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1,4-Dioxane
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123-91-1 Usage

Uses

1,4-Dioxane is used as a solvent for celluloseesters, oils, waxes, resins, and numerousorganic and inorganic substances. It is alsoused in coatings and as a stabilizer in chlorinatedsolvents.

Flammability and Explosibility

Dioxane is a highly flammable liquid (NFPA rating = 3). Its vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. Dioxane vapor forms explosive mixtures with air at concentrations of 2 to 22% (by volume). Fires involving dioxane should be extinguished with carbon dioxide or dry powder extinguishers. Dioxane can form shock- and heat-sensitive peroxides that may explode on concentration by distillation or evaporation. Samples of this substance should always be tested for the presence of peroxides before distilling or allowing to evaporate. Dioxane should never be distilled to dryness.

Chemical Properties

1,4-Dioxane is a colorless, stable liquid with a faint, pleasant odor. Although it has been known as far back as 1863, it was not until 1929 that is became commercially available. It is chemically a di-ether obtained by the loss of water from two molecules of ethylene glycol. It is completely soluble in water, as well as most organic solvents. It is freely soluble in mineral, vegetable, blown and heat-bodied oils, and oil soluble dyes. Most waxes are more readily soluble in dioxane when heated and examples of these are beeswax, carnauba, montan, paraffin, gilsonite, and Japan wax.

Uses

1,4-Dioxane, the six-member cyclic diether, is used as an aluminum inhibitor in chlorinated solvents like 1,1,1-trichloroethane and as a solvent for certain resins and polymers.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenicdata. Poison by intraperitoneal route. Moderately toxic by ingestion and inhalation. Mildly toxic by skin contact. Human systemic effects by inhalation: lachrymation, conjunctiva irritation, convulsions, hgh blood pressure, unspecified respiratory and gastrointestinal system effects. Mutation data reported. An eye and slun irritant. The irritant effects probably provide sufficient warning, in acute exposures, to enable a worker to leave exposure before being seriously affected. Repeated exposure to low concentrations has resulted in human fatahties, the organs chefly affected being the liver and kidneys. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with (H2 + Raney Ni), AgClO4. Can form dangerous peroxides when exposed to air. Potentially explosive reaction with nitric acid + perchloric acid, Raney nickel catalyst (above 210°C). Forms explosive mixtures with decaborane (impactsensitive), triethynylaluminum (sensitive to heating or drying). Violent reaction with sulfur trioxide. Incompatible with sulfur trioxide. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Incompatibilities

Dioxane can form potentially explosive peroxides upon long exposure to air. Dioxane may react violently with Raney nickel catalyst, nitric and perchloric acids, sulfur trioxide, and strong oxidizing reagents.

Uses

Suitable for HPLC, spectrophotometry, environmental testing

Waste Disposal

Excess dioxane and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

Reactivity Profile

1,4-Dioxane is a flammable liquid; when exposed to air 1,4-Dioxane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. The addition complex with sulfur trioxide (1:1) sometimes decomposes violently on storing at room temperature [Sisler, H. H. et al., Inorg. Synth., 1947, 2, p. 174]. Evaporation of boron trifluoride in aqueous 1,4-Dioxane with nitric acid led to an explosion upon addition of perchloric acid [MCA Guide, 1972, p. 312]. Explosive reaction with Raney nickel catalyst above 210° C {Mozingo R., Org. Synth., 1955, Coll. Vol. 3, p. 182].

uses

Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.

description

1,4-Dioxane is a hexahydroxy heterocyclic compound containing two oxygen heteroatoms. molecular formula C4H8O2,a colorless, flammable liquid, slight ether smell, photosensitive. Its Vapor can easily form explosive peroxides by absorbing oxygen in the air. Explosion limit 1.97%-1.97% (volume), It should be disposed by reducing agent in distillation process. Melting point 11.8 ℃, boiling point of 101 ℃ (750 mmHg), density 1.0337 (20/4 ℃), refractive index 1.4224, flash point12℃. Soluble in water, ethanol, ether and other organic solvents. It can form azeotrope with water (water content 18.6%) and the boiling point is 87.8 ℃. It turns bright yellow when reacting with tetranitromethane. Trace amount of 2,6-Di-tert-butyl-4-methylphenol(BHT) is often added to the commodity as a stabilizer. Low toxicity, half lethal dose (rats, oral) 4200 mg/kg. A possible carcinogen, an irritating chemical. 1,4-Dioxane can be prepared by dehydration of ethylene glycol by sulfuric acid and it is the indirect product in the production of epoxy ethane. As a good organic solvent, it has a wide application such as the solvent for cellulose acetate and lots of resins. It Is mainly used in the pharmaceutical industry as extraction agent, as a stabilizer in the production of 1,1,1 – trichloroethane as a volatile solvent in the production of polyurethane in place of dimethylformamide and tetrahydrofuran, as stripping agent in the crafts of coating and painting, as a solvent and dispersant in the dye industry, as a stabilizer in printing ink, and also as treatment agent for metal surface. In addition , it can also be used in cosmetics, spices manufacture, electroplating, etc.

Source

Improper disposal of products listed below may result in 1,4-dioxane leaching into groundwater.

Physical properties

Clear, colorless, very flammable, volatile liquid with a faint pleasant, ether-like odor. Experimentally determined detection and recognition odor threshold concentrations were 2.9 mg/m3 (800 ppbv) and 6.5 mg/m3 (1.8 ppmv), respectively (Hellman and Small, 1974).

Health Hazard

The toxicity of 1,4-dioxane is low in testanimals by all routes of exposure. However,in humans the toxicity of this compoundis severe. The target organs are theliver, kidneys, lungs, skin, and eyes. Exposureto its vapors as well as the absorptionthrough the skin or ingestion can cause poisoning,the symptoms of which include drowsiness,headache, respiratory distress, nausea,and vomiting. It causes depression of centralnervous system. There are reports of humandeaths from subacute and chronic exposures todioxane vapors at concentration levels rangingbetween 500 and 1000 ppm. Serious healthhazards may arise from its injurious effects onthe liver, kidneys, and brain. Rabbits died ofkidney injury resulting from repeated inhalationof 1,4-dioxane vapors for 30 days (Smyth1956). It is an irritant to the eyes, nose, skin,and lungs. In humans, a 1-minute exposure to5000-ppm vapors can cause lacrimation.LC50 value, inhalation (rats): 13,000 ppm/2 hLD50 value, oral (mice): 5700 mg/kg1,4-Dioxane is an animal carcinogen oflow potential. Ingestion of high concentrationsof this compound at a level of7000–18,000 ppm in drinking water for14–23 months caused nasal and liver tumorsin rats (ACGIH 1986). Guinea pigs developedlung tumors.

Production

1,4-Dioxane can be prepared by dehydration of ethylene glycol orpolyglycol ether by the catalysis of sulfuric acid and can also be prepared by direct dimerization of Ethylene oxide. The dimerization process was carried out in the presence of acid catalysts such as sulfuric acid, Sodium bisulfate, boron trifluoride, etc. Powdered sodium hydroxide can be added to 1,4-Dioxane of industrial grade to remove the acid and water, by filtering the solid and distillation to get prurified product.

Precautions

Workers Should be careful during handling of 1,4-Dioxane and avoid open flames, sparks and smoking. Workers should wear proper protectives since 1,4-Dioxane in known as hazardous, cause damage to eyes, respiratory tract, liver and kidney.

Definition

ChEBI: A dioxane with oxygen atoms at positions 1 and 4.

