1-(1-NAPHTHYL)-2-THIOUREA CAS 86-88-4
Introduction：Basic information about 1-(1-NAPHTHYL)-2-THIOUREA CAS 86-88-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
1-(1-NAPHTHYL)-2-THIOUREA Basic information
| Product Name: | 1-(1-NAPHTHYL)-2-THIOUREA |
| Synonyms: | 1-(1-naphthyl)-2-thio-ure;1-(1-naphthyl)thiourea;1-Naftil-tiourea;1-Naftylthioureum;1-naphthalenyl-thioure;1-Naphthalenylthiourea;1-Naphthyl-thioharnstoff;1-Naphthyl-thiouree |
| CAS: | 86-88-4 |
| MF: | C11H10N2S |
| MW: | 202.28 |
| EINECS: | 201-706-3 |
| Product Categories: | Sulphur Derivatives |
| Mol File: | 86-88-4.mol |
1-(1-NAPHTHYL)-2-THIOUREA Chemical Properties
| Melting point | 193 °C |
| Boiling point | 377.6±25.0 °C(Predicted) |
| density | 1.333 |
| refractive index | 1.5500 (estimate) |
| storage temp. | Poison room |
| solubility | 4.3 and 86 g/L in acetone and triethylene glycol, respectively (Windholz et al., 1983) |
| pka | 13.12±0.70(Predicted) |
| form | Crystals or Crystalline Powder |
| color | Grayish to beige-brown |
| Odor | bitter taste |
| Water Solubility | 600 mg/L at 20 °C (quoted, Windholz et al., 1983) |
| Merck | 14,722 |
| BRN | 778118 |
| Exposure limits | NIOSH REL: TWA 0.3 mg/m3, IDLH 100 mg/m3; OSHA PEL: TWA0.3 mg/m3 |
| Major Application | agriculture environmental |
| InChI | 1S/C11H10N2S/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14) |
| InChIKey | PIVQQUNOTICCSA-UHFFFAOYSA-N |
| SMILES | NC(=S)Nc1cccc2ccccc12 |
| CAS DataBase Reference | 86-88-4(CAS DataBase Reference) |
| IARC | 3 (Vol. 30, Sup 7) 1987 |
| EPA Substance Registry System | .alpha.-Naphthylthiourea (86-88-4) |
Safety Information
| Hazard Codes | T+ |
| Risk Statements | 28-40 |
| Safety Statements | 28-36/37-45-25-23 |
| OEB | C |
| OEL | TWA: 0.3 mg/m3 |
| RIDADR | 1651 |
| WGK Germany | 2 |
| RTECS | YT9275000 |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | I |
| HS Code | 29309090 |
| Storage Class | 6.1A - Combustible, acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 2 Oral Carc. 2 |
| Hazardous Substances Data | 86-88-4(Hazardous Substances Data) |
| Toxicity | Acute oral LD50 for Norwegian rats 6–8 mg/kg (Hartley and Kidd, 1987). |
| IDLA | 100 mg/m3 |
| Description | a-Naphthylthiourea (ANTU; also called DIRAX) is toxic byinhalation, ingestion, or skin contact. Due to its very narrowspectrum of activity, production was discontinued a long timeago. Exposure to ANTU causes pulmonary edema; therefore, itis often used as an experimental pneumotoxin. ANTU is a graycolored,prism-shaped, odorless powder with a bitter taste. Ithas a molecular weight of 202.28 and melting point of 200 ℃and does not ignite readily. However, on interaction withpotential oxidizing agents, it may cause fire and explosions,which can lead to hazardous decomposition products such assulfur dioxide, nitrogen dioxide, and carbon monoxide. Thestructure of ANTU contains the naphthalene chromophore,which absorbs UV light at ～311 nm. This suggests that ANTUcan undergo photolysis. |
| Chemical Properties | greyish to beige-brown crystals or cryst. powder |
| Chemical Properties | Alpha-naphthylthiourea (α-naphthalene thiourea) is a pure white or beige-brown solid/blue-gray powder. It is hard to dissolve in water, acid, and general organic solvents, butdissolves in boiling ethanol and alkaline solution. On decomposition, ANTU releases carbonmonoxide, toxic and irritating fumes and gases, and carbon dioxide. It is a rodenticideand a poison bait to lure rodents. |
| Chemical Properties | ANTU is a noncombustible, white crystallinesolid or gray powder. Odorless. |
| Physical properties | Colorless crystals when pure. Technical product is grayish-blue. Odorless solid. Bitter taste. |
| Uses | ANTU an organosulfur is a derivative of thiourea. It is a singledoserodenticide that is specifically used against Norway rats asa bait. However, it is futile against all other species of rodents.Because of its tendency to cause resistance and specificity onlytoward Norway rodents, this poison rapidly lost popularity andis no longer manufactured in the United States. |
| Uses | Rodenticide. Specific control for the adult Norway rat; less toxic to other rat species. |
| Definition | ChEBI: ANTU is a member of naphthalenes. |
| General Description | White crystal or powder; technical product is gray powder. Has no odor but a bitter taste. Used primarily as a rodenticide for control of adult Norway rats. Not produced commercially in the U.S. |
| Air & Water Reactions | Slightly soluble in water. |
| Reactivity Profile | 1-(1-NAPHTHYL)-2-THIOUREA is incompatible with the following: Strong oxidizers, silver nitrate . |
| Hazard | Toxic by ingestion |
| Health Hazard | Moderately toxic: probable oral lethal dose (human) 0.5-5 gm/kg, or between 1 ounce and 1 pint (or l lb.) for 150 lb. person. Chronic sublethal exposure may cause antithyroid activity. Can produce hyperglycemia of three times normal in three hours. People with chronic respiratory disease or liver disease may be especially at risk. |
