2-Amino-5-nitrothiazole
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2-Amino-5-nitrothiazole
structure -
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CAS No:
121-66-4
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Formula:
C3H3N3O2S
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Chemical Name:
2-Amino-5-nitrothiazole
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Synonyms:
2-Thiazolamine,5-nitro-;Thiazole,2-amino-5-nitro-;5-Nitro-2-thiazolamine;2-Amino-5-nitrothiazole;Enheptin;Entramin;5-Nitro-2-thiazolylamine;Amnizol soluble;Enheptin T;Nitramin IDO;5-Nitro-2-aminothiazole;2-Amino-5-nitro-1,3-thiazole;2-Amino-4-nitrothiazole;NSC 4;5-Nitro-thiazole-2-ylamine;8017-93-4;8023-00-5
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CAS No:
Description
greenish yellow, to orange or brown powderGreenish-yellow to orange-yellow fluffy powder or a brown chunky powder. Slightly bitter taste. Used as a veterinary medicine.
Greenish-yellow to orange-yellow fluffy powder or a brown chunky powder. Slightly bitter taste. Used as a veterinary medicine.
Greenish-yellow to orange-yellow fluffy powder or a brown chunky powder. Slightly bitter taste. Used as a veterinary medicine.|2-Amino-5-nitrothiazole is a member of thiazoles and a C-nitro compound.
2-Amino-5-nitrothiazole Basic Attributes
145.14
145.14
126797
204-490-9
1GR77A37Z5
4
2811
DTXSID6020066
Greenish-yellow to orange-yellow fluffy powder
29341000
Characteristics
113
0.8
Yellow Powder
1.583 (estimate)
202 °C (decomp)
345.1±15.0 °C(Predicted)
162.5±20.4 °C
1.6740 (estimate)
H2O: <0.1 g/100 mL at 20 ºC;95% ethanol: soluble 1g/150g at 20°C
Refrigerator
5.0X10-5 mm Hg at 25 deg C (est)
Peritoneal-mouse LD50: 200 mg/kg
Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes
Slightly bitter
Henry's Law constant = 5.34X10-12 atm-cu m/mol at 25 °C (est)
When heated to decomposition it emits very toxic fumes of NOx and SOx|Hydroxyl radical reaction rate constant = 2.0X10-13 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Amines, Phosphines, and Pyridines
2-AMINO-5-NITROTHIAZOLE may be sensitive to light. Incompatible with nitric acid and sulfuric acid. Also incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides. A preparative hazard (NTP, 1992).
Safety Information
2811
3
22-36/37/38-40-20/21/22
26-45-24/25-36/37
XJ2800000
Xn,Xi
Treasury is ventilated and dried at low temperature; stored separately from sulfuric acid and nitric acid
Irritant
Stable. Incompatible with strong acids, strong oxidizing agents, acid chlorides, acid anhydrides.
P301 + P312 + P330-P305 + P351 + P338
H302-H315-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.
Incompatible with /nitric and sulfuric acids/.
DHEW/NCI; Bioassay of 2-Amino-5-nitrothiazole for Possible Carcinogenicity (1978) Technical Rpt Series No. 53 DHEW Pub No. (NIH) 78-1359
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
|Warning|H302 (88.71%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 62 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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 spill this chemical, you should dampen the solid spill material with 5% acetic acid, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% acetic acid to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% acetic acid followed by washing 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 protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)
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)|Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Safety glasses with side-shields conforming to EN166
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
Accidental release measures. Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.
Avoid breathing dust/fume/gas/mist/vapors/spray. Wash skin thoroughly after handling.|Do not eat, drink or smoke when using this product.|Use only outdoors or in a well-ventilated area.|Handle with gloves. Choose body protection according to the amount and concentration of the dangerous substance at the work place.|For more Preventive Measures (Complete) data for 2-Amino-5-nitrothiazole (6 total), please visit the HSDB record page.