Purification Methods

It is prepared commercially either by dehydration of ethylene glycol with H2SO4 and heating ethylene oxide or bis(.-chloroethyl)ether with NaOH. The usual impurities are acetaldehyde, ethylene acetal, acetic acid, water and peroxides. Peroxides can be removed (and the aldehyde content decreased) by percolation through a column of activated alumina (80g per 100-200mL solvent), by refluxing with NaBH4 or anhydrous stannous chloride and distilling, or by acidification with conc HCl, shaking with ferrous sulfate and leaving in contact with it for 24hours before filtering and purifying further. Hess and Frahm [Chem Ber 71 2627 1938] refluxed 2L of dioxane with 27mL conc HCl and 200mL water for 12hours with slow passage of nitrogen to remove acetaldehyde. After cooling the solution, KOH pellets were added slowly and with shaking until no more would dissolve and a second layer had separated. The dioxane was decanted, treated with fresh KOH pellets to remove any aqueous phase, then transferred to a clean flask where it was refluxed for 6-12hours with sodium, then distilled from it. Alternatively, Kraus and Vingee [J Am Chem Soc 56 511 1934] heated it on a steam bath with solid KOH until fresh addition of KOH gave no more resin (due to acetaldehyde). After filtering through paper, the dioxane was refluxed over sodium until the surface of the metal was not further discoloured during several hours. It was then distilled from sodium. The acetal (b 82.5o) is removed during fractional distillation. Traces of *benzene, if present, can be removed as the *benzene/MeOH azeotrope by distillation in the presence of MeOH. Distillation from LiAlH4 removes aldehydes, peroxides and water. Dioxane can be dried using Linde type 4X molecular sieves. Other purification procedures include distillation from excess C2H5MgBr, refluxing with PbO2 to remove peroxides, fractional crystallisation by partial freezing and the addition of KI to dioxane acidified with aqueous HCl. Dioxane should be stored out of contact with air, preferably under N2. A detailed purification procedure is as follows: Dioxane is stood over ferrous sulfate for at least 2 days, under nitrogen. Then water (100mL) and conc HCl (14mL)/ litre of dioxane are added (giving a pale yellow colour). After refluxing for 8-12hours with vigorous N2 bubbling, pellets of KOH are added to the warm solution to form two layers and to discharge the colour. The solution is cooled rapidly with more KOH pellets being added (magnetic stirring) until no more dissolved in the cooled solution. After 4-12hours, if the lower phase is not black, the upper phase is decanted rapidly into a clean flask containing sodium, and refluxed over sodium (until freshly added sodium remained bright) for 1hour. The middle fraction is collected (and checked for minimum absorbency below 250nm). The distillate is fractionally frozen three times by cooling in a refrigerator, with occasional shaking or stirring. This material is stored in a refrigerator. Before use it is thawed, refluxed over sodium for 48hours, and distilled into a container. All joints are clad with Teflon tape. Coetzee and Chang [Pure Appl Chem 57 633 1985] dried the solvent by passing it slowly through a column (20g/L) of 3A molecular sieves activated by heating at 250o for 24hours. Impurities (including peroxides) are removed by passing the effluent slowly through a column packed with type NaX zeolite (pellets ground to 0.1mm size) activated by heating at 400o for 24hours or chromatographic grade basic Al2O3 activated by heating at 250o for 24hours. After removal of peroxides the effluent is refluxed for several hours over sodium wire, excluding moisture, distilled under nitrogen or argon and stored in the dark. One of the best tests of purity of dioxane is the formation of the purple disodium benzophenone complex during reflux and its persistence on cooling. (Benzophenone is better than fluorenone for this purpose and for the storing of the solvent.) [Carter et al. Trans Faraday Soc 56 343 1960, Beilstein 19 V 16.] TOXIC. Rapid purification: Check for peroxides (see Chapter 1 and Chapter 2 for test under ethers). Pre-dry with CaCl2 or better over Na wire. Then reflux the pre-dried solvent over Na (1% w/v) and benzophenone (0.2% w/v) under an inert atmosphere until the blue colour of the benzophenone ketyl radical anion persists. Distil, and store it over 4A molecular sieves in the dark.

Mechanism of action

An inhalation study in four male volunteers exposed to 50 ppm of dioxane determined that the majority (99.3%) of dioxane is eliminated by metabolism to β-hydroxyethoxyacetic acid (HEAA) with the remaining 0.7% being excreted through the urine (Young et al., 1977). Further studies suggest that the metabolism of dioxane is mediated by cytochrome P450 (Woo et al., 1978). The concentrations of HEAA were found to be 118% higher than the concentration of dioxane, suggesting rapid and extensive metabolism with a calculated metabolic clearance rate of 75 m/min. This same study concluded that repeated daily exposures to 50 ppm of dioxane would not cause adverse effects because accumulated concentrations would never exceed those attained at 50 ppm or less. β-Hydroxyethoxyacetic acid also accounted for >99% of the total urinary excretion of inhaled dioxane in rats (Young et al., 1978). Conversely, when dioxane is intravenously injected in rats, the metabolic clearance decreased indicating metabolic saturation at high doses (1000 mg/kg). Saturation was found to occur at doses >10 mg/kg/bw resulting in accumulation of 1,4-dioxane (HSDB, 1995).

storage

dioxane should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers. Containers of dioxane should be dated when opened and tested periodically for the presence of peroxides.

General Description

A clear colorless liquid with a faint ethereal odor. Flash point 55°F. Slightly denser than water and soluble in water. Vapors heavier than air. Susceptible to autooxidation to form peroxides.

Description

1,4-dioxane is a clear liquid with ether-like odour. It is highly flammable and forms explosive peroxides in storage (rate of formation increased by heating, evaporation, or exposure to light). 1,4-Dioxane is incompatible with oxidising agents, oxygen, halogens, reducing agents, and moisture. Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.

Carcinogenicity

1,4-Dioxane is reasonably anticipated to be a human carcinogen basedon sufficient evidence of carcinogenicity from studies in experimental animals.

Air & Water Reactions

Highly flammable. When exposed to air 1,4-Dioxane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Water soluble.

Uses

Stabilizer in chlorinated solvents. Solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, oil and spirit-sol dyes, and many other organic as well as some inorganic Compounds.

