759-22-8

Basic information

• Product Name: ACETIC ACID-DIISOPROPYLAMIDE
• Synonyms: Acetamide, N,N-diisopropyl-;ACETIC ACID-DIISOPROPYLAMIDE;N,N-DIISOPROPYLACETAMIDE;N,N-Bis(1-methylethyl)acetamide;N,N-di(propan-2-yl)acetamide;N,N-di(propan-2-yl)ethanamide;Acetic acid-diisoproylamide;N,N-Bisisopropyl-acetamide
• CAS NO: 759-22-8
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.23
• Mol File: 759-22-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 196 °C(lit.)
• Flash Point: 172 °F
• Appearance: /
• Density: 0.891 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.477mmHg at 25°C
• Refractive Index: n20/D 1.441(lit.)
• CAS DataBase Reference: ACETIC ACID-DIISOPROPYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETIC ACID-DIISOPROPYLAMIDE(759-22-8)
• EPA Substance Registry System: ACETIC ACID-DIISOPROPYLAMIDE(759-22-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 759-22-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 603, 1984 DOI: 10.1016/S0040-4039(00)99949-0

InChI:InChI=1/C8H17NO/c1-6(2)9(7(3)4)8(5)10/h6-7H,1-5H3

Upstream product

• 830-03-5 4-nitrophenol acetate 
• 108-18-9 diisopropylamine 
• 4232-27-3 2,4-dinitrophenyl acetate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 95777-15-4 N,N-Diisopropyl-2-((R)-toluene-4-sulfinyl)-acetamide 
• 23264-07-5 N,N-Diisopropylthioacetamid 
• 34251-46-2 N,N-diisopropylphenylacetamide 

Relevant articles and documents

Reactions of aryl phenylacetates with secondary amines in MeCN. Structure-reactivity relationship in the ketene-forming eliminations and concurrent E2 and E1cb mechanisms

Elimination reactions of aryl esters of arylacetic acids 1 and 2 promoted by R2NH in MeCN have been investigated kinetically. The reactions are second-order and exhibit β = 0.44-0.84, β(lg) = 0.41-0.50, and ρ(H) = 2.0-3.6. Bronsted β and β(lg) decrease with the electron-withdrawing ability of the β-aryl substituent. Hammett ρ(H) values remain nearly the same, but the β(lg) value increases as the base strength becomes weaker. Both ρ(H) and β decrease with the change of the leaving group from 4-nitrophenoxide to 2,4-dinitrophenoxide. The results are consistent with an E2 mechanism and a reaction coordinate with a large horizontal component corresponding to proton transfer. When the base-solvent system is changed from R2NH-MeCN to R2NH/R2NH2+-70 mol% MeCN(aq), the Bronsted β, ρ(H), and β(lg) decrease. Finally, the ketene-forming elimination reactions from p-nitrophenyl p-nitrophenylacetate promoted by R2NH/R2NH2+ buffers in 70 mol% MeCN(aq) have been shown to proceed by concurrent E2 and E1cb mechanisms.