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5-Nitrothiazol-2-ylamin
5-Nitrothiazol-2-amine · ENHEPTIN · ENHEPTYNE · 5-NITRO-1,3-THIAZOL-2-AMINE · Nitazoxanide Related Compound A (25 mg) (2-Amino-5-nitrothiazole) · NSC 4 · entramin · AKOS 203
Identifikatoren & physikalische Daten
| CAS No. | 121-66-4 |
|---|---|
| Summenformel | C3H3N3O2S |
| Durchschnittliche Molmasse | 145,14 g/mol |
| Monoisotopische Masse | 144,99459734 g/mol |
| SMILES | Nc1ncc([N+](=O)[O-])s1 |
| InChIKey | MIHADVKEHAFNPG-UHFFFAOYSA-N |
| PubChem CID | 8486 |
| ChEMBL | CHEMBL408049 |
| ChEBI | CHEBI:82386 |
| EC No. | 204-490-9 |
| DTXSID | DTXSID6020066 |
| Lokaler Name | 5-Nitrothiazol-2-ylamin |
Chemische & physikalische Eigenschaften
| XLogP | 0,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 113 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 125 |
| Stoffklassen | Nitrogen Compounds -> Thiazoles |
| LogP (Verteilungskoeffizient) | log Kow = 0.830.89 |
| Geschmack | Slightly bitter |
| Color/Form | Greenish-yellow to orange-yellow fluffy powder |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Very sparingly soluble in wateralmost insoluble in chloroform1 g dissolves in 150 g of 95% alcoholin 250 g ethersoluble in dilute mineral acids95% ethanol: soluble1g/150g at 20°C<0.1 g/100 mL at 20 ºC |
| Decomposition | When heated to decomposition it emits very toxic fumes of /nitroxides and sulfuric acid/. |
| Schmelzpunkt | 396 °F (decomposes) (NTP, 1992)202 °C (decomposes)195-200 °C (dec.) (lit.) |
| Dampfdruck | 0.000743 [mmHg] |
| Physical Description | 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] |
| Other Experimental Properties | When heated to decomposition it emits very toxic fumes of NOx and SOx |
| Siedepunkt | 345.1±15.0 °C(Predicted) |
| Dichte | 1.583 (estimate) |
| Brechungsindex | 1.6740 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,2-8°C |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 1.26±0.10(Predicted) |
| Farbe | Yellow |
| Merck | 14,457 |
| BRN | 126797 |
| Henry-Konstante | 1.9×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong acids, strong oxidizing agents, acid chlorides, acid anhydrides. |
| InChI | 1S/C3H3N3O2S/c4-3-5-1-2(9-3)6(7)8/h1H,(H2,4,5) |
| InChIKey | MIHADVKEHAFNPG-UHFFFAOYSA-N |
| SMILES | Nc1ncc(s1)[N+]([O-])=O |
| CAS Datenbank | 121-66-4(CAS DataBase Reference) |
| EPA chemische Informationen | 2-Amino-5-nitrothiazole (121-66-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (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. |
|---|---|
| Regulatorische Informationen | Chemical: 2-Thiazolamine, 5-nitro-Status: Active Update: 10-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/195162-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. |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Thiazolamine, 5-nitro-: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include irritation. |
| Gefahrenübersicht | Emergency treatment: Symptomatic drug ingestion[HSDB] No evidence for carcinogenicity in mice or female rats, but evidence for carcinogenicity in male rats[NTP] A skin and strong eye irritant[Alfa Aesar MSDS] |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| Special Reports | DHEW/NCIBioassay of 2-Amino-5-nitrothiazole for Possible Carcinogenicity (1978) Technical Rpt Series No. 53 DHEW Pub No. (NIH) 78-1359 |
| Reactivity Profile | 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). |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (89.2%) |
| Hazardous Reactivities and Incompatibilities | Incompatible with /nitric and sulfuric acids/. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| Erste Hilfe | 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. |
| Brandbekämpfungsverfahren | 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. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. |
| Reinigungsverfahren | 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. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations. |
| Preventive Measures | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | 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 |
| Umweltverhalten | 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). |
| Ongoing Test Status | 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] |
| Soil Adsorption/Mobility | 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. |
| Artificial Pollution Sources | 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. |
| Carcinogen Classification | 2-Amino-5-nitrothiazoleGroup 3: Not classifiable as to its carcinogenicity to humansVolume 31: (1983) Some Food Additives, Feed Additives and Naturally Occurring Substances1987 |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/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). |
| Non-Human Toxicity Excerpts | /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. |
| Evidence for Carcinogenicity | No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans. |
| Environmental Abiotic Degradation | 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). |
| Probable Routes of Human Exposure | 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) |
| Environmental Fate/Exposure Summary | 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 radicalsthe 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) |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29341000 |
| RTECS-Nr. | XJ2800000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 121-66-4(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
2-Amino-5-nitrothiazole was used as diazo component in the synthesis of monoazo disperse dyes. It was used as matrix during matrix-assisted laser desorption/ionization time-of-flight mass spectrometric study of oligonucleotide and protein.