Alpha-Naphthylthiourea
ANTU · ALPHA-NAPHTHYLTHIOUREA · AUTU · Bantu · Dirax · Alrato · u-5227 · Kripid
Identifiers & Physical Properties
| CAS No. | 30553-04-9 |
|---|---|
| Molecular formula | C11H10N2S |
| Average molar mass | 202.28 g/mol |
| Monoisotopic mass | 202.05646932 g/mol |
| SMILES | NC(=S)Nc1cccc2ccccc12 |
| InChIKey | PIVQQUNOTICCSA-UHFFFAOYSA-N |
| PubChem CID | 736366 |
| ChEMBL | CHEMBL3182781 |
| ChEBI | CHEBI:82256 |
| EC No. | 201-706-3 |
| DTXSID | DTXSID8020919 |
Chemical & Physical Properties
| XLogP | 1.7 |
|---|---|
| Topological polar surface area | 70.1 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 14 |
| Formal charge | 0 |
| Complexity | 217 |
| Pesticides | Pesticides -> Rodenticides |
| LogP (partition coefficient) | log Kow = 1.651.66 (calculated) |
| Odor | Odorlessbitter taste |
| Taste | Bitter taste |
| Density | Specific Gravity (water= 1): Greater than 1>1 g/cm³1.333 |
| Color/Form | Prisms from alcoholColorless ... solidWhite, crystalline or gray powder |
| Solubility | 0.06 % (NIOSH, 2024)In water, 600 mg/L at 25 °CSolubility in acetone = 2.43 g/100 mLin triethylene glycol = 8.6 g/100 mLfairly soluble in hot alcoholSlightly soluble in ethanol, ethyl ether, acetoneVery slightly soluble in most organic solventsSolubility in water: none4.3 and 86 g/L in acetone and triethylene glycol, respectively (Windholz et al., 1983)600 mg/L at 20 °C (quoted, Windholz et al., 1983) |
| Flash point | May burn but will not ignite readily (EPA, 1998) |
| Boiling point | Decomposes (NIOSH, 2024)400 °C @760 [mm Hg]377.6±25.0 °C(Predicted) |
| Decomposition | Hazardous decomposition products include: sulfur dioxide, oxides of nitrogen, and carbon monoxide.When heated to decomp ...it emits toxic fumes of /nitrogen oxides and sulfur oxides./ |
| Melting point | 388 °F (EPA, 1998)198 °C193 °C |
| Vapor density | 6.99 (EPA, 1998) - Heavier than airwill sink (Relative to Air) |
| Refractive index | 1.5500 (estimate) |
| Storage conditions | Poison room |
| pKa (acidity coefficient) | 13.12±0.70(Predicted) |
| Physical state | Crystals or Crystalline Powder |
| Color | Grayish to beige-brown |
| Merck | 14,722 |
| BRN | 778118 |
| Henry's law constant | 1.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Exposure limits | ACGIH:TLV-TWA 0.3 mg/m3OSHA:PEL-TWA 0.3 mg/m3NIOSH:REL-TWA 0.3 mg/m3 |
| Major applications | agricultureenvironmental |
| 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) |
| EWG's Food Scores | 2-3 |
| FDA UNII | UKY0H6XJ4J |
| IARC | 3 (Vol. 30, Sup 7) 1987 |
| EPA Substance Registry System | .alpha.-Naphthylthiourea (86-88-4) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS06,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H300-H351 |
| GHS precautionary statements | P264-P270-P201-P202-P280-P301+P310-P330-P308+P313-P405-P501 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Hazard symbols | T+ |
| Risk statements (R) | 28-40 |
| Safety statements (S) | 28-36/37-45-25-23 |
| Occupational exposure band (OEB) | C |
| Occupational exposure limit (OEL) | TWA: 0.3 mg/m3 |
| UN transport number | UN 1651 |
| Water hazard class (WGK) | 2 |
| RTECS number | YT9275000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 2 OralCarc. 2 |
| Packing group | II |
| Customs code | 29309090 |
| Storage class | 6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials |
| Hazardous substances data | 86-88-4(Hazardous Substances Data) |
| Toxicity | Acute oral LD50 for Norwegian rats 6–8 mg/kg (Hartley and Kidd, 1987). |
| Immediately dangerous to life or health concentration | 100 mg/m3 |
Safety & Regulations
| GHS classification | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatory information | The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT label | Poison |
| Fire hazards | Emits sulfur dioxide, oxides of nitrogen, and carbon monoxide fumes upon decomposition. It reacts with silver nitrate and strong oxidizers. Avoid decomposing heat. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· Combustible material: may burn but does not ignite readily.Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire. |
| Fire potential | /To fight fire use:/Powder, water spray, foam, carbon dioxide. |
| Health hazards | 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. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Hazards summary | The lethal oral dose in humans is about 4 g/kgTLV based on thyroid effects and nauseaIn high-dose feeding and intraperitoneal injection studies, animals develop liver injury, pleural and pericardial effusions, and pulmonary edema. [ACGIH] |
| DOT ID and guide | 1651 153 |
| Reactive group | Amides and Imides |
Applications & Uses
Description
a-Naphthylthiourea (ANTU; also called DIRAX) is toxic by inhalation, ingestion, or skin contact. Due to its very narrow spectrum of activity, production was discontinued a long time ago. Exposure to ANTU causes pulmonary edema; therefore, it is often used as an experimental pneumotoxin. ANTU is a graycolored, prism-shaped, odorless powder with a bitter taste. It has a molecular weight of 202.28 and melting point of 200 ℃ and does not ignite readily. However, on interaction with potential oxidizing agents, it may cause fire and explosions, which can lead to hazardous decomposition products such as sulfur dioxide, nitrogen dioxide, and carbon monoxide. The structure of ANTU contains the naphthalene chromophore, which absorbs UV light at ～311 nm. This suggests that ANTU can undergo photolysis.
Uses
ANTU an organosulfur is a derivative of thiourea. It is a singledose rodenticide that is specifically used against Norway rats as a bait. However, it is futile against all other species of rodents. Because of its tendency to cause resistance and specificity only toward Norway rodents, this poison rapidly lost popularity and is no longer manufactured in the United States.
Uses
Rodenticide. Specific control for the adult Norway rat; less toxic to other rat species.
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.