3774-53-6

Basic information

• Product Name: 4-HYDROXY-3-METHYLPHENYL THIOCYANATE
• Synonyms: 4-HYDROXY-3-METHYLPHENYL THIOCYANATE;2-Methyl-4-thiocyanatophenol;thiocyanic acid (4-hydroxy-3-methyl-phenyl) ester;4-Thiocyanato-O-cresol;2-Methyl-4-(thiocyano)phenol;4-Hydroxy-M-tolyl Thiocyanate;NSC 31040;NSC 4470
• CAS NO: 3774-53-6
• Molecular Formula: C₈H₇NOS
• Molecular Weight: 165.21
• Product Categories: Multisubstituted Benzene;Aromatics;Sulfur & Selenium Compounds
• Mol File: 3774-53-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 73-75°C
• Boiling Point: 305.4°Cat760mmHg
• Flash Point: 138.5°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.000455mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-HYDROXY-3-METHYLPHENYL THIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-METHYLPHENYL THIOCYANATE(3774-53-6)
• EPA Substance Registry System: 4-HYDROXY-3-METHYLPHENYL THIOCYANATE(3774-53-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 3774-53-6(Hazardous Substances Data)

Usage

Description

4-HYDROXY-3-METHYLPHENYL THIOCYANATE, also known as 4-hydroxy-3-methylbenzenethiocyanate, is an organic compound with the molecular formula C8H7NS. It is a light yellow solid that serves as an intermediate in the synthesis of various benzotriazoles, which are important compounds in the pharmaceutical, agrochemical, and chemical industries due to their diverse applications and unique properties.

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-3-METHYLPHENYL THIOCYANATE is used as an intermediate for the synthesis of various benzotriazoles, which are valuable in the development of pharmaceutical compounds. These benzotriazoles exhibit a wide range of biological activities, including anti-cancer, anti-inflammatory, and anti-microbial properties, making them essential components in the design and synthesis of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 4-HYDROXY-3-METHYLPHENYL THIOCYANATE is used as an intermediate for the preparation of benzotriazole-based compounds that possess insecticidal, fungicidal, and herbicidal properties. These compounds are crucial in the development of novel agrochemicals to protect crops from pests and diseases, ensuring increased yield and food security.
Used in Chemical Industry:
4-HYDROXY-3-METHYLPHENYL THIOCYANATE is utilized as an intermediate in the chemical industry for the synthesis of various benzotriazole derivatives. These derivatives find applications in areas such as corrosion inhibition, UV absorbers, and stabilizers for plastics, rubber, and coatings. The unique properties of benzotriazoles make them indispensable in the development of new materials and technologies in the chemical industry.

Synthesis Reference(s)

Synthetic Communications, 22, p. 2741, 1992 DOI: 10.1080/00397919208021538

InChI:InChI=1/C8H7NOS/c1-6-4-7(11-5-9)2-3-8(6)10/h2-4,10H,1H3

Upstream product

• 7726-95-6 bromine 
• 95-48-7 ortho-cresol 
• 333-20-0 potassium thioacyanate 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 51537-77-0 1-methoxy-2-methyl-4-thiocyanatobenzene 
• 1207268-90-3 methyl 2-methyl-2-(2-methyl-4-(1-(4-methyl-5-oxo-1-(4-trifluoromethylphenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzylthio)phenoxy)acetate 
• 1207268-95-8 ethyl 2,2-dimethyl-2-(3-methyl-4-(1-(2-(4-n-butyl-5-oxo-1-(4-trifluoromethyl-phenyl)-4,5-dihydrogen-1H-1,2,4-triazolyl))-benzylthio)-phenoxy)-acetate 
• 1207269-28-0 C₂₄H₂₀F₃N₃O₂S 
• 1207268-93-6 ethyl 2,2-dimethyl-2-(3-methyl-4-(1-(2-(4-methyl-5-oxo-1-(4-trifluoromethylphenyl)-4,5-dihydrogen-1H-1,2,4.triazolyl))-benzylthio)-phenoxy)-acetate 
• 1207269-27-9 C₄₈H₃₈F₆N₆O₄S₂ 
• 1207269-30-4 C₂₄H₂₀F₃N₃O₂S 
• 1207268-92-5 ethyl 2,2-dimethyl-2-(3-methyl-4-(1-(3-(4-methyl-5-oxo-1-(4-trifluoromethyl-phenyl)-4,5-dihydrogen-1H-1,2,4-triazolyl))-benzyloxy)-phenylthio)-acetate 
• 1207269-29-1 C₁₁H₁₄O₃S 
• 1207269-26-8 C₂₂H₂₆O₆S₂ 

Relevant articles and documents

N -Thiocyanato-dibenzenesulfonimide: A new electrophilic thiocyanating reagent with enhanced reactivity

A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2 for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.

N-Thiocyanatosaccharin: A "sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications

N-Thiocyanatosaccharin (R1) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a novel electrophilic thiocyanation reaction was achieved with high yields (up to 99%). The potential recycling of Saccharin, the wide scope of substrates, and the mild reaction conditions made this protocol much more practical.

Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles

An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct C[sbnd]H functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated in gram scale synthesis of a precursor of PPAR δ agonist in excellent yield.