4,4-Dimethyl oxazolidine

HCID 62010

Basic information

CAS
51200-87-4
Standard SMILES
CC1(C)COCN1
InChIKey
GUQMDNQYMMRJPY-UHFFFAOYSA-N
Molecular formula
C5H11NO
Average molar mass
101.15 g/mol
Monoisotopic mass
101.08406397

Names & identifiers

Preferred name
4,4-Dimethyl oxazolidine
IUPAC
4,4-dimethyl-1,3-oxazolidine
English name
4,4-Dimethyloxazolidine
Molecular formula
C5H11NO
Molecular weight
101.15

Names & synonyms

4,4-DIMETHYLOXAZOLIDINE51200-87-44,4-Dimethyl-1,3-oxazolidineOxazolidine ADimethyl oxazolidineOxadine AOxazolidine, 4,4-dimethyl-Oxaban AZoldine ZA4,4-dimethyl oxazolidineNuosept 101Oxaban-A
Show more names
SKL161notcleared4,4-dimethyloxazolidineanotclearedasinert)dimethyloxazolidineLABOTEST-BB LTBB000669
Caswell No. 374ABDTXSID0032314Truptan OX-INuosept 166Nuospet 101TRUPTAN OX96J42P99ZAEINECS 257-048-2

Database identifiers

CAS
51200-87-4
PubChem CID
62010
DTXSID
DTXSID0032314
ChEMBL
CHEMBL3560963
UNII
96J42P99ZA
EC Number
257-048-2
Nikkaji
J24.395G

Properties

Computed structural properties

XLogP
0.1
Topological polar surface area
21.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
7

Experimental & physicochemical properties

DensityBulk density = 0.99 g/mL
Color/FormColorless to slightly yellow liquid
Solubility · 2 items

Miscible with water in all proportions

Miscible with methanol, ethanol, propanol and acetone

Flash Point49 °C (120 °F) - closed cup
Boiling Point100.9 °C
DecompositionHazardous decomposition products: Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx)

Physicochemical properties

Boiling point
189.55 °C · 189.55°C (rough estimate)
Density
0.942 g/mL · 0.942 g/mL at 25 °C
refractive index
20 · n20/D 1.432
Flash point
120 °F · 120 °F
storage temp.
2 · 2-8°C, protect from light
pka
8.41 · 8.41±0.40(Predicted)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 2% (29 of 1462) of reports.

Danger

H226 (96%): Flammable liquid and vapor [Warning Flammable liquids];H302+H332 (37.3%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation];H302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (17.6%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (92.2%): Causes skin irritation [Warning Skin corrosion/irritation];H318 (97.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H332 (91.5%): Harmful if inhaled [Warning Acute toxicity, inhalation]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1462 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 29 of 1462 reports by companies.;There are 21 notifications provided by 1433 of 1462 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: Oxazolidine, 4,4-dimethyl-

Oxazolidine, 4,4-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxazolidine, 4,4-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27484

4,4-Dimethyloxazolidine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Oxazolidine, 4,4-dimethyl-: Human health tier II assessment
Hazards Summary · 1 item

A skin and severe eye irritant; Not sensitizing to guinea pig skin; Necrotic patches observed in 13-week dermal study of rats; Systemic LOAEL >100 mg/kg/day; No developmental toxicity observed in dermal study of rabbits; Mostly negative results in mutagenicity tests and not expected to be a mutagenic hazard from normal use; [Reference #1] Combustible liquid and vapor; Vapor poses an explosion hazard; A skin irritant; Causes burns to eyes; Harmful by inhalation; No allergic skin reactions observed in tests on humans; No birth defects or other developmental effects observed in experimental animals at doses maternally toxic; [Dow MSDS]

Special Reports · 1 item

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - 4,4-Dimethyloxazolidine, EPA 738-R-96-007 (August 1996). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of April 4, 2016: http://www.epa.gov/pesticides/reregistration/status.htm]

FIFRA Requirements · 2 items

Based on the reviews of the generic data for the active ingredient 4,4-dimethyloxazolidine, the Agency has sufficient information on the health effects of 4,4-dimethyloxazolidine and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that 4,4-dimethyloxazolidine products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing 4,4- dimethyloxazolidine for all current uses are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Dimethyloxazolidine is found on List C. Case No: 3095; Pesticide type: Antimicrobial; Case Status: RED Approved 6/96; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Dimethyloxazolidine; Data Call-in (DCI) Date(s): 9/3/92; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Hazard Classes and Categories · 2 items

