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123-91-1

Basic Information
CAS No.: 123-91-1
Name: 1,4-Dioxane
Article Data: 152
Cas Database
Molecular Structure:
Molecular Structure of 123-91-1 (1,4-Dioxane)
Formula: C4H8O2
Molecular Weight: 88.1063
Synonyms: Diethylene dioxide;p-Dioxan;NCI-C03689;1, 4-Diethylene dioxide;Silane,[1,3-dioxan-5-ylidenebis(methyleneoxy)]- bis-;Diossano-1,4;Dioxane;Dioxan-1, 4;Diethylene ether;1,4-Dioxan;Di (ethylene oxide);Tetrahydro-p-dioxin;Dioxaan-1,4;Tetrahydro-1,4-dioxin;Glycol ethylene ether;Dioxanne;Dioksan;Dioxane-1,4;Diokan;Dioxan;p-dioxane;Dioxyethylene ether;
EINECS: 204-661-8
Density: 0.995 g/cm3
Melting Point: 12 °C
Boiling Point: 102.9 °C at 760 mmHg
Flash Point: 12.2 °C
Solubility: soluble in water
Appearance: colourless liquid
Hazard Symbols: FlammableF,HarmfulXn
Risk Codes: 45-46-11-36/38-48/23/24/25-65-66-40-36/37-19-41-37/38-39/23/24/25-23/24/25-48/20/22-38-22-36/37/38
Safety: 9-16-36/37-46-45-53-7-62-26-24/25-23
Transport Information: UN 1993 3/PG 2
PSA: 18.46000
LogP: 0.03320
Synthetic route

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

A

123-91-1

1,4-dioxane

B

110-71-4

1,2-dimethoxyethane

C

115-10-6

Dimethyl ether

D

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%
75-21-8

oxirane

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;
107-21-1

ethylene glycol

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%
111-46-6

diethylene glycol

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;
112-27-6

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

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;
105-53-3

diethyl malonate

A

123-91-1

1,4-dioxane

B

1068-90-2

2-acetylaminomalonic acid diethyl ester

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

diethylene glycol dimethyl ether

A

123-91-1

1,4-dioxane

B

115-10-6

Dimethyl ether

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

ethylene glycol

A

123-91-1

1,4-dioxane

B

107-20-0

2-chloroethanal

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

ethylene glycol

A

123-91-1

1,4-dioxane

B

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;
107-21-1

ethylene glycol

A

497-26-7

2-methyl-1,3-dioxolane

B

123-91-1

1,4-dioxane

C

75-07-0

acetaldehyde

D

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
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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 201.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 11 , 1976,p. 247.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (oral); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-80 ,1978. . EPA Genetic Toxicology Program. Glycol ether compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 25 ppm (skin)
ACGIH TLV: TWA 20 ppm (skin); Confirmed Animal Carcinogen with Unknown Revelance to Humans
DFG MAK: 20 ppm (73 mg/m3); Not Classifiable as a Human Carcinogen
NIOSH REL: CL (Dioxane) 1 ppm/30M
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Dioxane (CAS NO.123-91-1), 1602.

Specification

The CAS registry number of Dioxane is 123-91-1. The IUPAC name is 1,4-dioxane. Its EINECS registry number is 204-661-8. In addition, the molecular formula is C4H8O2 and the molecular weight is 88.11. It is a kind of colourless liquid and belongs to the classes of Pharmaceutical Intermediates; Organics; API Intermediates; Dioxanes; Dioxanes & Dioxolanes; DioxanesCosmetics; Allergens; Alpha Sort; D; DAlphabetic; DIO - DIZEnvironmental Standards.

Physical properties about this chemical are: (1)ACD/LogP: -0.27; (2)ACD/LogD (pH 5.5): -0.27; (3)ACD/LogD (pH 7.4): -0.27; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 16.97; (7)ACD/KOC (pH 7.4): 16.97; (8)#H bond acceptors: 2; (9)Polar Surface Area: 18.46 Å2; (10)Index of Refraction: 1.404; (11)Molar Refractivity: 21.65 cm3; (12)Molar Volume: 88.5 cm3; (13)Polarizability: 8.58 ×10-24cm3; (14)Surface Tension: 31.2 dyne/cm; (15)Density: 0.995 g/cm3; (16)Flash Point: 12.2 °C; (17)Enthalpy of Vaporization: 34.16 kJ/mol; (18)Boiling Point: 102.9 °C at 760 mmHg; (19)Vapour Pressure: 38.2 mmHg at 25°C.

