Dimethoxane
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Dimethoxane
structure -
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CAS No:
828-00-2
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Formula:
C8H14O4
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Chemical Name:
Dimethoxane
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Synonyms:
1,3-Dioxan-4-ol,2,6-dimethyl-,4-acetate;m-Dioxan-4-ol,2,6-dimethyl-,acetate;1,3-Dioxan-4-ol,2,6-dimethyl-,acetate;6-Acetoxy-2,4-dimethyl-m-dioxane;2,6-Dimethyl-m-dioxan-4-ol acetate;Dimethoxane;Dioxin (bactericide);2,4-Dimethyl-6-acetoxy-1,3-dioxane;Giv Gard DXN-CO;Acetomethoxane;2,6-Dimethyl-m-dioxan-4-yl acetate;Dioxin;Giv Gard DXN;6-Acetoxy-2,4-dimethyl-1,3-dioxane;2,4-Dimethyl-6-m-dioxanyl acetate;Dioxin CO;6-Acetoxy-2,4-dimethyl-m-dioxane;Bioban DXN;(2,6-Dimethyl-1,3-dioxan-4-yl) acetate;2,6-Dimethyl-1,3-dioxan-4-yl acetate;DXN;37235-59-9
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CAS No:
Description
PHYSICAL DESCRIPTION: Clear light yellow to light amber slightly viscous liquid with a mustard-like odor. (NTP, 1992)
Dimethoxane is a clear light yellow to light amber slightly viscous liquid with a mustard-like odor. (NTP, 1992)
Dimethoxane is a clear light yellow to light amber slightly viscous liquid with a mustard-like odor. (NTP, 1992)|Dimethoxane is a member of dioxanes.
Dimethoxane Basic Attributes
174.19400
174.19
212-579-9
S0859MSI8I
DTXSID6020480
LIQUID|CLEAR YELLOW TO LIGHT AMBER LIQUID
Characteristics
44.76000
1.04700
Dimethoxane is a clear light yellow to light amber slightly viscous liquid with a mustard-like odor. (NTP, 1992)
1.0655 g/cm3 @ Temp: 20 °C
-7.15°C
74-75 °C @ Press: 6 Torr
52ºC
n20/D 1.433(lit.)
MISCIBLE WITH WATER, MANY ORG SOLVENTS
LD50 oral in rat: 1930mg/kg
MUSTARD-LIKE ODOR
Slowly hydrolyzes upon exposure to moisture. Water soluble.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
DIMETHOXANE is incompatible with strong acids and strong bases. (NTP, 1992)
Safety Information
III
3.2
UN 1993
36/37/38-40
S22;S26;S36
AH1350000
Xn
HYDROLYZES IN AQ SOLN TO PRODUCE ACETIC ACID & CORRESPONDING FREE ALCOHOL
P261-P281-P305 + P351 + P338
H226-H302-H315-H319-H335-H351
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
DHHS/NTP; Toxicology & Carcinogenesis Studies of Dimethoxane (Commercial Grade) in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 354 (1989) NIH Publication No. 89-2809
This chemical is combustible. (NTP, 1992)
|Warning|H226 (47.87%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 217 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P333+P313, P337+P313, P363, P370+P378, P403+P235, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicity
... Toxicology and carcinogenesis studies were conducted by administering commercial grade dimethoxane (80% pure, none of these impurities exceeded 3%) in corn oil gavage to groups of F344/N rats and B6C3F1 mice of each sex one time or 5 days/wk for ... 2 yr. ... Doses selected for the 2 yr studies were 0, 62.5, or 125 mg/kg dimethoxane in corn oil, given by gavage 5 days/wk to groups of 60 male rats; 0, 125, or 250 mg/kg to groups of 60 female rats; and 0, 250, or 500 mg/kg to groups of 58 or 60 mice of each sex. ... Conclusions: Under the conditions of these 2-year corn oil gavage studies, there was no evidence of carcinogenic activity of dimethoxane for male F344/N rats receiving 62.5 or 125 mg/kg or for female F344/N rats receiving 125 or 250 mg/kg per day. There was equivocal evidence of carcinogenic activily of dimethoxane for male B6C3Fl mice, as indicated by an increased incidence of forestomach neoplasms. There was no evidence of carcinogenic activity for female B6C3F1 mice receiving 250 or 500 mg/kg per day. ...
Dimethoxane will be released to the environment as a result of its use as a bacteriostatic and fungistatic preservative for cutting oil, resin emulsions, water-based paints, cosmetics and inks and as agasoline additive(1,2). It may also be released during its production, transport, formulation, and disposal(SRC).
