Et2O diethylether Physical and Chemical Properties
Et2O diethylether
Low‑boiling dialkyl ether commonly used as a non‑polar solvent in synthesis, extraction and analytical workflows for industrial and research laboratories.
| CAS Number | Not specified for this entry |
| Family | Dialkyl ethers |
| Typical Form | Colorless volatile liquid |
| Common Grades | EP |
Et2O (diethyl ether, IUPAC: ethoxyethane) is a small dialkyl ether belonging to the simple-ether structural class. Structurally it consists of an ether oxygen bridging two ethyl groups (\(R–O–R'\) with \(R=R'=\) ethyl), giving a formally neutral, aprotic molecule with two lone pairs on oxygen. The oxygen atom imparts limited polarity and a capacity to act as a hydrogen-bond acceptor, while two alkyl chains provide a predominately hydrocarbon surface that confers moderate lipophilicity and volatility. Electronic distribution is dominated by the oxygen lone pairs and the sigma framework of the alkyl groups; there are no acidic hydrogens and no formal charge in the neutral molecule.
Chemically, diethyl ether behaves as a relatively inert solvent under neutral conditions but is susceptible to specific reactions typical of simple ethers: acid-catalyzed cleavage, autoxidation to peroxides on exposure to air and light, and complexation/stabilization of organometallic reagents. Solvent properties combine modest polarity (oxygen lone pairs, hydrogen-bond accepting) with good compatibility with nonpolar organics, making it a common extraction and reaction medium. Historically it has seen use as a laboratory and industrial solvent and as an inhalation anesthetic; contemporary use is primarily as a solvent and reagent carrier in organic synthesis and process chemistry.
Common commercial grades reported for this substance include: EP.
Basic Physical Properties
Density
No experimentally established value for this property is available in the current data context.
Melting Point
No experimentally established value for this property is available in the current data context.
Boiling Point
No experimentally established value for this property is available in the current data context.
Vapor Pressure
No experimentally established value for this property is available in the current data context.
Flash Point
No experimentally established value for this property is available in the current data context.
Chemical Properties
Solubility and Phase Behavior
As a small dialkyl ether, this substance exhibits limited solubility in water due to competing hydrogen-bonding interactions of bulk water with itself; conversely it is highly miscible with most organic solvents (alcohols, hydrocarbons, chlorinated solvents, ethers). The oxygen atom provides hydrogen-bond acceptor capacity but the two ethyl groups dominate the molecular volume, so phase behavior is typical of low-polarity, volatile organic solvents used for liquid–liquid extraction and organic reaction media. Ethers commonly form azeotropes with water and other solvents under distillation; users should anticipate non-ideal vapor–liquid behavior when designing separations.
Reactivity and Stability
The substance is chemically stable under neutral, anhydrous conditions but exhibits two important practical instability pathways: - Autoxidation to form hydroperoxides and peroxides upon prolonged exposure to air, light, or trace metal catalysts. Peroxide formation is a safety and process hazard because peroxides can concentrate during storage or distillation and may detonate when concentrated. - Acid-catalyzed cleavage under strong protic acids (e.g., hydrogen halides, sulfonic acids) to give alcohols and alkyl halides or to promote ether cleavage pathways; therefore avoid strong acids during handling if retention of the ether is required.
It is relatively resistant to hydrolysis under neutral aqueous conditions, and it serves as a coordinating solvent for organometallic species (e.g., to stabilize Grignard reagents) due to the lone pairs on oxygen.
Thermodynamic Data
Standard Enthalpies and Heat Capacity
No experimentally established value for this property is available in the current data context.
Molecular Parameters
Molecular Weight and Formula
- Molecular formula: \(C_8H_{20}O_2\) (input representation).
- Molecular weight: \(148.24\,\mathrm{g}\,\mathrm{mol}^{-1}\) (as reported).
- Exact mass / Monoisotopic mass: \(148.146329876\).
