111-30-8

Basic information

• Product Name: Glutaraldehyde
• Synonyms: GLUTARDIALDEHYDE SOLUTION 25% FOR ELECTR;Glutaraldehyde 25% Min. / 50% Min.Tech/PharMa grade;Glutaric Dialdehyde, 50 Percent in Water;Glutaraldehyde, 50 wt.% solution in H2O;Glutaric Dialdehyde,50% aq. soln.;Glutaraldehyde, 50% aq. soln., 50% aq. soln.;GDA;Glutaraldehyde solution, 70% w/w
• CAS NO: 111-30-8
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 203-856-5
• Product Categories: Chemical raw materials;Fine Chemicals;Pharmaceutical Intermediates;INORGANIC & ORGANIC CHEMICALS;Biocide;Alphabetical Listings;Flavors and Fragrances;G-H;Carbohydrates A to Z;Carbohydrates G;Aldehydes;Biochemicals and Reagents;Building Blocks;C1 to C6;Carbohydrates;Carbonyl Compounds;Chemical Synthesis;Core Bioreagents;Monosaccharide;Organic Building Blocks;Research Essentials;&Buffers;Buffers and Reagents;Protein Electrophoresis;Proteomics;Reagents;Stains;Western Blotting;Routine Histology Stains;Hematology and Histology;Fixatives;Life Science Reagents for Immunohistochemistry (IHC);Tissue Processing;General Reagents;Life Science Reagents for Cell Culture;Life Science Reagents for Protein Electrophoresis;Life Science Reagents for Transfection;Life Science Reagents for Western Blotting;8618031153937;Glutaraldehyde ada@tuskwei.com whatsapp
• Mol File: 111-30-8.mol

Chemical Properties

• Melting Point: -15 °C
• Boiling Point: 100 °C
• Flash Point: 100°C
• Appearance: Clear to slight haze/Solution
• Density: 1.058 g/mL at 20 °C
• Vapor Density: 1.05 (vs air)
• Vapor Pressure: 0.583mmHg at 25°C
• Refractive Index: n20/D 1.450
• Storage Temp.: 2-8°C
• Water Solubility: miscible
• Merck: 14,4472
• BRN: 605390
• CAS DataBase Reference: Glutaraldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Glutaraldehyde(111-30-8)
• EPA Substance Registry System: Glutaraldehyde(111-30-8)

Safety Data

• Hazard Codes: T,N,Xn
• Statements: 36/37/38-42/43-34-23-22-50-23/25-41-37/38-20/22
• Safety Statements: 23-26-36/37-45-36/37/39-61
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: MA2450000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 111-30-8(Hazardous Substances Data)

Usage

Chemical Description

Glutaraldehyde is a C5 dialdehyde and a biomimetic equivalent of l-lysine.

Uses

Used in Medical and Dental Industry:
Glutaraldehyde is used as a broad-spectrum antimicrobial cold sterilant/disinfectant for hospital equipment, making it an essential component in maintaining a sterile environment in medical and dental settings. It is particularly effective against bacteria and viruses, including the human immunodeficiency virus (HIV).
Used in the Leather Industry:
Glutaraldehyde serves as a tanning agent for leather, contributing to the industry's production of various leather goods.
Used in Mortuary Science:
It is used as a tissue fixative, helping to preserve bodies for funeral and memorial services.
Used in the Cosmetics Industry:
Glutaraldehyde is used as a preservative in cosmetics, ensuring the longevity and safety of various beauty products.
Used in Pharmaceutical Applications:
It acts as a therapeutic agent for treating warts, hyperhidrosis (excessive sweating), and dermal mycotic infections.
Used in X-ray Processing:
Glutaraldehyde is utilized in X-ray processing solutions and film emulsion, playing a crucial role in the development of X-ray images.
Used in the Beauty Industry:
It is employed as a disinfectant, ensuring the cleanliness and safety of tools and equipment used in the beauty industry.
Used as a Cross-linking Agent:
Glutaraldehyde is used to cross-link proteins, which can be beneficial in various industrial applications.
Used in Industrial Water Treatment:
It is also utilized for industrial water treatment, contributing to the maintenance of clean and safe water systems.
Chemical Properties:
Glutaraldehyde is miscible in water and organic solvents, making it a versatile compound for various applications. However, it may be incompatible with strong oxidizers and strong bases. Alkaline solutions containing glutaraldehyde may react with alcohol, ketones, amines, hydrazines, and proteins, which should be taken into consideration when handling and using this compound.

