trans-1,4-Dichlorocyclohexane - ≥99%(GC) , CAS No.16890-91-8

CAS: 16890-91-8 Cat. No.: T161920 Formula: C₆H₁₀Cl₂ Peso molecolare: 153.05 PubChem CID: 519304

QUALITÀ & PUREZZA ≥99%(GC)

Synonyms

(1R,4R)-1,4-DICHLOROCYCLOHEXANE | Cyclohexane, 1,4-dichloro-, trans- | 1alpha,4alpha-Dichlorocyclohexane | 1,4-Dichlorocyclohexane | SCHEMBL20993361 | FT-0694018 | SCHEMBL9720381 | DTXSID70878819 | WQTINZDWAXJLGH-OLQVQODUSA-N | 1,4-Dichlorocyclohexane,c&t

Storage

Room temperature

Shipped In

Normal

Specifiche

Sinonimi

(1R,4R)-1,4-DICHLOROCYCLOHEXANE | Cyclohexane, 1,4-dichloro-, trans- | 1alpha,4alpha-Dichlorocyclohexane | 1,4-Dichlorocyclohexane | SCHEMBL20993361 | FT-0694018 | SCHEMBL9720381 | DTXSID70878819 | WQTINZDWAXJLGH-OLQVQODUSA-N | 1,4-Dichlorocyclohexane,c&t

Specifiche e purezza

≥99%(GC)

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥99%(GC)

Nomi e identificatori

Pubchem Sid

504759024

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504759024

Sorrisi canonici

C1CC(CCC1Cl)Cl

IUPAC Name

1,4-dichlorocyclohexane

InChIKey

WQTINZDWAXJLGH-UHFFFAOYSA-N

INCHI

1S/C6H10Cl2/c7-5-1-2-6(8)4-3-5/h5-6H,1-4H2

Isomeri SMILES

C1CC(CCC1Cl)Cl

PubChem CID

519304

Peso molecolare

153.05

Reaxy-Rn

1901383

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Classe Alkyl halides
      • Subclass Cyclohexyl halides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Classe: Alkyl halides
• Subclass: Cyclohexyl halides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclohexyl halides
• Alternative Parents: Organochlorides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexyl halide - Hydrocarbon derivative - Organochloride - Alkyl chloride - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen 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

Proprietà chimiche e fisiche

• Punto di ebollizione (°C): 60°C/3mmHg(lit.)
• Punto di fusione (°C): 103 °C
• Peso molecolare: 153.050 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 152.016 Da
• Monoisotopic Mass: 152.016 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 54.900
• 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 antibody/assay-specific protocols are associated with this small-molecule building block. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance and adapt to your specific methodology.

Biological Roles

Item-specific facts (from Product Data)

• Biological/biochemical role: Not specified for this item; for research use only.

General information (for context; not a claim of biological activity)

• trans-1,4-Dichlorocyclohexane is a hydrophobic, saturated organochlorine lacking specific functional groups typically associated with biochemical activity (e.g., aromatics or heteroatoms for H-bonding). It is expected to partition strongly into nonpolar phases (lipid-like environments) and poorly into aqueous media.
• In environmental chemistry studies, related organochlorines are used as model hydrophobic organic compounds (HOCs) to investigate sorption, partitioning (Kow), and volatilization behavior. Trans- vs cis‑isomers can exhibit distinct physical properties that modulate partitioning.
• Metabolic transformation in biological systems, when it occurs, generally proceeds via oxidative dechlorination or dehydrohalogenation catalyzed by mixed-function oxidases, producing more polar metabolites for excretion. However, specific metabolic pathways for this exact isomer are sparsely reported in the open literature.
• Because of its hydrophobicity, handling in bioassays commonly requires cosolvents (e.g., DMSO, ethanol) at low percentages with rigorous controls to avoid solvent artifacts.

Note: No medical, therapeutic, or toxicological claims are made. Use strictly in research settings with appropriate institutional approvals.

