4,4-Dimethoxy-2-butenal

Base Information

• Chemical Name: 4,4-Dimethoxy-2-butenal
• CAS No.: 4093-49-6
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.144
• Hs Code.: 2912499000
• European Community (EC) Number: 631-015-6
• Nikkaji Number: J570.702A,J867.999A
• Wikidata: Q76415937
• Mol file: 4093-49-6.mol

Synonyms:4093-49-6;4,4-Dimethoxy-2-butenal;(E)-4,4-dimethoxybut-2-enal;Fumaraldehyde Mono(dimethyl Acetal);FUMARALDEHYDEMONO(DIMETHYLACETAL);Fumaraldehyde mono(dimethylacetal);Fumaraldehyde Mono(dimethyl Acetal) (stabilized with HQ);fumaraldehyde dimethyl acetal;4,4-Dimethoxycrotonaldehyde;SCHEMBL1679853;SCHEMBL5157637;(e)-4,4-dimethoxy-2-butenal;(E)-4,4-dimethoxy-but-2-enal;MFCD00191439;(2E)-4,4-DIMETHOXYBUT-2-ENAL;CS-0357407;F0350;T72438

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

Chemical Property:

• Vapor Pressure: 0.393mmHg at 25°C
• Refractive Index: 1.423
• Boiling Point: 196.686°C at 760 mmHg
• Flash Point: 62.879°C
• PSA: 35.53000
• Density: 1.03
• LogP: 0.36040
• Storage Temp.: Refrigerator
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 94.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

FumaraldehydeMono(dimethylacetal) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(C=CC=O)OC
• Isomeric SMILES: COC(/C=C/C=O)OC
• Uses: Fumaraldehyde Mono(dimethyl acetal) (cas# 4093-49-6) is used in the crosslinked polyolefin separation membrane. It is also an intermediate in the synthesis of 4-Hydroxy Nonenal Mercapturic Acid (H296810), a mercapturic acid conjugate of 4-hydroxy nonenal (4-HNE) formed to clear 4-HNE from plasma via enterohepatic circulation.

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

There total 4 articles about 4,4-Dimethoxy-2-butenal 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: 95.0%

trans-butenedial bis-(dimethyl acetal) (6068-62-8) → (2E)-4,4-dimethoxybut-2-enal (18778-96-6,4093-49-6)

Guidance literature:

With amberlyst-15; In water; acetone; for 0.0833333h;

DOI:10.1055/s-1984-31059

Reference yield:

2,5-dihydro-2,5-dimethoxyfuran (332-77-4) → (2E)-4,4-dimethoxybut-2-enal (18778-96-6,4093-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / methanol / 1 h / Reflux

2: water / acetone / 2.5 h / 0 °C

With water; toluene-4-sulfonic acid; In methanol; acetone;

DOI:10.1039/c5cc01077b

Reference yield:

trans-butenedial bis-(dimethyl acetal) (6068-62-8) → fumaraldehyde (3675-14-7) + (2E)-4,4-dimethoxybut-2-enal (18778-96-6,4093-49-6)

Guidance literature:

With acidic Amberlyst-15 ion exchange resin; In water; acetone; at 0 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/tx00044a014

upstream raw materials:

furan

methanol

trans-butenedial bis-(dimethyl acetal)

2,5-dihydro-2,5-dimethoxyfuran

Downstream raw materials:

(E)-4,4-dimethoxy-but-2-enoic acid ethyl ester

(-)-methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(dimethoxymethyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Refernces

• 1、 -. "BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF". Paragraph 0083; 0095; 0118; 0119; 0120. . Retrieved 2018/10/26.
• 2、 -. "BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE". Paragraph 0095; 0118-0120. . Retrieved 2018/10/31.