1,3-Dimethoxypropan-2-amine

Inquiry

Cat Number

INT78531290

CAS Number

78531-29-0

If you have any other questions, please contact our experts.

Product Detail Description Scientific Support Customer Q&A

CAS Number

78531-29-0

Storage

2-8℃

Synonyms

2-Amino-1,3-dimethoxypropane;2-Propanamine, 1,3-dimethoxy-;1,3-Dimethoxy-2-propanamine

Molecular Formula

C5H13NO2

Molecular Weight

119.16

Appearance

Clear colorless to yellow liquid

Boiling Point

160.8℃

Relative Density

0.93

pKa

General Description

1,3-Dimethoxypropan-2-amine (also known as 2-amino-1,3-dimethoxypropane) is a symmetrical secondary amine featuring two terminal methoxy groups flanking a central 1,2-diamine-like backbone. The 2-amino-1,3-dimethoxy substitution pattern provides two methoxy groups capable of coordinating to metal ions, while the primary amine provides nucleophilicity and serves as a handle for further functionalization including amidation and sulfonylation.

Mechanism of Action

1,3-Dimethoxypropan-2-amine functions as a flexible amine building block in pharmaceutical synthesis. The symmetrical 1,3-dimethoxy substitution provides a degree of steric shielding around the central amine, which can influence the regioselectivity of downstream reactions and the conformational preference of resulting molecules. The methoxy groups are metabolically stable and contribute to lipophilicity.

Application

1,3-Dimethoxypropan-2-amine is used as an intermediate in the synthesis of pharmacologically active compounds, particularly those requiring a flexible ether-amine linker. It is used in the synthesis of nootropic (cognitive-enhancing) agents, local anesthetics, and surface-active agents. The dimethoxypropyl amine scaffold is also found in certain choline analogs and in the synthesis of cross-linking agents for polymer chemistry.

A potent BET inhibitor, dimethylpyridone benzimidazole 24 (1-BET469), was optimized from a hit series identified by encoded library technology. The synthesis involved coupling 1,3-dimethoxypropan-2-amine with 4-bromo-1-fluoro-2-nitrobenzene via nucleophilic aromatic substitution to form an aniline intermediate, followed by cyclization with 1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde to construct the benzimidazole core. Subsequent palladium-catalyzed C-N cross-coupling with morpholine gave the final compound. This 1,3-dimethoxypropan-2-amine-derived N1 substituent replaced the less metabolically stable 4-methylene THP group, significantly reducing off-target BAZ2A activity.

Fig. 1 1,3-Dimethoxypropan-2-amine in the synthesis of Dimethylpyridone Benzimidazole. (Wellaway C R.; et al. 2020)

References

Wellaway C R, et al. Discovery of a bromodomain and extraterminal inhibitor with a low predicted human dose through synergistic use of encoded library technology and fragment screening. Journal of Medicinal Chemistry, 2020, 63(2): 714-746.

What is the recommended storage condition for 1,3-Dimethoxypropan-2-amine?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of 1,3-Dimethoxypropan-2-amine?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

Is 1,3-Dimethoxypropan-2-amine compatible with common organic solvents used in pharmaceutical synthesis?

Solubility and compatibility information is available in the technical data sheet. For specific solvent compatibility questions, please contact our technical team.

What functional groups in 1,3-Dimethoxypropan-2-amine are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

Does your company offer custom packaging for 1,3-Dimethoxypropan-2-amine?

Yes, custom pack sizes are available. Specific quantity requirements can be discussed directly with our team to align with your production or research scale.