Buffer Applications

This compound is a hydrophobic organochlorine building block and is not used to prepare aqueous biological buffers. It has negligible water solubility and provides no acid/base functionality for buffering. For experimental work involving this compound in biological systems, select an appropriate aqueous buffer separately (e.g., PBS, HEPES) and deliver the compound via a suitable water-miscible cosolvent (DMSO/EtOH) or emulsifier as needed.

Green Alternatives

Context

• As a chlorinated alicyclic building block, trans-1,4-dichlorocyclohexane raises concerns typical of chlorinated organics (persistence, potential toxicity, halogenated waste streams).

Alternatives and strategies (general; balance benefits and trade-offs)

• Use alternative leaving groups: Prepare the 1,4-ditosylate or 1,4-dimesylate of cyclohexanediol as a precursor. These sulfonates are often more reactive in SN2 and can avoid chlorinated waste, though sulfonate synthesis employs acid chlorides/anhydrides and still requires careful waste management.
• Iodide in situ (Finkelstein): Exchange Cl→I under mild conditions to enable lower-temperature substitutions; reduces energy input but introduces iodide waste.
• Greener solvents: Favor 2‑MeTHF, CPME, EtOAc, or toluene over DMF/NMP/CH2Cl2 when reaction compatibility allows. Apply water/PEG biphasic systems with phase-transfer catalysis to reduce organic solvent use.
• Catalytic activation: Nickel-catalyzed cross-electrophile couplings under electrochemical or photochemical conditions can operate at lower temperatures and with fewer stoichiometric metals, reducing waste.
• Process intensification: Flow processing for exothermic substitutions or eliminations can enhance safety and reduce solvent inventory.

Comparison snapshot (general)

• Chloride substrate vs tosylate: chloride is cheaper, more stable; tosylate offers higher reactivity and often cleaner SN2 at lower temperature but introduces arylsulfonate byproducts.
• Polar aprotic (DMF/DMSO) vs greener ethers/esters: polar aprotic promote kinetics but carry health/environmental burdens; ethers/esters are greener but may slow reactions.

Pharmaceutical Uses

Item-specific facts (from Product Data)

• Pharmaceutical/excipient status: Not specified for this item; for research use only.

General context (non-clinical)

• As a simple chlorinated cycloalkane lacking functional handles beyond C–Cl bonds, trans-1,4-dichlorocyclohexane has no recognized role as a pharmaceutical excipient. However, chlorinated alicyclics can serve as synthetic intermediates en route to more complex molecules (e.g., 1,4‑disubstituted cyclohexanes) used in medicinal chemistry campaigns.
• In process development, analogous dihalides are sometimes leveraged for scaffold construction via substitution or elimination to access diamines, diols, or dithioethers that can be further elaborated into API intermediates. Any such use requires rigorous impurity and residual solvent control to meet pharmacopeial requirements.

Regulatory note

• No compendial monograph is known for this specific compound. If considered for GMP-related synthesis steps, establish in-house specifications (identity, isomeric purity, residual solvents, halide content) and validated analytical methods.

Physical Properties

Item-specific facts (from Product Data)

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

Literature/General properties (for reference only; not item specifications)

• Physical state: typically a low-melting solid or high-boiling liquid depending on isomeric purity and temperature; trans-1,4 is commonly reported as a crystalline solid at room temperature.
• Polarity: nonpolar to weakly polar (two C–Cl bonds; overall low polarity due to trans arrangement).
• Solubility: low in water; miscible with common nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, dichloromethane, chloroform, ethers).
• Volatility: substantially lower than lighter chlorinated solvents (e.g., DCM), consistent with a higher molecular weight and lack of aromaticity.
• Density: expected greater than water due to two chlorine atoms (literature for related chlorinated cycloalkanes: ~1.2–1.3 g/mL), but exact value for this item is not specified.
• Refractive behavior: typical of chlorinated alicyclics with elevated refractive index vs hydrocarbons (exact value not specified).

