6590-91-6

Basic information

• Product Name: 2,6-DICHLOROPHENYLTHIOUREA
• Synonyms: 2,6-DICHLOROPHENYLTHIOUREA;1-(2,6-DICHLOROPHENYL)-2-THIOUREA;N-(2,6-dichlorophenyl)thiourea;1,3-Dichloro-2-thioureidobenzene, 5-(Carbamothioylamino)-1,3-dichlorobenzene
• CAS NO: 6590-91-6
• Molecular Formula: C₇H₆Cl₂N₂S
• Molecular Weight: 221.11
• EINECS: -0
• Product Categories: API intermediates
• Mol File: 6590-91-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 157-159°C
• Boiling Point: 316.4 °C at 760 mmHg
• Flash Point: 145.2 °C
• Appearance: white
• Density: 1.563 g/cm³
• Vapor Pressure: 0.000411mmHg at 25°C
• Refractive Index: 1.73
• PKA: 11.57±0.70(Predicted)
• BRN: 2212144
• CAS DataBase Reference: 2,6-DICHLOROPHENYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLOROPHENYLTHIOUREA(6590-91-6)
• EPA Substance Registry System: 2,6-DICHLOROPHENYLTHIOUREA(6590-91-6)

Safety Data

• Hazard Codes: T
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: 6.1
• Hazardous Substances Data: 6590-91-6(Hazardous Substances Data)

Usage

General Description

2,6-Dichlorophenylthiourea is a chemical compound which is commonly used as a pesticide and also has applications in pharmaceutical and industrial processes. It is a white crystalline solid, and its chemical structure consists of a phenyl group with two chlorines attached to the 2 and 6 positions, and a thiourea functional group. 2,6-Dichlorophenylthiourea is known to inhibit the activity of the enzyme thyroid peroxidase, which is involved in the production of thyroid hormones. It is also used in the production of rubber and as a reagent in organic synthesis. However, it is important to note that 2,6-Dichlorophenylthiourea is toxic to aquatic organisms and can have harmful effects on the environment if not handled and disposed of properly.

InChI:InChI=1/C7H6Cl2N2S/c8-4-2-1-3-5(9)6(4)11-7(10)12/h1-3H,(H3,10,11,12)

Upstream product

• 540-72-7 sodium thiocyanide 
• 608-31-1 2,6-Dichloroaniline 
• 23822-56-2 ethyl 3-(2,6-dichlorophenyl)thioureidocarboxylate 
• 41542-10-3 N-(2,6-dichlorophenyl)-N'-benzoyl thiourea 
• 6590-95-0 2,6-dichlorophenylisothiocyanate 
• 33663-43-3 2,6-dichloroaniline hydrochloride 

Downstream Products

• 40524-27-4 3-(2,6-dichloro-phenyl)-4-methyl-thiazolidin-2-ylideneamine 
• 936638-01-6 2-(2,6-dichlorophenylamino)thiazol-4(5H)-one 
• 936638-01-6 2-(2,6 dichloro-phenylimino)-thiazolidin-4-one 
• 39075-78-0 2.6-Dichlorophenylguanidin 
• 123414-51-7 N-[(3aR,6aR)-3-(2,6-Dichloro-phenyl)-5,5-dioxo-hexahydro-5λ⁶-thieno[3,4-d]thiazol-(2Z)-ylidene]-acetamide 
• 82636-21-3 1-(2,6-Dichloro-phenyl)-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 75357-87-8 N-(2,6-Dichloro-phenyl)-pyrrolidine-1-carboxamidine 
• 736971-65-6 {2-[(2,6-dichlorophenyl)amino](1,3-thiazol-4-yl)}-N-[4-(trifluoromethyl)phenyl]-carboxamide 
• 736971-74-7 2-((2,6-dichlorophenyl)amino)thiazole-4-carboxylic acid 
• 936946-51-9 ethyl 2-((2,6-dichlorophenyl)amino)thiazole-4-carboxylate 
• 27806-88-8 1-(2,6-Dichloro-phenyl)-2-methyl-isothiourea; hydriodide 
• 27806-81-1 2,6-Dichlorphenyl-S-methylisothioharnstoff 
• 123414-45-9 (3aR,6aR)-3-(2,6-Dichloro-phenyl)-5,5-dioxo-hexahydro-5λ⁶-thieno[3,4-d]thiazol-2-ylideneamine; hydrobromide 
• 26169-94-8 3-(2,6-dichloro-phenyl)-[1,3]thiazinan-2-ylideneamine 

Relevant articles and documents

Disrupting the Conserved Salt Bridge in the Trimerization of Influenza A Nucleoprotein

Antiviral drug resistance in influenza infections has been a major threat to public health. To develop a broad-spectrum inhibitor of influenza to combat the problem of drug resistance, we previously identified the highly conserved E339?R416 salt bridge of the nucleoprotein trimer as a target and compound 1 as an inhibitor disrupting the salt bridge with an EC50 = 2.7 μM against influenza A (A/WSN/1933). We have further modified this compound via a structure-based approach and performed antiviral activity screening to identify compounds 29 and 30 with EC50 values of 110 and 120 nM, respectively, and without measurable host cell cytotoxicity. Compared to the clinically used neuraminidase inhibitors, these two compounds showed better activity profiles against drug-resistant influenza A strains, as well as influenza B, and improved survival of influenza-infected mice.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.