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1-Aziridineethanol

1-Aziridineethanol structure

1-Aziridineethanol 

structure
  • CAS No:

    1072-52-2

  • Formula:

    C4H9NO

  • Chemical Name:

    1-Aziridineethanol

  • Synonyms:

    1-Aziridineethanol;1-(2-Hydroxyethyl)ethylenimine;N-(2-Hydroxyethyl)aziridine;N-(2-Hydroxyethyl)ethylenimine;N-(β-Hydroxyethyl)aziridine;2-(Aziridin-1-yl)ethanol;NSC 50209;1-(2-Hydroxylethyl)aziridine;2-(Aziridin-1-yl)ethan-1-ol

Description

CLEAR COLOURLESS LIQUIDClear colorless to yellow liquid.


1-aziridine ethanol is a clear colorless to yellow liquid. (NTP, 1992)


1-aziridine ethanol is a clear colorless to yellow liquid. (NTP, 1992)|2-(1-Aziridinyl)ethanol is a tertiary amine.

1-Aziridineethanol Basic Attributes

87.12

87.12

214-009-4

R20BLL91L5

50209

2810

DTXSID0024551|DTXSID5093842

Colorless liquid

2933990090

Characteristics

23.2

-1.05 (est)

1-aziridine ethanol is a clear colorless to yellow liquid. (NTP, 1992)

1.088 g/cu cm at 25 deg C

154-156 °C @ Press: 760 Torr

67°C

1.456

Miscible with water

0.49 mm Hg at 25 deg C (est)

Oral-rat LD50: 74 mg/kg; Intravenous-Mouse LD50: 56 mg/kg

Flammable; burning produces toxic nitrogen oxide fumes

Henry's Law constant = 7.8x10-10 atm-cu m/mol at 25 °C (est)

pKa = 7.8 (tertiary amine) (est)

Hydroxyl radical reaction rate constant = 2.1x10-11 cu cm/molecule-sec at 25 °C (est)

Soluble in water. Hydrolyzes to give diethanolamine (NTP, 1992).

Alcohols and Polyols

Water-Reactive

1-AZIRIDINE ETHANOL is an amino alcohol. Amines are chemical bases. They neutralize acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Safety Information

II

6.1

2922

24/25-34

26-36/37/39-45-23

CM7000000

T

Ventilated, low temperature and dry; stored separately from food materials in warehouse

P210, P260, P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P307+P311, P310, P321, P330, P332+P313, P362, P370+P378, P403+P235, P405, P501

H227

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

This chemical is combustible. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P307+P311, P310, P321, P330, P332+P313, P362, P370+P378, P403+P235, P405, and P501

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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 store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (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)

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

Irritant to skin and eyes.

Toxicity

highly toxic

LD50 Rat oral 74 mg/kg|LD50 Mouse iv 56 mg/kg|LD50 Rabbit dermal 0.71 mg/kg

2-(1-AZIRIDINYL)ETHANOL IS NOT KNOWN TO OCCUR IN NATURE.

