6556-71-4

Usage

Structure

Cyclic trimer of formaldehyde

Physical State

Colorless, water-soluble liquid

Odor

Strong

Applications

a. Reagent in organic synthesis
b. Cross-linking agent in polymer production
c. Disinfectant
d. Chemical intermediate in organic compound production
e. Stabilizer in vinyl plastics production
f. Solvent in explosives manufacturing

Safety Precautions

Handle and store with care due to potential toxicity and flammability

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 201230-82-2 carbon monoxide 
• 110-83-8 cyclohexene 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 1356864-41-9 C₂₅H₃₅F₃O₄ 
• 1221590-46-0 C₂₅H₃₅F₃O₄ 
• 1221590-60-8 (S)-cyclohexyl(1-(hydroxymethyl)cyclohexyl)methanol 
• 1356864-32-8 (R)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol 
• 1221590-23-3 (S)-cyclohexyl-(1-methoxymethylcyclohexyl)methanol 

Relevant academic research and scientific papers

Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes

1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.

Stereoselective one-pot synthesis of highly differently substituted thiochromans

A highly stereoselective one-pot procedure to anti-configured thiochromans is described. This reaction functions at room temperature in the presence of catalytic amounts of trifluoroacetic acid. The transformation gives a selective but optional access to

Tetranuclear BINOL-titanium complex in selective direct aldol additions

(Chemical Equation Presented) The extremely robust and water-stable tetranuclear complex Ti4(μ-BINOLato)6(μ3- OH)4 (1) catalyzes the direct aldol addition with high degrees of regioselectivity at the sterically more encumbered α-side of unsymmetrical ketones. The formation of quaternary stereocenters is described. Oxygen-containing ene components can also be used as starting material in these reactions. When used with aliphatic aldehydes, acetals 18 or acetals of aldol adducts 20 were observed. As few as 0.2 mol % loadings with this catalyst 1 were enough to complete the reactions. Mechanistical aspects of the reactions are discussed.

A convenient solvent-free preparation of 1,3,5-trioxanes

In the presence of a small amount of trimethylsilyl chloride, aldehydes gave at room temperature in solvent-free conditions the corresponding 1,3,5-trioxanes with good to excellent yields.

Acetonyltriphenylphosphonium bromide in organic synthesis: A useful catalyst in the cyclotrimerization of aldehydes

Acetonyltriphenylphosphonium bromide (ATPB) is a useful catalyst for the cyclotrimerization of the aliphatic aldehydes under solvent-free condition. The aldehydes tethered with a variety of functionality such as olefin, ether, ester, bromide, azide and diester could also be cyclotrimerized under the catalysis of ATPB.

A high yield procedure for the Me3SiNTf2-induced carbon-carbon bond-forming reactions of silyl nucleophiles with carbonyl compounds: The importance of addition order and solvent effects

We demonstrate the efficiency of Me3SiNTf2 (0.3-1.0 mol%) as a strong Lewis acid catalyst for the Mukaiyama aldol and Sakurai-Hosomi allylation reactions, and that the slow addition of carbonyl compounds to a solution of acid catalys

Synthesis of 1,3,5-trioxanes: Catalytic cyclotrimerization of aldehydes

A series of 1,3,5-trioxanes derived from a single aldehyde, or from two aldehydes, were synthesized with methylrhenium trioxide as a catalyst. Cyclotrimerization of the aldehydes gave excellent yields under proper conditions, as did diethyl ketomalonate. A possible intermediate in the case of propionaldehyde was observed using 1H NMR spectroscopy. Water inhibits both forward and reverse reactions.

Hydroformylation of Cyclohexene Catalysed by Homogeneous Bimetallic Systems

Homogeneous bimetallic systems such as Co2(CO)8-Ru3(CO)12 and show high catalytic activity for the hydroformylation of cyclohexene compared with Co2(CO)8 alone.