19311-91-2

Basic information

• Product Name: N,N-DIETHYLSALICYLAMIDE
• Synonyms: N,N-DIETHYLSALICYLAMIDE;n,n-diethyl-2-hydroxy-benzamid;n,n-diethyl-salicylamid;o-hydroxy-n,n-diethylbenzamide;Salicylamide, N,N-diethyl-;2-Hydroxy-N,N-diethylbenzamide;Ai3-33468;Benzamide, N,N-diethyl-2-hydroxy-
• CAS NO: 19311-91-2
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 242-955-8
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 19311-91-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 93-97 °C(lit.)
• Boiling Point: 340℃
• Flash Point: 159℃
• Appearance: White to tan/Crystalline Powder
• Density: 1.096
• Vapor Pressure: 4.67E-06mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.73±0.30(Predicted)
• CAS DataBase Reference: N,N-DIETHYLSALICYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHYLSALICYLAMIDE(19311-91-2)
• EPA Substance Registry System: N,N-DIETHYLSALICYLAMIDE(19311-91-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: VN7320000
• Hazardous Substances Data: 19311-91-2(Hazardous Substances Data)

Usage

Description

N,N-Diethylsalicylamide, also known as N-Salicylidene-N-Diethylamine, is an organic compound with the chemical formula C11H15NO2. It is a colorless to pale yellow liquid with a characteristic amine-like odor. N,N-DIETHYLSALICYLAMIDE is known for its versatile chemical properties, making it a valuable intermediate in various chemical reactions and synthesis processes.

Uses

N,N-Diethylsalicylamide is used as a key intermediate in the synthesis of various organic compounds, pharmaceuticals, agrochemicals, and dyestuffs. Its unique chemical structure allows it to participate in a wide range of reactions, making it a valuable asset in the development of new products and materials.
Used in Organic Synthesis:
N,N-Diethylsalicylamide is used as a versatile intermediate for the synthesis of various organic compounds. Its reactivity and functional groups enable it to undergo a range of reactions, such as condensation, substitution, and rearrangement, leading to the formation of diverse chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N,N-Diethylsalicylamide is used as a building block for the development of new drugs and active pharmaceutical ingredients. Its unique structure and reactivity make it a promising candidate for the synthesis of novel therapeutic agents with potential applications in various medical fields.
Used in Agrochemicals:
N,N-Diethylsalicylamide is also utilized in the agrochemical industry for the synthesis of various pesticides, herbicides, and other crop protection agents. Its chemical properties allow it to be incorporated into the structures of these compounds, potentially enhancing their efficacy and selectivity.
Used in Dyestuff Industry:
In the dyestuff industry, N,N-Diethylsalicylamide is used as a starting material for the synthesis of various dyes and pigments. Its unique chemical structure and reactivity contribute to the development of new colorants with improved properties, such as enhanced color strength, lightfastness, and stability.

InChI:InChI=1/C7H7N3O4/c1-4-6(9(11)12)2-5(8)3-7(4)10(13)14/h2-3H,8H2,1H3

Upstream product

• 91731-53-2 2-acetoxy-benzoic acid diethylamide 
• 118-55-8 phenyl Salicylate 
• 109-89-7 diethylamine 
• 4349-62-6 2-benzyloxybenzoyl chloride 
• 1441-87-8 salicyloyl chloride 
• 1696-17-9 N,N-diethylbenzamide 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 51674-10-3 N,N-diethyl-2-methoxybenzamide 
• 54-21-7 sodium salicylate 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 108-95-2 phenol 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 444-30-4 2-(trifluoromethyl)phenol 

Downstream Products

• 610-99-1 1-(2-Hydroxy-phenyl)-propan-1-on 
• 101777-18-8 2-(2,3-dihydroxy-propoxy)-benzoic acid diethylamide 
• 102372-99-6 2-(2-hydroxy-3-o-tolyloxy-propoxy)-benzoic acid diethylamide 
• 51674-10-3 N,N-diethyl-2-methoxybenzamide 
• 101114-89-0 2-(2,3-epoxy-propoxy)-benzoic acid diethylamide 
• 88769-10-2 N,N-Diethyl-2-triethylsilanyloxy-benzamide 
• 128741-08-2 N,N-diethyl-2-<(2-methoxyethoxy)methoxy>benzamide 
• 4992-02-3 o-dimethylaminomethylphenol 
• 82819-70-3 O-(2-N,N-diethylcarbamoyl)phenyl N,N-diethylcarbamate 
• 88769-08-8 N,N-Diethyl-2-trimethylsilanyloxy-benzamide 
• 102471-07-8 1-(2-carbamoyl-phenoxy)-3-(2-diethylcarbamoyl-phenoxy)-propan-2-ol 
• 721448-74-4 2-{[tert-butyl(dimethyl)silyl]oxy}-N,N-diethylbenzamide 
• 721448-93-7 7-benzyloxy-3,3-bis-hydroxymethyl-3H-isobenzofuran-1-one 
• 721448-94-8 acetic acid 4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester 

Relevant articles and documents

Chemo- and Regioselective Anionic Fries Rearrangement Promoted by Lithium Amides under Aerobic Conditions in Sustainable Reaction Media

A straightforward and efficient protocol to promote the metalation/anionic Fries rearrangements of O-aryl carbamates, using for the first time a lithium amide as metalating agent under aerobic/ambient-friendly reaction conditions, is reported. This approach enables the sustainable preparation of salicylamide derivatives with high levels of chemoselectivity within ultrafast reaction times, working at room temperature in the presence of air/moisture, and using environmentally responsible cyclopentyl methyl ether as a solvent. Furthermore, the regioselective manipulation of O-2-tolyl carbamates has been accomplished using interchangeably alkyllithiums or lithium amides, with an unexpected beneficial contribution from the employment of biorenewable protic eutectic mixtures as non-innocent reaction media.

Aryl Carbamates: Mechanisms of Orthosodiations and Snieckus-Fries Rearrangements

Aryl carbamates are orthometalated by sodium diisopropylamide (NaDA) in tetrahydrofuran. The resulting arylsodiums undergo Snieckus-Fries rearrangement to give orthoacylated phenols in good yield. The intermediate arylsodiums and resulting orthoacylated phenolates are suggested to be monomeric. The rate-limiting step in the two-step sequence depends on the steric demands of the carbamoyl moiety and the substituents in the meta position of the arene. Rate studies reveal a dominant disolvated-monomer-based orthometalation followed by a di- or trisolvated arylsodium monomer-based rearrangement. Kinetic evidence of a NaDA-catalyzed Snieckus-Fries rearrangement suggests the intermediacy of mixed trimers. Competitive halide eliminations to form benzyne are also discussed.

Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing

In chemical synthesis, rapid intramolecular rearrangements often foil attempts at site-selective bimolecular functionalization.We developed a microfluidic technique that outpaces the very rapid anionic Fries rearrangement to chemoselectively functionalize iodophenyl carbamates at the ortho position. Central to the technique is a chip microreactor of our design, which can deliver a reaction time in the submillisecond range even at cryogenic temperatures.The microreactorwas applied to the synthesis of afesal, a bioactive molecule exhibiting anthelmintic activity, to demonstrate its potential for practical synthesis and production.