Ethylene glycol butyl ether(EB) - electronic grade,≥99% , CAS No.111-76-2

CAS: 111-76-2 Cat. No.: E1523608 Formula: C₆H₁₄O₂ Peso molecolare: 118.17 Beilstein Registry Number: 1732511 Numero EC: 203-905-0

GRADE & PURITY Electronic grade, ≥99%

Storage

Room temperature

Shipped In

FedEx DG Service

Specifications

Specifiche e purezza

electronic grade, ≥99%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

FedEx DG Service

Grado

Grado elettronico

Purezza

≥99%

Nomi e identificatori

Sorrisi canonici

CCCCOCCO

IUPAC Name

2-butoxyethanol

InChIKey

POAOYUHQDCAZBD-UHFFFAOYSA-N

INCHI

1S/C6H14O2/c1-2-3-5-8-6-4-7/h7H,2-6H2,1H3

Isomeri SMILES

CCCCOCCO

WGK Germania

1

RTECS

KJ8575000

Numero UN

2810

Gruppo di imballaggio

III

Peso molecolare

118.17

Beilstein

1732511

Reaxy-Rn

1732511

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1732511&ln=

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: Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkyl ether - Hydrocarbon derivative - Primary alcohol - Alcohol - 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: ether - primary alcohol

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

• Solubilità: Soluble in most organic solvents such as water, ethanol, and ether.
• Sensibilità: Moisture sensitive.
• Indice di rifrazione: 1.4198
• Punto di infiammabilità (°C): 61.1℃
• Punto di ebollizione (°C): 171°C
• Punto di fusione (°C): -75°C
• Peso molecolare: 118.170 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 118.099 Da
• Monoisotopic Mass: 118.099 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 37.500
• 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

No assay or immunoapplication protocols are provided for this solvent. Typical lab uses are process- and project-specific.

General guidance for common laboratory scenarios:

• As a vehicle for hydrophobic compounds in bioassays: Prepare a concentrated stock in EB, then dilute into aqueous buffer while monitoring final EB percentage and cell compatibility; include solvent controls.
• For polymer/coating tests: Blend EB with resin/monomer per formulation design; condition at controlled temperature/humidity; record evaporation/dry times relative to controls.
• Cleaning trials (electronics): Apply EB or EB-containing blend to contaminated substrates; allow contact; rinse with IPA or DI water; dry with filtered air or N2. Verify ionic residue by ROSE/ICS if required.

Because performance is formulation- and matrix-dependent, pilot tests and method validation are recommended.

Biological Roles

This product is intended for research use only. The following points summarize general biochemical fate of 2-butoxyethanol (literature; not product-specific and not clinical):

• Xenobiotic metabolism: As a primary alcohol, 2-butoxyethanol undergoes sequential oxidation via alcohol dehydrogenase (ADH) to the corresponding aldehyde and then via aldehyde dehydrogenase (ALDH) to 2-butoxyacetic acid. Conjugation pathways (e.g., glucuronidation) can further increase water solubility for excretion.
• Partitioning: Moderate hydrophilicity (logP ~0.8) and complete water miscibility enable broad tissue distribution in in vitro systems; it can cross biological membranes while remaining soluble in aqueous phases.
• Protein and membrane interactions: Hydrogen bonding and amphiphilic character permit interaction with phospholipid bilayers and proteins, which may influence cell permeability or enzyme activity in in vitro assays.
• In vitro use considerations: As a solvent vehicle, EB can solubilize hydrophobic test compounds while maintaining aqueous compatibility; however, it may affect cell viability or enzyme kinetics at modest concentrations—include solvent controls and minimize exposure.

No therapeutic, diagnostic, or clinical claims are made. Handle according to institutional biosafety and chemical hygiene practices when used in biological laboratories.

Buffer Applications

Ethylene glycol butyl ether is not a buffering agent and is not typically used to prepare defined pH buffer systems.