Toxicity
highly toxic
LD50 Mouse ip 200 mg/kg
A bioassay of 2-amino-5-nitrothiazole for possible carcinogenicity was conducted by administering the test chemical in feed to Fischer 344 rats and B6C3F1 mice. Groups of 50 rats and 50 mice of each sex were fed 2-amino-5-nitrothiazole at one of the following doses, either 300 or 600 ppm for rats, and either 50 or 100 ppm for mice. The rats were dosed for 110 wk, followed by 1 wk of observation; the mice were dosed for 104 wk. Matched controls consisted of 50 untreated rats and 50 untreated mice of each sex. All surviving rats were /sacrificed/ at wk 111, all surviving mice at wk 104. The mean body weights of the groups of rats and mice fed 2-amino-5-nitrothiazole in the diet were slightly lower than those of controls throughout most of the period of admin. No other clinical signs related to admin of the chemical were noted. There was a dose related trend in mortality only in the male rats; however, sufficient numbers of rats were at risk in all groups for development of late appearing tumors. In male rats, there was a significant dose related trend (p=0.044) in the incidence of malignant lymphomas, lymphocytic leukemias, or undifferentiated leukemias, although the results of direct comparisons of incidences in each of the dosed groups with those in controls were not significant. There was also a significant dose related trend in the incidence of granulocytic leukemia in the male rats (p=0.014) and a significantly incr incidence of this tumor (p=0.023) in the high dose group (matched controls 2/50, low dose 4/50, high dose 9/49). When the incidences of all neoplasms of the hematopoietic system (lymphomas and leukemias) were combined, greater significance was attained for both the dose related trend (p=0.001) and direct comparison (p=0.002) of the incidence of the high dose group with that of matched controls (controls 13/50, low dose 9/50, high dose 28/49). The reliability of the incidence of hematopoietic tumors in the male controls was supported by that for male controls observed in a similar bioassay of another test chemical at the same laboratory (13/50). The incidences of the combined hematopoietic tumors in dosed female rats were not significant when compared with the incidence in the matched controls. In female rats, there was a significant dose related trend in the incidence of chromophobe adenomas of the pituitary (p=0.016) and a higher incidence (p=0.021) in the high dose group than in matched controls (controls 19/45, low dose 29/47, high dose 29/44). The incidence of this lesion in dosed male rats was much lower than that in dosed females, and the dose related trend (p=0.48) was only marginally significant (controls 3/46, low dose 3/45, high dose 8/43). The incidences of chromophobe adenomas of the pituitary which were observed in control groups of rats used in a similar bioassay of another test chemical at the same laboratory were 13/49 (27%) for the males and 26/50 (52%) for the females. Because of the variability in incidences of the tumor among different control groups, the occurrence of chromophobe adenomas of the pituitary in the dosed female rats cannot be clearly associated with admin of the /test cmpd/. Also in femalerats there was a higher incidence of endometrial stomal polyps of the uterus in the low dose group (p=0.023) than in the matched controls (controls 2/50, low dose 9/49, high dose 3/50). Since, however, only three high dose animals had this tumor, the occurrence of uterine tumors in the low dose group cannot clearly be associated with admin of the test chemical. In mice, no neoplasms were observed at a statistically significant incidence in the dosed groups when compared with controls. It is concluded It is concluded that under the conditions of this bioassay, the occurrence of tumors of the hematopoietic system, ie, lymphoma and granulocytic leukemia, in dosed male Fischer 344 rats was associated with administration of 2-amino-5-nitrothiazole. /The cmpd/ was not carcinogenic in female Fischer 344 rats or in male or female B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
2-Amino-5-nitrothiazole's production and use in synthesis(1) and as a veterinary medication(2) may result in its release to the environment through various waste streams.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrothiazole is expected to have high mobility in soil(SRC). Volatilization of 2-amino-5-nitrothiazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.3X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Amino-5-nitrothiazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrothiazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.3X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.83(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Amino-5-nitrothiazole is not expected to hydrolyze in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-amino-5-nitrothiazole, which has an estimated vapor pressure of 5.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-amino-5-nitrothiazole 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 80 days(SRC), calculated from its rate constant of 2.0X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-amino-5-nitrothiazole may be removed from the air by wet or dry deposition(SRC). 2-Amino-5-nitrothiazole contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 2-amino-5-nitrothiazole with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 80 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Amino-5-nitrothiazole is not expected to hydrolyze in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Amino-5-nitrothiazole contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for 2-amino-5-nitrothiazole(SRC), using a log Kow of 0.83(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 2-amino-5-nitrothiazole can be estimated to be 60(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-amino-5-nitrothiazole is expected to have high mobility in soil.
