Ethane, 1-chloro-1-ethoxy- - ≥95% , CAS No.7081-78-9

CAS: 7081-78-9 Cat. No.: E1051615 Formula: C₄H₉ClO Peso molecolare: 108.570 Numero EC: 230-378-4

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: CCOC(C)Cl
• IUPAC Name: 1-chloro-1-ethoxyethane
• InChIKey: URGLIMIKUNFFMT-UHFFFAOYSA-N
• INCHI: 1S/C4H9ClO/c1-3-6-4(2)5/h4H,3H2,1-2H3
• Peso molecolare: 108.570

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Dialkyl ethers
• Alternative Parents: Organochlorides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkyl ether - Hydrocarbon derivative - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
• 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: 108.570 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 108.034 Da
• Monoisotopic Mass: 108.034 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 30.700
• 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 antibody/assay protocols (WB, IHC, IF, FC) are relevant to this small-molecule reagent. For practical usage, refer to the Reaction & Applications and Reaction Conditions sections for synthetic procedures.

Biological Roles

This product is a small synthetic halogenated ether used as a protecting-group reagent in organic synthesis. It does not serve a recognized physiological or metabolic role in biology.

General notes for researchers (literature/generic):

• Reactivity: As a potential alkylating agent under acidic activation, it may react with nucleophilic biomolecules; therefore, it should be handled only for in vitro chemical synthesis and never for biological exposure studies without appropriate approvals and containment.
• Biodegradation/toxicity: Halogenated ethers may be persistent and display aquatic toxicity; consult SDS and local regulations for disposal.

If the research involves downstream biochemical assays:

• Thorough removal of this reagent and its byproducts (e.g., by aqueous workup, silica gel chromatography, or vacuum stripping) is recommended prior to introducing synthetic products into biological test systems.

No medical/clinical uses are implied; per Product Data, it is for research use only.

Buffer Applications

Not typically applicable. Ethane, 1-chloro-1-ethoxy- is not a buffering agent and is reactive under acidic conditions. It is used as a synthetic reagent in organic media, not for preparing aqueous buffers or biological buffer systems. For relevant guidance, see the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections.

Green Alternatives

Context: 1-chloro-1-ethoxyethane is effective but halogenated and typically requires acid activation. Greener strategies can deliver the same protecting group or a functional equivalent with reduced hazard or waste.

Options (literature comparison):

• Ethyl vinyl ether (EVE)

  • How it works: Acid-catalyzed addition of ROH across the enol ether gives the 1-ethoxyethyl acetal directly.
  • Pros: Avoids halogenated reagent; benign byproducts; often catalytic acid loadings.
  • Cons: Volatile and flammable; still requires acid; odor; may require controlled addition to manage exotherm.

• Acetaldehyde diethyl acetal (Acetal, CH3CH(OEt)2)

  • How it works: Transacetalization with ROH under acid catalysis.
  • Pros: Readily available; often milder; avoids chlorinated feedstock.
  • Cons: Equilibrium-limited; requires water removal (molecular sieves/Dean–Stark) for high yields.

• 2-Methyltetrahydrofuran (2-MeTHF) or CPME as greener solvents

  • Role: Use as the reaction medium while employing EVE or Acetal above.
  • Pros: Bio-based (2-MeTHF), better safety/air emissions than DCM; good water removal.
  • Cons: Can coordinate to strong Lewis acids; reaction rates may differ from DCM.

Trade-offs:

• The chloroether reagent often proceeds rapidly at low temperature and can exhibit high chemoselectivity. Greener routes may require solvent and water management but reduce halogenated waste and corrosive HCl formation.

Pharmaceutical Uses

No excipient or pharmacopeial grade information is provided for this item; refer to CoA/Spec Sheet if required.

General context (non-clinical, literature):

• Role in drug discovery chemistry: employed as a protecting-group reagent for alcohols during multi-step synthesis of small molecules. The 1-ethoxyethyl (EE) group provides acid-labile protection orthogonal to base-sensitive motifs.
• Manufacturing considerations: If used in GMP or scale-up settings, residual levels in drug substance/intermediates would be controlled by ICH Q3A/B principles for process impurities and ICH Q3C for solvents (note: this reagent is a reagent, not a classed residual solvent). Cleaning validation should account for its potential to hydrolyze to HCl and volatile organics under acidic washdown.

