83594-04-1

Basic information

• Product Name: 4-METHYLPENTANOIC ANHYDRIDE
• Synonyms: 4-METHYLPENTANOIC ANHYDRIDE;4-Methylpentanoic anhydride (4-Methylvaleric anhydride);4-METHYLPENTANOIC ANHYDRIDE 4-METHYLVALERIC ANHYDRIDE
• CAS NO: 83594-04-1
• Molecular Formula: C₁₂H₂₂O₃
• Molecular Weight: 214.3
• Mol File: 83594-04-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 244.886°C at 760 mmHg
• Flash Point: 106.883°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: 1.434
• CAS DataBase Reference: 4-METHYLPENTANOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLPENTANOIC ANHYDRIDE(83594-04-1)
• EPA Substance Registry System: 4-METHYLPENTANOIC ANHYDRIDE(83594-04-1)

Safety Data

• Hazardous Substances Data: 83594-04-1(Hazardous Substances Data)

Usage

General Description

4-Methylpentanoic anhydride, also known as Pivalic Anhydride, is a chemical compound with the molecular formula C9H16O3. It is a colorless liquid with a pungent odor, and is commonly used in organic synthesis as a reagent for acylation reactions. It is also used as a protecting group for alcohols and amines in organic chemistry. It is a highly reactive compound, and should be handled with care due to its potential to cause irritation to the skin, eyes, and respiratory system. Additionally, it should be stored in a cool, dry place away from incompatible materials.

InChI:InChI=1/C12H22O3/c1-9(2)5-7-11(13)15-12(14)8-6-10(3)4/h9-10H,5-8H2,1-4H3

Upstream product

• 646-07-1 4-Methylpentanoic acid 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 25228-71-1 4-Methyl-pentanoic acid [3-(4-methyl-pentanoylamino)-phenyl]-amide 
• 591-50-4 iodobenzene 
• 2412-80-8 methyl 4-methylpentanoate 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Relevant articles and documents

Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.