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
• Article Data: 14

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

General Description

2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE is a chemical compound with the molecular formula C12H24O3. It is an organic compound that consists of a trioxane ring with three propyl groups attached to it. 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE is often used as a crosslinking agent in the production of epoxy resins, which are commonly used in adhesives, coatings, and electronic materials. It is also used as a curing agent in the manufacturing of polyurethane foams and in the production of plasticizers. Additionally, 2,4,6-TRIPROPAN-2-YL-1,3,5-TRIOXANE has potential applications in pharmaceuticals and as a solvent for specialty chemicals. However, it is important to handle this compound with caution, as it may pose health and environmental risks if not used properly.

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

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

Downstream Products

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

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.

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.

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.