No therapeutic claims are made. This product is supplied strictly for research and laboratory synthesis.

Physical Properties

Item-specific specifications are not provided in the Product Data; consult the CoA/Spec Sheet for authoritative values for this lot.

Literature/general reference (for context only; not item specifications):

• Appearance: typically a colorless, volatile liquid (literature)
• Molecular formula: C4H9ClO (literature)
• Molecular weight: ~108.57 g/mol (literature, computed)
• Density: often near 0.95–1.00 g/mL at 20–25 °C (literature ranges for low-MW chloroethers; confirm on CoA)
• Boiling point: commonly reported in the ~90–110 °C range at 1 atm for related 1-chloroethyl ethers (literature; verify exact value on CoA)
• Refractive index (nD20): typically ~1.41–1.43 for comparable chloroethyl ethers (literature; verify)
• Solubility: low in water; miscible with many organic solvents (e.g., DCM, toluene, Et2O, hexanes, THF) (literature)

Important notes:

• The above are typical literature values provided to support planning and hazard assessment; they are not specifications for this SKU. Always verify critical parameters (bp for distillation, density for dosing, refractive index for ID) against the certificate of analysis for the specific lot you receive.

Quality and Grades

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

Interpretation and implications (general guidance for this compound class):

• For protection-group reagents like 1-chloro-1-ethoxyethane, low moisture and low acid content are often critical to maintain controlled reactivity and minimize background hydrolysis to alcohol/acetaldehyde and HCl. If an inhibitor or base is present (rare but possible), it will be declared on the CoA/SDS.
• If HPLC or GC assay is reported on the CoA, it typically reflects organic purity; residual solvents and acidity (as HCl) may also be shown. Trace-halide or peroxide specifications are not typical for this reagent; water content (Karl Fischer) may be provided.
• For sensitive applications (e.g., protecting highly functionalized alcohols), consider verifying: assay, acidity (as HCl), water content, and color/APHA. If chromatography is planned, low UV background is generally expected for such aliphatic ethers.

Lot-to-lot control:

• Aladdin provides batch-specific documentation; request the CoA to confirm exact specifications, analytical methods, and any stabilizer content for this SKU.

Reaction and Applications

Primary use (literature): installation of the 1-ethoxyethyl (EE) protecting group on alcohols to give mixed acetals RO–CH(CH3)–OEt. The reagent acts as an electrophile; activation with Brønsted or Lewis acids promotes formation of a 1-ethoxyethyl cation or ion pair that is trapped by the target alcohol.

Typical application scenarios:

• Protection of primary/secondary alcohols: Treat ROH with 1.5–3.0 equiv of 1-chloro-1-ethoxyethane in anhydrous dichloromethane with catalytic p-TsOH or ZnCl2 at 0–25 °C. Workup by neutralization and aqueous washes affords RO–CH(CH3)–OEt. The EE group is stable to many bases/nucleophiles yet removable with aqueous acid.
• Protecting polyfunctional molecules: EE ethers can tolerate organometallic steps or basic conditions where silyl ethers might be less suitable; acid-labile deprotection (e.g., 0.5–2 M HCl/MeOH, AcOH/H2O, or catalytic p-TsOH in wet solvents) regenerates ROH and gives ethyl vinyl ether or acetaldehyde/ethanol byproducts.

Additional uses:

• Alkylation of oxygen nucleophiles (phenols, carboxylates) under Lewis acid mediation to form mixed acetals/orthoesters in specific contexts.
• Temporary masking of hemiacetals in carbohydrate chemistry where EE provides orthogonal lability relative to silyl/benzyl protections.

Practical tips:

• Exclude moisture; trace water accelerates hydrolysis and reduces yield.
• Use slight excess of reagent and titrate acid catalyst; excessive acidity promotes side reactions (self-alkylation, elimination to ethyl vinyl ether).
• Monitor by TLC/GC; product often shows distinct Rf vs alcohol and can be tracked by disappearance of OH signals in IR/NMR.

