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Merck

121967

Aminoacetaldehyde dimethyl acetal

99%

Synonym(s):

2,2-Dimethoxyethylamine

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About This Item

Linear Formula:
NH2CH2CH(OCH3)2
CAS Number:
22483-09-6
Molecular Weight:
105.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847473
EC Number:
245-026-5
Beilstein/REAXYS Number:
741868
MDL number:
MFCD00008135
Assay:
99%

Key Documents

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InChI

1S/C4H11NO2/c1-6-4(3-5)7-2/h4H,3,5H2,1-2H3

InChI key

QKWWDTYDYOFRJL-UHFFFAOYSA-N

SMILES string

COC(CN)OC

assay

99%

Quality Level

200

refractive index

n20/D 1.417 (lit.)

bp

135-139 °C/95 mmHg (lit.)

density

0.965 g/mL at 25 °C (lit.)

functional group

acetal, amine, ether

Related Categories

General description

Aminoacetaldehyde dimethyl acetal reacts with sulfone, followed by hydrolysis and reductive amination by adding desired piperazine derivative to yield piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine.

Aminoacetaldehyde dimethyl acetal is used as a building block for the synthesis of various acylated and sufonylated oxyenamides.

Application

Aminoacetaldehyde dimethyl acetal was used in a study to develop a fluorescent substrate for aldehyde dehydrogenase. It was used in preparation of chitosan-dendrimer hybrids having various functional groups such as carboxyl, ester and poly(ethylene glycol). It was used in an efficient 3-step synthesis of a bicyclic proline analog from L-ascorbic acid and in 3-component reaction catalyzed by MgClO4 leading to α-aminophosphonates.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 2 petroleums + Hazardous rank III + Water insoluble liquid

fsl

121967-BULK: + 121967-25ML: + 121967-VAR: + 121967-10KG: + 121967-100ML: + 121967-500ML:

jan

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Hitoshi Sashiwa et al.
Biomacromolecules, 4(5), 1244-1249 (2003-09-10)
Chitosan-dendrimer hybrids having various functional groups such as carboxyl, ester, and poly(ethylene glycol) groups were prepared successfully using dendrimer acetal by reductive N-alkylation. The synthetic procedure could be accomplished by one-step reaction without organic solvent. The degree of substitution of
R W Storms et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(16), 9118-9123 (1999-08-04)
Because hematopoietic stem cells are rich in aldehyde dehydrogenase (ALDH) activity, we developed a fluorescent substrate for ALDH, termed BODIPY aminoacetaldehyde (BAAA), and tested its potential for isolating primitive human hematopoietic cells. A population of cells with low orthogonal light
Chi B Vu et al.
Bioorganic & medicinal chemistry letters, 14(19), 4835-4838 (2004-09-03)
Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been shown to be potent and selective adenosine A(2a) receptor antagonists. We now demonstrate that potent and selective A(2a) receptor antagonists could still be obtained when the arylpiperazines are separated from the triazolotriazine core
Synthesis, 3122-3122 (2006)
Maria C Llinàs et al.
Drug delivery, 25(1), 1137-1146 (2018-05-22)
A dual doxorubicin/camptothecin (DOX/CPT) pH-triggered drug delivery mesoporous silica nanoparticle (MSN)-based nano-vehicle has been prepared. In this drug-delivery system (DDS), CPT is loaded inside the pores of the MSNs, while DOX is covalently attached to the surface of an aldehyde-functionalized
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