Preparation of Dioxane: it is produced by the acid-catalysed dehydration of diethylene glycol, which in turn arises from the hydrolysis of ethylene oxide. And it can be prepared by ethane-1,2-diol. This reaction will need catalyst Nafion-H. The reaction time is 5 hours at reaction temperature of 135 °C. The yield is about 50%.

Dioxane can be prepared by ethane-1,2-diol

Uses of Dioxane: it is an occasionally used solvent for a variety of practical applications as well as in the laboratory. And it can be used to get [1,4]dioxan-2-one. This reaction will need reagents Me3SiONO2 and CrO3 and solvent acetonitrile. The reaction time is 24 hours at ambient temperature. The yield is about 53%.

Dioxane can be used to get [1,4]dioxan-2-one

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and irritating to eyes, skin and respiratory system. And it has danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed. It may cause cancer, heritable genetic damage and lung damage if swallowed. Avoid exposure - obtain special instruction before use. During using it, wear suitable protective clothing and gloves and avoid contact with skin and eyes. You should not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer). If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If swallowed, do not induce vomiting, you should seek medical advice immediately and show this container or label. Keep container tightly closed. Keep container in a well-ventilated place. When store it, keep away from sources of ignition-No smoking.

You can still convert the following datas into molecular structure:
(1)SMILES: O1CCOCC1
(2)InChI: InChI=1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
(3)InChIKey: RYHBNJHYFVUHQT-UHFFFAOYAN

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LCLo inhalation 44gm/m3/7H (44000mg/m3) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
"Beitrag zur Toxikologischen Wirkung Technischer Losungsmittel, Dissertation," Klimmer, O., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1937Vol. -, Pg. -, 1937.
cat LD50 oral 2gm/kg (2000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 21, Pg. 173, 1939.
cat LDLo intravenous 1500mg/kg (1500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: IRRITABILITY
Journal of Hygiene. Vol. 35, Pg. 540, 1935.
guinea pig LD50 oral 3150mg/kg (3150mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
human LCLo inhalation 470ppm/3D (470ppm) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LIVER: OTHER CHANGES
Pollution Engineering. Vol. 7(9), Pg. 22, 1975.
human TCLo inhalation 470ppm (470ppm) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: OTHER CHANGES
AMA Archives of Industrial Health. Vol. 20, Pg. 445, 1959.
human TCLo inhalation 5500ppm/1M (5500ppm) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Public Health Reports. Vol. 45, Pg. 2023, 1930.
mammal (species unspecified) LC50 inhalation 20500mg/m3 (20500mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse LC50 inhalation 37gm/m3/2H (37000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 63, 1982.
mouse LD50 intraperitoneal 790mg/kg (790mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 6, Pg. 342, 1947.
mouse LD50 oral 5300mg/kg (5300mg/kg)   Indian Journal of Experimental Biology. Vol. 16, Pg. 54, 1978.
rabbit LD50 oral 2gm/kg (2000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 21, Pg. 173, 1939.
rabbit LD50 skin 7600uL/kg (7.6mL/kg)   Union Carbide Data Sheet. Vol. 12/17/1971,
rabbit LDLo intravenous 1500mg/kg (1500mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Journal of Hygiene. Vol. 35, Pg. 540, 1935.
rat LC50 inhalation 46gm/m3/2H (46000mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Kosmicheskaya Biologiya I Aviakosmicheskaya Meditsina. Space Biology and Aerospace Medicine. Vol. 11(6), Pg. 53, 1977.
rat LD50 intraperitoneal 799mg/kg (799mg/kg)   Environmental Research. Vol. 40, Pg. 411, 1986.
rat LD50 oral 4200mg/kg (4200mg/kg)   Industrial Health. Vol. 32, Pg. 145, 1994.