Notes

• Precise BP/MP, density, refractive index, and partition data are formulation- and isomer-purity-dependent and are Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

Item-specific facts (from Product Data)

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

Guidance on grades (general)

• Research grade: suitable for most synthetic, analytical, or materials R&D uses. When stereochemical outcomes matter (cis/trans), ensure the isomeric purity is documented on the CoA.
• Analytical/GC grade: emphasizes low background impurities volatile under GC conditions; relevant if you plan to use this compound as a reference or internal standard in environmental or materials analyses.
• Isomeric purity: The trans vs cis ratio profoundly affects physical properties and reactivity (conformation, elimination pathways). If your work is stereosensitive (e.g., conformational studies, mechanistic kinetics), request/isolate documentation of isomeric purity and residual cis isomer content.
• Stabilizers: Not typically required for saturated chlorocarbons; if a stabilizer or inhibitor is present, it should be declared. For this item: Not specified for this item; refer to CoA/Spec Sheet.

What to check on receipt

• Verify CAS (16890-91-8), identity (NMR/GC-MS), isomeric assignment (1H/13C NMR coupling patterns consistent with trans-1,4), and purity (GC, HPLC). Document water content (Karl Fischer) only if moisture-sensitive applications are planned.

Reaction and Applications

General applications (literature; guidance only)

• Nucleophilic substitution: Secondary C(sp3)–Cl centers can undergo SN2 with strong nucleophiles (e.g., azide, thiolates, iodide under Finkelstein-like conditions) to deliver 1,4-disubstituted cyclohexanes (e.g., 1,4-diazides → 1,4-diamines after reduction; 1,4-dithiol derivatives).
• Elimination (E2): Strong bases (e.g., t‑BuOK, LDA) can promote double dehydrohalogenation to yield cyclohexenes/dienes (e.g., 1,4‑cyclohexadiene), though rates are modest for chlorides; elevated temperatures may be required. Competing substitution must be managed by base choice/solvent.
• Reduction/dehalogenation: Metals or hydrides (Zn/AcOH, Zn/NH4Cl, Mg/MeOH, catalytic hydrogenation on Pd/C under H2) can effect partial or full dechlorination to cyclohexane.
• Radical chemistry: Initiators (AIBN/peroxides, photoredox) can generate carbon radicals from C–Cl under appropriate catalysts, enabling functionalization or dehalogenation (Ni/photoredox dual catalysis for C(sp3)–Cl activation).
• Cross-electrophile coupling (advanced): Nickel catalysis can couple secondary chlorides with aryl/vinyl electrophiles or organozincs under reductive conditions; requires methodological optimization due to sterics.
• Conformational studies: The trans-1,4 arrangement (often diequatorial) serves as a benchmark substrate in teaching and research on cyclohexane conformations and energetics.

Practical notes

• Activation: Converting chlorides to better leaving groups (tosylates/iodides) can accelerate substitutions if chlorides prove sluggish.
• Stereochemical outcomes: Trans-1,4 substitution often preserves the anti relationship; SN2 at secondary centers in a ring proceeds with inversion at each reacting carbon—plan sequences accordingly.
• Workup: For reactions in polar aprotic solvents, thorough aqueous washes and scavengers for residual halides/nucleophiles improve product purity.

Reaction Conditions

General conditions (literature guidance; adjust per your system)

• Nucleophilic substitution (SN2):
  • Solvents: DMSO, DMF, NMP, or THF (for more reactive nucleophiles).
  • Nucleophiles: NaN3, KSCN, NaI, RS−, CN− (observe strict safety control with toxic nucleophiles).
  • Temperature: ambient to 80–120 °C depending on nucleophile strength and solvent; secondary chlorides often require heating.
  • Additives: phase-transfer catalysts (e.g., TBAB) can accelerate reactions in biphasic systems; iodide salts can promote halide exchange.
• Elimination (E2):
  • Bases: t‑BuOK, KOEt, LDA, DBU.
  • Solvents: DMSO, DMF, t‑BuOH, or THF.
  • Temperature: typically elevated (60–120 °C); monitor by GC to manage over-elimination or side reactions.
• Reduction/dehalogenation:
  • Metals: Zn in acetic acid or ammonium chloride aqueous-organic mixtures; Mg/MeOH.
  • Catalytic hydrogenation: Pd/C or Raney Ni under H2 (1–10 bar), room temperature to 60 °C, producing mono- or dechlorinated products depending on conditions.
• Cross-electrophile coupling (advanced):
  • Catalysts: NiBr2•glyme or NiCl2 with bipyridine/phen ligands; reductant Zn or electrochemical.
  • Solvents: DMA, DMF, MeCN; temperatures 0–60 °C; rigorous exclusion of air/moisture recommended.

