second activation if needed.

• Buchwald–Hartwig amination:

  • Catalyst: Pd(OAc)2 (1–3 mol%) with BrettPhos or RuPhos.
  • Base: NaOtBu or Cs2CO3; solvent: toluene or CPME; 90–110 °C.

• Olefin metathesis (cross-metathesis):

  • Catalyst: Grubbs II/HO-G-II (2–5 mol%).
  • Solvent: DCM, toluene, or green alternatives (EtOAc/2-MeTHF); rt to 40 °C; 2–12 h.

Yields: substrate- and partner-dependent; 60–90% commonly reported for well-optimized couplings and hydroborations on related systems. Always run small-scale scouts to define conditions for this exact substrate.

Safety and Handling

Item-specific hazard information from Product Data:

• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• GHS classification/pictograms: Not specified for this item; refer to SDS.

General safety considerations for aryl–alkenes (literature/practice; defer to SDS):

• Likely hazards: combustible liquid; may cause skin/eye irritation; harmful if inhaled/ingested. Treat as a general organic liquid with potential narcotic effects at high vapor concentrations.
• PPE: lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and avoid aerosol generation.
• Incompatibilities: strong oxidizers (may cause exotherm); strong electrophiles; radical initiators (risk of unwanted polymerization of the terminal alkene under radical conditions); very strong bases can induce side reactions (e.g., elimination/addition at the olefin) in reactive mixtures.
• Handling: avoid heat, sparks, and open flame. Ground/bond containers during transfer if in bulk. Minimize exposure to air/UV if long-term stability is a concern (allylic substrates can undergo slow autoxidation under harsh conditions).
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Spill response: absorb with inert material (vermiculite, sand); ventilate area; collect for disposal per local regulations. Refer to SDS for authoritative guidance.

Solvent Selection

This compound is a nonpolar-to-moderately nonpolar aryl–alkene. It is a substrate/solute, not used as a solvent; solvent selection should focus on dissolving it effectively while supporting the intended reaction or purification.

General solvent compatibility (literature/practice):

• High solubility: hexanes, heptane, cyclohexane, toluene/xylene, ethyl acetate, MTBE, diethyl ether, THF, dichloromethane, chloroform.
• Poorly soluble: water; highly polar protic media (unless emulsified with surfactants).

Selection tips by application:

• Pd-catalyzed cross-couplings (on aryl–Cl): toluene, xylene, dioxane or CPME with strong biaryl phosphine ligands; polar aprotics (DMF/DMAc) may enhance rates but complicate workup.
• Olefin functionalizations (hydroboration, epoxidation): etheric solvents (THF/2-MeTHF) or CH2Cl2 for peracid epoxidations; avoid chlorinated solvents under strong base.
• Purification: normal-phase silica flash with hexanes/EtOAc gradients; aryl dichloro increases Rf vs non-chlorinated analogs; consider silver nitrate-doped plates to visualize alkene if needed.

Quick comparison (general):

• Toluene: excellent solubility, high bp for elevated-temperature couplings.
• 2-MeTHF/MTBE: greener ethers, good for hydroboration and organometallics.
• DCM: efficient for peracid epoxidation and extractions; consider greener alternatives if feasible.

Storage and Reconstitution

Item-specific storage/shipping:

• Storage conditions: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.
• Shipped in: Normal (ambient) conditions.

General handling and stability (literature/practice):

• Protect from prolonged exposure to heat and direct sunlight. For multi-month storage, consider blanketing headspace with inert gas (N2/Ar) to minimize slow oxidative changes typical of alkenes.
• If an inhibitor is listed on the CoA (not specified here), remove before polymerization/catalysis if problematic (e.g., pass through a short plug of basic alumina).
• Reconstitution: Not applicable; typically used neat or as a solution in organic solvents (e.g., hexanes, toluene, THF, DCM). Prepare stock solutions under dry, inert atmosphere for air/moisture-sensitive downstream chemistry.
• Freeze–thaw: Not generally required; avoid unnecessary freezing which can stress containers. If crystallization/solidification occurs at low temperature, warm gently to ambient and mix thoroughly before use.

Always refer to the product’s CoA and SDS for definitive storage and stability data specific to the supplied lot.

Structure and Identity

4-(2,6-Dichlorophenyl)-1-butene is an aryl–alkene building block bearing a terminal olefin and a 2,6-dichloro-substituted phenyl ring, offering two orthogonal functional domains for synthesis.

Item-specific (from Product Data):

• SKU: D1298927
• Product Name: 4-(2,6-Dichlorophenyl)-1-butene
• CAS: 117269-67-7
• PubChem CID: 14224113
• InChIKey (as provided): 464350 (note: appears non-standard/truncated; verify on CoA/SDS)
• Storage: Room temperature
• Shipped in: Normal
• Research Use: For research use only

Computed/literature identifiers and features (for reference; not item specifications):

• Typical molecular formula (literature/computed): C10H10Cl2
• Typical molecular weight (literature/computed): ~201.09 g/mol
• Representative SMILES (literature/computed): C=CCCc1c(Cl)cccc1Cl
• Structural features: terminal alkene (1-butene moiety), disubstituted phenyl ring with ortho,ortho-dichloro pattern (2,6-Cl2); no stereocenters; conjugation between aryl ring and alkyl chain is interrupted (sp3 at benzylic carbon), olefin is isolated (terminal).

2D description in words (general): a 2,6-dichlorobenzene ring is attached via a –CH2–CH2– tether to a terminal vinyl group (–CH2=CH2), giving an aryl–(CH2)2–CH2–CH2=CH2 connectivity with the ring chlorinated at the two ortho positions.

Synthetic Utility

Strategic value arises from two orthogonal functional manifolds:

• Terminal alkene (chemoselective handle):
  • Anti-Markovnikov additions (hydroboration–oxidation → primary alcohols; hydroazidation/hydroamination under radical or metal catalysis).
  • Electrophilic oxidations (epoxidation, dihydroxylation) leading to β-functionalized derivatives.
  • C–C formations via radical additions (e.g., Giese-type), cross-metathesis, and ozonolysis to carbonyl fragments.
• Two aryl chlorides (2,6-disposition):
  • Enable stepwise or simultaneous cross-couplings (Suzuki–Miyaura to aryl/alkyl boronates; Buchwald–Hartwig to amines), with steric hindrance often imparting selectivity between the two C–Cl bonds.
  • Serve as precursors to ortho-disubstituted motifs after coupling, valuable in ligand frameworks (e.g., biaryl phosphines) or congested scaffolds.

Retrosynthetic considerations:

• The substrate can be disconnected to a 2,6-dichlorobenzyl unit plus a two-carbon linker to a vinyl group; hence it is a convenient convergence point for routes requiring late-stage olefin introduction or aryl diversification.

Practical notes:

• Aryl–Cl activation benefits from electron-rich bulky phosphines (e.g., BrettPhos, XPhos) or NHC ligands; bases such as NaOtBu, K3PO4, or Cs2CO3 in toluene/dioxane are typical.
• Olefin transformations should be sequenced to avoid catalyst/ligand incompatibilities; protect sensitive functionalities introduced on the aryl ring before strong oxidations of the olefin.

Target Specificity

Not applicable. This product is a small organic molecule, not a biological targeting reagent (e.g., antibody, ligand probe). No antigen/epitope or species reactivity parameters apply.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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 117269-67-7, the molecular formula is C10H10Cl2, and the molecular weight is 201.09 g/mol. InChIKey ZRBPFCPGZWEQLV-UHFFFAOYSA-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.