7580-12-3

Basic information

• Product Name: 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE
• Synonyms: Triisopropyl-s-trioxane;2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE;2,4,6-Triisopropyl-s-trioxane;2,4,6-Tris(1-methylethyl)-1,3,5-trioxane;Paraisobutyraldehyde;Sunsubly B;1,3,5-Trioxane, 2,4,6-triisopropyl-;1,3,5-Trioxane, 2,4,6-tris(1-methylethyl)-
• CAS NO: 7580-12-3
• Molecular Formula: C₁₂H₂₄O₃
• Molecular Weight: 216.31716
• EINECS: 231-479-6
• Mol File: 7580-12-3.mol

Chemical Properties

• Melting Point: 64℃
• Boiling Point: 244.9 °C at 760 mmHg
• Flash Point: 80 °C
• Appearance: /
• Density: 0.916 g/cm³
• Vapor Pressure: 0.0463mmHg at 25°C
• Refractive Index: 1.424
• CAS DataBase Reference: 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE(7580-12-3)
• EPA Substance Registry System: 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE(7580-12-3)

Safety Data

• Hazardous Substances Data: 7580-12-3(Hazardous Substances Data)

Usage

Uses

Used in Adhesives and Coatings Industry:
2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE is used as a crosslinking agent for the production of epoxy resins, which are essential components in the formulation of high-performance adhesives and coatings. Its ability to form strong crosslinks enhances the durability, chemical resistance, and mechanical properties of the final products.
Used in Electronic Materials Industry:
In the electronic materials industry, 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE serves as a crosslinking agent in the production of epoxy resins used for encapsulation and potting of electronic components. This helps protect the components from environmental factors, such as moisture and chemicals, and ensures their reliable performance.
Used in Polyurethane Foam Manufacturing:
2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE is used as a curing agent in the manufacturing of polyurethane foams. Its presence accelerates the reaction between isocyanates and polyols, resulting in the formation of a stable foam structure with desirable properties, such as low density, good mechanical strength, and excellent thermal insulation.
Used in Plasticizers Production:
2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE is also utilized in the production of plasticizers, which are additives used to increase the flexibility and workability of various types of plastics. 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE contributes to the development of plasticizers with improved performance characteristics, such as enhanced compatibility with polymers and reduced volatility.
Used in Pharmaceutical Industry:
2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE has potential applications in the pharmaceutical industry, where it can be used as an intermediate in the synthesis of various drug molecules. Its unique structure and reactivity make it a valuable building block for the development of new pharmaceutical compounds.
Used as a Specialty Chemicals Solvent:
In the field of specialty chemicals, 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE serves as a solvent for various applications. Its ability to dissolve a wide range of substances makes it suitable for use in processes that require the dissolution or extraction of specific compounds.
However, it is crucial to handle 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE with caution, as it may pose health and environmental risks if not used properly. Proper safety measures and disposal methods should be followed to minimize any potential hazards associated with this compound.

InChI:InChI=1/C12H24O3/c1-7(2)10-13-11(8(3)4)15-12(14-10)9(5)6/h7-12H,1-6H3

Synthetic route

isobutyraldehyde (78-84-2) → 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3)

Conditions	Yield
With beryllium iodide In chloroform-d1 at 20℃; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube;	100%
With dodecatungstosilic acid for 1h; Ambient temperature;	99.9%
With N,N,N',N'',N''-pentamethyl-N,N''-bis(3-sulfopropyl)diethylenetriaminium tris(trifluoromethanesulfonate) In neat (no solvent) at 20℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Green chemistry;	97.6%

pivalaldehyde (630-19-3) → 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3)

Conditions	Yield
With [P(2-pyridyl)3W(CO)(NO)2](2+)(BF4(1-))2 at 20℃; for 24h;	86%

trimethylsilyl isothiocyanate (2290-65-5) + isobutyraldehyde (78-84-2) → 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + bis(1-isothiocyanato-2-methylpropyl) ether

Conditions	Yield
zinc(II) chloride at 90℃; for 0.5h; Product distribution; effect of temperature on product distribution;	A 36% B 22%

isobutyraldehyde (78-84-2) → 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6)

Conditions	Yield
bentonitic earth Irradiation;	A 21% B 12%

isobutyraldehyde (78-84-2) + n-butyl(crotyl)tin dichloride → 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + E-5-Hydroxy-6-methyl-hepten-2 (75851-75-1, 85924-66-9, 66248-77-9) + (2S,6R)-4-Chloro-2,6-diisopropyl-3-methyl-tetrahydro-pyran + (2S,6S)-4-Chloro-2,6-diisopropyl-3-methyl-tetrahydro-pyran

