This compound belongs to the class of organic compounds known as hemiaminals. These are compounds comprising the hemiaminal functional group, with the general formula R2C(OH)NR2 where R can by a hydrogen or an alkyl group.
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
Not applicable as a bioassay reagent. No validated biological applications (e.g., WB, IHC, IF, FC) or recommended dilutions are provided in the Product Data. For chemical synthesis applications, see the Reaction & Applications and Reaction Conditions sections for general guidance.
Biological Roles
This compound is an aliphatic tertiary amine ether designed for use as a synthetic reagent/intermediate. It is not a biological buffer, metabolite, or biomolecule and has no inherent biological role in standard metabolic pathways.
General chemistry perspective
Tertiary amines can be protonated to form ammonium salts; such salts may show altered solubility and partitioning, but these are physicochemical properties rather than biological functions.
No enzyme cofactors, receptor ligands, or canonical biochemical roles are associated with simple methoxymethyl tertiary amines in the literature.
Research use limitation
For research use only. Not intended for food, drug, cosmetic, or household use.
If your project involves biological systems, handle with caution: tertiary amines can be membrane-active and may disrupt biological membranes at sufficient concentrations (general consideration). Determine cytotoxicity and compatibility empirically for your specific system if incidental exposure is possible.
Buffer Applications
Not typically applicable. This product is not a dedicated buffering agent, and no validated pKa/pH buffering range has been established for this specific compound in the Product Data. While tertiary amines can be protonated (conjugate acid pKa for dimethylamino groups is often ~9–10, literature), reproducible buffer systems use well-characterized amine salts (e.g., Tris, TEA) with defined buffering ranges.
For work requiring pH control, select established buffers appropriate to your pH window (e.g., phosphate, Tris, HEPES) and reserve this compound for its intended role as a synthetic reagent/intermediate.
Green Alternatives
When considering protecting-group or C1-transfer chemistry, reagent choice affects safety and environmental footprint.
Context (general)
Traditional MOM installation commonly uses chloromethyl methyl ether (MOMCl), a highly hazardous, volatile, and regulated alkylating agent. Non-halogenated precursors that generate MOM electrophiles in situ under acid activation are of interest as safer alternatives.
Comparative assessment (literature/general)
(Dimethylamino)methyl methyl ether (this reagent)
Pros: Halogen-free; tertiary amine can be protonated and removed as a benign salt; potential to tune reactivity via choice of acid; reduced corrosion/halide waste compared with MOMCl.
Cons: Typically requires strong acids/Lewis acids; may produce dimethylamine emissions (odor, amination of equipment if uncontrolled); possibly lower reactivity/selectivity vs preformed halides; flammability considerations for low-boiling amines.
Alternatives
Dimethoxymethane (DMM): greener solvent-like reagent; under strong acid can deliver MOM groups but often less selective and equilibrium-limited.
Paraformaldehyde + MeOH under acid: inexpensive and halogen-free; mixtures can be harder to control; water generation can reduce protecting yields.
Commercial MOM reagents with stabilized leaving groups (e.g., MOM-OTf in situ): high reactivity but generates acid/halide wastes and requires stringent controls.
Practical green tips
Use catalytic, recoverable acids (e.g., polymer-supported sulfonic acids) where feasible.
Employ closed systems with amine scrubbing to minimize VOC emissions.
Choose solvents from preferred lists (e.g., Me-THF, CPME, EtOAc) compatible with acid catalysis and substrate.
Pharmaceutical Uses
No pharmacopeial grade or excipient status is provided in the Product Data. This material is supplied for research use only and is not intended for human or veterinary use.
General remarks (formulation chemistry context)
Aliphatic tertiary amines are occasionally leveraged in process development as bases, acid scavengers, or transient protecting-group carriers. However, translating such reagents into GMP manufacturing requires comprehensive impurity, residuals, and toxicology controls.
If used upstream as a protecting-group reagent (e.g., to introduce MOM groups), process design typically ensures complete removal or transformation to benign salts, followed by rigorous purge studies.
Documentation
For any consideration beyond laboratory research, consult regulatory guidance and develop appropriate specifications for identity, purity, residual solvents, and elemental impurities. None of these are specified here for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific specifications (exact numeric values) are not provided in the Product Data for this SKU. Refer to the CoA/Specification Sheet for authoritative values.
Item-specific statements from Product Data
Storage: Room temperature
Literature/computed properties (for general reference; not item-specific specs)
Empirical formula: C4H11NO (computed from structure)
Molecular weight: ~89.14 g/mol (computed)
Physical state/appearance: typically a low-boiling, colorless liquid for small aliphatic tertiary amine ethers (literature expectation)
Boiling point: Not specified for this item; refer to CoA/Spec Sheet. Small C4 tertiary amines/ethers often boil below 120 °C (literature trend).
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density (20–25 °C): Not specified for this item; refer to CoA/Spec Sheet.
Refractive index (nD): Not specified for this item; refer to CoA/Spec Sheet.
Solubility: Tertiary amines of this size are generally miscible with many organic solvents and exhibit appreciable water solubility due to amine basicity (literature trend). Quantitative solubility for this item is not specified; consult CoA.
pKa (conjugate acid): Tertiary dimethylamino centers commonly have pKaH ≈ 9–10 (literature). Exact value for this structure not specified.
LogP: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, GC area %, and impurity limits.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Shipped in: Not specified for this item; refer to product label/CoA.
Interpreting grade (general guidance)
For low-boiling amine ethers used as building blocks or protecting-group reagents, common grades include: synthetic grade (general use), ≥95–99% assay (for reproducible transformations), and anhydrous grades for acid-sensitive protocols. If UV transparency is needed (e.g., analytical HPLC mobile phase modifier studies), low-UV grades minimize baseline noise.
Stabilizers/inhibitors: Some ether-containing reagents are packaged under inert gas or with trace stabilizers to mitigate peroxide formation. Presence/absence of stabilizer materially impacts downstream reactivity in acid-promoted transformations; verify on the CoA.
What to check on receipt (practical tips)
Verify assay, water (Karl Fischer), amine number, and residual solvent on the CoA when relevant to your procedure.
Inspect for color or odor changes that can indicate oxidation or contamination, especially after repeated openings.
For moisture- or acid-sensitive sequences, consider distillation over base/drying agents immediately prior to use.
Reaction and Applications
General application domain
A versatile tertiary amine ether used as a methoxymethyl (MOM)-transfer or aminomethylation synthon under acid activation, and as a nucleophilic/base component in organic synthesis.
Literature-based reactivity patterns (general; not item-specific claims)
Acid activation of the –CH2–N(CH3)2 moiety can generate an iminium-like intermediate. In the presence of nucleophiles (e.g., alcohols, phenols), substitution can afford MOM-protected derivatives with expulsion of dimethylamine. Strong Brønsted acids (e.g., HClO4, HBF4) or Lewis acids (e.g., BF3·OEt2) are commonly employed in analogous systems.
As a dimethylaminomethyl source (Mannich-type chemistry), iminium formation with carbonyl partners followed by C–C bond formation can introduce –CH2NMe2, which can be further manipulated (e.g., quaternization, oxidative deamination, or hydrolysis).
Alkylation of the tertiary amine yields quaternary ammonium salts, useful phase-transfer agents or isolable intermediates, depending on counterion.
Practical tips
Control acidity carefully: excess strong acid can lead to competitive cleavage to methanol and dimethylamine or polymeric byproducts.
Maintain anhydrous conditions for selective MOM transfer to water-sensitive substrates; water will capture the electrophile and reduce yields.
Remove expelled dimethylamine by gas sweep or reduced pressure to drive equilibria; scrub outlet streams appropriately.
Representative contexts
Protection of alcohols/phenols as MOM ethers (acid-catalyzed).
Introduction of aminomethyl functionality via Mannich-type additions followed by downstream transformations.
