This compound belongs to the class of organic compounds known as borinic acid esters. These are compounds comprising the boronic acid ester functional group RB(R')OR'' (R,R',R''=organyl; X= any O,N,Hal residue).
External Descriptors
Not available
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.
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Application Protocols
No assay-specific or bioanalytical application protocols apply to this small-molecule reagent.
For synthetic use, a representative literature-style procedure outline is provided (adapt to your substrates; not item-specific):
Dry a flame-dried flask under argon. Charge with anhydrous solvent (e.g., THF) and the carbonyl substrate (1.0 equiv).
Cool to −78 °C. Add Et2BOMe (1.2–1.5 equiv) via syringe under argon.
Generate base in situ (e.g., add i-Pr2NEt, then titrate n-BuLi) or add preformed LDA to create the boron enolate (monitor by TLC/11B NMR).
Add the electrophile (e.g., an aldehyde, 1.1 equiv) dropwise at −78 to −40 °C. Stir until complete.
Quench oxidatively with H2O2/NaOH at 0 °C, then warm to rt; extract, dry, and purify.
Always validate on small scale and consult primary literature for your specific substrate class.
Biological Roles
This product is a small-molecule organoboron reagent intended for synthetic chemistry. It does not have established physiological or metabolic roles.
No known role in metabolic pathways or signaling in living systems (general knowledge for dialkylalkoxyboranes).
Reactivity toward biomolecules (general caution): as a Lewis acid, it may complex with nucleophilic sites (e.g., alcohols, amines), but such interactions are non-specific and are not utilized in biological systems.
Research note: For research use only (per Product Data). Not intended for food, drug, or clinical applications.
Buffer Applications
Not typically applicable. Diethylmethoxyborane is an air- and moisture-sensitive organoboron reagent that hydrolyzes in water and is unsuitable for aqueous buffer systems. For relevant information, see Reaction & Applications and Synthetic Utility for its role in organic synthesis.
Green Alternatives
When designing stereoselective C–C bond formations, Et2BOMe offers a milder, often less corrosive alternative to classical Lewis acids (e.g., TiCl4, SnCl4). However, it remains air/moisture sensitive and flammable. Consider the following options based on your objective:
Comparison (general, literature-based):
Target: anti-selective aldol reactions
Et2BOMe (this item): high selectivity; mild conditions; moisture sensitive; generates boron waste manageable by oxidative workup.
BF3·OEt2: strong Lewis acid; broader substrate activation; corrosive; HF risk; more challenging waste stream.
TiCl4/SnCl4: powerful activation; often harsher, more wasteful halide salts; poorer compatibility with sensitive motifs.
Target: installation of boron functionality (for cross-coupling)
B2pin2 (bis(pinacolato)diboron): bench-stable solid; greener handling; widely used to install boronates for Suzuki coupling; but different reactivity profile than Et2BOMe.
Solvent greening
Replace CH2Cl2 with toluene, 2-MeTHF, or CPME where feasible. 2-MeTHF/CPME offer lower peroxide tendency than ethers like THF/Et2O and improved sustainability.
Trade-offs:
Et2BOMe delivers outstanding stereocontrol in aldol chemistry that is not always matched by greener reagents; a hybrid strategy (e.g., greener solvent, minimal excess, efficient quench) can reduce environmental impact while retaining selectivity.
Pharmaceutical Uses
Direct pharmaceutical or excipient use is not typical for this moisture-sensitive organoboron reagent.
Role in process chemistry (general): May be used in API intermediate synthesis for stereoselective aldol/Michael steps under strictly anhydrous conditions. Any such use occurs upstream in synthesis and not in final dosage forms.
Pharmacopeial status: Not a compendial excipient. No monograph use known.
All uses are for research and laboratory synthesis only; not for clinical or therapeutic applications.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General/literature properties (for context; not item specifications)
Physical state: low-viscosity, air- and moisture-sensitive liquid (typical for dialkylalkoxyboranes).
Volatility: generally moderate; handle in closed systems or under inert gas to limit hydrolysis/oxidation.
Solubility profile: miscible with common aprotic organic solvents (e.g., hexanes, toluene, diethyl ether, THF; literature/generic for organoboranes). Hydrolyzes in protic solvents and water.
Density, refractive index, bp/mp, pKa, logP: Not specified for this item; refer to CoA/Spec Sheet.
Notes for practitioners
Expect pronounced sensitivity to moisture; even trace water increases hydrolysis rate, altering effective concentration in solution-phase reactions.
For accurate dosing, use gastight syringes or calibrated addition funnels under inert atmosphere. Verify concentration/purity by 11B NMR or titration when critical.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for this reagent class (general)
Organoboron Lewis acids used for stereoselective synthesis (e.g., aldol reactions) benefit from low hydrolyzable impurity levels and tight control of alkoxy content. Trace water significantly impacts performance.
If offered as “anhydrous” or “air/moisture sensitive,” expect inert gas packaging (this item is Argon charged) and low residual water; verify via Karl Fischer as needed.
For spectroscopic or enantioselective applications, review UV cutoff and metal content if relevant to your method. If not provided, analyze in-house.
Verification and documentation
Request and review the CoA for assay method, residual solvents, titratable boron content, and water by KF.
Before critical stereoselective steps, consider a small-scale validation run and 11B/1H NMR check to confirm integrity and absence of hydrolysis.
Reaction and Applications
Key uses center on leveraging the Lewis acidity and B–O bond of diethylmethoxyborane (Et2BOMe) to generate boron enolates and to enable highly stereoselective carbon–carbon bond formations.
Boron enolate generation (literature): Et2BOMe reacts with carbonyl compounds in the presence of base (e.g., LDA, i-Pr2NEt with n-BuLi) to give diethylboron enolates. These intermediates add to aldehydes/ketones with excellent diastereocontrol in aldol reactions (often favoring anti-aldol with appropriate enolate geometry).
Aldol reactions: Boron-mediated aldols are renowned for high selectivity and mild conditions. Low temperatures (−78 to −20 °C) and aprotic solvents (THF, CH2Cl2) are common. Subsequent oxidative workup (e.g., H2O2/NaOH) liberates the aldol product.
Michael additions: Boron enolates participate in 1,4-additions to enones with improved selectivity relative to lithium enolates, reducing side reactions.
Acylation and alkylation: The boron enolate’s softer character can modulate chemoselectivity in acyl transfer and SN2 alkylations of stabilized electrophiles.
Enolate geometry control: Complexation to boron often preserves Z-enolate geometry, translating to predictable anti/syn outcomes per Evans/Masamune models (literature guidance).
Functional group compatibility: Compared to TiCl4/SnCl4, Et2BOMe conditions are milder, often tolerating silyl ethers, acetals, and sensitive heterocycles.
Practical notes:
Titrate active boron content if the material has been stored for extended periods.
Use rigorous inert techniques; trace moisture compromises both concentration and selectivity.
Plan for oxidative or transboronation workup to remove boron and avoid product complexation.
Reaction Conditions
General literature guidance for boron-enolate chemistry using Et2BOMe (adapt to substrate specifics; not item specs):
Atmosphere: strictly inert (argon recommended; matches Product Data “Argon charged”). Dry glassware and anhydrous solvents are essential.
Solvents: THF, diethyl ether, toluene, or CH2Cl2. Choose based on temperature control and substrate solubility.
Temperatures: −78 to −20 °C for enolate formation and aldol addition; 0 to +25 °C for subsequent transformations as tolerated.
i-Pr2NEt + n-BuLi (mixed solvent) or other hindered amine/alkyllithium systems to modulate aggregation and geometry.
Stoichiometry: Often slight excess of Et2BOMe to ensure complete complexation and to scavenge trace water.
Additions: Slow addition of electrophile (e.g., aldehyde) at low temperature; maintain rigorous exclusion of moisture.
Workup: Oxidative (H2O2/NaOH) liberates alcohols/aldols and converts boron to borates; alternatively, buffered methanol/water quench followed by extraction.
Typical outcomes: High diastereoselectivity (anti or syn depending on enolate geometry and models); yields often high when moisture is excluded (consult substrate-specific literature).
Monitoring/analytics:
11B NMR: diagnostic shifts for tri-coordinate B species and after enolate formation.
Quench tests and KF titration to assess water content if selectivity drifts.
Safety and Handling
GHS/SDS status for this item
Signal word: Not specified for this item; refer to SDS.
Hazard statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General hazards and precautions (organoborane class; not a substitute for SDS)
Reactivity: air- and moisture-sensitive. Hydrolysis yields flammable gases and boron-containing byproducts; exothermic upon contact with water or protic media.
Flammability: organic boranes/borinates are typically flammable liquids. Strictly avoid ignition sources.
Peroxide formation: not an ether; peroxide formation is not a primary hazard. The main risks are hydrolysis and flammability.
Incompatibilities: water, alcohols, strong oxidizers, strong bases/acids without inert technique; oxidants can cause vigorous reactions.
PPE and engineering controls
Use in a certified fume hood under inert gas (argon recommended; item is Argon charged per Product Data).
Wear safety glasses or face shield, flame-resistant lab coat, and appropriate chemical-resistant gloves (e.g., nitrile); double-glove for extended handling.
Use air-free techniques (Schlenk line/glovebox). Ensure syringes/cannulas are dry and oxygen-free.
First-aid (overview; follow SDS/site policy)
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye: immediate irrigation with copious water for ≥15 min; remove contaminated clothing; obtain medical evaluation.
