1,2-Dichloropentane - ≥95% , CAS No.1674-33-5

CAS: 1674-33-5 Cat. No.: D1358078 Formula: C₅H₁₀Cl₂ Molecular Weight: 141.04 EC Number: 605-481-6

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

CCCC(CCl)Cl

IUPAC Name

1,2-dichloropentane

InChIKey

PPLBPDUKNRCHGG-UHFFFAOYSA-N

INCHI

1S/C5H10Cl2/c1-2-3-5(7)4-6/h5H,2-4H2,1H3

Molecular Weight

141.04

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Class Organochlorides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Class: Organochlorides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organochlorides
• Alternative Parents: Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydrocarbon derivative - Organochloride - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as organochlorides. These are compounds containing a chemical bond between a carbon atom and a chlorine 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

Chemical and Physical Properties

• Molecular Weight: 141.040 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 140.016 Da
• Monoisotopic Mass: 140.016 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 37.100
• 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

No assay or bioanalytical application protocols are specified for this item. For synthetic transformations, see the Reaction Conditions and Synthetic Utility sections for general, literature-based procedural guidance. Always tailor conditions to your substrate scope and consult primary literature.

Biological Roles

This product is an industrial/organic synthesis intermediate and does not have native biochemical roles.

General toxicology/biotransformation context (literature; not product-specific)

• Chlorinated alkanes are typically xenobiotics. If absorbed, they may undergo oxidative metabolism (e.g., via cytochrome P450) yielding chlorinated alcohols/aldehydes/acids, with potential for dehydrochlorination.
• Physicochemical properties (hydrophobic, volatile) suggest preferential partitioning into lipid phases and potential for CNS depressant effects at high exposure, as with many small chlorinated hydrocarbons.
• Environmental fate: Hydrolysis is slow under neutral conditions; primary degradation pathways are volatilization and oxidative degradation. Some chlorinated alkanes exhibit aquatic toxicity; appropriate waste management is required.

No claims are made for biological activity or clinical use. For laboratory research applications only.

Buffer Applications

Not typically applicable. 1,2-Dichloropentane is a nonpolar organic reagent and does not function as a buffering agent or pH stabilizer. For work involving this compound, focus on reaction solvent choice, phase-transfer conditions, or extraction systems rather than aqueous buffer selection.

Green Alternatives

Context

• 1,2-Dichloropentane is a halogenated hydrocarbon. While effective as a synthetic intermediate, chlorinated substrates and the solvents typically used with them may raise environmental, safety, and waste-disposal concerns.

Greener strategy considerations (literature/general)

• Solvent choices:
  • Prefer 2-MeTHF or CPME over THF/diethyl ether for metal-mediated steps—lower peroxide risk and improved safety profiles.
  • Consider propylene carbonate, MeCN, or green amide alternatives (e.g., NEP) as replacements for DMF/NMP where feasible.
• Activation alternatives:
  • Replace chloride with more reactive, less persistent leaving groups formed in situ (e.g., mesylates/tosylates from the corresponding alcohol in a telescoped sequence), avoiding isolation of chlorinated intermediates.
• Reaction design:
  • Employ catalytic, atom-economical couplings (e.g., nickel-catalyzed cross-electrophile coupling) rather than multi-step sequences with stoichiometric metal halide waste.

Illustrative comparison (general)

• Conventional: Finkelstein (NaI/acetone) → iodide intermediate; waste: NaCl, iodide residues; acetone VOC.
• Alternative: Direct nickel-catalyzed cross-electrophile coupling in 2-MeTHF with Mn/Zn reductant; fewer isolation steps; avoids iodide intermediate.

Trade-offs

• Greener solvents may alter rates/selectivities and require re-optimization.
• Avoiding iodides can reduce reactivity; catalysts/ligands must be tuned accordingly.

Pharmaceutical Uses

Not formulated as an excipient or processing aid in typical pharmaceutical contexts.

General manufacturing context (literature; not product-specific)

• If used at all, halogenated hydrocarbons like this would appear only as synthetic intermediates in API route development. They are not acceptable residual solvents per ICH Q3C beyond strict limits; their use would require validated removal and residual testing (e.g., headspace GC).
• Process considerations: Selection of greener, pharmaceutically preferred solvents and leaving groups is encouraged to minimize chlorinated hydrocarbon handling and residual risk.

No therapeutic or clinical claims are made for this product.

Physical Properties

Item-specific specifications

• Appearance, purity/grade, water/peroxide/metals/UV specs: Not specified for this item; refer to CoA/Spec Sheet.

Literature/estimated reference properties for 1,2-dichloropentane (for context; not product specifications)

• Molecular formula: C5H10Cl2
• Molecular weight: ~141.04 g/mol (literature)
• Physical state: Typically a colorless liquid (literature)
• Boiling point: Reported around 155–160 °C (literature; varies with isomeric composition and measurement)
• Melting point: Expected below 0 °C (literature; often < −60 °C for similar dichloroalkanes)
• Density (20 °C): Approximately 1.10–1.16 g/mL (literature range for C5 vic-dichloroalkanes)
• Refractive index n20 D: ~1.445–1.460 (literature)
• Vapor pressure: Lower than lighter dichloroalkanes; qualitative: moderate volatility (literature)
• Solubility: Practically insoluble in water; miscible with many organic solvents (ethers, aromatics, chlorinated solvents) (literature)
• LogP (octanol/water): Expected moderate hydrophobicity; estimated 2–3 (literature/estimations for alkyl dichlorides)
• pKa: Not applicable (non-ionizable neutral organic).

Notes

• Values above are provided solely as general literature guidance; they are not specifications for this SKU. Consult the product’s CoA/SDS for definitive data.

Quality & Grades

Item-specific quality information

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

Guidance on typical grades for small chlorinated organics (general)

• Reagent grade: Suitable for most synthetic applications; impurities are controlled to general limits.
• High-purity (≥99%) or low-residue grades: Preferred for kinetic studies or when downstream transformations are sensitive to trace protic or metal impurities.
• GC/HPLC designation: When present, implies low non-volatile residue and low UV background (relevant if used as solvent or internal standard matrix; not typical for this compound).

Impurity considerations (general)

• Potential impurities: Isomeric dichloropentanes (e.g., 1,3-), unreacted monochlorides, residual halogenated solvents, moisture.
• Analytical control: GC for isomeric purity and residual solvents; Karl Fischer for water (if relevant); halide assay by argentometry; density/refractive index cross-check.

Recommendation

• Verify the supplied CoA for assay, identity (GC/MS), and any stabilizer notes before use in moisture- or base-sensitive reactions.

Reaction & Applications

General reactivity profile (literature)

• Functional motif: Vicinal alkyl dichloride (primary and secondary). Offers differential reactivity: C1 (primary) generally more prone to SN2; C2 (secondary) more prone to elimination or slower substitution.

Representative transformations

• Nucleophilic substitutions (SN2):
  • Halide exchange: 1,2-dichloropentane → 1-chloro-2-iodopentane using NaI in acetone (Finkelstein). The iodide can then undergo further cross-couplings.
  • Formation of azides, thiols, thioethers, cyanides, and amines using NaN3, RS−, CN−, or amines in polar aprotic solvents.
• Elimination (E2):
  • Dehydrohalogenation with strong base (e.g., KOH/EtOH or t-BuOK) affords pentenes; regioisomer distribution depends on base/solvent and temperature.
• Dihydroxylation via halohydrin route:
  • Stepwise hydrolysis/substitution can yield chlorohydrins and subsequently diols under aqueous AgNO3 or other halide-activating conditions.
• Metal-mediated chemistry:
  • Zinc insertion to form organozinc species is more feasible at the primary site; these can participate in Negishi-type couplings after halide activation (often improved by converting Cl → Br/I first).
• Radical/cross-electrophile coupling:
  • Ni-catalyzed reductive couplings with aryl halides under Zn/Mn can forge C(sp3)–C(sp2) bonds from the primary chloride, with careful control to suppress β-hydride elimination (literature precedents for similar substrates).

Practical tips

• Dry, oxygen-free conditions minimize side reactions in metal-mediated pathways.
• Consider a two-step activation (convert Cl→I) to enhance reactivity/selectivity where needed.
• Monitor by GC to resolve isomer distributions and partial substitution products.

Reaction Conditions

General guidance from literature (not product-specific; optimize per your system)

SN2 substitutions at C1 (primary chloride)

• Typical solvents: DMF, DMSO, MeCN. Dry conditions preferred.
• Nucleophiles/bases: NaI (halide exchange), NaN3, KCN/NaCN, NaSR, primary/secondary amines.
• Temperature/time: 25–80 °C, 2–24 h depending on nucleophile; higher for secondary site.
• Notes: Finkelstein in acetone: 3–10 equiv NaI, reflux to drive precipitation of NaCl.

Secondary-site activation (C2)

• Convert to iodide: NaI/acetone or I2/PPh3 (Appel-type) on the corresponding alcohol derivative; facilitates subsequent substitution/cross-coupling.
• Phase-transfer: TBAI or TBAB in toluene/water with concentrated NaN3 or NaCN can accelerate.

Elimination (E2) to pentenes

• Conditions: KOH/EtOH (reflux) or t-BuOK/t-BuOH (50–80 °C); 2–8 h.
• Outcome: Mixtures of 1- and 2-pentene isomers; distribution depends on base, temperature, and solvent polarity.

Metal-mediated routes

• Organozinc formation: Zn/activators (Cu, Ni salts) in THF, 0–25 °C to reflux; then Negishi coupling with Pd/Ni catalysts.
• Cross-electrophile coupling: Ni(II) precatalyst, bipyridine/pybox ligands, Mn or Zn reductant, DMA/DMF/2-MeTHF, 20–60 °C.

Workup/analysis

• Quench nucleophiles with aqueous NH4Cl; extract with nonpolar solvent; dry (Na2SO4/MgSO4). Analyze by GC/GC–MS to track isomeric outcomes and residual chlorinated species.

Safety & Handling

Item-specific hazard data

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

General safety information for chlorinated alkanes (literature; not product-specific)

• Hazards: Many low-molecular-weight chlorinated hydrocarbons are harmful if inhaled or ingested, cause skin/eye irritation, and may have narcotic effects at high vapor concentrations. Combustion/thermal decomposition can generate hydrogen chloride and phosgene.
• Incompatibilities: Strong bases and nucleophiles (can cause substitution/elimination), finely divided reactive metals, strong oxidizers, and strong reducing agents. Avoid contact with alkoxides or hot alcoholic KOH unless reaction is intended (E2 elimination risk).
• PPE: Chemical-resistant gloves (e.g., nitrile), splash goggles, lab coat. Use in a fume hood to control vapors.
• First aid (overview):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Remove contaminated clothing; wash with soap/water.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention for irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire response: Use alcohol-resistant foam, dry chemical, or CO2. Cool containers with water spray.

Always consult the SDS for authoritative, product-specific hazard and response information.

Solvent Selection

Applicability

• 1,2-Dichloropentane is primarily a reactive building block, not a routine laboratory solvent. This section focuses on choosing solvents for reactions where 1,2-dichloropentane is the substrate.

General solvent guidance (literature)

• SN2 substitutions at C1 (primary chloride) and C2 (secondary chloride) are favored by polar aprotic solvents (e.g., DMSO, DMF, NMP, acetonitrile). These increase nucleophilicity and rate for backside attack, particularly at the primary site.
• E2 eliminations to form pentenes are promoted in protic or mixed solvents with strong base (EtOH/KOH, t-BuOK/t-BuOH, or non-protic solvents like DMSO with alkoxides).
• Halide exchange (Finkelstein) to iodide typically employs acetone or MEK where NaI is soluble and NaCl precipitates, driving equilibrium.
• Radical or metal-catalyzed transformations (e.g., Ni-catalyzed cross-electrophile coupling) often use polar aprotic or ethereal media (DMA, DMF, THF, 2-MeTHF) under inert atmosphere.

Quick comparison (general)

• DMF/DMSO: Maximize SN2 rates; higher boiling points enable elevated temperatures.
• Acetone: Ideal for halide exchange (drives precipitation of NaCl).
• Alcoholic KOH: Convenient for E2 but less selective; may cause competing substitution.
• 2-MeTHF/CPME: Useful greener ethers for metal-catalyzed or radical chemistry; improved safety versus THF/Et2O.