Synthesis Reference(s)

Tetrahedron, 48, p. 3503, 1992 DOI: 10.1016/S0040-4020(01)88489-1

Air & Water Reactions

Polymerizes in the presence of water.

Reactivity Profile

GLUTARALDEHYDE may discolor on exposure to air. Pentanedial polymerizes on heating. Pentanedial is incompatible with strong oxidizing agents. Pentanedial polymerizes in the presence of water.

Health Hazard

Glutaraldehyde is a strong irritant to the nose,eyes, and skin. In rabbits, 250 μg and 500 mg in 24 hours produced severe irritation in theeyes and skin, respectively. The corrosiveeffect on human skin of 6 mg over 3 dayswas severe. However, the acute toxicity ofglutaraldehyde by the oral and dermal routesis low to mild. Ohsumi and Kuroki (1988)determined that the symptoms of acute toxicityof this compound were less severethan those of formaldehyde. But the restraintof growth was more pronounced in micetreated with glutaraldehyde. An oral LD50value of 1300 mg/kg was reported for mice.Inhalation of this compound can cause upperrespiratory tract irritation, headache, and nervousness.Mice exposed at 33 ppm showedsymptoms of hepatitis.

Fire Hazard

Literature sources indicate that Pentanedial is nonflammable.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Glutaraldehyde is an effective protein crosslinker and finds application in techniques like enzyme immobilisation microscopy, histochemistry and cytochemistry. It exists in different forms under acidic or neutral conditions. It is a biocide widely used as a disinfectant in hospitals and industries and is toxic to aquatic organisms. Its allergic nature leads to hypersensitivity reactions. Contact of glutaraldehyde vapors in endoscopy contributes to Colitis.

Contact allergens

Glutaraldehyde is a well-know sensitizer in cleaners and health workers. It can also be found in X-ray developers or in cosmetics.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by inhalation, skin contact, and subcutaneous routes. Experimental teratogenic and reproductive effects. A severe eye and human skin irritant. Mutation data reported. When heated to decomp osition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Potential Exposure

Glutaraldehyde is used in leather tanning; in embalming fluids; as a germicide; as a cross-linking agent for protein and polyhydroxy materi als; as a fixative for tissues; and as an intermediate. Buffered solutions are used as antimicrobial agents in hospitals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Likely impurities are oxidation products-acids, semialdehydes and polymers. It can be purified by repeated washing with activated charcoal (Norit) followed by vacuum filtration, using 15-20g charcoal/100mL of glutaraldehyde solution. Distil it at 60-65o/15mm, discarding the first 5-10%, then dilute with an equal volume of freshly distilled water at 70-75o, using magnetic stirring under nitrogen. The solution is stored at low temperature (3-4o), in a tightly stoppered container, and protected from light. Standardise by titration with hydroxylamine. [Anderson J Histochem Cytochem 15 652 1967, Beilstein 1 IV 3659.]

Incompatibilities

Water contact forms a polymer solution. A strong reducing agent. Incompatible with strong acids; caustics, ammonia, amines, and strong oxidizers. Note: Alkaline solutions of glutaraldehyde (i.e., activated glutar aldehyde) react with alcohol, ketones, amines, hydrazines, and proteins.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2

Synthetic route

Conditions	Yield
With sodium dihydrogenphosphate In water at 20 - 92℃; under 150.015 Torr; Temperature; Large scale;	95.4%
With cation-exchange resin KU-2 and KU-2-8 In water at 20 - 30℃;	40%
With water at 150℃;

1,1,5,5-tetramethoxy-pentane (4454-02-8) → Glutaraldehyde (111-30-8)

Conditions	Yield
With acetic acid In water for 1h;	86%
With boric acid; oxalic acid
With boric acid; oxalic acid

cyclopentene (142-29-0) → Glutaraldehyde (111-30-8)

Conditions	Yield
With 1H-imidazole; sodium periodate; MnCl-TPP-(PEO750)4 In water; acetonitrile at 20℃; for 24h;	99%
With W-MCM41; dihydrogen peroxide In tert-butyl alcohol at 35℃; for 24h;	71%
With sodium periodate; water In 1,2-dichloro-ethane at 20℃; for 1h;	70.9%

cyclopentene (142-29-0) → cyclopent-2-enone (930-30-3) + Glutaraldehyde (111-30-8)

