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2-Hydroxy-5-methoxybenzaldehyde

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Organic compound and isomer of vanillin
2-Hydroxy-5-methoxybenzaldehyde
Names
Preferred IUPAC name 2-Hydroxy-5-methoxybenzaldehyde
Other names 5-Methoxysalicylaldehyde; 2-Formyl-4-methoxyphenol; 6-Hydroxy-m-anisaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.537 Edit this at Wikidata
EC Number
  • 211-589-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-6H,1-2H3Key: FZHSPPYCNDYIKD-UHFFFAOYSA-N
  • InChI=1S/C8H8O3/c1-11-7-2-3-8(10)6(4-7)5-9/h2-5,10H,1H3Key: AFUKNJHPZAVHGQ-UHFFFAOYAN
SMILES
  • COC1=CC(=C(C=C1)O)C=O
Properties
Chemical formula C8H8O3
Molar mass 152.149 g·mol
Appearance Yellow to yellow-green liquid
Density 1.219 g/mL
Melting point 4 °C (39 °F; 277 K)
Boiling point 250 °C (482 °F; 523 K)
Refractive index (nD) 1.578
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2-Hydroxy-5-methoxybenzaldehyde is an organic compound and an isomer of vanillin.

Synthesis and reactions

The chemical is produced by the Reimer-Tiemann reaction on 4-methoxyphenol with a 79% yield.

It reacts with malononitrile to form 2-imino-6-methoxy-2H-1-benzopyran-3-carbonitrile. It can be reduced by sodium borohydride in ethanol to form 2-hydroxy-5-methoxybenzyl alcohol.

See also

References

  1. Wynberg, Hans; Meijer, Egbert W. (2005). The Reimer–Tiemann Reaction. p. 16. doi:10.1002/0471264180.or028.01. ISBN 9780471264187.
  2. Dinparast, Leila; Hemmati, Salar; Zengin, Gokhan; Alizadeh, Ali Akbar; Bahadori, Mir Babak; Kafil, Hossein Samadi; Dastmalchi, Siavoush (2019). "Rapid, Efficient, and Green Synthesis of Coumarin Derivatives via Knoevenagel Condensation and Investigating Their Biological Effects". ChemistrySelect. 4 (31): 9211–9215. doi:10.1002/slct.201901921. ISSN 2365-6549. S2CID 202077668.
  3. Cheng, Yan; Ono, Masahiro; Kimura, Hiroyuki; Kagawa, Shinya; Nishii, Ryuichi; Kawashima, Hidekazu; Saji, Hideo (2010). "Fluorinated Benzofuran Derivatives for PET Imaging of β-Amyloid Plaques in Alzheimer's Disease Brains". ACS Medicinal Chemistry Letters. 1 (7): 321–325. doi:10.1021/ml100082x. ISSN 1948-5875. PMC 4007906. PMID 24900214.


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