20383-28-2

Basic information

• Product Name: N,N-DIISOPROPYLBENZAMIDE
• Synonyms: N,N-DIISOPROPYLBENZAMIDE;TIMTEC-BB SBB008238;N,N-Bis(1-methylethyl)benzamide;N,N-di(propan-2-yl)benzamide;N,N-Diisopropylbenzamide 98%
• CAS NO: 20383-28-2
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.3
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 20383-28-2.mol
• Article Data: 61

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 148-152°C 18mm
• Flash Point: 148-152°C/18mm
• Appearance: /
• Density: 0.9923 (rough estimate)
• Vapor Pressure: 0.000662mmHg at 25°C
• Refractive Index: 1.5175 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.26±0.70(Predicted)
• Water Solubility: Soluble in water 301 mg/L @ 25°C.
• BRN: 2048090
• CAS DataBase Reference: N,N-DIISOPROPYLBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIISOPROPYLBENZAMIDE(20383-28-2)
• EPA Substance Registry System: N,N-DIISOPROPYLBENZAMIDE(20383-28-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 20383-28-2(Hazardous Substances Data)

Usage

General Description

N,N-Diisopropylbenzamide is a chemical compound with the formula C13H19NO that is commonly used as a pharmaceutical intermediate. These compounds serve as an essential bridge in drug discovery and formulation. It is also found in many pesticides due to its insecticidal properties. It exists as a crystalline substance at room temperature and its properties may vary based on substituents on the aromatic ring. However, it is imperative to handle these chemicals with caution due to their toxicity and potential hazards to the environment.

InChI:InChI=1/C13H19NO/c1-10(2)14(11(3)4)13(15)12-8-6-5-7-9-12/h5-11H,1-4H3

Upstream product

• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 108-18-9 diisopropylamine 
• 116858-79-8 tributyl-N,N-di-isopropylcarbamoylstannane 
• 116858-82-3 (N,N-diisopropylcarbamoyl)(trimethyl)stannane 
• 119-61-9 benzophenone 
• 932-31-0 ortho-tolylmagnesium bromide 
• 155496-72-3 2-(tert-butylsulfonyl)-N,N-diisopropylbenzamide 
• 93-58-3 benzoic acid methyl ester 
• 4111-54-0 lithium diisopropyl amide 
• 15563-32-3 N,N-diisopropyl-4-thiobenzamide 
• 98-88-4 benzoyl chloride 
• 455-32-3 benzoyl fluoride 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 161431-82-9 2-tert-Butylsulfanyl-N,N-diisopropyl-benzamide 
• 5398-11-8 3-phenylphthalide 
• 103258-06-6 2-formyl-N,N-diisopropylbenzamide 
• 864130-86-9 N,N-diisopropyl-2-(toluene-4-sulfinyl)-benzamide 
• 410074-77-0 N,N-diisopropyl 2-(3-methoxynaphthalen-2-yl)benzamide 
• 410074-78-1 N,N-diisopropyl 2-(4-bromo-3-methoxynaphthalen-2-yl)benzamide 
• 410074-83-8 5-benzylamino-6-methoxybenzo[a]fluoren-11-one 
• 103681-98-7 2-diisopropylaminocarbonylphenylboronic acid 
• 680218-51-3 N,N-diisopropyl-2-(dicyclohexylphosphanyl)benzamide 
• 20320-39-2 o-(N,N-diisopropylcarbamoyl)benzoic acid 
• 1527480-10-9 C₁₃H₁₇⁽²⁾HBrNO 
• 79839-67-1 N,N-diisopropyl-2,6-dideuteriobenzamide 
• 1374637-94-1 N,N-diisopropyl-2-(2-(triisopropylsilyl)ethynyl)benzamide 

Relevant articles and documents

Conformational Equilibria and Torsional Barriers of the Isopropyl Groups in N,N-Diisopropylbenzamide and its Thio and Seleno Analogues

The conformations of the isopropyl groups and the barriers to conformational interconversion in N,N-diisopropylbenzamide (1), and its thio (2) and seleno (3) analogues have been studied by dynamic 1H NMR spectroscopy.In 1 only one conformation is observed

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.