Flam. Liq. 3 (96%);Acute Tox. 4 (97.9%);Acute Tox. 4 (17.6%);Skin Irrit. 2 (92.2%);Eye Dam. 1 (97.5%);Acute Tox. 4 (91.5%)

Acute toxicity (ingestion) - category 4;Acute toxicity (dermal) - category 4;Acute toxicity (inhalation) - category 4;Eye irritation - category 2A;Skin irritation - category 2;Skin sensitisation - category 1

Safety & protection

Fire Fighting Procedures · 3 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray to cool unopened containers.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Cleanup Methods · 1 item

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains; Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

Disposal Methods · 2 items

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.

Preventive Measures · 4 items

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Personal Protective Equipment (PPE) · 4 items

Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Complete suit protecting against chemicals. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Toxicology

Ecotoxicity Values · 5 items

LD50; Species: /Colinus virginianus/ (Bobwhite quail) oral 705 mg/kg

LC50; Species: /Lepomis macrochirus/ (Bluegill sunfish); Conditions: freshwater, static; Concentration: 59 ppm for 96 hr /77.2% active ingredient/ /from table/

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout); Conditions: freshwater, /static/; Concentration: 95 ppm for 96 hr /technical/ /from table/

LC50; Species: /Cyprinodon variegatus/ (Sheepshead minnow); Conditions: saltwater, static; Concentration: 218 (171-248) ppm for 96 hr /82% purity/ /from table/

For more Ecotoxicity Values (Complete) data for 4,4-Dimethyl oxazolidine (9 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that 4,4-dimethyl oxazolidine is expected to have very high mobility in soil(SRC). However, adsorption is affected by the acidity of the soil/substrate(SRC). The pKa of 4,4-dimethyl oxazolidine is 9.35(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. 4,4-Dimethyl oxazolidine is expected to volatilize from dry soil surfaces(SRC) based upon a estimated vapor pressure of 7.58 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2015).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that 4,4-dimethyl oxazolidine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 9.35(3) indicates 4,4-dimethyl oxazolidine will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Bioconcentration in aquatic organisms is not expected as 4,4-dimethyl oxazolidine hydrolyzes extremely rapidly in water(3). Biodegradation data in water were not available(SRC, 2015).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4,4-dimethyl oxazolidine, which has an estimated vapor pressure of 7.58 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4,4-dimethyl oxazolidine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.3 hrs(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4,4-Dimethyl oxazolidine does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Toxicity Summary · 1 item

IDENTIFICATION AND USE: 4,4-Dimethyl oxazolidine is a colorless to slightly yellow liquid. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. 4,4-Dimethyl oxazolidine is used as an antimicrobial to control bacteria and fungi in oil recovery drilling muds, packer fluids, secondary oil recovery injection water, adhesives, metalworking cutting fluids, latex paints, resin emulsions, wet-end additives and industrial processing chemicals or in specialty industrial products. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: In rats and rabbits it produced skin irritation, combined with reduced bodyweight gain in rats. In rats microscopic examination of treated skin revealed inflammation, ulceration, and acanthosis in both males and females, confirming the clinical observations of scabs on the skin and necrotic patches. Rats in the 195 mg/kg/day dosage group (dermal) showed moderate and severe skin reaction that included thickening and ulcerations, and histopathology revealed severe ulcerative response in the skin. In addition, these animals had enlarged lung, heart, liver, spleen and adrenals.Two studies showed that 4,4-dimethyl oxazolidine was tested in the Ames test with no apparent mutagenic potential in S. typhimurium strains TA-1535, TA-1537, TA-1538, TA-98 and TA-100 up to 10 ug/plate, both with or without activation. 4,4-dimethyl oxazolidine was tested in the L5178Y Mouse lymphoma assay with mutagenic potential with or without activation. Another study used 4,4-dimethyl oxazolidine in the chromosomal aberration assay in Chinese hamster ovary cells finding mutagenic potential with or without activation. When tested in the micronucleus test in mouse bone marrow, 4,4-dimethyl oxazolidine had no apparent mutagenic potential at 500 mg/kg.