Ingestion: do not induce vomiting; rinse mouth; seek medical care promptly.
Fire-fighting
Suitable media: dry chemical, CO2. Water may be ineffective and can exacerbate hydrolysis; trained responders only.
Combustion byproducts may include boron oxides and carbon oxides.
Always consult the official SDS for authoritative safety information.
Solvent Selection
Diethylmethoxyborane is a neutral, moderately Lewis acidic organoboron that is soluble in common nonpolar and ethereal solvents. Solvent choice strongly affects stability and reaction outcomes.
Polarity class (general): nonpolar to moderately polar aprotic environments preferred.
Chlorinated solvents: CH2Cl2 can be used for boron enolate chemistry at low temperatures, keeping moisture scrupulously excluded.
Avoid: protic solvents (alcohols, water) due to rapid hydrolysis; strongly coordinating bases unless forming boron enolates intentionally.
Comparison (general considerations):
THF vs toluene: THF accelerates formation of boron enolates but increases hydrolysis risk; toluene affords improved bench stability but may require longer times or higher temperatures.
Hexanes vs ether: hexanes maximize stability during storage/transfer; ether facilitates low-temperature dosing but demands rigorously anhydrous conditions.
Practical tips:
Dry all solvents (molecular sieves or distillation; verify by KF where critical).
For kinetic control (e.g., anti-selective aldol additions), use low temperatures in ether/CH2Cl2 under strict inert atmosphere.
Storage and Reconstitution
Item-specific storage/shipping
Storage conditions: Room temperature, Argon charged (per Product Data). Keep container tightly closed under an inert atmosphere.
Shipped: Normal (per Product Data).
General handling/storage guidance (organoboranes)
Protect from moisture and air. Minimize headspace exchange; consider septum-capped bottles for syringe withdrawal under argon.
Store in a dry, well-ventilated area away from oxidizers, acids, bases, and ignition sources.
If transferring to a drying tube/ampoule, ensure vessel is thoroughly dried; backfill with argon after each use.
Reconstitution
Supplied neat unless otherwise stated. If preparing solutions (e.g., 0.5–1.0 M in toluene, THF, or CH2Cl2), use anhydrous, oxygen-free solvents. Prepare under argon and store in sealed, inerted containers.
Verify concentration by titration or NMR if solution is stored for extended periods; hydrolysis may gradually reduce active boron content.
Follow the product label and SDS for any additional, item-specific instructions.
Structure and Identity
Item-specific identifiers (from Product Data)
SKU: D164492
Product name: Diethylmethoxyborane
CAS: 7397-46-8
PubChem CID: 522516
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (general reference)
Common name/descriptor: diethyl(methoxy)borane; Et2B-OMe
Molecular formula (literature): C5H13BO
Molecular weight (literature): ~99.8 g/mol
Core structural features: tricoordinate boron bearing two ethyl substituents and one methoxy substituent (R2B–OR′). The boron is sp2-hybridized with an empty p-orbital, conferring Lewis acidity.
2D structural description: a central boron atom singly bonded to two ethyl groups (–CH2CH3) and one oxygen atom; the oxygen is further bound to a methyl group (–O–CH3). No rings or stereocenters.
Category/Type inference (general)
Compound class: organoboron Lewis acid; dialkylalkoxyborane.
Typical roles: boron source for boron enolates; promoter of stereoselective aldol/Michael additions; precursor to organoboron transformations.
Synthetic Utility
Functional features enabling synthetic value:
Lewis acidity at boron (empty p-orbital) promotes formation of boron enolates from carbonyl compounds under basic conditions, providing enhanced selectivity versus lithium/sodium enolates.
The methoxy ligand serves as a leaving group during enolate formation/transformation, while diethyl substitution imparts solubility and modulates reactivity.
anti-Selective aldol reactions: Formation of Z-boron enolates followed by addition to aldehydes affords anti-aldols with high diastereoselectivity; oxidative workup releases free aldols.
Michael additions: Soft boron enolates engage α,β-unsaturated carbonyls with good chemoselectivity.
Acylations/Alkylations of enolates: Boron coordination suppresses side reactions and over-alkylation.
Auxiliary and chiral catalysis compatibility: Operates under conditions compatible with many chiral auxiliaries (e.g., Evans oxazolidinones), facilitating predictable stereochemical outcomes.
Practical synthesis notes:
Generate boron enolates at −78 to −20 °C; titrate base carefully to avoid over-deprotonation or O-bound enolate scrambling.
After C–C bond formation, oxidative workup (H2O2/NaOH) or methanolysis/aqueous workup efficiently removes boron; include chelating agents if emulsions persist.
Monitor by TLC/GC or in situ 11B/1H NMR to track enolate formation and consumption.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not target biological epitopes or molecular targets in the sense of antibodies, enzymes, or ligands. No clone/isotype/species information applies.
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