The Henry's Law constant for 2-amino-5-nitrothiazole is estimated as 5.3X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-amino-5-nitrothiazole is expected to be essentially nonvolatile from water surfaces(2). 2-Amino-5-nitrothiazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.0X10-5 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to 2-amino-5-nitrothiazole may occur through dermal contact with this compound at workplaces where 2-amino-5-nitrothiazole is produced or used. (SRC)
Drug Information
Radiation-Sensitizing Agents|/Experimental therapy/ 2-amino-5-nitrothiazole was evaluated as a hypoxic radiosensitizer using bacteria. The findings suggests that nitrothiazoles might be an interesting class of nitroheterocyclic radiosensitizers, but molecules with increased solubility & improved pharmacokinetics would be necessary for efficacy in vivo.|(VET): Antihistomonad in turkeys. For trichomoniasis in pigeons.
VET: Do not give to egg laying birds.
SYMPTOMS: Symptoms of exposure to this compound may include irritation. ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion, inhalation or skin absorption. It may cause irritation. It is a positive animal carcinogen. When heated to decomposition it emits very toxic fumes of carbon monoxide, carbon dioxide, nitrogen oxides and sulfur oxides. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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)
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
2-amino-5-nitrothiazole
2-Amino-5-nitrothiazole Use and Manufacturing
DEACETYLATION OF 2-ACETAMIDO-5-NITROTHIAZOLE|Prepared by deacetylation of 2-acetamido-5-nitrothiazole: Hubbard; Steahly, US patents 2,573,641; 2,573,656-7 (all 1951 to Monsanto).|Early production of /2-Amino-5-nitrothiazole/ was based on nitration of 2-acetylaminothiazole and careful hydrolysis. Direct nitration of 2-aminothiazole gives a cleaner product and is best achieved by adding 2-aminothiazole nitrate to concentrated sulfuric acid at 0 - 10 °C. This process and the nitration of o-anisidine are the only large-scale processes based on rearrangement of an amine nitrate, and both are potentially hazardous due to the possibility of runaway exothermic reactions.
Used as an important intermediate for the preparation of azo heterocyclic dyes
(1975) No Data|(1977) No Data|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4712]
ENHEPTIN PREMIX, NITRAMIN, NITRAMINE
2-Thiazolamine, 5-nitro-: INACTIVE|To make water solution 15% stock solution in propylene glycol should first be prepared.|DO NOT GIVE TO EGG LAYING BIRDS. ALARMING, BUT HARMLESS, PINK DROPPINGS MAY BE NOTED DURING THERAPY. DISCONTINUE FEEDING AT LEAST 1 WK BEFORE SLAUGHTERING TREATED BIRDS TO AVOID UNDESIRABLE TISSUE RESIDUES IN FOOD FOR HUMAN CONSUMPTION.|ON 14 NOV 1980, US FOOD & DRUG ADMIN ANNOUNCED WITHDRAWAL OF ITS APPROVAL OF USE OF A PREMIX CONTAINING 2-AMINO-5-NITROTHIAZOLE IN TURKEY FEED (...ORIGINALLY APPROVED IN 1950) AS AN AID IN PREVENTION OF BLACKHEAD.
2-AMINO-5-NITROTHIAZOLE IN FEED, SPECTROPHOTOMETRY AT 388.5 NM.
Computed Properties
Molecular Weight:145.14
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:144.99459752
Monoisotopic Mass:144.99459752
Topological Polar Surface Area:113
Heavy Atom Count:9
Complexity:125
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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