17709-95-4

Basic information

• Product Name: N,N-DIMETHYL-2-PHENYL(THIOACETAMIDE)
• Synonyms: N,N-DIMETHYL-2-PHENYLETHANETHIOAMIDE;N,N-DIMETHYL-2-PHENYL(THIOACETAMIDE);N,N-DIMETHYL-2-PHENYL(THIOACETAMIDE), 98+;N,N-Dimethylbenzenethioacetamide
• CAS NO: 17709-95-4
• Molecular Formula: C₁₀H₁₃NS
• Molecular Weight: 179.28
• Mol File: 17709-95-4.mol

Chemical Properties

• Melting Point: 78-80°
• Boiling Point: 262.9°Cat760mmHg
• Flash Point: 112.8°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: N,N-DIMETHYL-2-PHENYL(THIOACETAMIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-2-PHENYL(THIOACETAMIDE)(17709-95-4)
• EPA Substance Registry System: N,N-DIMETHYL-2-PHENYL(THIOACETAMIDE)(17709-95-4)

Safety Data

• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S22:Do not inhale dust.; S36/37:Wear suitable protective clothing and gloves.
• HazardClass: IRRITANT
• Hazardous Substances Data: 17709-95-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 4061, 1980 DOI: 10.1016/0040-4039(80)88066-X

InChI:InChI=1/C10H13NS/c1-11(2)10(12)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3

Upstream product

• 100-42-5 styrene 
• 122-78-1 phenylacetaldehyde 
• 124-40-3 dimethyl amine 
• 98-86-2 acetophenone 
• 25445-77-6 4-phenyl-1,2,3-thiadiazole 
• 36838-59-2 N-styrylmorpholine 
• 137-26-8 Thiram 
• 103-63-9 1-phenyl-2-bromoethane 
• 68-12-2 N,N-dimethyl-formamide 
• 4137-10-4 DIMCARB 
• 68542-14-3 2-Phenyl-1-methylthio-1-(acetoxymethylthio)-ethylene 
• 136970-31-5 1-Methylselanyl-2-phenyl-ethanethione 
• 536-74-3 phenylacetylene 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 1126-71-2 N,N-dimethylphenethylamine 
• 18925-69-4 N,N-dimethyl-2-phenylacetamide 
• 66598-12-7 2-Dimethylamino-2-methylthiostyrol 
• 35776-03-5 5-N,N-dimethylamino-4-phenyl-1,2-dithiole-3-thione 
• 85892-15-5 erythro-N,N-dimethyl-2-phenyl-3-methylthiopent-4-enamide 
• 85892-14-4 threo-N,N-dimethyl-2-phenyl-3-methylthiopent-4-enamide 
• 86943-11-5 erythro-N,N-dimethyl-2,3-diphenylthiopent-4-enamide 
• 86943-12-6 threo-N,N-dimethyl-2-phenyl-3-methylthiopent-4-enamide 
• 76454-89-2 Sodium; (E)-1-dimethylamino-2-phenyl-ethenethiolate 
• 76454-87-0 Lithium; (E)-1-dimethylamino-2-phenyl-ethenethiolate 
• 79070-81-8 potassium 1-dimethylamino-2-phenylethenethiolate 
• 4410-99-5 2-mercaptophenylethane 
• 131657-45-9 N¹,N¹-dimethyl-2-phenyl-N²-tosylacetamidine 
• 22191-68-0 (2R,3R)-3-Hydroxy-N,N-dimethyl-2,3-diphenyl-thiopropionamide 

Relevant articles and documents

A facile access to thieno[2,3-b]indoles via sulfur-mediated decarboxylative cyclization of α, β-unsaturated carboxylic acids with indoles

An efficient synthesis of thieno[2,3-b]indoles via a one-pot three-component reaction was well established. By using inexpensive and commercial available indoles and α, β-unsaturated carboxylic acids in the presence of elemental sulfur, various functional groups were achieved in moderate to good yields.

Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur

A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.

The thioamidation ofgem-dibromoalkenes in an aqueous medium

The direct integration of sulphur and amine groups with 1,1-dibromoalkenes for thioamide synthesis has been achieved in an aqueous medium. The presented green protocol emphasizes the suitability of aqueous media for the thioamidation reaction and enables greater selectivity with synthetic utility. A wide range of thioamides in moderate to excellent yields has been achieved using readily available starting materials, with the use of no organic solvents, catalysts, or additives.

Elemental Sulfur-Promoted Benzoxazole/Benzothiazole Formation Using a C=C Double Bond as a One-Carbon Donator

An efficient method to assemble diverse benzoxazoles/benzothiazoles in good yields was developed via oxidative cyclization with 2-aminothiophenols or 2-iodoanilines as raw materials. In this protocol, elemental sulfur was used as the effective oxidant and C atoms on the C=C double bond were introduced as a one-carbon donator.

Three-Component Thieno[2,3-b]indole Synthesis from Indoles, Alkenes or Alkynes and Sulfur Powder under Metal-Free Conditions

A Bronsted acid promoted three-component synthesis of substituted thieno[2,3-b]indole has been developed starting from indoles, alkenes or alkynes, and sulfur powder. N,N-Dimethylformamide plays an important role to convert the starting materials into the fused products. Various functional groups attached to substrates were well tolerated to afford the corresponding products in moderate to good yields under very simple reaction conditions. (Figure presented.).

Solvent-controlled highly regio-selective thieno[2,3-: B] indole formation under metal-free conditions

An efficient three-component thieno[2,3-b]indole formation method was developed under metal-free conditions. The cascade cyclization was enabled by acid-promoted annulation of indoles, ketones and sulfur powder, which enabled modular synthesis of 2-substituted and 3-substituted thieno[2,3-b]indoles with excellent regioselectivity and broad functional group tolerance. DMF solvent played an important role in the regioselectivity control.

Sulfur promoted decarboxylative thioamidation of carboxylic acids using formamides as amine proxy

An efficient decarboxylative thioamidation of arylacetic and cinnamic acids has been developed employing formamides as amine surrogate and sulfur as promoter. Thioamides with variant structural features are obtained under mild reaction conditions without the use of transition metal catalysts and oxidants.

Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides

An improved and efficient method for the synthesis of thioamides is presented. For this transformation, dimethylamine as the key intermediate is generated in situ from dimethylformamide (DMF). All the tested substrates produced the desired products with excellent isolated yields.

Synthesis of thioamides via one-pot A3-coupling of alkynyl bromides, amines, and sodium sulfide

We herein describe a novel method for the synthesis of thioamides by a three component condensation of alkynyl bromides, amines, and Na 2S·9H2O. The developed method is applicable for a wide range of amines and alkynyl bromides bearing different functional groups furnishing the corresponding products in moderate to excellent yields. The Royal Society of Chemistry.

Decarboxylative thioamidation of arylacetic and cinnamic acids: A new approach to thioamides

A new decarboxylative strategy has been developed for the synthesis of thioamides via a three-component reaction involving arylacetic or cinnamic acids, amines and elemental sulfur powder, without the need of a transition metal and an external oxidant.