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Salicylaldehyde



Salicylaldehyde
Chemical name 2-Hydroxybenzaldehyde
Other names Salicylaldehyde
Salicylic aldehyde
Chemical formula C7H6O2
Molecular mass 122.12 g/mol
CAS number [90-02-8]
Density 1.146 g/cm3
Melting point -7 °C
Boiling point 196-197 °C
SMILES OC1=C(C=O)C=CC=C1
Related compounds Salicylic acid
Benzaldehyde
Salicylaldoxime
Disclaimer and references

Salicylaldehyde, or 2-hydroxybenzaldehyde, is the chemical compound with the formula C6H4CHO-2-OH [1]. This colourless oily liquid has a bitter almond odor. Salicylaldehyde is a key precursor to a variety chelating agents, some of which are commercially important. It can be prepared from phenol and chloroform by heating with sodium hydroxide in a Reimer-Tiemann reaction.

Additional recommended knowledge

Salicylaldehyde is a common highly-functionalized arene that has often been exploited as a precursor to still other chemicals, which are shown in the figure, from the left: catechol, benzofuran, a salicylaldehydimine (R = alkyl or aryl), 3-carbethoxycoumarin.

Other hydroxybenzaldehydes

Three isomers exist of hydroxybenzaldehyde with the hydroxyl group in the ortho, meta, or para position.


ortho-hydroxybenzaldehydemeta-hydroxybenzaldehydepara-hydroxybenzaldehyde
Synonymssalisylaldehyde3-hydroxybenzaldehyde 4-hydroxybenzaldehyde
CAS number[90-02-8][100-83-4] [123-08-0]
Appearancecolorless oily liquidlight-tan crystals yellow to tan powder
Density1.146 g/cm3 1.226 ± 0.06 g/cm3
Melting point -7 °C100-103 °C 112-116 °C
Boiling point196-197 °C191 °C 50 mm Hg310.00 - 311.00 °C
hydroxybenzaldehydes [5] [6].


3-Hydroxybenzaldehyde has been prepared from m-nitrobenzaldehyde in a sequence of nitro group [[organic reduction, diazotisation of the amine and its hydrolysis [7] [8]

References

  1. ^ Merck Index, 11th Edition, 8295.
  2. ^ Dakin, H. D. (1941). "Catechol". Org. Synth.; Coll. Vol. 1: 149. 
  3. ^ Horning, E. C.; Horning, M. G.; Dimmig, D. A. (1955). "3-Carbethoxycoumarin". Org. Synth.; Coll. Vol. 3: 165. 
  4. ^ Burgstahler, A. W.; Worden, L. R. (1973). "Coumarone". Org. Synth.; Coll. Vol. 5: 251. 
  5. ^ http://www.sigmaaldrich.com
  6. ^ http://www.thegoodscentscompany.com/data/rw1040191.html
  7. ^ Organic Syntheses, Coll. Vol. 3, p.453 (1955); Vol. 25, p.55 (1945). http://www.orgsynth.com/orgsyn/orgsyn/prepContent.asp?prep=cv3p0453
  8. ^ Organic Syntheses, Coll. Vol. 3, p.564 (1955); Vol. 29, p.63 (1949). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0564
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Salicylaldehyde". A list of authors is available in Wikipedia.
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