7456-83-9

Basic information

• Product Name: 2,2'-oxybisacetaldehyde
• Synonyms: 2,2'-oxybisacetaldehyde;Diglycolaldehyde;Einecs 231-230-1;2,2'-oxydiacetaldehyde
• CAS NO: 7456-83-9
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.08864
• EINECS: 231-230-1
• Mol File: 7456-83-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2'-oxybisacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-oxybisacetaldehyde(7456-83-9)
• EPA Substance Registry System: 2,2'-oxybisacetaldehyde(7456-83-9)

Safety Data

• Hazardous Substances Data: 7456-83-9(Hazardous Substances Data)

Usage

Appearance

Colorless liquid

Odor

Pungent

Flammability

Highly flammable

Uses

Reagent in organic synthesis (e.g. production of pharmaceuticals and fragrance compounds), intermediate in manufacturing of polymer resins, crosslinking agent in coatings and adhesives

Safety precautions

Skin and eye irritant, should be handled with caution to avoid exposure

Upstream product

• 126-58-9 Dipentaerythritol 
• 1708-29-8 2,5-dihydrofuran 
• 27725-58-2 3,4-dihydroxy-tetrahydrofuran 
• 7456-84-0 2,6-dihydroxy-1,4-dioxane 
• 7697-37-2 nitric acid 
• 4358-64-9 cis-1,4-anhydroerythritol 
• 78082-47-0 diglycolaldehyde bis(di-isopropyl acetal) 
• 78082-46-9 bis-(2,2-dimethoxy-ethyl) ether 

Downstream Products

• 78082-46-9 bis-(2,2-dimethoxy-ethyl) ether 
• 56999-16-7 2-(2,2-diethoxyethoxy)-1,1-diethoxyethane 
• 56999-14-5 cis-2,6-diethoxy-1,4-dioxane 
• 5581-22-6 trans-2,6-diethoxy-1,4-dioxane 
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• 80875-73-6 3'-deamino-3'-(4-morpholinyl)-13-dihydrodoxorubicin 
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• 88254-07-3 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin 
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• 132817-55-1 7-O-<3-(3(R/S)-cyanomorpholin-4-yl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl>-ε-rhodomycinone 

Relevant articles and documents

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Iron-mediated and -catalyzed metalative cyclization of electron- withdrawing-group-substituted alkynes and alkenes with grignard reagents

Treatment of ethyl (E)-5,5-bis[(benzyloxy)methyl]-8-(N,N-diethylcarbamoyl)- 2-octen-7-ynoate with an iron reagent generated from FeCl2 and tBuMgCl in a ratio of 1:4 (abbreviated as FeCl2/4 tBuMgCl) afforded ethyl [4,4-bis[(benzyloxy)methyl]-2-[(E)-(N,N-diethylcarbamoyl)methylene] cyclopent-1-yl]acetate in good yield. Deuteriolysis of an identical reaction mixture afforded the bis-deuterated product ethyl [4,4-bis[(benzyloxy)methyl]-2- [(E)-(N,N-diethylcarbamoyl)deuteriomethylene]cyclopent-1-yl]deuterioacetate, thus confirming the existence of the corresponding dimetalated intermediate. The latter intermediate can react with halogens or aldehydes to facilitate further synthetic transformations. The amount of FeCl2 was reduced to catalytic levels (10 mol% relative to enyne), and catalytic cyclizations of this sort proceeded with yields comparable to those of the aforementioned stoichiometric reactions. The cyclization of diethyl (E,E)-2,7-nonadienedioate with a stoichiometric amount of FeCl2/4 tBuMgCl, followed by the addition of sBuOH as a proton source, afforded a mixture of 2-(ethoxycarbonyl)- 3-bicyclo[3.3.0]octanone and its enol form in good yield. The use of aldehyde or ketone in place of sBuOH afforded 2-(ethoxycarbonyl)-3-bicyclo[3.3.0]octanone, which has an additional hydroxyalkyl side chain. Additionally, the metalation of a carbon-carbon unsaturated bond in N,N-diethyl-5,5-bis[(benzyloxy)methyl]-7,8- epoxy-2-octynamide or (E)-3,3-dimethyl-6-(N,N-diethylcarbamoyl)-5-hexenyl p-toluenesulfonate with FeCl2/4 tBuMgCl or FeCl2/4 PhMgBr was followed by an intramolecular alkylation with an epoxide or alkyl p-toluenesulfonate to afford 5,5-bis[(benzyloxy)methyl]-3-[(E)-(N,N- diethylcarbamoyl)methylene]-1-cyclohexanol or N,N-diethyl(3,3- dimethylcyclopentyl)acetamide after hydrolysis. In both cases, the remaining metalated portion α to the amide group was confirmed by deuteriolysis and could be utilized for an alkylation with methyl iodide.