Conditions	Yield
With tert.-butylhydroperoxide In acetonitrile at 82℃; for 6h; Inert atmosphere;
With tert.-butylhydroperoxide In acetonitrile at 29.84℃; for 36h; Reagent/catalyst;	A n/a B 5.6 %Chromat.
With Ca0.3Co0.7Fe2O4; dihydrogen peroxide In N,N-dimethyl-formamide at 60℃; for 10h; Schlenk technique;

2-ethoxy-2,3-dihydro-4H-pyran (103-75-3) → Glutaraldehyde (111-30-8)

Conditions	Yield
With hydrogenchloride
Multi-step reaction with 2 steps 1: TsOH / Heating 2: (hydrolysis) View Scheme
Multi-step reaction with 2 steps 1: TsOH / Heating 2: (hydrolysis) View Scheme
With acetic acid In methanol; water
With acetic acid In methanol; water

1 ,5-pentanediol (111-29-5) → Glutaraldehyde (111-30-8)

Conditions	Yield
With sodium hydroxide; sodium ruthenate(VI); potassium hexacyanoferrate(III) at 30℃; Equilibrium constant; Kinetics; Further Variations:; concentration dependence;
With Pd-Ce nanoparticles supported on functional Fe-MIL-101-NH2 In water; acetonitrile at 60℃; under 1034.32 Torr;
at 20℃;

cyclopentene (142-29-0) → 1,5-pentanedioic acid (110-94-1) + Glutaraldehyde (111-30-8)

Conditions	Yield
With periodic acid In tetrachloromethane; water; acetonitrile at 25℃; for 1h;

cyclopentene (142-29-0) → cis-1,2-cyclopentanediol (5057-98-7) + Glutaraldehyde (111-30-8)

Conditions	Yield
With cis-[Ru(1,4,7-trimethyl-1,4,7-triazacyclononane)O2(trifluoroacetate)]ClO4 In acetonitrile at 20℃; for 14h;	A 10% B 73%

2,2'-trimethylene-bis-1,3-dioxolane (6543-04-0) → Glutaraldehyde (111-30-8)

Conditions	Yield
With C11H10N2O2Pd(1+)*ClO4(1-); water In [D3]acetonitrile at 50℃; for 2h;	95 %Spectr.

Cyclopentene oxide (285-67-6) → Glutaraldehyde (111-30-8)

Conditions	Yield
With 1-(3-sulfopropyl)-2-methyl-3-isopropylimidazolium periodate In water at 35℃; for 12h;	99 %Chromat.

cyclopentene (142-29-0) → cyclopent-2-enone (930-30-3) + Glutaraldehyde (111-30-8) + cyclopentanone (120-92-3)

Conditions	Yield
With Ca0.3Co0.7Fe2O4; dihydrogen peroxide In N,N-dimethyl-formamide at 90℃; for 8h; Temperature; Schlenk technique;

cis-1,2-cyclopentanediol (5057-98-7) → Glutaraldehyde (111-30-8)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; for 0.25h; Inert atmosphere;	92%
With C21H12Cl6NO4V In toluene at 100℃; under 760.051 Torr; Reagent/catalyst; chemoselective reaction;	70%
With N-Bromosuccinimide; water; potassium carbonate; triphenylbismuthane In acetonitrile for 2h;	63%

cyclopentane-1,2-diol (4065-92-3) → Glutaraldehyde (111-30-8) + C15H24O4

Conditions	Yield
With oxygen; [(n-Bu)4N]3H2[IMo6O24] In acetonitrile at 80℃; under 1520.1 Torr; for 15h;	A 17 % Chromat. B 83 % Chromat.

piperidine (110-89-4) → Glutaraldehyde (111-30-8)

Conditions	Yield
With 3-carboxypyridinium dichromate In acetonitrile at 20℃; for 0.0833333h;	97%
With zinc dichromate trihydrate at 20℃; grinding; neat (no solvent); chemoselective reaction;	90%
With oxygen; potassium iodide; sodium nitrite In water; acetonitrile for 12h; Reflux;	70%