1-Aziridineethanol's former production and use as a chemical intermediate(1,2) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.0(SRC), determined from a structure estimation method(2), indicates that 1-aziridineethanol is expected to have very high mobility in soil(SRC). However, the estimated pKa of 1-aziridineethanol is 7.8 (tertiary amine)(3), indicating that this compound will exist partially in cation form in the environment and cations generally have lower mobility in soils than their neutral counterparts(4). Volatilization of 1-aziridineethanol from moist soil surfaces is not expected to be an important fate process(SRC) because cations do not volatilize and based on an estimated Henry's Law constant of 7.8x10-10 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(5). 1-Aziridineethanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.49 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2006).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.0(SRC), determined from a structure estimation method(2), indicates that 1-aziridineethanol is not expected to adsorb to suspended solids and sediment(SRC). However, the estimated pKa of 1-aziridineethanol is 7.8 (tertiary amine)(3), indicating that this compound will exist partially in cation form in the environment and cations generally adsorb to sediment more strongly than their neutral counterparts(4). Volatilization from water surfaces is not expected(5) because cations do not volatilize and based upon an estimated Henry's Law constant of 7.8x10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). According to a classification scheme(7), an estimated BCF of 3.1(SRC), from an estimated log Kow of -1.1(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Measured hydrolysis data were not located for 1-aziridineethanol. However, the measured hydrolysis rate constant of the structurally similar compound ethylenimine is 5.2X10-7 sec-1 at 25 °C(10), which corresponds to a half-life of 15 days. Biodegradation data were not available(SRC, 2006).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-aziridineethanol, which has an estimated vapor pressure of 0.49 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-aziridineethanol 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 6 hours(SRC), calculated from its rate constant of 2.1x10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Aziridineethanol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 1-aziridineethanol with photochemically-produced hydroxyl radicals has been estimated as 2.1x10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Measured hydrolysis data were not located for 1-aziridineethanol. However, the measured hydrolysis rate constant of the structurally similar compound ethylenimine is 5.2X10-7 sec-1 at 25 °C(2), which corresponds to a half-life of 15 days. 1-Aziridineethanol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3.1 was calculated for 1-aziridineethanol(SRC), using an estimated log Kow of -1.1(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-aziridineethanol can be estimated to be 2.0(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-aziridineethanol is expected to have very high mobility in soil. However, the estimated pKa of 1-aziridineethanol is 7.8 (tertiary amine)(3), indicating that this compound will exist partially in cation form in the environment and cations generally have lower mobility in soil than their neutral counterparts(4).

The Henry's Law constant for 1-aziridineethanol is estimated as 7.8x10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). The pKa of 1-aziridineethanol is 7.8 (tertiary amine)(2), indicating that this compound will exist partially as a cation in the environment. Based on this Henry's Law constant and the fact that anions do not volatilize, 1-aziridineethanol is expected to be essentially nonvolatile from moist soil or water surfaces(3). 1-Aziridineethanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.49 mm Hg(SRC), determined from a fragment constant method(4).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 442 workers (63 of these are female) were potentially exposed to 1-aziridineethanol in the US(1). Occupational exposure to 1-aziridineethanol may have occured through inhalation and dermal contact with this compound at workplaces where 1-aziridineethanol was produced or used(SRC).

Drug Information

SYMPTOMS: Chronic exposure to this compound can produce liver damage. ACUTE/CHRONIC HAZARDS: This compound is an irritant to the skin, nose, mucous membranes and eyes. When heated to decomposition this compound emits toxic fumes. (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: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. 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. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin bums with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/SIGNS AND SYMPTOMS/ Toxic. Irritant to skin and eyes.

1-Aziridineethanol Use and Manufacturing

Uses

Chemical intermediate.

Production

(1973) MORE THAN 4.54X10+7 GRAMS (CONSUMPTION)|(1975) No Data|(1986) 10 thousand-500 thousand pounds|(1990) 10 thousand-500 thousand pounds

1-Aziridineethanol: INACTIVE|1-Aziridineethanol, homopolymer: INACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|It has been tested as insect chemosterilant...but it is not used commercially...because of problems association with...application to insects...toxicity and environmental effects.

CHROMATOGRAPHIC SEPARATION ON ION-EXCHANGE RESINS .../&/ GAS-LIQ CHROMATOGRAPHY...HAVE BEEN DESCRIBED; SHIMOMURA ET AL, "LIQ-EXCHANGE CHROMATOGRAPHY OF AZIRIDINES & ETHANOLAMINES," ANALYT CHEM 45, 501-505, 1973; ZAGER ET AL, "THE PHARMACOLOGY OF 2-AZIRIDINYL ETHANOL," J PHARMACOL EXP THER, 166: 205-216, 1969.

Computed Properties

Molecular Weight:87.12
XLogP3:-0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:87.068413911
Monoisotopic Mass:87.068413911
Topological Polar Surface Area:23.2
Heavy Atom Count:6
Complexity:42.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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