• Role in aqueous systems: EB may be employed as a co-solvent to enhance solubility of hydrophobic analytes or reagents within buffered solutions.
• Practical tip: When adding EB to buffers, verify final pH, ionic strength, and phase behavior; EB can alter activity coefficients and may change apparent pKa values of solutes.

For buffer formulation guidance, consider standard buffering agents (e.g., phosphate, Tris, HEPES). EB’s most relevant sections are Solvent Selection and Reaction & Applications.

Green Alternatives

Selection of a greener solvent depends on performance needs (polarity, water miscibility, evaporation rate) and EHS profile. The following are literature-based, general comparisons (not item-specific):

Comparison snapshot:

• Ethyl lactate: Bio-derived, readily biodegradable; polar, good solvency; fully miscible with water. Often a greener replacement where ester stability is acceptable. Higher hydrolysis sensitivity than EB under basic conditions.
• Propylene glycol n-butyl ether (PnB/DPnB): Lower acute toxicity profile in some jurisdictions; similar solvency and slower evaporation; may be less irritating than EB. Typically partially miscible with water depending on isomer.
• 2-Methyltetrahydrofuran (2-MeTHF): Bio-based option for many organometallic reactions; immiscible with water, lower peroxide tendency than THF; not a direct replacement when water miscibility and protic character are needed.
• Dimethyl carbonate (DMC): Green reagent/solvent with favorable EHS; aprotic and more volatile; limited water miscibility; suitable for certain carbonate/alkylation chemistry.

Trade-offs:

• EB’s strong coupling ability (water + hydrophobes) and protic nature are hard to match; greener choices may require process redesign (co-solvent systems, temperature changes).
• Always validate cleaning efficacy, drying time, residue levels (NVR), and material compatibility (elastomers, plastics) when changing solvents.

Guidance:

• Use solvent selection guides (e.g., CHEM21, GSK) to score candidates across safety, health, environment, and process metrics.
• Consider recovery/recycle (distillation) to reduce environmental footprint when EB remains the best technical fit.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided in the Product Data for this item.

General context (literature; not product-specific):

• Glycol ethers like 2-butoxyethanol are not commonly used as pharmaceutical excipients due to EHS considerations. Where solvents/co-solvents are required, pharmacopeial alcohols (ethanol), glycols (propylene glycol, PEG 400), or esters (ethyl lactate) are more typical.
• EB may be encountered in non-pharmaceutical coatings/cleaning steps within device manufacturing, but such uses are process-specific and require thorough residue and biocompatibility assessments.

If contemplating use in GMP or medical-device contexts:

• Confirm material compliance, residual solvent limits, and extractables/leachables by validated methods.
• Obtain and review the lot-specific CoA/specification. If pharmacopoeial grades are required, select appropriately certified materials.

This product is sold for research use only and is not intended for use in humans or clinical applications.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are typical literature values for 2-butoxyethanol (for reference only; not specifications):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: ~118.17 g/mol (literature)
• Boiling point: ~171–172 °C at 1 atm (literature)
• Melting point: ~−74 °C (literature)
• Density: ~0.900 g/mL at 20 °C (literature)
• Refractive index (n20 D): ~1.419 (literature)
• Vapor pressure: ~0.8–1.0 mmHg at 20–25 °C (literature)
• Dielectric constant: ~17–18 at 20 °C (literature)
• LogP (octanol/water): ~0.8 (literature)
• Water solubility: Miscible with water (literature)
• Viscosity: ~3 mPa·s at 25 °C (literature)
• Hansen/Hildebrand solubility: δT ~22 MPa^1/2; strong polar/H-bonding components (literature)

Notes for practitioners:

• As a glycol ether/alcohol, EB is hydrophilic enough to co-dissolve water while also solvating apolar organics, making it an effective coupling solvent.
• Hygroscopic tendency is moderate; composition can drift with water uptake—verify Karl Fischer if water content is critical (spec not provided; consult CoA if needed).
• UV cutoff and trace impurity limits: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade: Electronic grade (per Product Data)

What electronic grade generally implies (context for professionals):

• Emphasis on low ionic and particulate contamination to minimize corrosion, residues, and leakage currents in electronic assembly/processing and in semiconductor-related wet steps.
• Controlled levels of metal ions, halides, and nonvolatile residues to reduce risk of device contamination and to support ESD-safe cleaning and flux removal. Exact limits vary by supplier/product line.