Reaction Conditions

General literature guidance for forming 1-ethoxyethyl ethers from alcohols using 1-chloro-1-ethoxyethane (adjust for substrate sensitivity; verify with pilot trials):

• Solvents: Anhydrous dichloromethane, 1,2-dichloroethane, toluene, or diethyl ether. Choose non-protic, low-water media.
• Catalyst systems: p-TsOH·H2O (0.5–10 mol%), camphorsulfonic acid (CSA), BF3·Et2O (5–20 mol%), ZnCl2 (10–50 mol%). Stronger Lewis acids accelerate but can increase side reactions; start low and titrate.
• Reagent stoichiometry: 1.5–3.0 equivalents relative to ROH to drive conversion and offset competitive hydrolysis.
• Temperature: 0–25 °C for acid-sensitive substrates; up to 40–60 °C in toluene for robust substrates.
• Time: 0.5–12 h depending on alcohol and catalyst; monitor by TLC/GC or in situ IR.
• Water control: 3 Å molecular sieves (0.5–1.0 g/mL solvent) or rigorous drying of glassware/solvents; inert atmosphere recommended.
• Workup: Neutralize with solid NaHCO3 or dilute NaHCO3 solution; wash with brine; dry over MgSO4/Na2SO4; concentrate under reduced pressure at ≤35 °C to minimize premature deprotection.
• Typical isolated yields: 70–95% reported for unhindered primary/secondary alcohols; lower for sterically hindered or highly electron-poor substrates (literature values; not item specifications).

Deprotection (for planning): dilute aqueous acid (e.g., 0.5–2 M HCl in MeOH/H2O or AcOH/H2O, rt to 40 °C) to return ROH cleanly.

Safety and Handling

Safety data for this specific item are not specified in the Product Data. Always review the product SDS for definitive hazard, classification, and response measures.

General hazards for halogenated ethers and 1-chloroethyl reagents (literature/generic guidance):

• Likely flammable liquid and vapor; handle away from ignition sources; use grounding/bonding during transfer.
• Irritation: vapors and liquid may be irritating to eyes, skin, and respiratory tract; some chloroethers are lacrimatory.
• Reactivity: under acidic conditions, can generate a carbocation; may alkylate nucleophiles. Contact with moisture/acids can lead to hydrolysis and release of HCl; use appropriate ventilation.

PPE and engineering controls:

• Work in a fume hood. Wear chemical-resistant gloves (e.g., nitrile), safety goggles/face shield, and a lab coat.
• Use explosion-proof refrigeration/ventilation if storing in large quantities.

Storage and incompatibilities:

• Per Product Data: store at room temperature. Keep tightly closed, dry, and under inert atmosphere if possible to minimize hydrolysis.
• Incompatible with strong acids/bases (promote decomposition or rapid reaction), strong oxidizers, and active nucleophiles.

First aid (overview; follow SDS):

• Eyes/skin: rinse with water for ≥15 min; remove contaminated clothing.
• Inhalation: move to fresh air; seek medical attention if symptoms persist.
• Ingestion: do not induce vomiting; rinse mouth and seek medical attention.

Solvent Selection

This product is a reactive halogenated ether reagent rather than a routine process solvent. It is not generally chosen as a bulk solvent. Instead, select an appropriate reaction solvent when using it as an electrophile.

General miscibility/handling (literature):

• Typically miscible with nonpolar and moderately polar organic solvents (DCM, chloroform, toluene, diethyl ether, MTBE, THF). Poorly soluble in water.

Choosing a solvent for 1-ethoxyethyl protection of alcohols:

• Non-coordinating chlorinated solvents (DCM, 1,2-dichloroethane) are common with Brønsted/Lewis acid catalysts (e.g., p-TsOH, BF3·Et2O, ZnCl2).
• Aromatics (toluene) can be advantageous at slightly elevated temperatures if higher reactivity is needed and water removal is aided by Dean–Stark when alternative acetal methods are used.
• Ethers (Et2O, MTBE) may be used under mild conditions but can coordinate to strong Lewis acids; monitor rate and selectivity.

