4,4-Dimethoxy-2-butanone

Base Information

• Chemical Name: 4,4-Dimethoxy-2-butanone
• CAS No.: 5436-21-5
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29145000
• European Community (EC) Number: 226-605-1
• NSC Number: 59721,21538
• UNII: 0IZ188B2ZA
• DSSTox Substance ID: DTXSID8052196
• Nikkaji Number: J150.136D
• Wikidata: Q27236836
• Metabolomics Workbench ID: 46240
• Mol file: 5436-21-5.mol

Synonyms:4,4-Dimethoxy-2-butanone;5436-21-5;4,4-dimethoxybutan-2-one;Acetylacetaldehyde dimethyl acetal;2-Butanone, 4,4-dimethoxy-;1,1-Dimethoxy-3-butanone;Acetoacetaldehyde dimethyl acetal;3-Oxobutyraldehyde dimethyl acetal;4,4-Dimethoxybutanone;Formylacetone dimethyl acetal;Acetylacetaldehyddimethylacetal;Acetoacetaldehyde, 1-(dimethyl acetal);3-Ketobutyraldehyde dimethylacetal;3-Ketobutyraldehyde dimethyl acetal;3-Oxobutanal dimethyl acetal;FEMA No. 3381;Acetylacetaldehyde dimethylacetal;beta-Oxobutyraldehyde dimethyl acetal;NSC 21538;NSC 59721;4,4-dimethoxy-butan-2-one;Acetoacetaldehyde 1-(dimethyl acetal);3-oxobutanal, dimethyl acetal;EINECS 226-605-1;.beta.-Oxobutyraldehyde dimethyl acetal;UNII-0IZ188B2ZA;AI3-22760;0IZ188B2ZA;3-Oxobutyraldehyde dimethylacetal;BUTANAL,2-OXO,DIMETHYL ACETAL;MFCD00008789;NSC-21538;NSC-59721;3-Oxobutyraldehyde 1-(dimethylacetal);2-Butanone,4-dimethoxy-;Acetoacetaldehyde, 1-(dimethyl acetal) (6CI,7CI,8CI);4,4-Dimethxoy-2-butanone;4,4,-dimethoxy-2-butanone;SCHEMBL122205;1-acetyl-2,2-dimethoxyethane;acetylacetoaldehyde-dimethylacetal;DTXSID8052196;acetyl acetaldehyde dimethylacetal;FEMA 3381;CHEBI:173539;4,4-Dimethoxy-2-butanone, 9CI;acetyl acetaldehyde dimethyl acetal;acetyl acetoaldehyde dimethyl acetal;HY-Y0035;NSC21538;NSC59721;BBL011444;STL146555;beta -oxobutyraldehyde dimethyl acetal;AKOS000119879;AC-5732;FS-4100;LS-3012;OXOBUTANAL DIMETHYL ACETAL, 3-;CS-0008327;D1157;FT-0617066;3-OXOBUTANAL, DIMETHYL ACETAL [FHFI];EN300-19628;3-OXOBUTYRALDEHYDE 1-(DIMETHYL ACETAL);D72464;A830123;4,4-Dimethoxy-2-butanone, technical grade, >=90%;W-105638;Q27236836;F0001-1430

Chemical Property of 4,4-Dimethoxy-2-butanone

Chemical Property:

• Appearance/Colour: Clear colorless to yellow liquid
• Vapor Pressure: 1.35mmHg at 25°C
• Melting Point: -82 °C
• Refractive Index: n20/D 1.414(lit.)
• Boiling Point: 172.1 °C at 760 mmHg
• Flash Point: 49.4 °C
• PSA: 35.53000
• Density: 0.959 g/cm³
• LogP: 0.58440
• Storage Temp.: Flammables area
• Water Solubility.: decomposes
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 86.3

Purity/Quality:

99%, ^*data from raw suppliers

4,4-Dimethoxy-2-butanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=O)CC(OC)OC
• Uses: Acetaldehyde dimethyl acetal is used as a flavoring agent. It is also used in the preparation of (R)-4,4-dimethoxy-2-butanol, pyrazoles and pyrimidines. Further, it is used in the preparation of N,N-diethyl-[2-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]-pyrimidin-3-yl]acetamide and acetoacetaldehyde. 4,4-Dimethoxy-2-butanone (β-ketobutyracetal) may be used in the preparation of:(R)-4,4-dimethoxy-2-butanolpyrazoles and pyrimidines[7,16-dihydro- 6,15( 17)-dimetbyldibenzo[b,i]-[1,4,8,11]tetrilazacyclotetradecinato-N5,N9,N14,N18]nickel{II)

Technology Process of 4,4-Dimethoxy-2-butanone

There total 28 articles about 4,4-Dimethoxy-2-butanone 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: 99.0%

methanol (67-56-1) + trans-4-methoxy-3-buten-2-one (51731-17-0) → acetylacetaldehyde dimethyl acetal (5436-21-5)

Guidance literature:

pyrrolidine; methanesulfonic acid; at 20 ℃; for 28h;

DOI:10.1016/j.tetlet.2006.08.134

Reference yield: 95.0%

3-butenal dimethyl acetal (72380-56-4) → acetylacetaldehyde dimethyl acetal (5436-21-5)

Guidance literature:

With tert.-butylhydroperoxide; C₂₁H₁₉N₅Pd⁽²⁺⁾*2BF₄^(1-); In decane; acetonitrile; at 70 ℃; for 24h; Temperature;

DOI:10.1021/acscatal.0c02729

Reference yield: 90.0%

2-methyl-propan-1-ol (78-83-1) + (Z)-4-methoxybut-3-en-2-one (57155-06-3) → acetylacetaldehyde dimethyl acetal (5436-21-5) + 4-isobutoxy-but-3-en-2-one (85716-38-7) + 4-isobutoxy-4-methoxybutan-2-one

Guidance literature:

for 10h; Yields of byproduct given; Heating;

DOI:10.1016/0040-4020(82)80194-4

upstream raw materials:

methanol

1-methoxy-buten-3-yne

tetrachloromethane

4-chloro-3-buten-2-one

Downstream raw materials:

5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine

2-Methylpyrimido<1,2-a>benzimidazol

2,5-dimethyl-pyrano[3,2-b]pyrrole-3-carboxylic acid ethyl ester

ethyl 2,6-dimethylnicotinate

Refernces

• 1、 -. "Synthesis method of 4,4-dimethoxy-2-butanone". Paragraph 0017-0037. . Retrieved 2021/11/06.
• 2、 Bera, Jitendra K.,Dutta, Indranil,Kunnikuruvan, Sooraj,Reshi, Noor U Din,Saha, Sayantani,Yadav, Suman. "Electronic Asymmetry of an Annelated Pyridyl-Mesoionic Carbene Scaffold: Application in Pd(II)-Catalyzed Wacker-Type Oxidation of Olefins". . p. 11385 - 11393. Retrieved 2020/11/23.