1,1'-<1,7-dimethyl-(1,7-diaza-2,6-dioxo-hepta-1,7-diyl) bis-(3-methyl-3H-imidazol-1-ium)> diiodide → Glutaraldehyde (111-30-8)

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -10 - 20℃; for 0.5h;	72%

trans-cyclopentane-1,2-diol (5057-99-8) → Glutaraldehyde (111-30-8)

Conditions	Yield
With C21H12Cl6NO4V In toluene at 100℃; under 760.051 Torr; Reagent/catalyst; chemoselective reaction;	72%
With sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 2h;	43%
With cobalt(III) acetate In acetic acid at 50℃; Rate constant; Mechanism;
With cobalt(III) acetate In acetic acid at 25℃; Kinetics; Thermodynamic data; Mechanism; var. temp.; ΔH(excit.), ΔS(excit.), ΔG(excit.);

Glutaraldehyde bisulfite complex (7420-89-5) → Glutaraldehyde (111-30-8)

Conditions	Yield
With cation exchange resin In benzene at 70℃; for 3.5h;	80%

piperidine (110-89-4) + 3-nitro-benzaldehyde (99-61-6) + diethyl oxaloacetate (108-56-5) → Glutaraldehyde (111-30-8)

Conditions	Yield
With acetic acid In ethanol

2-methoxy-3,4-dihydro-2H-pyran (4454-05-1) + methanol (67-56-1) → cis- and trans-2,6-Dimethoxytetrahydropyran (6581-57-3) + Glutaraldehyde (111-30-8)

Conditions	Yield
With water at 41℃;

isopropyl alcohol (67-63-0) + cyclopentene (142-29-0) → cyclopentane-1,2-diol (4065-92-3) + 2-Isopropoxy-cyclopentanol (142052-70-8) + Glutaraldehyde (111-30-8)

Conditions	Yield
With dihydrogen peroxide; tungsten(VI) oxide at 35℃; for 20h;	A 16.2% B 10.2% C 68.4%

cyclopentene ozonide → Glutaraldehyde (111-30-8)

Conditions	Yield
With Lindlar's catalyst; ethyl acetate Hydrogenation;
With titanium(III) chloride; sodium acetate; acetic acid at 40℃; Reagens 4: Wasser;
With water

2-methoxy-3,4-dihydro-2H-pyran (4454-05-1) + methanol (67-56-1) → 1,1,5,5-tetramethoxy-pentane (4454-02-8) + 5,5-dimethoxypentanal (50789-30-5) + Glutaraldehyde (111-30-8)

Conditions	Yield
With water at 90 - 93℃;

6,7-dioxa-bicyclo[3.2.2]nonane (283-35-2) → ethene (74-85-1) + cis-1,4-dihydrocycloheptane (31351-04-9) + cycloheptane-1,4-dione (14950-46-0) + Glutaraldehyde (111-30-8)

Conditions	Yield
With cobalt(II) 5,10,15,20-tetraphenylporphyrin In chloroform at 60℃; for 13h;	A 4% B 60% C 8% D 4%

1 ,5-pentanediol (111-29-5) → tetrahydro-2H-2-pyranol (694-54-2) + Glutaraldehyde (111-30-8)

Conditions	Yield
With oxygen; (t-Bu)4; Cl(ON)Ru(salen) substituted with Me4 In diethyl ether at 20℃; Irradiation;	A 95 % Spectr. B 5 % Spectr.

diazomethane (186581-53-3, 908094-01-9) + cyclopentene (142-29-0) → methyl 4-formylbutanoate (6026-86-4) + Dimethyl glutarate (1119-40-0) + Glutaraldehyde (111-30-8)

Conditions	Yield
Stage #1: cyclopentene With ozone In dichloromethane at -78℃; Stage #2: With Merrifield resin-bound piperidine In dichloromethane at 20℃; for 24h; Stage #3: diazomethane In dichloromethane; ethyl acetate	A 59% B 14% C 23%

1,1,5,5-tetraethoxypentane (4454-01-7) → Glutaraldehyde (111-30-8)

Conditions	Yield
With cation-exchange resin KU-2 and KU-2-8 In water at 20 - 30℃; for 2.5h;	40%

cis-1,2-cyclopentanediol (5057-98-7) → 2-Methylsulfanylmethoxy-cyclopentanol (85260-38-4) + Glutaraldehyde (111-30-8)

Conditions	Yield
With dimethyl sulfoxide; molybdenum peroxide In toluene Heating;	A 35% B 10%

ethanol (64-17-5) + cyclopentene (142-29-0) → cyclopentane-1,2-diol (4065-92-3) + 2-Ethoxycyclopentanol (78782-09-9) + Glutaraldehyde (111-30-8)

Conditions	Yield
With dihydrogen peroxide; tungsten(VI) oxide at 35℃; for 20h;	A 18.7% B 34.6% C 47.4%

cyclopentene (142-29-0) + tert-butyl alcohol (75-65-0) → trans-cyclopentane-1,2-diol (5057-99-8) + Glutaraldehyde (111-30-8) + trans-2-tert-butoxycyclopentanol

Conditions	Yield
With dihydrogen peroxide; tungsten(VI) oxide; silica gel In tert-butyl alcohol at 34.85℃; for 24h; Product distribution; Further Variations:; Catalysts; Solvents;	A n/a B 60% C n/a

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) → Glutaraldehyde (111-30-8)

Conditions	Yield
With hydrogenchloride at 80℃; for 1.5h;

4-amino-1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole (850362-77-5) + Glutaraldehyde (111-30-8) → 1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-4-(piperidin-1-yl)-1H-indazole (850363-25-6)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In ethanol; water at 20℃; for 7h;	89%
With hydrogen; 5%-palladium/activated carbon In ethanol; water at 20℃; for 7h;	89%
With hydrogen; 5% palladium over charcoal In ethanol; water at 20℃; for 7h;	89%

Upstream product

• 123-91-1 1,4-dioxane 
• 5057-99-8 trans-cyclopentane-1,2-diol 
• 546-67-8 lead(IV) tetraacetate 
• 4454-05-1 2-methoxy-3,4-dihydro-2H-pyran 
• 103-75-3 2-ethoxy-2,3-dihydro-4H-pyran 
• 6635-57-0 1,5-pentanedioxime 
• 64-17-5 ethanol 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 6286-43-7 1,2,3-trihydroxycyclohexane 
• 854704-82-8 N,N'-dimethyl-N,N'-diphenyl-glutaramide 
• 103266-56-4 1,3-bis-(1,3-diphenyl-imidazolidin-2-yl)-propane 
• 142-29-0 cyclopentene 
• 21502-33-0 5c-ethoxy-pent-4-enal 
• 21502-34-1 5t-ethoxy-pent-4-enal 

Downstream Products

• 108-55-4 glutaric anhydride, 
• 110-94-1 1,5-pentanedioic acid 
• 38150-01-5 (1α,2β,3α)-2-nitro-1,3-cyclohexanediol 
• 579-21-5 Lobelanine 
• 6035-31-0 2,2′-(piperidine-2,6-cis-diyl)bis(1-phenylethanone) 
• 495-50-1 2,2′-(piperidine-2,6-trans-diyl)bis(1-phenylethanone) 
• 41980-31-8 2,6-dicyanopiperidine 
• 5085-07-4 glutaraldehyde bis-(2,4-dinitro-phenylhydrazone) 
• 552-70-5 pseudopelletierine 
• 110-86-1 pyridine 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 31285-34-4 4,4'-(2-methyl-2-nitro-cyclohexane-1,3-diyl)-bis-morpholine 
• 18961-35-8 3-morpholin-4-yl-2-nitro-cyclohexanol 
• 18531-80-1 DL-1-Nitro-1ref-aethyl-cyclohexandiol-(2cis,6trans) 

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A novel WO3/SiO2 was designed for the catalytic oxidation of cyclopentene by H2O2 to glutaraldehyde In comparison with those homogeneous catalysts, it seems more suitable for the industrial process owing to the high yield of glutaraldehyde and easy separation of the present catalyst from reaction products.