Note: the provided molecular formula and mass correspond to two ethoxyethane units represented jointly in the input (see Structural Features).
LogP and Polarity
No direct logP value is provided in the current data context. Computed polar descriptors supplied indicate a low overall polarity for the combined representation: topological polar surface area (TPSA) = 18.5 and hydrogen-bond acceptor count = 2 with hydrogen-bond donor count = 0. These descriptors are consistent with an ether that is a modest hydrogen-bond acceptor but overall dominated by nonpolar alkyl character, giving moderate lipophilicity and good solubility in organic phases.
Structural Features
- SMILES: CCOCC.CCOCC
- InChI: InChI=1S/2C4H10O/c21-3-5-4-2/h23-4H2,1-2H3
- InChIKey: OLAMWIPURJGSKE-UHFFFAOYSA-N
The SMILES string contains a dot (.) separating two identical fragments, indicating the input representation corresponds to two ethoxyethane units presented together rather than a single covalently linked larger molecule. Computed structural descriptors: heavy atom count = 10; rotatable bond count = 4; topological polar surface area = 18.5; complexity = 11.1; covalently-bonded unit count = 2. The molecule is an aprotic ether featuring an sp3-hybridized oxygen bound to two ethyl groups, enabling lone-pair coordination to Lewis acids and organometallic reagents.
Identifiers and Synonyms
Registry Numbers and Codes
- InChI: InChI=1S/2C4H10O/c21-3-5-4-2/h23-4H2,1-2H3
- InChIKey: OLAMWIPURJGSKE-UHFFFAOYSA-N
- SMILES: CCOCC.CCOCC
- IUPAC name (computed descriptor): ethoxyethane
Synonyms and Structural Names
Depositor-supplied synonyms available in the current data context: - Et2O diethylether - Et2O Diethyl ether - SCHEMBL21406 - OLAMWIPURJGSKE-UHFFFAOYSA-N
(No CAS number is provided in the current data context.)
Industrial and Commercial Applications
Representative Uses and Industry Sectors
No concise application summary is available in the current data context; in practice this substance is selected based on its general solvent properties described above. At the class level, simple dialkyl ethers are commonly used as organic solvents for extraction, low-temperature reactions, and as media for organometallic chemistry. Historically, diethyl ether was used as an inhalation anesthetic; modern industrial and laboratory use is dominated by solvent and reagent roles.
Role in Synthesis or Formulations
As a coordinating, aprotic solvent with moderate lipophilicity and volatility, this substance is used to dissolve nonpolar and moderately polar organics, to stabilize reactive intermediates (notably certain organometallic reagents), and as a reaction medium for alkylations and reductions where a nonprotic environment is required. It is often employed in extraction workflows and process steps where low boiling point and ease of removal by distillation are advantageous.
Safety and Handling Overview
Acute and Occupational Toxicity
Dialkyl ethers are generally central nervous system depressants by inhalation at sufficient concentrations and can cause dizziness, drowsiness, and respiratory effects; skin contact may produce irritation or defatting. Because of volatility, inhalation exposure is a primary occupational concern; engineering controls (local exhaust, closed systems) and appropriate personal protective equipment (gloves, eye protection) are recommended. No specific LD50 or occupational exposure limit is provided in the current data context.
Storage and Handling Considerations
Key practical safety considerations for ethers: - Flammability: ethers are volatile and flammable; control ignition sources, grounding/bonding during transfer, and use appropriate ventilation. - Peroxide formation: ethers readily form peroxides on prolonged exposure to air and light. Store in tightly closed containers, preferably under inert atmosphere or with inhibitor as appropriate for the grade; inspect and test for peroxides before distillation or concentration steps and dispose of peroxide-containing waste per local regulations. - Segregation: store away from strong oxidizers and strong acids; avoid conditions that promote acid-catalyzed cleavage or unwanted reactions. For detailed hazard, transport and regulatory information, users should refer to the product-specific Safety Data Sheet (SDS) and local legislation.
