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86-88-4

86-88-4 Structure

86-88-4 Structure
IdentificationMore
[Name]

1-(1-NAPHTHYL)-2-THIOUREA
[CAS]

86-88-4
[Synonyms]

1-(1-NAPHTHYL)-2-THIOUREA
1-(1-NAPHYTHYL)-2-THIOUREA
1-NAPHTHYL-2-THIOUREA
1-NAPHTHYLTHIOUREA
ALPHA-NAPHTHYLTHIOUREA
A-NAPHTHYLTHIOCARBAMIDE
A-NAPHTHYLTHIOUREA
ANTU
ANTURAT(R)
BANTU(R)
CHEMICAL 109(R)
LABOTEST-BB LT02090877
NAPHTHALEN-1-YL-THIOUREA
α-Naphthylthiourea
RATTRACK(R)
1-(1-naphthyl)-2-thio-ure
1-(1-naphthyl)thiourea
1-Naftil-tiourea
1-Naftylthioureum
1-naphthalenyl-thioure
[EINECS(EC#)]

201-706-3
[Molecular Formula]

C11H10N2S
[MDL Number]

MFCD00041824
[Molecular Weight]

202.28
[MOL File]

86-88-4.mol
Chemical PropertiesBack Directory
[Appearance]

ANTU is a noncombustible, white crystalline solid or gray powder. Odorless.
[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)
[form ]

Crystals or Crystalline Powder
[pka]

13.12±0.70(Predicted)
[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: TWA 0.3 mg/m3
[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)
Hazard InformationBack Directory
[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, but dissolves in boiling ethanol and alkaline solution. On decomposition, ANTU releases carbon monoxide, toxic and irritating fumes and gases, and carbon dioxide. It is a rodenticide and a poison bait to lure rodents.
[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.
[Reactivity Profile]

ANTU(86-88-4) is incompatible with the following: Strong oxidizers, silver nitrate .
[Air & Water Reactions]

Slightly soluble in water.
[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. Exposures to 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 CNS disturbances, convulsions, tachycardia, dyspnea, vertigo, tinnitus, weakness, disorientation, lethargy, drowsiness, and fi nally coma and death. The target organs include the blood, kidneys, CNS, liver, lungs, cardiovascular system, and blood-forming organs.
[Potential Exposure]

ANTU or its formulations are used as a rodenticide.
[Fire Hazard]

Emits sulfur dioxide, oxides of nitrogen, and carbon monoxide fumes upon decomposition. ANTU reacts with silver nitrate and strong oxidizers. Avoid decomposing heat.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
[Shipping]

UN1651 Naphthylthiourea, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
[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.
[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.
[Waste Disposal]

Incinerate in a furnace equipped with an alkaline scrubber. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
[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 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
[Uses]

Rodenticide. Specific control for the adult Norway rat; less toxic to other rat species.
[Definition]

ChEBI: ANTU is a member of naphthalenes.
[Carcinogenicity]

ANTU was not carcinogenic in rodent feeding studies.4 Cases of bladder tumors among rat catchers exposed to ANTU have been attributed to b-naphthylamine, a manufacturing impurity of ANTU. In bacterial assays ANTU induced mutations.
[Environmental Fate]

Chemical/Physical. The hydrolysis rate constant for ANTU at pH 7 and 25°C was determined 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)
[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 metabolic activation via the hepatic and lung microsomal enzymes. Two important metabolites are formed: ANU and atomic sulfur. ANTU pulmonary toxicity may result, in part, from covalent binding of sulfur or a metabolite containing carbonyl carbon of ANTU to macromolecules of liver and lung microsomes. The covalent binding of atomic sulfur released in the cytochrome P450 monooxygenase-catalyzed metabolism of thiono-sulfur compounds is responsible for monooxygenase activity being inhibited. Damage to liver and possibly lung edema and neoplasia result from the covalent binding of the electrophilic S-oxides, S-dioxides or carbene derivatives of these S-oxides and S-dioxides to tissue macromolecules.
However, it is not known if these metabolites are seen in humans. ANTU is believed to act on certain enzyme systems involving the sulfhydryl group similar to other sulfhydryl inhibitors, such as alloxan, iodoacetamide, and oxophenarsine, which cause pulmonary edema. Hence the mechanism of action of causing pulmonary edema from the toxic effects of these sulfhydryl inhibitors and ANTU is assumed to be similar. Additionally, ANTU-induced lung damage has been linked to the formation of oxygen free radicals produced via the cyclooxygenase pathway. Following exposure to ANTU, there are a number of biochemical events, such as alteration in carbohydrate metabolism, adrenal stimulation, and interaction of the chemical with sulfhydryl groups, but none of these appear to bear any relationship to the observed signs of toxicity.
Safety DataBack Directory
[Hazard Codes ]

T+
[Risk Statements ]

R28:Very Toxic if swallowed.
R40:Limited evidence of a carcinogenic effect.
[Safety Statements ]

S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S25:Avoid contact with eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
[RIDADR ]

1651
[WGK Germany ]

2
[RTECS ]

YT9275000
[TSCA ]

Yes
[HazardClass ]

6.1
[PackingGroup ]

I
[HS Code ]

29309090
[storage]

α-Naphthalene thiourea should be kept stored in a tightly closed container in a locked poison room, in a cool, dry, well-ventilated area away from incompatible substances.
[Precautions]

Workers should use/handle α-naphthalene thiourea with adequate ventilation. During use, dust generation and accumulation should be minimum, and avoid contact with the eyes, skin, and clothing.
[Safety Profile]

Poison by ingestion and intraperitoneal routes. Moderately toxic to humans by an unspecified route. Questionable carcinogen with experimental tumorigenic data. Mutagenic data. A rodenticide used extensively. Death is caused by pulmonary edema. Chronic toxicity has been known to cause dermatitis and a decrease in the white blood cells. When heated to decomposition it emits toxic fumes of NOx and SOx.
[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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ammonium thiocyanate-->Sodium thiocyanate-->1-Naphthylamine-->Potassium thiocyanate-->2-AMINONAPHTHALENE HYDROCHLORIDE
[Preparation Products]

1-Naphthyl isothiocyanate-->2-AMINO-BETA-NAPHTHOTHIAZOLE
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

α-naphthylthiourea(86-88-4).msds
Spectrum DetailBack Directory
[Spectrum Detail]

1-(1-NAPHTHYL)-2-THIOUREA(86-88-4)MS
1-(1-NAPHTHYL)-2-THIOUREA(86-88-4)1HNMR
1-(1-NAPHTHYL)-2-THIOUREA(86-88-4)IR1
1-(1-NAPHTHYL)-2-THIOUREA(86-88-4)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

1-(1-Naphthyl)-2-thiourea,97%(86-88-4)
[Alfa Aesar]

N-(1-Naphthyl)thiourea, 97%(86-88-4)
[Sigma Aldrich]

86-88-4(sigmaaldrich)
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