1-(1-Naphthyl)-2-thiourea

Base Information

• Chemical Name: 1-(1-Naphthyl)-2-thiourea
• CAS No.: 86-88-4
• Molecular Formula: C11H10 N2 S
• Molecular Weight: 202.28
• Hs Code.: 29309090
• European Community (EC) Number: 201-706-3
• ICSC Number: 0973
• NSC Number: 3287
• UN Number: 1651
• UNII: UKY0H6XJ4J
• DSSTox Substance ID: DTXSID8020919
• Nikkaji Number: J4.268D
• Wikipedia: Alpha-Naphthylthiourea
• Wikidata: Q413532
• ChEMBL ID: CHEMBL3182781
• Mol file: 86-88-4.mol

Synonyms:1-naphthylthiourea;alpha-naphthyl thiourea;alpha-naphthylthiourea;ANTU;Dirax

Chemical Property of 1-(1-Naphthyl)-2-thiourea

Chemical Property:

• Appearance/Colour: WHITE, ODOURLESS CRYSTALLINE POWDER
• Vapor Pressure: 6.69E-06mmHg at 25°C
• Melting Point: 193 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 377.6 °C at 760 mmHg
• PKA: 13.12±0.70(Predicted)
• Flash Point: 182.1 °C
• PSA: 70.14000
• Density: 1.333 g/cm³
• LogP: 3.26860
• Storage Temp.: Poison room
• Solubility.: 4.3 and 86 g/L in acetone and triethylene glycol, respectively (Windholz et al., 1983)
• Water Solubility.: 600 mg/L at 20 °C (quoted, Windholz et al., 1983)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 202.05646950
• Heavy Atom Count: 14
• Complexity: 217
• Transport DOT Label: Poison

Purity/Quality:

ANTU ^*data from reagent suppliers

Safty Information:

• Pictogram(s): TLV: 0.3 mg/m³.
• Hazard Codes: T+
• Statements: 28-40
• Safety Statements: 28-36/37-45-25-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Rodenticides
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2NC(=S)N
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: Exposure could cause lung oedema. Medical observation is indicated.
• 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.
• Physical properties: Colorless crystals when pure. Technical product is grayish-blue. Odorless solid. Bitter taste.
• Uses: Rodenticide 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. Rodenticide. Specific control for the adult Norway rat; less toxic to other rat species.

Technology Process of 1-(1-Naphthyl)-2-thiourea

There total 22 articles about 1-(1-Naphthyl)-2-thiourea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ammonium thiocyanate (1147550-11-5) + 1-amino-naphthalene (134-32-7) → naphthalen-1-yl-thiourea (86-88-4)

Guidance literature:

ammonium thiocyanate; With benzoyl chloride; In acetone; for 0.333333h; Reflux;

1-amino-naphthalene; In acetone; for 1h; Reflux;

With sodium hydroxide; In water; at 80 ℃; for 0.5h;

DOI:10.1021/acs.cgd.7b01180

Reference yield: 95.0%

1-isothiocyanatonaphthalene (551-06-4) → naphthalen-1-yl-thiourea (86-88-4)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 20 ℃; for 49h;

DOI:10.1002/chir.22794

Reference yield: 94.0%

1-(N-(1-naphthyl)thiocarbamoyl)-1H-benzotriazole (1078157-23-9) → naphthalen-1-yl-thiourea (86-88-4)

Guidance literature:

With sodium carbonate; ammonium chloride; In neat (no solvent); for 1h; Milling; Green chemistry;

DOI:10.1039/c6gc00089d

upstream raw materials:

N-acetyl-N'-[1]naphthyl-thiourea

ammonium thiocyanate

1-amino-naphthalene

1-isothiocyanatonaphthalene

Downstream raw materials:

[1]naphthyl-(4-phenyl-thiazol-2-yl)-amine

[5-(4-fluoro-phenyl)-thiazol-2-yl]-naphthalen-1-yl-amine

5,5-Bis-(4-hydroxy-phenyl)-3-naphthalen-1-yl-2-thioxo-imidazolidin-4-one

[3-Methylsulfanyl-1-(3-naphthalen-1-yl-thioureido)-propyl]-phosphonic acid diphenyl ester

Refernces

• 1、 Bagherzadeh, Nastaran,Sardarian, Ali Reza,Inaloo, Iman Dindarloo. "Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea". supporting information. p. 11852 - 11858. Retrieved 2021/07/12.
• 2、 Drabowicz, Józef,Kudzin, Marcin H.,Kudzin, Zbigniew H.,Pokora-Sobczak, Patrycja. "High-performance liquid chromatographic enantioseparation of N-aryl-thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide-based chiral stationary phases". supporting information. p. 131 - 140. Retrieved 2017/12/28.