Environmental fate

Biological. Heukelekian and Rand (1955) reported a 10-d BOD value of 0.00 g/g which is 0.0% of the ThOD value of 1.89 g/g. Photolytic. Irradiation of pure 1,4-dioxane through quartz using a 450-W medium-pressure mercury lamp gave meso and racemic forms of 1-hydroxyethyldioxane, a pair of diastereomeric dioxane dimers (Mazzocchi and Bowen, 1975), dioxanone, dioxanol, hydroxymethyldioxane, and hydroxyethylidenedioxane (Houser and Sibbio, 1977). When 1,4-dioxane is subjected to a megawatt ruby laser, 4% was decomposed yielding ethylene, carbon monoxide, hydrogen, and a trace of formaldehyde (Watson and Parrish, 1971). Chemical/Physical. Anticipated products from the reaction of 1,4-dioxane with ozone or OH radicals in the atmosphere are glyoxylic acid, oxygenated formates, and OHCOCH2CH2OCHO (Cupitt, 1980). Storage of 1,4-dioxane in the presence of air resulted in the formation of 1,2- ethanediol monoformate and 1,2-ethane diformate (Jewett and Lawless, 1980). Stefan and Bolton (1998) studied the degradation of 1,4-dioxane in dilute aqueous solution by OH radicals. Degradation follows pseudo-first-order kinetics at a rate of 8.7 x 10-3/sec. Within 5 min of direct photolysis of hydrogen peroxide to generate OH radicals, almost 90% of the 1,4-dioxane reacted. Four primary intermediate formed were 1,2-ethanediol monoformate, 1,2-ethanediol diformate, formic acid, and methoxyacetic acid. These compounds were attacked by OH radicals yielding glycolic, glyoxylic, and acetic acids which led to oxalic acid as the last intermediate. Malonic acid was also identified as a minor intermediate. Twelve minutes into the reaction, the pH decreased rapidly to 3.25 from 5.0, then less rapidly to 3.25 after 23 min. After 1 h, the pH rose to 4.2 min. The decrease of pH during the initial stages of reaction is consistent with the formation of organic acids. Oxidation of organic acid by OH radicals led to an increase of pH. The investigators reported that the lower pH at the end of the experiment was due to carbonic acid formed during the mineralization process.

Definition

dioxan: A colourless toxic liquid,C4H8O2; r.d. 1.03; m.p. 11°C; b.p.101.5°C. The molecule has a sixmemberedring containing fourCH2groups and two oxygen atoms at oppositecorners. It can be made fromethane-1,2-diol and is used as a solvent.
InChI:InChI=1/C4H8O2/c1-3-5-4-2;2*1-2/h3-4H2,1-2H3;2*1-2H2

123-91-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (39118)  1,4-Dioxane, ACS, 99+%    123-91-1 500ml 475.0CNY Detail
Alfa Aesar (39118)  1,4-Dioxane, ACS, 99+%    123-91-1 1L 736.0CNY Detail
Alfa Aesar (39118)  1,4-Dioxane, ACS, 99+%    123-91-1 *4x500ml 1411.0CNY Detail
Alfa Aesar (39118)  1,4-Dioxane, ACS, 99+%    123-91-1 4L 2010.0CNY Detail
Alfa Aesar (43821)  1,4-Dioxane, anhydrous, 99.8%, packaged under Argon in resealable ChemSeal? bottles    123-91-1 100ml 423.0CNY Detail
Alfa Aesar (43821)  1,4-Dioxane, anhydrous, 99.8%, packaged under Argon in resealable ChemSeal? bottles    123-91-1 1L 950.0CNY Detail
Alfa Aesar (43821)  1,4-Dioxane, anhydrous, 99.8%, packaged under Argon in resealable ChemSeal? bottles    123-91-1 *4x1L 3073.0CNY Detail
Alfa Aesar (22913)  1,4-Dioxane, HPLC Grade, 99% min    123-91-1 1L 813.0CNY Detail
Alfa Aesar (22913)  1,4-Dioxane, HPLC Grade, 99% min    123-91-1 4L 2462.0CNY Detail
Alfa Aesar (22913)  1,4-Dioxane, HPLC Grade, 99% min    123-91-1 *4x1L 2595.0CNY Detail
Alfa Aesar (43167)  1,4-Dioxane, HPLC Grade, 99% min, packaged under Argon in resealable ChemSeal? bottles    123-91-1 250ml 424.0CNY Detail
Alfa Aesar (43167)  1,4-Dioxane, HPLC Grade, 99% min, packaged under Argon in resealable ChemSeal? bottles    123-91-1 1L 854.0CNY Detail

123-91-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-Dioxane

1.2 Other means of identification

Product number -
Other names DIOXANE, 1,4-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. 1,4-Dioxane is used as a solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, some dyes, and other organic and inorganic compounds.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123-91-1 SDS

123-91-1Synthetic route

C4H10O2*C10H15(1-)*C24BF20(1-)*Si(2+)

C4H10O2*C10H15(1-)*C24BF20(1-)*Si(2+)