For this specific item:

• Detailed impurity specifications (e.g., moisture ppm, metal ion ppb, UV absorbance, NVR) are Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

Use considerations:

• For microelectronics or lithium-battery work, verify water and metal content against your process window. Request a current CoA for the lot.
• For analytical workflows (e.g., trace analysis), electronic grade may be adequate, but HPLC/UV grade may be preferred if low background absorbance is critical; confirm UV specs where applicable.
• For moisture-sensitive reactions, dry before use (e.g., molecular sieves) and confirm Karl Fischer content, as glycol ethers are hygroscopic.

Documentation: Lot-specific CoA and, where relevant, an internal specification sheet are recommended prior to GMP-adjacent or cleanroom deployment.

Reaction and Applications

Research and process uses leverage EB’s dual functionality (ether + primary alcohol) and its broad solvency profile.

As a solvent/co-solvent:

• Base/acid-catalyzed organic reactions in mixed aqueous/organic media (e.g., transesterifications, condensations) where EB maintains homogeneity.
• Polymerization environments for acrylics, styrenics, and urethanes, improving monomer/initiator compatibility and film formation (literature).
• Phase-coupling medium in biphasic systems, aiding mass transfer for reactions involving salts or polar reagents.

As a reagent (through the –CH2CH2OH):

• Ester formation to give 2-butoxyethyl esters using carboxylic acids or acyl chlorides (e.g., acid chloride, Et3N or pyridine; or DCC/EDC with DMAP catalysis). These esters can function as plasticizers or intermediates.
• Williamson-like etherification after generating the alkoxide (NaH, KOtBu, or Na/K in alcohol) to install 2-butoxyethoxy groups on electrophiles (RX, sulfonates). Control elimination by using mild base and low temperature.
• Oxidation of the primary alcohol to 2-butoxyacetaldehyde (e.g., Swern, Dess–Martin, TEMPO/bleach) or further to 2-butoxyacetic acid (e.g., TEMPO/NaClO/NaClO2), providing access to glycolate derivatives.

Practical considerations:

• Water miscibility enables in situ aqueous workups; however, product extraction may require salting out or switching solvents.
• Peroxide formation is possible on extended storage; test and remove peroxides before concentrating or heating to reflux.
• For moisture-sensitive couplings, predry EB (3Å/4Å sieves) and maintain inert atmosphere.

Reaction Conditions

The following generalized conditions are compiled from literature and typical lab practice; they are not specifications for this item.

• Esterification (2-butoxyethyl esters):

  • Acid chloride (RCOCl), 0–25 °C to rt, base (Et3N or pyridine), catalytic DMAP optional, EB as both reagent and solvent or use an inert solvent (DCM, toluene). Workup with aqueous bicarbonate and brine; yields commonly high (70–95%).
  • Fischer esterification with carboxylic acids: p-TsOH (1–5 mol%), Dean–Stark not applicable in EB/water; instead, employ azeotropic removal with toluene/xylene co-solvent or molecular sieves; 60–120 °C; 6–24 h.

• Oxidation of the primary alcohol:

  • Swern (DMSO, oxalyl chloride, Et3N): −78 to 0 °C; yields 70–90% aldehyde.
  • DMP (Dess–Martin): CH2Cl2, rt; 1–3 h; good to excellent yields.
  • TEMPO/NaOCl: biphasic H2O/EtOAc or MeCN/H2O with buffer pH ~9–10; 0–25 °C; aldehyde or acid depending on co-oxidant (NaClO2 for acid).

