Acetaldehyde oxime

Structural formula
( Z ) -isomer (left) and ( E ) -isomer (right)
General
Surname	Acetaldehyde oxime
other names	Acetaldoxime
Molecular formula	C 2 H 5 NO
Brief description	colorless liquid
External identifiers / databases
CAS number 107-29-9 5780-37-0 [( E ) -form] 5775-72-4 [( Z ) -form] EC number 203-479-6 ECHA InfoCard 100.003.164 PubChem 7863 Wikidata Q27103709
properties
Molar mass	59.07 g mol −1
Physical state	liquid
density	0.969 g cm −3
Melting point	12 ° C (α-form) 45 ° C (β-form) 47 ° C [mixture of ( E ) and ( Z ) isomer]
boiling point	115 ° C
Vapor pressure	13 hPa (25 ° C)
solubility	easily soluble in water (185 g l −1 at 25 ° C) soluble in ethanol soluble in most organic solvents
Refractive index	1.426 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-302-331 P: 210-304 + 340-308 + 310
Toxicological data	740 mg kg −1 ( LD 50 ,  rat ,  oral ) 100 mg kg −1 ( LD 50 ,  mouse , ip )
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

Acetaldehyde oxime is a chemical compound from the group of oximes . It occurs in two stereoisomeric forms ( cis - and trans -).

Extraction and presentation

Acetaldehyde oxime can be obtained by reacting acetaldehyde with hydroxylamine . The synthesis produces a mixture of ( Z ) -isomer and ( E ) -isomer:

In the resulting mixture of isomers, the ( Z ) isomer usually dominates .

properties

Acetaldehyde oxime is a colorless, flammable liquid that is easily soluble in water. It comes in two forms that melt at 12 ° C or 45 ° C. The two stereoisomers both have a planar molecular structure and their energy difference is only 0.7 kcal / mol. The commercially available products have a ( Z ) :( E ) ratio of 10-20: 1. The oxime slowly decomposes at room temperature in air.

use

Acetaldehyde is useful as an intermediate for the synthesis of organic compounds such as pesticides Methom , Thiodicarb , and Alanycarb used.

safety instructions

The vapors of acetaldehyde oxime can form an explosive mixture with air ( flash point 40 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on acetaldehyde oxime in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
2. ^ ^{A b c} Richard P. Pohanish: Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens . William Andrew, 2011, ISBN 978-1-4377-7869-4 , pp. 3033 ( limited preview in Google Book search).
3. ↑ ^{a b c} Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons, Ltd, 2001, ISBN 978-0-470-84289-8 , Acetaldoxime, doi : 10.1002 / 047084289x.ra004 / abstract (English).
4. ↑ Richard J. Lewis: Hazardous Chemicals Desk Reference . John Wiley & Sons, 2008, ISBN 0-470-33445-2 , pp. 1462 ( limited preview in Google Book Search).
5. ↑ Data sheet Acetaldehyde oxime, mixture of syn and anti, 99% from Sigma-Aldrich , accessed on April 15, 2017 ( PDF ).
6. ↑ ^{a b c} Entry on acetaldehyde oxime in the Hazardous Substances Data Bank , accessed April 15, 2017.
7. ^ ^{A b} Charles S. Gibson: Essential Principles of Organic Chemistry . Cambridge University Press, 2016, ISBN 978-1-316-60386-4 , pp. 160 ( limited preview in Google Book Search).
8. ^ Super Course in Chemistry for the IIT-JEE: Organic Chemistry . 2011, ISBN 81-317-5979-2 , pp. 34 ( limited preview in Google Book search).
9. ↑ wiley.com: Acetaldoxime , accessed April 15, 2017
10. ^ Zvi Rappoport, Joel F. Liebman: The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids . John Wiley & Sons, 2008, ISBN 0-470-74195-3 , pp. 17 ( limited preview in Google Book search).
11. ↑ M. Madalena Caldeira, Victor MS Gil: Self-association and relative stability of the isomeric structures of acetaldoxime. In: Tetrahedron. 32, 1976, p. 2613, doi: 10.1016 / 0040-4020 (76) 88037-4 .