Fumaraldehyde bis(dimethyl acetal)

Base Information

• Chemical Name: Fumaraldehyde bis(dimethyl acetal)
• CAS No.: 6068-62-8
• Molecular Formula: C8H16O4
• Molecular Weight: 176.213
• Hs Code.: 2901299090
• European Community (EC) Number: 626-693-5
• DSSTox Substance ID: DTXSID70421182
• Nikkaji Number: J1.925.956K,J534.090J
• Wikidata: Q76312123
• Mol file: 6068-62-8.mol

Synonyms:Fumaraldehyde bis(dimethyl acetal);6068-62-8;(E)-1,1,4,4-tetramethoxybut-2-ene;starbld0003038;SCHEMBL1679775;SCHEMBL3989087;DTXSID70421182;2-Butenedial bis(dimethyl acetal);MFCD00075507;AKOS015913624;1,1,4,4-Tetramethoxy-trans-2-butene;(2E)-1,1,4,4-tetramethoxybut-2-ene;Fumaraldehyde bis(dimethyl acetal), 95%;CS-0357322;F0329

Chemical Property of Fumaraldehyde bis(dimethyl acetal)

Chemical Property:

• Vapor Pressure: 0.158mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Boiling Point: 100-103 °C15 mm Hg(lit.)
• Flash Point: 169 °F
• PSA: 36.92000
• Density: 1.01 g/mL at 25 °C(lit.)
• LogP: 0.78040
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 176.10485899
• Heavy Atom Count: 12
• Complexity: 102

Purity/Quality:

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

Fumaraldehyde bis(dimethyl acetal) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(C=CC(OC)OC)OC
• Isomeric SMILES: COC(/C=C/C(OC)OC)OC
• Uses: Fumaraldehyde bis(dimethyl acetal) may be used in the syntheses of C20-carotene and crocetin or descrocetin esters. It may be used in the preparation of fumaraldehyde dimethylacetal, (FDMA), by partial acid hydrolysis.

Technology Process of Fumaraldehyde bis(dimethyl acetal)

There total 5 articles about Fumaraldehyde bis(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: 79.0%

furan (110-00-9) + methanol (67-56-1) → trans-butenedial bis-(dimethyl acetal) (6068-62-8)

Guidance literature:

furan; methanol; With bromine; at -40 - -10 ℃; for 3h;

With sodium carbonate; at 20 ℃; for 0.5h;

DOI:10.1039/c6ob00086j

Reference yield: 70.0%

2,5-dihydro-2,5-dimethoxyfuran (332-77-4) + trimethyl orthoformate (149-73-5) → trans-butenedial bis-(dimethyl acetal) (6068-62-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 0.166667h; Reflux;

DOI:10.1021/acs.orglett.0c02553

Reference yield: 26.0%

(E)-1,2-diphenyl-ethene (103-30-0) + N-methylpyrrolidine N-oxide (7529-17-1) → trans-butenedial bis-(dimethyl acetal) (6068-62-8) + (1R,2R,7aR)-1,2-Diphenyl-hexahydro-pyrrolizine (97531-03-8,97531-05-0,97531-08-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 3h; Title compound not separated from byproducts;

upstream raw materials:

furan

methanol

(E)-1,2-diphenyl-ethene

N-methylpyrrolidine N-oxide

Downstream raw materials:

(2E)-4,4-dimethoxybut-2-enal

(2S,4S,5R)-2-((E)-3,3-Dimethoxy-propenyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester

fumaraldehyde

(Z)-4,4-Dimethoxy-3-phenylselanyl-but-2-enal

Refernces

• 1、 -. "BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF". Paragraph 0083; 0095; 0116; 0117. . Retrieved 2018/10/26.
• 2、 -. "BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE". Paragraph 0095; 0116-0117. . Retrieved 2018/10/31.