Note

• Select solvent based on desired pathway (substitution vs elimination) and catalyst/base system. Always confirm compatibility with your base/nucleophile and temperature profile.

Storage & Reconstitution

Item-specific storage

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

General handling guidance (literature/general best practice)

• Keep container tightly closed in a well-ventilated area; minimize headspace to limit volatilization.
• Store away from strong bases, strong nucleophiles, and oxidizers. Protect from heat and ignition sources. Avoid prolonged exposure to light/UV during long-term storage.
• If moisture sensitivity is a concern for your application, store over an inert atmosphere or include a desiccant; verify by Karl Fischer if needed.

Reconstitution

• Not applicable (neat liquid). If solidification occurs at low temperature, gently warm to ambient and homogenize before use.

Shelf-life

• Not specified for this item; refer to CoA/Spec Sheet. As with similar chlorinated hydrocarbons, periodic GC check for purity is prudent for long-term stored material.

For research use only.

Structure & Identity

Overview: 1,2-Dichloropentane is a saturated, linear C5 alkyl chain bearing a vicinal primary/secondary dichloride motif (Cl–CH2–CH(Cl)–CH2–CH2–CH3). It exists as a pair of enantiomers (R/S) at C2 and is commonly handled as a racemate.

Item-specific identifiers (from Product Data)

• SKU: D1358078
• Product name: 1,2-Dichloropentane
• CAS: 1674-33-5
• PubChem CID: 15481
• InChIKey: 283612 (as provided)
• Storage conditions: Room temperature
• Research use note: For research use only

Computed/literature structural data (not item-specific)

• Molecular formula (literature): C5H10Cl2
• Approx. molecular weight (literature): 141.04 g/mol
• Representative SMILES (literature): ClCC(Cl)CCC

Structural features (general chemistry)

• Functional groups: Two alkyl chloride moieties (one primary at C1, one secondary at C2).
• Stereochemistry: One stereogenic center at C2; racemic unless specified.
• 2D description: A five-carbon straight chain; chlorine substituents on adjacent C1 and C2 positions (vicinal dichloride).

Synthetic Utility

Functional group leverage

• Vicinal dichloride offers site-selective manipulation:
  • Primary C–Cl (C1): Favorable for SN2 displacement to install diverse groups (I, Br via halide exchange; N3; CN; SR; NR2), enabling downstream diversification.
  • Secondary C–Cl (C2): Amenable to substitution under stronger conditions or via activation (e.g., conversion to iodide/mesylate), or to E2 elimination for alkene synthesis.

Strategic roles (literature)

• Handle for stepwise differentiation: Sequential substitution at C1 then C2, allowing modular assembly of 1,2-disubstituted pentane motifs.
• Alkene precursor: Controlled E2 affords internal vs terminal pentenes; subsequent hydrofunctionalizations (hydroboration–oxidation, epoxidation) expand functionality.
• Cross-coupling linchpin: After halide activation (Cl→I/Br) or formation of organozinc, participate in Negishi/Kumada-type couplings to forge C(sp3)–C bonds.
• Cyclization templates: Intramolecular displacement can be engineered to form small/medium rings when tethered nucleophiles are introduced at C5 or beyond.

Tactics to improve outcomes

• Use phase-transfer catalysis for hard nucleophiles (e.g., CN−, N3−) in biphasic systems to accelerate substitution at C1.
• Employ iodide catalysis (NaI catalytic) to in situ activate the secondary chloride.
• Monitor and control elimination by temperature and base sterics; bulky bases bias Hofmann vs Zaitsev outcomes.

Target Specificity

Not applicable. This product is a small-molecule organic reagent, not a biological targeting agent. No antigen/epitope, clone, isotype, or species reactivity information applies.

Frequently Asked Questions

How should this product be stored?

Store at room temperature.

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

The CAS Number is 1674-33-5, the molecular formula is C5H10Cl2, and the molecular weight is 141.04 g/mol. InChIKey PPLBPDUKNRCHGG-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.

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.