4388-88-9

Basic information

• Product Name: Di-tert-butylglyoxal
• Synonyms: 2,2,5,5-Tetramethyl-3,4-hexanedione;2,2,5,5-Tetramethylhexane-3,4-dione;Bipivaloyl;Di-tert-butylglyoxal;Pivalil
• CAS NO: 4388-88-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Mol File: 4388-88-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: -1°C
• Boiling Point: 239.9°C (rough estimate)
• Flash Point: 67°C
• Appearance: /
• Density: 0.8776
• Vapor Pressure: 0.446mmHg at 25°C
• Refractive Index: 1.4157 (estimate)
• CAS DataBase Reference: Di-tert-butylglyoxal(CAS DataBase Reference)
• NIST Chemistry Reference: Di-tert-butylglyoxal(4388-88-9)
• EPA Substance Registry System: Di-tert-butylglyoxal(4388-88-9)

Safety Data

• Hazardous Substances Data: 4388-88-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 385, 1959 DOI: 10.1021/jo01085a029Synthesis, p. 209, 1971 DOI: 10.1055/s-1971-21697

InChI:InChI=1/C10H18O2/c1-9(2,3)7(11)8(12)10(4,5)6/h1-6H3

Upstream product

• 815-66-7 pivaloin 
• 7732-18-5 water 
• 815-17-8 trimethylpyruvic acid 
• 112423-73-1 (1S,4S)-1,4,6-Tri-tert-butyl-2,3-dioxa-5-aza-bicyclo[2.2.0]hex-5-ene 
• 35373-26-3 2-tert-butyl-4,4-dimethyl-pent-1-en-3-one 
• 17530-24-4 di-tert-butylacetylene 
• 3378-20-9 2,3-di-tert-butyl-1,3-butadiene 

Downstream Products

• 75-98-9 Trimethylacetic acid 
• 815-66-7 pivaloin 
• 7498-61-5 (+/-)-4,5-di-tert-butyl-5-chloro-5H-furan-2-one 
• 51884-33-4 4-diazo-2,2,5,5-tetramethyl-hexan-3-one 
• 1026163-32-5 4-(1,1-dimethylethyl)-4-hydroxy-2,2,5,5-tetramethyl-3-hexyl N-(4-toluenesulfonyl)carbamate 
• 815-24-7 Di-t-butyl ketone 
• 37494-10-3 6-hydroxy-2,2,5,5-tetramethyl-1-cyclohexanone 

Relevant articles and documents

Ozonolyses of α-Oxo-alkenes: On the Existence of α-Oxo-ozonides

Ozonolyses of nine acyclic (1a-i) and two cyclic (14, 29) α-oxo-alkenes on polyethylene or in pentane afforded in eight cases (1d-i, 14, 29) isolable α-oxo-ozonides. α-Diozonides (9) are obtained from five of the acyclic α-oxo-alkenes (1a, b, d, g, h).All isolated ozonides are labile; the 2,4-dinitrophenylhydrazones of the α-oxo-ozonides, however, are very stable.Decomposition of the α-oxo-ozonides affords not only the hitherto known fragments, but non-peroxidic isomers (8) of the ozonides, too.

Characterization of Intermediates in the Reaction of Ozone with Di-tert-butylacetylene. A Novel Pivaloylating System

Reaction of di-tert-butylacetylene (1a) with ozone in -40 deg C aprotic solvents upon warming leads to pivalic anhydride, pivalil, and pivalic acid, with evolution of isobutane, isobutene, carbon dioxide, and carbon monoxide.Spectral and chemical evidence indicated the presence of at least two labile intermediates in the reaction.Ozonolysis of the alkyne in the presence of compounds containing a hydroxyl function led to their pivaloyl derivatives with incorporation of both tert-butyl groups, probably via fragmentation of an adduct of ROH to an intermediate carbonyl oxide.