5-Nitrothiazol-2-ylamin

log Kow = 0.83

0.89

less than 1 mg/mL at 68 °F (NTP, 1992)

Very sparingly soluble in water; almost insoluble in chloroform; 1 g dissolves in 150 g of 95% alcohol; in 250 g ether; soluble in dilute mineral acids

396 °F (decomposes) (NTP, 1992)

202 °C (decomposes)

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 solid; [Merck Index] Yellow crystalline powder; [Alfa Aesar MSDS]

Warning

H302 (89.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 65 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 2-Thiazolamine, 5-nitro-

Status: Active Update: 10-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/19516

2-Thiazolamine, 5-nitro-: 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.

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.

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.

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.

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.

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.

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

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 following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=121-66-4]

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.

2-Amino-5-nitrothiazole

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 31: (1983) Some Food Additives, Feed Additives and Naturally Occurring Substances

1987

1987

2-Amino-5-nitrothiazole

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).

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).

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 50 male and 50 female B6C3F1 hybrid mice, 53 days of age, were fed diets containing 50 or 100 mg/kg ... for 104 wk ... 50 mice of each sex served as matched controls. No significant dose-related trend in mortality was seen for animals of either sex by the end of the study ... No significant increase in the incidence of tumors in treated mice of either sex was observed when compared with controls.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ...35 weanling female Sprague-Dawley rats were fed diet containing ... 1140 mg/kg for 1 wk, then 750 mg/kg until 9th wk, then 1000 mg/kg until 46th wk, followed by control diet until end of study at 66 wk (total cumulative dose per rat, 4.6 g) ... 39 weanling female rats ... /were/ controls. Long-acting penicillin was administered im to all rats to control infection. Rats ... exhibited initial growth retardation which required reduction of dose and continued to weigh about 15% less than control rats ... No significant survival difference was seen at 66 wk. 7 solitary mammary fibroadenomas and 1 mammary adenocarcinoma were observed in 8/35 treated rats and 2 fibroadenomas in 39 controls ... 6/35 treated animals developed renal pelvis hyperplasia, 2/35 renal pelvis transitional-cell carcinomas, and 2/35 pulmonary alveolar-cell carcinomas. [The working group noted the short duration of this experiment.]

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 50 male and 50 female Fischer 344 rats, 50 days of age, were fed diets containing 300 or 600 mg/kg ... for 110 wk, followed by 1 wk of control diet ... 50 rats of each sex /were/ controls. In male rats, there was a dose-related trend in mortality by the end of the study. Statistically significant increases in tumor incidence were observed for the following neoplasms: (1) dose-related trends ... in incidences of malignant lymphomas, lymphocytic leukemias, and undifferentiated leukemias in males ... (b) dose-related trend in the incidence of granulocytic leukemia in males ... (c) dose-related trend ... in the incidence of chromophobe adenomas of the pituitary gland in ... females ... and males /treated and controls/ ... (d) higher incidence of endometrial stromal polyps of uterus in low-dose females ... than ... controls. [The working group noted that the average incidence of pituitary gland tumors in historical control groups was 40% in females and 20.3% in males and the average incidence of endometrial stromal polyps in female Fischer rats was 12.7-14.9%.]

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ 2-amino-5-nitrothiazole (ANT), along with several other nitroheterocyclic compounds with relatively low single-electron redox potential, was tested for embryotoxicity in cultured rat embryos. The effects were compared with those of other 5-membered heterocycles. Sprague-Dawley rat embryos were explanted on day 10 of gestation and grown in culture medium to which the test compounds were added. After 26 hr in culture, the embryos were removed and examined for malformations. Six of the 7 embryos cultured were viable after exposure to 1 mM concentration of ANT and all six were abnormal. Five exhibited bilateral prosencephalic hypoplasia and one had abnormal rotation of flexure. Growth parameters were significantly lower than controls, but ANT failed to elicit axial asymmetry.

For more Non-Human Toxicity Excerpts (Complete) data for 2-Amino-5-nitrothiazole (8 total), please visit the HSDB record page.

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).

2-Amino-5-nitrothiazole's production and use in synthesis and as a veterinary medication may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 5.0X10-5 mm Hg at 25 °C indicates 2-amino-5-nitrothiazole will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase 2-amino-5-nitrothiazole will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 80 days. Particulate-phase 2-amino-5-nitrothiazole will be removed from the atmosphere by wet or dry deposition. 2-Amino-5-nitrothiazole contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 2-amino-5-nitrothiazole is expected to have high mobility based upon an estimated Koc of 60. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 5.3X10-12 atm-cu m/mole. If released into water, 2-amino-5-nitrothiazole is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. 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)

Used to treat parasitic infections in turkeys and pigeons; [Merck Index] Formerly used as an additive to turkey feed (approval cancelled in 1980) and in the synthesis of nithiazide, niridazole, and atrican; [HSDB]

HAS BEEN USED IN SYNTH OF NITHIAZIDE, NIRIDAZOLE, ATRICAN

THERAPEUTIC CATEGORY: Antihistomonad in turkeys. For trichomoniasis in pigeons

MEDICATION

MEDICATION (VET)

(1975) No Data

(1977) No Data

(1975) No Data

(1977) No Data

(1975) No Data

(1977) No Data

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4710]

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.

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.