A

1,4-dioxane
123-91-1

1,4-dioxane

B

1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

C

Dimethyl ether
115-10-6

Dimethyl ether

D

Cp*Si(1+)* B(C6F5)4(1-)

Cp*Si(1+)* B(C6F5)4(1-)

Conditions
ConditionsYield
In dichloromethane-d2 for 120h;A n/a
B n/a
C n/a
D 100%
oxirane
75-21-8

oxirane

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With BPA; triethylamine In water; isopropyl alcohol at 55 - 65℃; under 1500.15 Torr; for 8h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Autoclave; Large scale;99%
With sulfuric acid; water
beim Erwaermen einer Suspension von Bleicherde in Dioxan;
ethylene glycol
107-21-1

ethylene glycol

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 5h; Inert atmosphere; Sealed tube;99%
Nafion-H at 135℃; for 5h;50%
With aluminium phosphate aluminium oxide catalyst Product distribution; Heating;2%
diethylene glycol
111-46-6

diethylene glycol

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 10h; Inert atmosphere; Sealed tube;99%
With hafnium tetrakis(trifluoromethanesulfonate) In neat (no solvent) at 180℃; for 4.5h;85%
With sulfuric acid durch kontinuierliche Destillation;
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 6h; Inert atmosphere; Sealed tube;99%
With Sulfate; zirconium(IV) oxide at 180℃; for 1.41667h; cyclodehydration;
diethyl malonate
105-53-3

diethyl malonate

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With acetic acid; sodium nitrite In waterA n/a
B 86%
diethylene glycol dimethyl ether
111-96-6

diethylene glycol dimethyl ether

A

1,4-dioxane
123-91-1

1,4-dioxane

B

Dimethyl ether
115-10-6

Dimethyl ether

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate In hexane at 100℃; for 48h; Glovebox;A 75%
B n/a
ethylene glycol
107-21-1

ethylene glycol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2-chloroethanal
107-20-0

2-chloroethanal

Conditions
ConditionsYield
With tetrachloromethane; bis(acetylacetonate)oxovanadium at 100℃; for 1h;A 20%
B 72%
ethylene glycol
107-21-1

ethylene glycol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

diethylene glycol
111-46-6

diethylene glycol

Conditions
ConditionsYield
With sulfuric acid In neat (no solvent) at 150℃; under 1147.61 Torr; for 24h; Time; Autoclave;A 9%
B 65%
With Cs-P-Si at 300℃; under 75006 Torr;
ethylene glycol
107-21-1

ethylene glycol

A

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

B

1,4-dioxane
123-91-1

1,4-dioxane

C

acetaldehyde
75-07-0

acetaldehyde

D

diethylene glycol
111-46-6

diethylene glycol

Conditions
ConditionsYield
With tungsten trioxide on silica; hydrogen In water at 340℃; Temperature; Inert atmosphere;A 38.8%
B 28.7%
C 44.9%
D n/a
oxirane
75-21-8

oxirane

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2-fluoroethanol
371-62-0

2-fluoroethanol

Conditions
ConditionsYield
With hydrogen fluoride under 380 Torr; Product distribution;A 37%
B 5%
3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

methylamine
74-89-5

methylamine

A

1,4-dioxane
123-91-1

1,4-dioxane

B

4-methyl-morpholine
109-02-4

4-methyl-morpholine

C

1,1'-oxybisethene
109-93-3

1,1'-oxybisethene

D

2-chloroetyl vinyl ether
110-75-8

2-chloroetyl vinyl ether

Conditions
ConditionsYield
With sodium hydroxide In water at 90 - 95℃; for 4h;A 12%
B 25%
C 20%
D 7%
oxirane
75-21-8

oxirane

perfluoropropylene
116-15-4

perfluoropropylene

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2-(1,1,2,3,3,3-hexafluoropropyl)-1,4-dioxane
94412-88-1

2-(1,1,2,3,3,3-hexafluoropropyl)-1,4-dioxane

C

3,3,4,5,5,5-hexafluoropentan-2-one
60249-67-4

3,3,4,5,5,5-hexafluoropentan-2-one

Conditions
ConditionsYield
Irradiation;A 16%
B 5%
C 0.8%
oxirane
75-21-8

oxirane

triethyloxonium fluoroborate
368-39-8

triethyloxonium fluoroborate

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With diethyl ether
Cbz-L-Gln
2650-64-8

Cbz-L-Gln

N-L-asparaginyl-S-benzyl-L-cysteine methyl ester
86961-92-4

N-L-asparaginyl-S-benzyl-L-cysteine methyl ester

A

1,4-dioxane
123-91-1

1,4-dioxane

B

S-benzyl-N-[N2-(N2-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester
2658-34-6

