Pivalaldehyde

Structural formula
General
Surname	Pivalaldehyde
other names	Trimethylacetaldehyde 2,2-dimethylpropanal 2,2-dimethylpropionaldehyde
Molecular formula	C 5 H 10 O
Brief description	colorless liquid
External identifiers / databases
CAS number 630-19-3 EC number 211-134-6 ECHA InfoCard 100.010.123 PubChem 12417 Wikidata Q2097441
properties
Molar mass	86.13 g mol −1
Physical state	liquid
density	0.793 g cm −3 (25 ° C)
Melting point	6 ° C
boiling point	74 ° C (973 hPa)
Vapor pressure	14.8 kPa (20 ° C)
solubility	almost insoluble in water
Refractive index	1.378 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-315-335 P: 210-261
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Pivalaldehyde (also pivalaldehyde ) is a chemical compound from the group of aldehydes . With its isomers valeraldehyde ( n- pentanal), isovaleraldehyde and 2-methylbutyraldehyde , it forms the group of pentanals .

use

By reacting pivaldehyde with enantiomerically pure lactic acid , mandelic acid or proline , a sterically fixed acetal is obtained which is used in stereoselective synthesis. The α-hydroxycarboxylic acids ( S ) -lactic acid (R = CH ₃ ) or ( S ) -mandelic acid (R = C ₆ H ₅ = Ph) react diastereoselectively as follows:

Individual evidence

1. ↑ ^{a b c d e f g} Data sheet trimethylacetaldehyde from Sigma-Aldrich , accessed on December 1, 2012 ( PDF ).
2. ↑ ^{a b} Entry on pivalaldehyde at TCI Europe, accessed on December 2, 2012.
3. ↑ Dieter Seebach , Reto Naef: Enantioselective Generation and Diastereoselective Reactions of Chiral Enolates Derived from α-Heterosubstituted Carboxylic Acids , Helvetica Chimica Acta , 1981 , 64 , pp. 2704-2708 ( doi : 10.1002 / hlca.19810640829 ).