TERRESTRIAL FATE: If released on soil, dimethoxane would readily leach. Based on limited data, it may biodegrade. Although information on rates are unavailable, dimethoxane may also hydrolyze. Hydrolysis of the ring would be favored under acidic conditions and ester hydrolysis would be favored under alkaline conditions. (SRC)|AQUATIC FATE: If released in water, dimethoxane would be expected to hydrolyze. Hydrolysis of the ring would be favored under acidic conditions and ester hydrolysis would be favored under alkaline conditions. Information on hydrolysis of the acetal-containing ring structure is lacking. The base-catalyzed hydrolytic half-life of the ester linkage is estimated to be 7.4 days at pH 8. Based on the results of a screening test, dimethoxane may also biodegrade. Volatilization from water and adsorption to sediment are not expected to be important fate processes. (SRC)|ATMOSPHERIC FATE: Dimethoxane will react with photochemically-produced hydroxyl radicals in the atmosphere, resulting in an estimated atmospheric half-life of 7.9 hr(1). Since dimethoxane is miscible in water(2), one would expect it to wash out in rain(SRC).
Dimethoxane hydrolyzes in water to form active aldehyde-containing compounds plus some acetic acid(1). Acetals, to which dimethoxane is related, are hydrolyzed easily by acid, but are extremely stable under basic conditions(2). The hydrolysis of the ester linkage of dimethoxane is base-catalyzed and the estimated reaction rate is 1.079 L/mol-sec(3). The half-life for the hydrolysis of this moiety of dimethoxane is therefore 74 days at pH 7 and 7.4 days at pH 8(3,SRC). No hydrolysis rates were located for dimethoxane or similar compounds. In the atmosphere, dimethoxane reacts with photochemically-produced hydroxyl radicals with an estimated rate constant of 48.9X10-12 cu cm/molecule-s at 25 °C(4). Assuming a hydroxyl radical concn of 5X10+5 radicals/cu cm, the half-life of dimethoxane in the atmosphere would be 7.9 hr(SRC).
Using an estimated log Kow of 0.49(1,SRC), one would estimate a BCF of 1.4 for dimethoxane using a recommended regression equation(2). This would indicate that dimethoxane would not bioconcentrate in aquatic organisms(2).
The Koc for dimethoxane estimated from molecular structure is 0.56(1). According to a suggested classification scheme(2), this estimated Koc indicates that dimethoxane would be highly mobile in soil.
The Henry's Law constant for dimethoxane estimated from structure activity relationships is 1.24X10-7 atm-cu-m/mol(1). Using this value of the Henry's Law constant, one would estimate a volatilization half-life of 390 days for dimethoxane from a model river 1 m deep with a 1 m/s current and a 3 m/s wind(3,SRC). Therefore dimethoxane would be essentially nonvolatile from water. The vapor pressure of dimethoxane is estimated to be 0.14 mm Hg(3). Considering this and its low adsorptivity to soil, some dimethoxane may volatilize from the soil surface(SRC).
Exposure to dimethoxane would be primarily occupational via dermal contact with products containing this chemical. The general population may be exposed to dimethoxane if they use cosmetics or other products containing this preservative. (SRC)
Drug Information
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes. It may also cause allergic sensitization. ACUTE/CHRONIC HAZARDS: This compound may cause irritation to the skin and eyes. When heated to decomposition it emits acrid smoke. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
dimethoxane
Dimethoxane Use and Manufacturing
REACTION OF 2,4-DIMETHYL-6-HYDROXY-META-DIOXANE WITH ACETIC ANHYDRIDE IN PYRIDINE|C.S. Marvel J Org Chem 4, 252 1939); Spath et al., Ber 76, 57 (1943). Description: Am Perfum Cosmet 77, no 12, 32-34 (1962), C.A. 58,8848c (1963).|CHAFETZ ET AL, US PATENT 3,036,904 (1962 TO TEXACO).
Dimethoxane is used as an antimicrobial agent in water-based paints, dyestuffs, fabric softeners, sizings, and spinning emulsions. Preservative for cutting oils, resin emulsions, water-based paints, cosmetics, inks. Effective range of concentration: 0.03-0.1%. Gasoline additive: Chafetz et al., US 3036904 (1962 to Texaco).
(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
PURITY: ...AVAIL IN US AS TECHNICAL GRADE CONTAINING 93% OF PURE CHEM. PREPN: ...WAS PREPARED IN 1943 BY REACTION OF 2,4-DIMETHYL-6-HYDROXY-META-DIOXANE WITH ACETIC ANHYDRIDE IN PYRIDINE.
1,3-Dioxan-4-ol, 2,6-dimethyl-, 4-acetate: ACTIVE|...ALSO USED TO PREVENT CONTAMINATION OF WATER-BASED PRINTING INKS & PAINTS. ... DIMETHOXANE WAS RECOMMENDED FOR USE IN COSMETICS IN PAST. IN US...REGISTERED AS ANTIMICROBIAL AGENT 'FOR MFR USE ONLY'. ...IS NOT KNOWN TO OCCUR IN NATURE.
Computed Properties
Molecular Weight:174.19
XLogP3:1.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:174.08920892
Monoisotopic Mass:174.08920892
Topological Polar Surface Area:44.8
Heavy Atom Count:12
Complexity:168
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes