Methylaminoacetaldehyde Dimethyl Acetal CAS 122‑07‑6

Product Overview

Methylaminoacetaldehyde dimethyl acetal is a dual‑functional aliphatic intermediate integrating secondary methyl‑amino group and dimethyl acetal moiety. The acetal group can release active aldehyde under acidic conditions, while N‑methyl secondary amine supports amination, cyclization and coupling transformation. This unique structure makes it an indispensable raw material for constructing imidazole and other nitrogen‑heterocyclic skeletons. It is widely adopted in pharmaceutical intermediate manufacturing, heterocyclic methodology research and reference‑substance preparation for drug‑impurity analysis, both for laboratory‑scale synthesis and pilot‑scale production.

Basic Product Information

1. Product Name: Methylaminoacetaldehyde Dimethyl Acetal
2. CAS NO.: 122‑07‑6
3. Synonym: (2,2‑dimethoxyethyl)(methyl)amine;1,1‑Dimethoxy‑2‑methylaminoethane
4. Molecular Formula: C₅H₁₃NO₂
5. Molecular Weight: 119.16
6. Structural formula:
7. Purity: ≥98% (GC)
8. Appearance: Colorless to pale‑yellow clear liquid
9. Density: 0.928 g/mL (25℃)
10. Boiling point: 140 ℃(760 mmHg)
11. Refractive index: n₂₀/D 1.414
12. Flash Point: 29 ℃
13. Melting point: -73 ℃
14. Solubility: Miscible with water, methanol, dichloromethane, THF
15. MDL Number: MFCD00008485
16. HS Code: 2922199090

Frequently Asked Questions (FAQ)

Question 1: What makes this acetal‑amine intermediate different from ordinary amino‑acetal reagents?
Answer: It carries N‑methyl secondary amine instead of primary amine. After acid‑triggered deprotection, the in‑situ‑generated aldehyde and secondary amine can rapidly complete intramolecular cyclization. It avoids extra N‑methylation steps for target heterocycles, shortening synthetic routes for methyl‑substituted nitrogen‑heterocyclic products.

Question 2: What pitfalls should be avoided during laboratory operations?
Answer: It is flammable and irritant to skin, eyes and respiratory tract. Since acetal is sensitive to acid, do not expose samples to acidic aqueous environment for long time, otherwise premature hydrolysis to aldehyde impurity will occur. All operations are recommended inside fume hood with fire‑proof measures because of low flash‑point.

Question 3: What is the mainstream synthetic route and its pros and cons?
Answer: Industrial and lab main route is pressure‑driven amination: chloroacetaldehyde dimethyl acetal reacts with excess methylamine in autoclave under heating condition, followed by neutralization and vacuum distillation purification. This process delivers high yield, yet requires pressure equipment and handles volatile methylamine. Small‑scale researchers mostly purchase commercial product rather than self‑preparation.

Question 4: Why does long‑term storage lead to rising impurity content?
Answer: This product is sensitive to air and moisture. Trace water plus carbon dioxide from air can slowly trigger partial acetal hydrolysis and amine oxidation, generating aldehyde and polymeric impurities. Repeated opening of bottle cap accelerates degradation. Inert‑gas‑sealed cold storage greatly prolongs service life.

Question 5: How to arrange reaction sequence of amino site and acetal site?
Answer: Two typical strategies are available. Under neutral or weak‑alkaline environment, perform amine‑involved coupling or cyclization first, then release aldehyde by subsequent acid treatment. If acidic condition is applied at early stage, acetal will hydrolyze immediately. Users must prioritize amine‑group transformation before introducing acid into system.

Application Cases

Application Case 1: Key precursor for antithyroid drug Methimazole synthesis
This compound serves as critical starting material for manufacturing methimazole, a classic hyperthyroidism‑treatment drug. After acetal deprotection under controlled acidic condition, the intermediate participates in ring‑closure cyclization reaction to build N‑methyl imidazole‑2‑thiol core skeleton. Strict quality control of this raw material directly reduces related‑substance impurities in final API.

Application Case 2: Synthesis library of substituted imidazole heterocyclic compounds
In copper‑catalyzed cyclization system, it reacts with various nitrile substrates to produce multi‑substituted imidazole derivatives. The built‑in N‑methyl group avoids additional methylation procedures. This protocol supports quick construction of imidazole compound libraries for high‑throughput screening of anti‑infective and anti‑inflammatory lead molecules in medicinal chemistry projects.

Application Case 3: Substrate for Petasis borono‑Mannich multicomponent reaction
It acts as amine component in Petasis reaction, assembling with glyoxylic acid and aryl boronic acid to yield N‑methyl‑N‑(2,2‑dimethoxyethyl) glycine derivatives. These modified amino‑acid fragments can be further derivatized for peptide‑mimetic study, offering convenient access to non‑natural amino‑acid building‑blocks.

Application Case 4: Preparation of drug‑impurity reference standard for quality control
It corresponds to known process‑related impurity A of methimazole API. High‑purity material can be used as reference standard for HPLC qualitative‑quantitative analysis in pharmaceutical‑quality‑control laboratories, helping factories monitor impurity profiles during drug production and satisfy pharmacopoeia testing requirements.

Application Case 5: Construction of complex fused aza‑cyclazine ring systems
Via condensation with oxazolopyridinium salt substrates, it constructs aza[3.3.2]cyclazine fused‑ring framework, generating functionalized amino‑indolizine intermediates. Such polycyclic nitrogen‑containing skeletons are valuable for early‑stage exploration of new‑type fluorescent dyes and bio‑active heterocyclic candidates, mostly at academic‑research lab scale.

Safety and Storage

1. Keep container tightly sealed, store under inert nitrogen‑blanketing condition. Recommended long‑term storage temperature: 2‑8℃; short‑term room‑temperature storage is allowed.
2. Protect from moisture, air exposure and acidic materials. Keep far away from heat source, open flame and strong oxidizing agents due to low flash‑point.
3. Wear protective gloves, goggles and work inside fume‑hood when handling. Avoid inhalation of vapors and direct skin contact.
4. For transportation: classified as flammable irritant liquid. Prevent container breakage and liquid leakage. Prohibit co‑transport with acid and oxidants. Avoid high‑temperature exposure during transit.

Product Manager Information

Product Manager: Emma Song
Email: emma@coreychem.com