Methylaminoacetaldehyde dimethyl acetal

Base Information

• Chemical Name: Methylaminoacetaldehyde dimethyl acetal
• CAS No.: 122-07-6
• Molecular Formula: C5H13NO2
• Molecular Weight: 119.164
• Hs Code.: 29225000
• European Community (EC) Number: 204-520-0
• NSC Number: 66270
• UNII: 6V8Q54KHCL
• DSSTox Substance ID: DTXSID3051620
• Nikkaji Number: J93.680D
• Wikidata: Q27265573
• Mol file: 122-07-6.mol

Synonyms:122-07-6;Methylaminoacetaldehyde dimethyl acetal;2,2-Dimethoxy-N-methylethanamine;(Methylamino)acetaldehyde dimethyl acetal;Ethanamine, 2,2-dimethoxy-N-methyl-;(2,2-dimethoxyethyl)(methyl)amine;2,2-Dimethoxyethylmethylamine;2,2-Dimethoxy-N-methylethylamine;N-Methylaminoacetaldehyde dimethyl acetal;2,2-DIMETHOXYETHYL(METHYL)AMINE;2-(Methylamino)acetaldehyde dimethyl acetal;Acetaldehyde, (methylamino)-, dimethyl acetal;UNII-6V8Q54KHCL;6V8Q54KHCL;(2,2-dimethoxyethyl)methylamine;HSDB 5406;1,1-Dimethoxy-2-methylaminoethane;EINECS 204-520-0;(2,2-Dimethoxy-ethyl)-methyl-amine;1-(methylamino)-2,2-dimethoxyethane;NSC 66270;NSC-66270;N-(2,2-dimethoxyethyl)-N-methylamine;methylamino acetaldehyde dimethyl acetal;EC 204-520-0;N-(2,2-Dimethoxyethyl)methylamine;2,2-dimethoxy-N-methyl-ethanamine;2,2-dimethoxy-N-methylethan-1-amine;METHYLAMINOACETALDEHYDE DIMETHYLACETAL;SCHEMBL356543;DTXSID3051620;HUMIEJNVCICTPJ-UHFFFAOYSA-;SARCOSINAL DIMETHYL ACETAL;Ethanamine,2-dimethoxy-N-methyl-;N-Methyl-2,2-dimethoxyethanamine;(2,2-dimethoxy-ethyl)-methylamine;N-(2,2-dimethoxyethyl)methanamine;AMY41272;NSC66270;2,2-Dimethoxy-N-methylethanamine #;N-(2,2-dimethoxyethyl) methanamine;N-Methyl-N-2,2-dimethoxyethylamine;BBL027717;MFCD00008485;STK802333;AKOS009064862;(methylamino)acetaldehyde dimethylacetal;CS-W011213;Methylaminoacetaldehyde dimethyl acetal;N-methylaminoacetaldehyde dimethylacetal;SB75556;METHYL(2,2-DIMETHOXYETHYL)AMINE;(methylamino)-acetaldehyde dimethylacetal;VS-08583;THIAMAZOLE IMPURITY A [EP IMPURITY];(N-methylamino)-acetaldehyde dimethyl acetal;FT-0631697;M0884;(N-methyl-amino)-acetaldehyde dimethyl acetal;(Methylamino)acetaldehyde dimethyl acetal, 97%;2,2-DIMETHOXYETHYL(METHYL)AMINE [HSDB];EN300-114193;(N-METHYLAMINO)ACETALDEHYDE DIMETHYL ACETAL;W-108438;Q27265573;F0001-0355;Z138091358;Thiamazole impurity A, European Pharmacopoeia (EP) Reference Standard

Chemical Property of Methylaminoacetaldehyde dimethyl acetal

Chemical Property:

• Appearance/Colour: yellow needles or powder
• Vapor Pressure: 6.26mmHg at 25°C
• Melting Point: -73 °C
• Refractive Index: n20/D 1.414(lit.)
• Boiling Point: 140 °C at 760 mmHg
• PKA: 8.29±0.20(Predicted)
• Flash Point: 29.4 °C
• PSA: 30.49000
• Density: 0.896 g/cm³
• LogP: 0.21560
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Water Solubility.: miscible
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 119.094628657
• Heavy Atom Count: 8
• Complexity: 45.7

Purity/Quality:

99% ^*data from raw suppliers

2,2-Dimethoxy-N-methylethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36-36/37/38
• Safety Statements: 26-36-37/39-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CNCC(OC)OC
• Description: Methylaminoacetaldehyde dimethyl acetal can be used as a pharmaceutical synthesis intermediate, such as the preparation of methimazole, the chemical name is 1-methylimidazole-2-thiol, which is an antithyroid drug, and its mechanism of action is to inhibit thyroid endoperoxide Enzymes, thereby hindering the oxidation of iodide absorbed into the thyroid and the coupling of tyrosine, hindering the synthesis of thyroxine (T4) and triiodothyronine (T3). Animal experiments have observed that B lymphocytes synthesize antibodies, reduce the level of thyroid-stimulating antibodies in the blood circulation, and restore the suppressor T cells to normal.
• Uses: 2,2-Dimethoxy-N-methylethanamine is an impurity formed in the synthetic process of Methimazole (M260300), a thiourea antithyroid agent that prevents iodine organification, (Methylamino)acetaldehyde dimethyl acetal can be used as a reactant to synthesize: Aza[3.3.2] cyclazines by reacting with 5-methyloxazolo[3,2-a]pyridinium salts via synthesis of functionalized 5-aminoindolizines intermediates. N-(2,2-Dimethoxyethyl)-N-methyl-3,4-dimethoxyphenylglycine by Petasis reaction with glyoxylic acid and 3,4-dimethoxyphenylboronic acid. Substituted imidazoles via copper-catalyzed reaction with various nitriles.

Technology Process of Methylaminoacetaldehyde dimethyl acetal

There total 4 articles about Methylaminoacetaldehyde dimethyl acetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

chloroacetaldehyde dimethyl acetal (97-97-2) + methylamine (74-89-5) → N-(methyl)aminoacetaldehyde dimethyl acetal (122-07-6)

Guidance literature:

In water; at 80 - 85 ℃; for 16h; Autoclave;

Reference yield:

C10H21NO4 → N-(methyl)aminoacetaldehyde dimethyl acetal (122-07-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c7ob00593h

Reference yield:

1-bromo-2,2-dimethoxyethane (7252-83-7) + methylamine (74-89-5) → bis-(2,2-dimethoxy-ethyl)-methyl-amine (70887-96-6) + N-(methyl)aminoacetaldehyde dimethyl acetal (122-07-6)

Guidance literature:

With methanol; at 140 ℃; im Autoklaven;

upstream raw materials:

1-bromo-2,2-dimethoxyethane

methylamine

chloroacetaldehyde dimethyl acetal

Downstream raw materials:

O-benzyl-N-(2,2-dimethoxyethyl)-N-methyl-2-(3,4-dimethoxyphenyl)glycinol

N-(2,2-dimethoxyethyl)-N-methyl-2-(3,4-dimethoxyphenyl)glycinol

2-Mercapto-1-methylimidazole

1-methyl-2-aminoimidazole

Refernces

• 1、 McPherson, Christopher G.,Caldwell, Nicola,Jamieson, Craig,Simpson, Iain,Watson, Allan J. B.. "Amidation of unactivated ester derivatives mediated by trifluoroethanol". supporting information. p. 3507 - 3518. Retrieved 2017/04/26.