Reaction Conditions
The following are literature-style, general guidance notes for chemistry involving tertiary amine hemiaminal ethers; they are not item-specific specifications. Optimize for your substrate and scale.
MOM installation on alcohols/phenols (acid-activated)
Solvent: CH2Cl2, MeCN, or toluene are typical. Avoid highly nucleophilic solvents (MeOH) that can compete.
Acid promoter: BF3·OEt2 (0.1–1.0 equiv), TfOH (cat. to 0.5 equiv), or strong protic acids like HClO4 (carefully dosed). Weaker acids often give low conversion.
Temperature: 0 °C to ambient; cooling controls exotherm during acid addition.
Time: 0.5–6 h, depending on substrate nucleophilicity and sterics.
Workup: Neutralize acid; vent or scrub dimethylamine formed; wash, dry, and concentrate. Purify by distillation or chromatography as substrate dictates.
Mannich-type aminomethylation
Components: carbonyl compound (to form iminium), nucleophile (enolizable carbonyl, aromatics under EAS), acid catalyst (e.g., p-TsOH, BF3·OEt2).
Solvent: MeCN, DCE, or toluene.
Temperature: 0–60 °C.
Notes: Control water content; water shifts equilibria back to starting materials.
Solvent: MeCN, acetone, EtOAc; often proceeds at rt to reflux.
Isolation: Precipitation of salts with non-coordinating counterions can simplify purification.
Yields
Highly substrate- and condition-dependent; consult primary literature for your substrate class.
Safety and Handling
Always consult the SDS for authoritative safety, hazard, and first-aid information for this product.
Item-specific hazard data from Product Data
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety guidance for tertiary amine ethers (literature/general)
Likely hazards: Flammable liquid and vapor are common for low-MW amine ethers; vapors may be irritating to eyes, skin, and respiratory tract. Tertiary amines are bases and can cause chemical irritation on contact.
PPE: Use chemical splash goggles, nitrile gloves, lab coat; handle in a fume hood to avoid inhalation of vapors.
Incompatibilities: Strong oxidizers; strong acids (may form salts, heat on neutralization). Avoid halogenating agents and acylating agents unless controlled for synthesis.
Ethers and peroxide formation: Many ethers can form peroxides on prolonged storage with air and light (literature). Periodic testing is prudent for long-stored, opened containers; keep tightly closed and protected from light.
Spill/first aid (overview): For skin/eye contact, rinse with water for ≥15 minutes and remove contaminated clothing; seek medical attention. For inhalation, move to fresh air. For ingestion, do not induce vomiting; seek medical attention. Eliminate ignition sources during spills; absorb with inert material.
Handling tips
Ground/bond containers when dispensing flammable liquids.
In synthetic use, quenching acid/base carefully controls exotherms; add reagent to acid slowly if protonation or in situ generation of cationic species is intended.
Solvent Selection
This product is primarily a reactive intermediate/reagent rather than a bulk solvent. However, understanding its solvation and compatibility helps in process design.
Polarity/miscibility (literature/general)
The tertiary amine confers basicity and hydrogen-bond-acceptor capacity; the ether increases organic solubility. Such C4 amine ethers are typically miscible with most polar organic solvents (THF, MeCN, acetone, alcohols) and dissolve in many nonpolar solvents (toluene, ethers). Water miscibility is often appreciable for tertiary amines of this size, especially in protonated form; confirm experimentally.
Choosing media for reactions involving this reagent
Acid-promoted transformations (e.g., in situ generation of cationic intermediates): use non-nucleophilic solvents with controlled acidity, such as CH2Cl2, toluene, or MeCN, and add Brønsted/Lewis acid cautiously.
Nucleophilic substitution or protection chemistry with alcohol substrates: dichloromethane or MeCN can balance solubility and control; protic solvents (MeOH, EtOH) can compete; evaluate based on desired selectivity.
Salt formation (protonation): polar solvents (EtOAc, MeCN, IPA) aid isolation/crystallization of ammonium salts with appropriate acids.