Monitoring and workup

• Monitor by GC/GC–MS or 1H NMR (CDCl3 or C6D6). Quench reactive bases cautiously. Extract into nonpolar organics; wash to remove salts/nucleophiles. Purify by column chromatography or recrystallization depending on product properties.

Expected yields

• Strongly method-dependent; secondary C–Cl substrates often furnish moderate to good yields after optimization. Consult primary literature for analogous substrates.

Safety and Handling

Item-specific facts (from Product Data)

• GHS Classification, Signal Word, H-statements, Pictograms: Not specified for this item; refer to SDS.

General safety guidance (consult SDS for authoritative information)

• Likely hazards: chlorinated alicyclics can cause skin/eye irritation and may be harmful if swallowed, inhaled, or absorbed through skin. Avoid aerosols and vapors; use in a fume hood.
• PPE: safety goggles, lab coat, suitable chemically resistant gloves (e.g., nitrile), and appropriate footwear. Avoid skin contact; wash thoroughly after handling.
• Handling: minimize inhalation and exposure. Prevent release to the environment—halogenated organics can be persistent. Use secondary containment for bulk operations.
• Incompatibilities: strong bases (risk of dehydrohalogenation), strong nucleophiles (SN reactions), strong oxidizers (combustion enhancement), alkali metals/reducing agents (possible dehalogenation). Avoid open flames and sources of ignition.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: remove contaminated clothing; wash with soap and water.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if easy; continue rinsing; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Spills: absorb with inert material (vermiculite, sand), collect in halogenated waste container. Ventilate area.
• Waste: dispose of as halogenated organic waste per institutional and local regulations.

Special risks

• Not an ether—no specific peroxide-formation risk expected. Avoid prolonged heating with strong bases which can promote elimination to dienes.

Solvent Selection

Relevance

• trans-1,4-Dichlorocyclohexane is a hydrophobic, nonpolar-to-weakly-polar organic substrate. Solvent choice affects its solubility and reactivity in substitutions, eliminations, and reductions.

General solvent compatibility (literature; guidance only)

• Highly suitable: nonpolar/apolar aprotic solvents (hexanes, heptane, cyclohexane, toluene) for physical handling, recrystallization (where applicable), or radical chemistry.
• Moderately polar aprotic: dichloromethane, chloroform, ethyl acetate, THF, CPME—useful for nucleophilic substitutions with stronger nucleophiles or for metal-mediated reductions where some polarity is beneficial.
• Polar aprotic for SN2/E2 on secondary chlorides: DMSO, DMF, NMP can increase reaction rates with potent nucleophiles/bases, but assess elimination side-products. Observe safety and work-up complexity.
• Poor: water and highly protic media (unless using phase-transfer catalysis), due to very low aqueous solubility.

Selection tips

• For conformational or spectroscopic studies: CDCl3 or C6D6 are typical NMR solvents providing good solubility and well-resolved spectra.
• For nucleophilic substitutions: choose a polar aprotic solvent and a strong, unhindered nucleophile; consider phase-transfer catalysis if working biphasically.
• For eliminations (E2): employ strong bases in polar aprotic solvents while controlling temperature to manage competing substitution.

Small comparison (general)

• DCM/CHCl3: good solvency, easy workup; higher volatility/toxicity considerations.
• Toluene/hexanes: greener profile, lower polarity; may limit reaction rates for polar mechanisms.
• Ethers (THF/CPME): balance between solvency and process safety; ethers aid organometallic steps but introduce peroxide management for certain ethers (not CPME).