When to choose alternatives:

• If a greener profile is required, consider generating the 1-ethoxyethyl acetal from ethyl vinyl ether under acid catalysis in ethanol or toluene, avoiding halogenated reagents.
• For highly acid-sensitive substrates, milder acetalization routes (e.g., 2-methoxypropene for MOM/MPM-type protections) may offer better chemoselectivity.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Container: Store in a tightly sealed, chemically resistant bottle. Use PTFE-lined caps to minimize ingress of moisture and acid-catalyzed corrosion.
• Atmosphere: Keep dry; consider storing under inert gas (N2/Ar) to limit hydrolysis and HCl formation. Avoid prolonged exposure to air/humidity.
• Light: Store away from direct sunlight to minimize potential degradation.
• Stability considerations (literature): Halogenated acetals can slowly hydrolyze to ethanol/acetaldehyde (or ethyl vinyl ether) and HCl in the presence of moisture or acid; periodic quality checks (GC, 1H NMR, acidity) are recommended for long-term storage.
• Reconstitution: Not applicable; supplied neat as a liquid reagent. If solidification/crystallization is observed at low temperature, gently warm to ambient and mix thoroughly before use.
• Handling before use: Dry syringes/needles/glassware; minimize headspace exchange; dispense quickly to reduce moisture uptake.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet and SDS. Given typical flammability/volatility of low-MW chloroethers, ground shipping under standard flammable-liquid regulations is common (check SDS/transport classification).

Structure and Identity

Short introduction: Ethane, 1-chloro-1-ethoxy- is a small, halogenated mixed acetal/ether commonly used to install the 1-ethoxyethyl protecting group on alcohols.

• Preferred name: 1-chloro-1-ethoxyethane (also known as 1-chloroethyl ethyl ether)
• CAS: 7081-78-9 (Product Data)
• PubChem CID: 23478 (Product Data)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists “367214,” which is not a complete InChIKey.)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C4H9ClO (literature)
• Molecular weight: ~108.57 g/mol (literature, computed from formula)

Structural features (general description):

• Functional groups: one tertiary-like electrophilic center (C-1) bearing both a chloro substituent and an ethoxy substituent; overall a mixed haloacetal/ether.
• Carbon skeleton: a two-carbon parent (ethane) where C-1 carries Cl and an –OCH2CH3 group, and C-2 is a methyl group. In 2D, the key stereogenic center is the substituted C-1; commercial material may be racemic unless stated otherwise.
• Reactivity handle: the C–Cl at an acetal-like center is activated under Lewis/Brønsted acid, generating a stabilized 1-ethoxyethyl cation capable of transferring the 1-ethoxyethyl protecting group to nucleophiles (notably alcohols).

Synthetic Utility

Key functional features:

• Electrophilic center: The 1-ethoxyethyl carbon bearing chlorine can generate a stabilized cation under acid catalysis, enabling transfer of the 1-ethoxyethyl moiety to nucleophiles.
• Protecting group chemistry: Efficient formation of 1-ethoxyethyl ethers (RO–CH(CH3)–OEt) from alcohols affords an acid-labile protecting group with stability toward many bases, nucleophiles, and moderate reductants.

Named/related transformations (literature):

• Acetalization via chloroacetal pathway: acid- or Lewis acid-catalyzed substitution where ROH traps the developing cation.
• Orthogonal deprotection: EE ethers cleave under dilute mineral acids or catalytic p-TsOH in wet organic solvents; compatible with conditions that retain benzyl (hydrogenolysis-sensitive) or silyl (fluoride-sensitive) protections when carefully chosen.

Strategic applications:

• Carbohydrate and polyol chemistry where selective, temporary protection is required to guide regioselective functionalization.
• Late-stage functionalization sequences in which acid-labile unmasking is planned after base-driven couplings, metalations, or rearrangements.

Practical considerations:

• Moisture control and acid loading are crucial; use molecular sieves or rigorously dry solvent to suppress hydrolysis.
• Quench protocols should neutralize residual acidity to prevent deprotection during workup.
• For chiral contexts, note that the reagent is typically racemic; the installed EE group at carbon is not stereogenic at oxygen but the acetal carbon may scramble under strong acid.

Target Specificity

Not applicable. This product is a small-molecule synthetic reagent and does not have biological target specificity (no antigen/epitope/isotype properties).