Comparison to alternatives (general)
Versus chloromethylating agents (e.g., MOMCl): this non-halogenated amine ether may offer handling advantages and reduced corrosivity, but typically requires acid activation; reactivity is lower without activation.
Versus dimethoxymethane/paraformaldehyde: provides a dimethylamino leaving group context; reactivity and selectivity differ—choose per mechanism needs.
Storage and Reconstitution
Item-specific storage information (from Product Data)
Storage Conditions: Room temperature.
Additional handling guidance (general)
Keep container tightly closed in a well-ventilated place. Minimize headspace oxygen for long-term storage to limit potential peroxide formation typical of ether-containing liquids (general precaution).
Protect from moisture and strong acids/bases unless intentionally used; tertiary amines readily form salts with acids.
If long-term storage after opening is anticipated, consider inert gas blanket and storage in amber glass.
Reconstitution
Supplied neat (no reconstitution required). If solidification or phase separation is observed at low temperature, gently warm to ambient and mix thoroughly before use.
Shipping
Shipped in: Not specified for this item; refer to product label and SDS.
Stability
Shelf-life and specific impurity limits are not specified for this item; refer to CoA/Spec Sheet. Periodic peroxide testing is prudent for opened bottles stored for extended periods (general ether precaution).
Structure and Identity
A tertiary amine bearing a methoxymethyl substituent, formally the dimethylamino hemiaminal ether of formaldehyde (structural motif: CH3–O–CH2–N(CH3)2).
Item-specific identifiers (from Product Data)
SKU: D1248482
CAS: 62393-45-7
InChIKey: 436149 (as provided)
Category: Chemical and Biochemical Reagents (research use only)
Literature/computed identifiers (general reference; not item-specific specs)
Common name: (Dimethylamino)methyl methyl ether; dimethyl(methoxymethyl)amine
Molecular formula (computed from structure): C4H11NO
Functional groups: tertiary amine [N(CH3)2], aliphatic ether (methoxy group), methylene linker (–CH2–) between O and N.
No stereogenic centers; acyclic, conformationally flexible.
The tertiary amine is basic and nucleophilic; the ether oxygen is weakly Lewis basic. Under acidic conditions, an iminium-like species can be generated at the –CH2–N center, enabling substitution or protection chemistry.
2D description in words (general)
A three-atom chain O–CH2–N links a terminal methoxy group (–OCH3) to a dimethylamino group [–N(CH3)2]. The nitrogen carries two methyl substituents and a methoxymethyl substituent, giving a tertiary amine with no N–H bonds.
Synthetic Utility
Functional handle analysis (general)
Tertiary amine: basic, nucleophilic; forms stable ammonium salts; undergoes alkylation to quaternary ammonium salts.
Methoxymethyl ether segment: under strong acids/Lewis acids, can generate a stabilized cationic species enabling substitution with oxygen or carbon nucleophiles.
Protecting-group chemistry
Acid activation of (dimethylamino)methyl methyl ether can provide a route to install MOM groups on alcohols/phenols in situ, with dimethylamine as the leaving fragment (literature precedent for related reagents). This offers a halogen-free alternative to MOMCl; optimization of acid, solvent, and temperature is critical to suppress side reactions.
C1 and aminomethyl transfer chemistry
In Mannich-type reactions, iminium formation with carbonyl partners can introduce –CH2NMe2, which is convertible into other functionalities (e.g., N-oxidation, Hofmann elimination after quaternization, or hydrolytic unmasking to carbonyl derivatives).
Retrosynthetic value
Serves as a masked formaldehyde equivalent in combination with dimethylamine and methanol under acid catalysis. Its tertiary amine allows controlled generation/scavenging of cationic intermediates without introducing halide.
Downstream manipulations
Quaternization (e.g., MeI, MeOTf) affords isolable ammonium salts; subsequent Hofmann or Cope eliminations can be used to forge alkenes from appropriately substituted frameworks (general strategy).
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not have biological target specificity, antigen/epitope information, species reactivity, clone, or isotype. No such details are provided in the Product Data.
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