Conditions	Yield
Yield given. Further byproducts given. Yields of byproduct given;

isobutyraldehyde (78-84-2) → 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + E-5-Hydroxy-6-methyl-hepten-2 (75851-75-1, 85924-66-9, 66248-77-9) + (2S,6R)-4-Chloro-2,6-diisopropyl-3-methyl-tetrahydro-pyran + (2S,6S)-4-Chloro-2,6-diisopropyl-3-methyl-tetrahydro-pyran

Conditions	Yield
With n-butyl(crotyl)tin dichloride Yield given. Further byproducts given. Yields of byproduct given;

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + trimethylsilyl isothiocyanate (2290-65-5) → bis(1-isothiocyanato-2-methylpropyl) ether

Conditions	Yield
With tin(ll) chloride for 1.5h; Ambient temperature;	70%

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + potassium permanganate → 2-methyllactic acid (594-61-6)

Conditions	Yield
at 130℃; im Rohr;

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + bromine (7726-95-6) → 2-bromo-2-methylpropanal (13206-46-7) + 2-bromo-1,1-diethoxy-2-methyl-propane (98561-16-1) + monobromo-paraisobutyraldehyde

Conditions	Yield
nachfolgend Einw. von Alkohol;

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + bromine (7726-95-6) → bis-(1,2-dibromo-2-methyl-propyl) ether (6304-38-7) + 2-bromo-2-methylpropanal (13206-46-7) + 2-bromo-1,1-diethoxy-2-methyl-propane (98561-16-1) + monobromo-paraisobutyraldehyde

Conditions	Yield
at 30℃;

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) → monomer isobutyraldehyde

Conditions	Yield
at 150℃; im Rohr;

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + sulfuric acid (7664-93-9) → monomer isobutyraldehyde

carbon disulfide (75-15-0) + 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + bromine (7726-95-6) → trimer(ic) α-bromo-isobutyraldehyde

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate → Reaxys ID: 11649497

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate → Reaxys ID: 11649498

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate + poly(ethylene-co-vinyl acetate) → EVA; SB-5; 2,3,5,6-tetrafluoro-4-methylbenzyl-(1R)-trans-3-(1-propenyl(Z/E=8/1))-2,2-dimethylcyclopropanecarboxylate; 2,4,6-triisopropyl-1,3,5-trioxane

Conditions	Yield
With SB-5

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate + Reaxys ID: 15740905 → EMMA; 2,3,5,6-tetrafluoro-4-methylbenzyl-(1R)-trans-3-(1-propenyl(Z/E=8/1))-2,2-dimethylcyclopropanecarboxylate; 2,4,6-triisopropyl-1,3,5-trioxane; WD203-1

Conditions	Yield
With WD203-1

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + linear low density polyethylene + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate → Reaxys ID: 11364417

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + linear low density polyethylene + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate → Reaxys ID: 11364468

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + low density polyethylene + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate → low density polyethylene; 2,3,5,6-tetrafluoro-4-methylbenzyl-(1R)-trans-3-(1-propenyl(Z/E=8/1))-2,2-dimethylcyclopropanecarboxylate; 2,4,6-triisopropyl-1,3,5-trioxane; UB-1

Conditions	Yield
With UB-1

2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) + low density polyethylene + 2,3,5,6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate → polyethylene; 2,3,5,6-tetrafluoro-4-methylbenzyl-(1R)-trans-3-(1-propenyl(Z/E=8/1))-2,2-dimethylcyclopropanecarboxylate; 2,4,6-triisopropyl-1,3,5-trioxane; V-1

Conditions	Yield
With V-1

methanol (67-56-1) + 2,4,6-triisopropyl-1,3,5-trioxane (7580-12-3) → (R)-1-methoxy-2,2,4-trimethyl-pentan-3-ol (1221590-31-3) + (S)-1-methoxy-2,2,4-trimethyl-pentan-3-ol (1221590-22-2)

Conditions	Yield
With lithium perchlorate; (-)-menthol trimethylsilyl ether; trifluoroacetic acid at 20℃; for 2h; optical yield given as %ee; enantioselective reaction;

Upstream product

• 630-19-3 pivalaldehyde 
• 78-84-2 isobutyraldehyde 
• 2290-65-5 trimethylsilyl isothiocyanate 

Downstream Products

• 6304-38-7 bis-(1,2-dibromo-2-methyl-propyl) ether 
• 13206-46-7 2-bromo-2-methylpropanal 
• 98561-16-1 2-bromo-1,1-diethoxy-2-methyl-propane 
• 594-61-6 2-methyllactic acid 