Storage and Reconstitution

Item-specific facts (from Product Data)

• Storage conditions: Room temperature
• Shipped: Normal conditions

General guidance (supplemental; not item specifications)

• Container: Store tightly closed in an amber glass bottle to minimize volatilization and photolytic degradation risk. Use PTFE-lined caps to resist halogenated organics.
• Atmosphere: Typically stable in air; for long-term storage, a dry environment is recommended to prevent adventitious hydrolysis in the presence of strong bases or nucleophiles.
• Segregation: Keep away from strong bases, strong nucleophiles, and oxidizers. Maintain secondary containment for halogenated organics.
• Reconstitution/solubilization: If supplied as a solid, dissolve in a suitable organic solvent (e.g., dichloromethane, chloroform, toluene, THF, ethyl acetate) to prepare stock solutions. For biological assays, prepare concentrated stocks in DMSO or ethanol, then dilute into buffer immediately before use, keeping final cosolvent ≤1–2% v/v as assay permits.
• Freeze–thaw: Not typically required. If preparing solutions for extended storage, keep at 2–8 °C in sealed amber vials; check for precipitation/crystallization before use.
• Stability checks: Periodically verify identity/purity by GC or NMR if stored for >12 months or exposed to heat. Refer to the CoA/Spec Sheet for item-specific stability data if available.

Structure and Identity

Item-specific facts (from Product Data)

• Product name: trans-1,4-Dichlorocyclohexane (SKU: T161920)
• CAS: 16890-91-8
• Storage: Room temperature; shipped under normal conditions
• InChIKey (as provided): 405571
• SMILES: 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/General identity data (for reference only; not item specifications)

• Typical molecular formula: C6H10Cl2
• Typical molecular weight: 153.05 g/mol
• Representative SMILES (non-stereospecific): ClC1CCC(CC1)Cl; trans stereochemistry implies substituents are on opposite faces of the ring (diequatorial in the preferred chair).
• Structural features: saturated six-membered cyclohexane ring bearing two chlorine substituents at the 1- and 4-positions; the trans isomer places the two C–Cl bonds anti to each other across the ring. In a chair conformation, the thermodynamically favored form is generally diequatorial (minimizing 1,3‑diaxial interactions).

2D structure description

• Six-carbon ring (cyclohexane) with chlorines at carbons 1 and 4. The two chlorines are disposed on opposite faces (trans), yielding no net dipole along the 1,4-axis. No aromaticity, no heteroatoms other than two chlorides, and no formal stereocenters outside of conformational chirality in the chair forms.

Synthetic Utility

Key functional elements

• Two secondary C(sp3)–Cl leaving groups positioned trans-1,4 on a cyclohexane ring. The trans relationship facilitates anti-periplanar arrangements in certain elimination events and enables symmetrical disubstitution patterns.

Transformations (literature; guidance only)

• Double SN2 displacements to form 1,4‑disubstituted cyclohexanes: azides → diamines; thiolates → dithioethers; cyanide → dinitriles (with caution and appropriate safety measures for CN− handling).
• Halide exchange (Cl→I) to enhance reactivity toward softer nucleophiles; uses NaI in acetone or polar aprotic media, potentially stepwise via monohalide stages.
• Double elimination to 1,4‑cyclohexadiene or conjugated systems under strong basic conditions; stereoelectronic control via chair conformations can influence regioisomer distribution (1,3‑ vs 1,4‑diene formation).
• Reductive strategies: Zn, Mg, or catalytic hydrogenation to partially or fully remove chlorides, useful for protecting/deprotecting strategies on the cyclohexane scaffold.
• Modern C(sp3)–Cl activation: nickel catalysis (with ligands such as bipyridines) under reductive conditions to forge C–C bonds with aryl/alkyl partners.

Retrosynthetic perspective

• Serves as a masked 1,4‑di-functionalized cyclohexane synthon. Strategic substitution enables installation of orthogonal handles for subsequent diversification (e.g., diamines → ureas, diols → carbonates/ethers). The trans topology gives access to diequatorial products with defined 3D shape—a valuable attribute in medicinal chemistry for conformational control.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and does not have biological target specificity, epitopes, or antibody-related attributes.