Pd-Ce nanoparticles supported on functional Fe-MIL-101-NH2: An efficient catalyst for selective glycerol oxidation

Metal organic framework Fe-MIL-101-NH2 was prepared at different reaction time. The morphology of the Fe-MIL-101-NH2 slightly changed following a longer reaction time; the crystal structure remained. Neocuproine ligand coordinating palladium complex has demonstrated high activity in selective glycerol oxidation towards 1,3-dihydroxyacetone (DHA). Neocuproine ligand was attached to MOF Fe-MIL-101-NH2 by forming an amide (CO[sbnd]NH) bond in this work. The functional Fe-MIL-101-NH2 was used as catalyst supports to hold palladium and cerium nanoparticles. The resulting composite of the Pd-Ce/Fe-MIL-101[sbnd]N[dbnd]CHNeocuproine was found to be a high efficient catalyst in the selective oxidation conversion of glycerol to dihydroxyacetone in comparison with catalysts Pd/Fe-MIL-101[sbnd]N[dbnd]CHNeocuproine and Pt-Bi/C. The catalysts and products were analyzed by FT-IR, XRD, SEM, TEM and 1H, 13C NMR spectroscopy. In addition, the supported catalyst is recyclable with sustainable activity.

Atmospheric chemistry of bifunctional cycloalkyl nitrates

Reported here are some aspects of the atmospheric chemistry of the cycloalkyl nitrates trans-2-hydroxy-cyclopentyl-1-nitrate (HCPN), 2-oxo-cyclohexyl-1-nitrate (OCHN) and trans-1-methyl-cyclohexyl-1,2-dinitrate (MCHDN). Their UV absorption spectra have been measured and rate coefficients for their reaction with OH radicals have been determined at 302 K in 1000 mbar of synthetic air. The tropospheric lifetimes of the cycloalkyl nitrates have been estimated from calculations of their photolysis frequencies and first-order OH-radical loss rates. HCPN will not photolyse under atmospheric conditions and for OCHN and MCHDN 24 h globally-averaged photolysis lifetimes of 1.6 and 7.7 days, respectively, have been estimated. The globally-averaged 24 h lifetimes due to reaction with OH radicals are approximately 4 days for both HCHN and OCHN and 8 days for MCHDN. Therefore, for OCHN and MCHDN both photolysis and reaction with OH radicals will be significant atmospheric sinks. For HCHN wet deposition may also be important due to the increased solubility of this compound.

Synthesis, x-ray crystallography, and computational analysis of 1-azafenestranes

The tandem [4+2]/[3+2] cycloaddition of nitroalkenes has been employed in the synthesis of 1-azafenestranes, molecules of theoretical interest because of planarizing distortion of their central carbon atoms. The synthesis of c,c,c,c-[5.5.5.5]-1-azafenestrane was completed in good yield from a substituted nitrocyclopentene, and its borane adduct was analyzed through X-ray crystallography, which showed a moderate distortion from ideal tetrahedral geometry. The syntheses of two members of the [4.5.5.5] family of 1-azafenestranes are also reported, including one with a trans fusion at a bicyclic ring junction which brings about considerable planarization of one of the central angles (16.8° deviation from tetrahedral geometry). While investigating the [4.5.5.5]-1-azafenestranes, a novel dyotropic rearrangement that converts nitroso acetals into tetracyclic aminals was discovered. Through conformational analysis, a means to prevent this molecular reorganization was formulated and realized experimentally with the use of a bulky vinyl ether in the key [4+2] cycloaddition reaction. Finally, DFT calculations on relative strain energy for the 1-azafenestranes, as well as their predicted central angles, are disclosed.

Preparation of Heterogeneous Mesoporous Silica-Supported 12-Tungstophosphoric Acid Catalyst and Its Catalytic Performance for Cyclopentene Oxidation

Keggin-structured 12-tungstophosphoric acids were immobilized onto the surface of amine-modified mesoporous sieve SBA-15 as onium salts. All the catalyst materials were characterized by X-ray diffraction, N2 physisorption, Fourier transform infrared spectroscopy, thermal gravimetric analysis, and X-ray photoelectron spectroscopy for their structural integrity and physicochemical properties. Characterization of the catalysts confirmed an ordered hexagonal mesostructure for SBA-15 and that the Keggin structure of the heteropolyanions on the amine-modified SBA-15 was preserved. The catalytic activities of the catalysts were evaluated for the liquid-phase oxidation of cyclopentene with 50% hydrogen peroxide as the oxidant in tert-butanol. A 100% conversion of cyclopentene and an 81% selectivity for glutaraldehyde were obtained and these were higher than that for the catalysts prepared by direct impregnation. The stability and reusability of the catalysts were studied and the catalysts could be reused at least five times, which indicates their excellent reusability. The influence of reaction temperature and reaction time was also investigated. In addition, a reaction mechanism was proposed.