Relevant articles and documents

Beryllium-Induced Conversion of Aldehydes

Aldehydes play a key role in the human metabolism. Therefore, it is essential to know their reactivity with beryllium compounds in order to assess its effects in the body. The reactivity of simple aldehydes towards beryllium halides (F, Cl, Br, I) was studied through solution and solid-state techniques and revealed distinctively different reactivities of the beryllium halides, with BeF2 being the least and BeI2 the most reactive. Rearrangement and aldol condensation reactions were observed and monitored by in situ NMR spectroscopy. Crystal structures of various compounds obtained by Be2+-catalyzed cyclization, rearrangement, and aldol addition reactions or ligation of beryllium halides have been determined, including unprecedented one-dimensional BeCl2 chains and the first structurally characterized example of an 1-iodo-alkoxide. Long-term studies showed that only aldehydes without a β-H can form stable beryllium complexes, whereas other aldehydes are oligo- and polymerized or decomposed by beryllium halides.

A convenient approach for the synthesis of 1,3,5-trioxanes under solvent-free conditions at room temperature

A series of environmentally benign bis-SO3H-functionalized Bronsted acidic ionic liquids were synthesized by using aliphatic polyamines and 1,3-propanesultone as the source chemicals. These ionic liquids acted as efficient inexpensive and recyclable catalysts for cyclotrimerization of aliphatic aldehydes at room temperature under solvent-free conditions. The reactions proceeded smoothly with good to excellent isolated yields (66.9-97.6 %=) and were generally complete in 1.5 h when the amount of ionic liquids was 0.1 mol%. The ionic liquids could be recovered readily and reused five times without any significant loss in their catalytic activity. Graphical abstract: [Figure not available: see fulltext.]

Novel acidic ionic liquids as efficient and recyclable catalysts for the cyclotrimerization of aldehydes

A mild, efficient, and ecofriendly procedure for cyclotrimerization of aldehydes was realized by using a series of novel Brnsted acidic ionic liquids (BAILs) consisting of double-SO3H groups in cations as catalysts. Good conversion of aldehydes and selectivity of trialkyl-1,3,5-trioxanes were achieved by using 1mol% of BAILs. In addition, the catalyst system could be recycled and reused at least eight times without apparent loss of activity. Taylor & Francis Group, LLC.

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.

InCl3 as an efficient catalyst for cyclotrimerization of aldehydes: Synthesis of 1,3,5-Trioxane under solvent-free conditions

1,3,5-Trioxanes derived from aldehydes were synthesized using indium trichloride as a catalyst. Cyclotrimerization of the aldehydes gave excellent yields under neat conditions within a short span of time. Copyright Taylor & Francis, Inc.

Tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization catalyzed by an organotungsten Lewis acid

The tris(2-pyridyl)phosphine complex [P(2-py)3 W(CO)(NO)2](BF4)2 acts as a Lewis acid catalyst precursor for the tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization, which lead to the formation of a series of hyper-branched star polymers.

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.

Cyclotrimerization of Aliphatic Aldehydes Catalysed by Keggin-type Heteropoly Acids and Concomitant Phase Separation

The acid-catalysed cyclotrimerization of aliphatic aldehydes has been examined through comparison of heteropoly acids with other acid catalysts.A Keggin-type heteropoly acid such as phosphomolybdic acid catalyses the cyclotrimerization of aldehydes, such as ethanal, propanal, butanal, 2-methylpropanal, 2,2-dimethylpropanal, hexanal, octanal, and decanal, to produce the respective 2,4,6-trialkyl-1,3,5-trioxanes in high yields.Catalysts turnover number of the heteropoly acid is more than 10000 for propanal cyclotrimerization.In addition to the high catalytic activities, the reaction mixture spontaneously separates into two phases, a produ ct phase and a catalyst phase, at high conversions of aldehyde.For propanal cycltrimerization, the reaction mixture separates into two liquid phases, and the recovered catalyst phase may be repeatedly applied to the reaction without additional care in isolation of the catalyst.The phase separation phenomenon has been concluded to be caused by the insolubility of the heteropoly acid coordinated with propanal in the product 2,4,6-triethyl-1,3,5-trioxane.

Synthesis of 1,3,5-trioxanes: A new, simple method using a bentonitic earth as catalyst

A simple method for synthesizing aliphatic as well as aromatic 1,3,5-trioxanes using as catalyst a bentonitic earth is reported. The yields ranged from good to excellent.