| Health Hazard | α-Naphthalene thiourea, a rodenticide, is very toxic and is fatal if swallowed. Exposuresto ANTU cause poisoning with symptoms that include, but are not limited to, headache,weakness, dizziness, shortness of breath, cyanosis, blood abnormalities, methemoglobinemia,irritation of the digestive tract, liver and kidney damage, cardiac and CNSdisturbances, convulsions, tachycardia, dyspnea, vertigo, tinnitus, weakness, disorientation,lethargy, drowsiness, and fi nally coma and death. The target organs include theblood, kidneys, CNS, liver, lungs, cardiovascular system, and blood-forming organs. |
| Fire Hazard | Emits sulfur dioxide, oxides of nitrogen, and carbon monoxide fumes upon decomposition. 1-(1-NAPHTHYL)-2-THIOUREA reacts with silver nitrate and strong oxidizers. Avoid decomposing heat. |
| Safety Profile | Poison by ingestion andintraperitoneal routes. Moderately toxic tohumans by an unspecified route.Questionable carcinogen with experimentaltumorigenic data. Mutagenic data. Arodenticide used extensively. Death iscaused by pulmonary edema. Chronic toxicity has been known to cause dermatitisand a decrease in the white blood cells.When heated to decomposition it emitstoxic fumes of NOx and SOx. |
| Potential Exposure | ANTU or its formulations are used asa rodenticide. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24°48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray. |
| Carcinogenicity | ANTU was not carcinogenic in rodentfeeding studies.4 Cases of bladder tumorsamong rat catchers exposed to ANTU havebeen attributed to b-naphthylamine, a manufacturingimpurity of ANTU. In bacterialassays ANTU induced mutations. |
| Environmental Fate | Chemical/Physical. The hydrolysis rate constant for ANTU at pH 7 and 25°C wasdetermined to be 8 × 10–5/hour, resulting in a half-life of 361 days (Ellington et al., 1988) Emits very toxic fumes of nitrogen and sulfur oxides when heated to decomposition(Lewis, 1990) |
| storage | α-Naphthalene thiourea should be kept stored in a tightly closed container in a lockedpoison room, in a cool, dry, well-ventilated area away from incompatible substances. |
| Shipping | UN1651 Naphthylthiourea, Hazard Class: 6.1;Labels: 6.1-Poisonous materials. |
| Purification Methods | Crystallise ANTU from EtOH. [Beilstein 12 III 2941, 12 IV 3086.] |
| Toxicity evaluation | ANTU toxicity in the rat is thought to depend on metabolicactivation via the hepatic and lung microsomal enzymes. Twoimportant metabolites are formed: ANU and atomic sulfur.ANTU pulmonary toxicity may result, in part, from covalentbinding of sulfur or a metabolite containing carbonyl carbon ofANTU to macromolecules of liver and lung microsomes. Thecovalent binding of atomic sulfur released in the cytochromeP450 monooxygenase-catalyzed metabolism of thiono-sulfurcompounds is responsible for monooxygenase activity beinginhibited. Damage to liver and possibly lung edema andneoplasia result from the covalent binding of the electrophilicS-oxides, S-dioxides or carbene derivatives of these S-oxidesand S-dioxides to tissue macromolecules. However, it is not known if these metabolites are seen inhumans. ANTU is believed to act on certain enzyme systemsinvolving the sulfhydryl group similar to other sulfhydrylinhibitors, such as alloxan, iodoacetamide, and oxophenarsine,which cause pulmonary edema. Hence the mechanismof action of causing pulmonary edema from the toxiceffects of these sulfhydryl inhibitors and ANTU is assumed tobe similar. Additionally, ANTU-induced lung damage hasbeen linked to the formation of oxygen free radicals producedvia the cyclooxygenase pathway. Following exposure toANTU, there are a number of biochemical events, such asalteration in carbohydrate metabolism, adrenal stimulation,and interaction of the chemical with sulfhydryl groups, butnone of these appear to bear any relationship to the observedsigns of toxicity. |
| Incompatibilities | Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions.Keep away from alkaline materials, strong bases,strong acids, oxoacids, epoxides, silver nitrate. |
| Waste Disposal | Incinerate in a furnaceequipped with an alkaline scrubber. Consult with environmentalregulatory agencies for guidance onacceptable disposal practices. Generators of waste containingthis contaminant (≥100 kg/mo) must conform withEPA regulations governing storage, transportation, treatment,and waste disposal. |
| Precautions | Workers should use/handle α-naphthalene thiourea with adequate ventilation. Duringuse, dust generation and accumulation should be minimum, and avoid contact with theeyes, skin, and clothing. |
1-(1-NAPHTHYL)-2-THIOUREA Preparation Products And Raw materials
| Raw materials | Ammonium thiocyanate-->Sodium thiocyanate-->1-Naphthylamine-->Potassium thiocyanate-->2-AMINONAPHTHALENE HYDROCHLORIDE |
| Preparation Products | 1-Naphthyl isothiocyanate-->2-AMINO-BETA-NAPHTHOTHIAZOLE |