Ongoing Test Status · 1 item

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of December 17, 2015: http://actor.epa.gov/dashboard/]

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4,4-dimethyl oxazolidine can be estimated to be 9(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4,4-dimethyl oxazolidine is expected to have very high mobility in soil. The pKa of 4,4-dimethyl oxazolidine is 9.35(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). However, adsorption is affected by the acidity of the soil/substrate(SRC).

Artificial Pollution Sources · 1 item

4,4-Dimethyl oxazolidine's production and use in some floor wax(1) and latex paint(2) products may result in its release to the environment through various waste streams; its use as an antimicrobial in industrial processes and water systems(3) will result in its direct release to the environment(SRC). Products containing this compound include oil recovery drilling muds, packer fluids, secondary oil recovery injection water, adhesives, metalworking cutting fluids, latex paints, resin emulsions and wet-end additives(2).

Regulatory information

Regulatory Information · 4 items

Chemical: Oxazolidine, 4,4-dimethyl-

Oxazolidine, 4,4-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxazolidine, 4,4-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27484

4,4-Dimethyloxazolidine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

FIFRA Requirements · 2 items

Based on the reviews of the generic data for the active ingredient 4,4-dimethyloxazolidine, the Agency has sufficient information on the health effects of 4,4-dimethyloxazolidine and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that 4,4-dimethyloxazolidine products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing 4,4- dimethyloxazolidine for all current uses are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Dimethyloxazolidine is found on List C. Case No: 3095; Pesticide type: Antimicrobial; Case Status: RED Approved 6/96; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Dimethyloxazolidine; Data Call-in (DCI) Date(s): 9/3/92; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Safety data

wgk
2
tsca
TSCA listed
rtecs
RP7211000
ridadr
1993
hs_code
2934999090
risk_code
10-20/21/22-36/37/38

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as antimicrobial for control of slime forming bacteria and fungi in oil recovery drilling muds and secondary injection water, packer fluids, metalworking cutting fluids, adhesives, resin emulsions, latex paints, wet-end additives, and industrial processing chemicals; [Reference #1]

Metal Machining [Category: Heat or Machine];Petroleum Production and Refining [Category: Industry];Painting (Pigments, Binders, and Biocides) [Category: Paint];Working with Glues and Adhesives [Category: Other];Using Disinfectants or Biocides [Category: Clean]

For 4,4-dimethyloxazolidine (USEPA/OPP Pesticide Code: 114801) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

4,4-Dimethyloxazolidine is an antimicrobial used in oil recovery drilling muds, packer fluids, secondary oil recovery injection water, adhesives, metalworking cutting fluids, latex paints, resin emulsions, wet-end additives/industrial processing chemicals and specialty industrial products to control bacteria and fungi.

... could be used in liquids for the production of textiles.

Antimicrobial preservatives useful in cosmetics: dimethyl oxazolidine. /From table/

U.S. Production2023: 1,141,710 lb;2022: 2,719,357 lb;2021: 823,741 lb;2020: 1,111,720 lb
Consumer UsesOther
Industry UsesOther;Binder
Formulations/Preparations · 5 items

Bioban CS-1135 Antimicrobial (Dow Chemical Company, The): Active ingredient: 4,4-dimethyloxazolidine 76.0%.

Troysan 186 Formula II (Troy Chemical Corporation): Active ingredient: 4,4-dimethyloxazolidine 68.0%.

Mergal 187 (Troy Chemical Corporation): Active ingredient: 4,4-dimethyloxazolidine 59.0%.

Troysan 192 II (Troy Chemical Corporation): Active ingredient: 4,4-dimethyloxazolidine 73.7%.

Soluble concentrate/liquid.

Household ProductsInformation on 5 consumer products that contain Dimethyl Oxazolidine in the following categories is provided:;• Inside the Home

Applications

UsesOxazolidine A is a reagent that is used inantimicrobial mixtures. It is particular useful for fighting Aspergillus brasiliensis.

Uses4,4-Dimethyl-oxazolidine is a preservative for latex paints and emulsions and for cooling fluids (component in Bioban CS 1135).

Suppliers83 total

北京华美互利生物化工010-56205725 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

9 records

Compound notes

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