S-benzyl-N-[N2-(N2-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester

Conditions
ConditionsYield
With tetrahydrofuran; chloroformic acid ethyl ester; triethylamine Reagens 4: H2O;
ethanol
64-17-5

ethanol

ethylamine
75-04-7

ethylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
at 57℃; Rate constant;
ethylene glycol
107-21-1

ethylene glycol

(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

A

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

B

1,4-dioxane
123-91-1

1,4-dioxane

C

acetaldehyde
75-07-0

acetaldehyde

ethylene glycol
107-21-1

ethylene glycol

ethylene dibromide
106-93-4

ethylene dibromide

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
at 160℃; im Rohr;
ethylene glycol
107-21-1

ethylene glycol

ethylene dibromide
106-93-4

ethylene dibromide

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2-(2′-(2″-bromoethoxy)ethoxy)ethanol
57641-67-5

2-(2′-(2″-bromoethoxy)ethoxy)ethanol

C

2-(2-bromoethoxy)ethan-1-ol
57641-66-4

2-(2-bromoethoxy)ethan-1-ol

D

2-bromoethanol
540-51-2

2-bromoethanol

Conditions
ConditionsYield
at 160℃;
2-(2-Chloroethoxy)ethanol
628-89-7

2-(2-Chloroethoxy)ethanol

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With potassium hydroxide; water
With sodium hydroxide; water
formaldehyd
50-00-0

formaldehyd

Propiolaldehyde diethyl acetal
10160-87-9

Propiolaldehyde diethyl acetal

diethylamine
109-89-7

diethylamine

A

1,4-dioxane
123-91-1

1,4-dioxane

B

4-diethylamino-but-2-ynal diethyl acetal
5799-78-0

4-diethylamino-but-2-ynal diethyl acetal

3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With sodium hydroxide at 200 - 220℃;
With sodium hydroxide; water at 200℃;
With copper(II) oxide
(R)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol
76738-28-8

(R)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

(1R,2R)-2-amino-3-dichloroacetoxy-1-(4-nitro-phenyl)-propan-1-ol; hydrochloride
119324-39-9

(1R,2R)-2-amino-3-dichloroacetoxy-1-(4-nitro-phenyl)-propan-1-ol; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether; water
cyclobutanone
1191-95-3

cyclobutanone

C4H9O2(1+)*C2H3N

C4H9O2(1+)*C2H3N

A

1,4-dioxane
123-91-1

1,4-dioxane

B

C4H7O(1+)*C2H3N

C4H7O(1+)*C2H3N

Conditions
ConditionsYield
at 24.9℃; Thermodynamic data; ΔG0;
cyclobutanone
1191-95-3

cyclobutanone

[1,4]Dioxan-1-ium
71815-79-7

[1,4]Dioxan-1-ium

A

1,4-dioxane
123-91-1

1,4-dioxane

B

cyclobutanone; protonated form
64725-63-9

cyclobutanone; protonated form

Conditions
ConditionsYield
at 24.9℃; Thermodynamic data; ΔG0;
1,4-dioxane
123-91-1

1,4-dioxane

dioxane-trichloroborane adduct

dioxane-trichloroborane adduct

Conditions
ConditionsYield
With boron trichloride at -78 - 0℃;100%
1,4-dioxane
123-91-1

1,4-dioxane

nickel
7440-02-0

nickel

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

2,3,5,6-tetrafluoroterephthalaldehyde
3217-47-8

2,3,5,6-tetrafluoroterephthalaldehyde

2,3,5,6-tetrafluoro-1,4-benzenedimethanol
92339-07-6

2,3,5,6-tetrafluoro-1,4-benzenedimethanol

Conditions
ConditionsYield
100%
1,4-dioxane
123-91-1

1,4-dioxane

3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole
247922-29-8

3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole

1-methyl-5-hydroxypyrazole
33641-15-5

1-methyl-5-hydroxypyrazole

topramezone
210631-68-8

topramezone

Conditions
ConditionsYield
With carbon monoxide; potassium carbonate; triethylamine; triphenylphosphine; palladium(II) chloride In water100%
With hydrogenchloride; potassium carbonate; triethylamine; bis(triphenylphosphine)palladium(II) dichloride In water
1,4-dioxane
123-91-1

1,4-dioxane

N-methyl-L-leucine
3060-46-6

N-methyl-L-leucine

N-methyl-L-leucine methyl ester
35026-08-5

N-methyl-L-leucine methyl ester

Conditions
ConditionsYield
In hydrogenchloride; methanol100%
1,4-dioxane
123-91-1

1,4-dioxane

methyl 3-(1-adamantyl)-4-vinylbenzoate
135109-96-5

methyl 3-(1-adamantyl)-4-vinylbenzoate

methyl 3-(1-adamantyl)-4-ethylbenzoate
135077-86-0

methyl 3-(1-adamantyl)-4-ethylbenzoate

Conditions
ConditionsYield
palladium on charcoal100%
1,4-dioxane
123-91-1

1,4-dioxane

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
72287-26-4, 95464-05-4

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride

trifluoromethanesulfonic acid 3-(2-cyanothien-3-yl)phenyl ester

trifluoromethanesulfonic acid 3-(2-cyanothien-3-yl)phenyl ester

dichloro[1,1'-bis(diphenylphiosphino)ferrocene]palladium

dichloro[1,1'-bis(diphenylphiosphino)ferrocene]palladium

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]thiophene-2-carbonitrile

3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]thiophene-2-carbonitrile

Conditions
ConditionsYield
With potassium acetate100%
1,4-dioxane
123-91-1

1,4-dioxane

4-(6,7-dimethoxy-4-quinazolinyl)-N-(4-ethoxycarbonylphenyl)-1-piperazinecarboxamide
205255-23-8

4-(6,7-dimethoxy-4-quinazolinyl)-N-(4-ethoxycarbonylphenyl)-1-piperazinecarboxamide

N-(4-Carboxyphenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide

N-(4-Carboxyphenyl)-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide

Conditions
ConditionsYield
With lithium hydroxide monohydrate In water100%
1,4-dioxane
123-91-1

1,4-dioxane

isobutylaluminum dichloride
1888-87-5

isobutylaluminum dichloride

isobutyl aluminum dichloride 1,4-dioxane complex

isobutyl aluminum dichloride 1,4-dioxane complex

Conditions
ConditionsYield
slow addn. of Al-compound under Ar to an excess of dioxane at 0°C with stirring; evapn. in vacuo; elem. anal.;100%
1,4-dioxane
123-91-1

1,4-dioxane

(CO)5WC[OB(C4H9)2]CH3(OC4H8)

(CO)5WC[OB(C4H9)2]CH3(OC4H8)

(CO)5WC[OB(C4H9)2]CH3(O2C4H8)

(CO)5WC[OB(C4H9)2]CH3(O2C4H8)

Conditions
ConditionsYield
In pentane at -40°C; evapn., drying at -40.degreeC under high vac. for 20 h, elem. anal.;100%
1,4-dioxane
123-91-1

1,4-dioxane

diisobutylaluminium hydride
1191-15-7

diisobutylaluminium hydride

(2,6-Me2C6H3)N(SiMe3)(Si(OH)3)

(2,6-Me2C6H3)N(SiMe3)(Si(OH)3)

[(2,6-Me2C6H3)N(SiMe3)SiO3Al*dioxane]4

[(2,6-Me2C6H3)N(SiMe3)SiO3Al*dioxane]4

Conditions
ConditionsYield
In 1,4-dioxane; hexane byproducts: H2, i-C4H10; N2-atmosphere; refluxing (6 h); evapn. (vac.), drying (vac., 24 h). recrystn. (hexane / dioxane, 5°C); elem. anal.;100%
1,4-dioxane
123-91-1

1,4-dioxane

diisobutylaluminium hydride
1191-15-7

diisobutylaluminium hydride

(2,4,6-Me3C6H2)N(SiMe3)(Si(OH)3)

(2,4,6-Me3C6H2)N(SiMe3)(Si(OH)3)

[(2,4,6-Me3C6H2)N(SiMe3)SiO3Al*dioxane]4

[(2,4,6-Me3C6H2)N(SiMe3)SiO3Al*dioxane]4

Conditions
ConditionsYield
In 1,4-dioxane; hexane byproducts: H2, i-C4H10; N2-atmosphere; refluxing (6 h); evapn. (vac.), drying (vac., 24 h). recrystn. (hexane / dioxane, 5°C); elem. anal.;100%
1,4-dioxane
123-91-1

1,4-dioxane

isopropylindium dichloride
132280-88-7

isopropylindium dichloride

[((CH3)2CH)InCl2(C4H8O2)]

[((CH3)2CH)InCl2(C4H8O2)]

Conditions
ConditionsYield
In 1,4-dioxane Ar atm.;; layering (n-pentane, -30°C);100%
1,4-dioxane
123-91-1

1,4-dioxane

zinc tetraphenylporphyrin
14074-80-7

zinc tetraphenylporphyrin

Bis(κO-dioxane)-(α,β,γ,δ-tetraphenylporphinato)zinc(II)
1045486-95-0

Bis(κO-dioxane)-(α,β,γ,δ-tetraphenylporphinato)zinc(II)

Conditions
ConditionsYield
at 20℃; for 240h;100%
In 1,4-dioxane Zn complex dissolved in excess of 1,4-dioxane; soln. heated up to boiling temp.; excess of the solvent removed after cooling by flow of air;
1,4-dioxane
123-91-1

1,4-dioxane

(4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone
1241914-71-5

(4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone

(R,S)-(4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanol hydrochloride

(R,S)-(4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile100%
1,4-dioxane
123-91-1

1,4-dioxane

C4H8O2*O3Se

C4H8O2*O3Se

Conditions
ConditionsYield
With sulfur dioxide; selenium trioxide at 20℃; Schlenk technique; Sealed tube; Inert atmosphere;100%
1,4-dioxane
123-91-1

1,4-dioxane

A

t-butyl 4-({5-[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]-7-methoxy-1H-pyrazolo[4,3-d]pyrimidin-1-yl}methyl)piperidine-1-carboxylate

t-butyl 4-({5-[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]-7-methoxy-1H-pyrazolo[4,3-d]pyrimidin-1-yl}methyl)piperidine-1-carboxylate

B

ethyl 1-[7-methoxy-1-(piperidin-4-ylmethyl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carboxylate hydrochloride

ethyl 1-[7-methoxy-1-(piperidin-4-ylmethyl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carboxylate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; ethyl acetateA n/a
B 100%
1,4-dioxane
123-91-1

1,4-dioxane

C39H54GeO6Si2

C39H54GeO6Si2

C27H26GeO6*0.65C4H8O2

C27H26GeO6*0.65C4H8O2

Conditions
ConditionsYield
Stage #1: C39H54GeO6Si2 With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: 1,4-dioxane
100%
1,4-dioxane
123-91-1

1,4-dioxane

1,3-dimethyluracil
874-14-6

1,3-dimethyluracil

1,3-dimethyl-5-(2,5-dioxanyl)uracil
124851-80-5

1,3-dimethyl-5-(2,5-dioxanyl)uracil

Conditions
ConditionsYield
With dibenzoyl peroxide for 4h; Heating;99%
1,4-dioxane
123-91-1

1,4-dioxane

t-butyl cis-5-(5-hydroxy-3-pyridinyl)hexahydropyrrolo[3,4-c]-pyrrole-2(1H)-carboxylate
370879-71-3

t-butyl cis-5-(5-hydroxy-3-pyridinyl)hexahydropyrrolo[3,4-c]-pyrrole-2(1H)-carboxylate

cis-2-(5-hydroxy-3-pyridinyl)octahydropyrrolo[3,4-c]pyrrole dihydrochloride

cis-2-(5-hydroxy-3-pyridinyl)octahydropyrrolo[3,4-c]pyrrole dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; ethyl acetate99%
1,4-dioxane
123-91-1

1,4-dioxane

3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazole
195714-54-6

3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazole

3-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride
195713-66-7

3-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride99%
1,4-dioxane
123-91-1

1,4-dioxane

Pd2 (dba)3

Pd2 (dba)3

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

4,4'-Dimethoxybiphenyl
2132-80-1

4,4'-Dimethoxybiphenyl

Conditions
ConditionsYield
With cesium fluoride In hexane; ethyl acetate99%
1,4-dioxane
123-91-1

1,4-dioxane

(R)-(-)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-7,7'-dimethyl-1,1'-binaphthyl

(R)-(-)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-7,7'-dimethyl-1,1'-binaphthyl

(R)-(+)-2-diphenylphosphinyl-2'-hydroxy-7,7'-dimethyl-1,1'-binaphthyl

(R)-(+)-2-diphenylphosphinyl-2'-hydroxy-7,7'-dimethyl-1,1'-binaphthyl

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In methanol99%
1,4-dioxane
123-91-1

1,4-dioxane

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

4,4'-Dimethoxybiphenyl
2132-80-1

4,4'-Dimethoxybiphenyl

Conditions
ConditionsYield
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In hexane; ethyl acetate99%
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In hexane; ethyl acetate99%
1,4-dioxane
123-91-1

1,4-dioxane

nickel dichloride

nickel dichloride

nickel chloride dioxane adduct

nickel chloride dioxane adduct

Conditions
ConditionsYield
With trimethyl orthoformate at 65℃; for 3.5h; Heating / reflux;99%
1,4-dioxane
123-91-1

1,4-dioxane

{tetra-n-butylammonium}{osmiumnitrido(chloro)4}
42531-46-4

{tetra-n-butylammonium}{osmiumnitrido(chloro)4}

tetra-n-butylammonium octachlorodinitrido(1,4-dioxane)diosmate(VI)
136656-57-0

tetra-n-butylammonium octachlorodinitrido(1,4-dioxane)diosmate(VI)

Conditions
ConditionsYield
In acetone addn. of dioxane to soln. of Os-complex, stirring; evapn. to dryness under argon, elem. anal.;99%

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