• Williamson etherification (forming 2-butoxyethoxy derivatives):

  • Generate alkoxide with NaH (60% dispersion) or KOtBu in THF/DMF; 0–25 °C. Alkylate with primary sulfonates/halides. Suppress elimination by using primary electrophiles and lower temperatures.

• Acidic cleavage (for deprotection or analysis):

  • Concentrated HI or HBr, reflux; produces 1-butanol/2-bromoethanol derivatives; use with caution.

Solvent role:

• EB may serve as co-solvent with water, alcohols, ethers, or aromatics. Dry EB over 3Å/4Å sieves for moisture-sensitive steps. Degas if radical/polymerization chemistry is moisture/oxygen-sensitive.

Safety and Handling

Authoritative safety information resides in the product SDS. The Product Data does not list GHS details for this item. The following summary reflects typical literature/SDS classifications for 2-butoxyethanol (for reference; not product-specific):

• Typical GHS classification (literature): Acute Tox. 4 (oral, dermal, inhalation); Skin Irrit. 2; Eye Irrit. 2.
• Typical hazard statements (literature): H302, H312, H332 (harmful if swallowed/in contact with skin/if inhaled); H315 (causes skin irritation); H319 (causes serious eye irritation).
• Pictogram (literature): GHS07 (exclamation mark).

Handling and PPE:

• Use in a fume hood; avoid inhalation of vapors and aerosols.
• Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles/face shield.
• Prevent skin/eye contact; remove contaminated clothing and wash skin promptly.

Incompatibilities and reactivity:

• Avoid strong oxidizers, strong bases/acids during storage.
• Like many ethers, glycol ethers can slowly form peroxides on prolonged air/oxygen exposure; test and manage peroxides for long-opened containers. Store away from light/air when feasible.

First-aid overview (consult SDS for full guidance):

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin: Wash with soap/water; seek medical advice for irritation.
• Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; get medical attention.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Fire safety: Combustible liquid; use alcohol-resistant foam, CO2, dry chemical. Cool containers with water spray.

Solvent Selection

Ethylene glycol butyl ether is a mid-polar, protic glycol ether solvent with strong hydrogen-bonding capability and broad solvency.

• Polarity/character: Polar protic; strong H-bond donor/acceptor; dielectric constant ~17–18 (literature).
• Miscibility: Fully miscible with water and many organics (alcohols, ketones, esters, aromatics). Useful as a coupling solvent between aqueous and hydrophobic phases.
• Boiling range: High bp (~171–172 °C, literature) allows elevated-temperature processing and slower evaporation compared to IPA/EtOH.

When to choose EB:

• To solubilize mixed polar/apolar matrices (resins, inks, polymer precursors) or to improve flow/leveling in coatings.
• As a process aid for cleaning/degassing steps where some water content is present but stronger solvency than short-chain alcohols is required.
• As a co-solvent enabling homogeneous phase in base- or acid-catalyzed transformations containing salts/water.

Comparison (literature, general):

• vs. IPA/EtOH: EB offers higher solvency for hydrophobic substrates and slower evaporation; however, it is more irritating and less volatile (slower dry).
• vs. DMSO/DMF: EB is less polar and less coordinating; often easier to remove, lower boiling than DMSO, but higher than most esters/ketones.
• vs. 2-MeTHF/EtOAc: EB is water-miscible and protic; better for coupling polar with apolar components; less preferred when strictly aprotic conditions are needed.

Practical tips:

• Monitor water content for moisture-sensitive chemistry.
• For precision cleaning, rinse residues with a more volatile solvent (e.g., IPA) or DI water as appropriate.

Storage and Reconstitution

• Storage conditions (per Product Data): Room temperature.
• Shipped in: FedEx DG Service (hazmat-compliant transport).
• Container: Keep tightly closed in original container to minimize moisture uptake and oxidation. Use air- and moisture-tight seals; consider inert gas blanket for long-term storage after opening.
• Light/air: Store away from direct sunlight; limit headspace oxygen to reduce potential peroxide formation over extended periods.
• Stabilizer/inhibitor: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance check: Not specified for this item; refer to CoA/Spec Sheet. Inspect for discoloration or turbidity before use.
• Reconstitution: Not applicable—product is supplied as a ready-to-use liquid solvent. If drying is required, treat with activated 3Å/4Å molecular sieves and verify by Karl Fischer (spec not provided).
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Periodically test for peroxides if stored for long durations after opening.
• Research use note: For research use only.

Disposal: Collect as organic solvent waste. Follow institutional and local regulations.

Structure and Identity

Ethylene glycol butyl ether (also known as 2-butoxyethanol, EGBE, EB) is a glycol ether comprising a primary alcohol tethered to an n-butyl ether chain.

• SKU: E1523608
• CAS: 111-76-2
• PubChem CID: 8133
• Synonyms (literature): 2-Butoxyethanol; Butyl cellosolve; EGBE; Ethylene glycol monobutyl ether (EGMBE)
• Molecular formula (literature): C6H14O2
• Molecular weight (literature): 118.17 g/mol
• SMILES (literature): CCCCOCCO
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (descriptive):

• Functional groups: one primary alcohol (-CH2CH2OH) and one alkyl ether (–O–n-Bu).
• Skeleton: linear n-butyl chain attached via oxygen to a 2-hydroxyethyl unit (HO–CH2–CH2–O–(CH2)3–CH3).
• H-bonding: hydrogen bond donor (1) and acceptor (2), enabling strong interactions with water and polar organic solvents.
• No stereocenters; achiral.

Category fit: Glycol ether solvent suitable for cleaning, processing, and synthetic applications where moderate polarity, high solvency, and water miscibility are advantageous.

Note on identifiers: Where values are labeled “literature,” they are provided for general reference and are not item-specific specifications.

Synthetic Utility

Key functional elements and their reactivity (literature):

• Primary alcohol handle (–CH2CH2OH):

  • Esterifications: With acids (Fischer, acid chloride, anhydrides) or via DCC/EDC + DMAP to give 2-butoxyethyl esters.
  • Oxidations: To aldehyde (Swern, DMP) or acid (TEMPO/bleach; Jones) yielding 2-butoxyacetaldehyde/2-butoxyacetic acid.
  • Carbonate/Carbamate formation: Using phosgene equivalents (e.g., CDI, triphosgene) or dimethyl carbonate under base to afford cyclic/acyclic derivatives.

• Ether oxygen (–O–nBu):

  • Generally inert under many conditions; however, under strong acid it can undergo cleavage (e.g., HI/HBr) to liberate alcohols/alkyl halides.

• As a leaving group precursor:

  • Conversion of the –CH2CH2OH to halide or sulfonate (Ms/ Ts) followed by substitution can install the 2-butoxyethyl fragment onto nucleophiles.

Solvent-enabled utility:

• EB’s water miscibility allows single-phase reactions with inorganic bases or salts that otherwise require phase-transfer catalysis. It can improve rates/selectivity in reactions sensitive to microheterogeneity.

Process notes:

• Workups may require electrolyte addition to break emulsions or “salt out” organics.
• If distilling EB or EB-containing mixtures, assess and treat peroxides. Use an inhibitor or add a small amount of a reducing agent if appropriate, and avoid distilling to dryness.

Overall, EB is a versatile building block and medium for transformations that benefit from a protic, high-boiling, water-miscible solvent.

Target Specificity

Not an antibody, enzyme, or probe. No biological target specificity applies to this solvent/reagent.

• Target/epitope/clone/isotype: Not applicable.
• Species reactivity: Not applicable.

For relevant information, see Solvent Selection, Reaction & Applications, and Synthetic Utility.