4-(2-Hydroxyethoxy)benzaldehyde Chemical Properties

Melting point:

36-38°C

Boiling point:

335.2±17.0 °C(Predicted)

Density 

1.194±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

14.14±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H10O3/c10-5-6-12-9-3-1-8(7-11)2-4-9/h1-4,7,10H,5-6H2

InChIKey

VCDGTEZSUNFOKA-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(OCCO)C=C1

LogP

0.730 (est)

CAS DataBase Reference

22042-73-5(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-(2-hydroxyethoxy)- (22042-73-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2912490090

4-(2-Hydroxyethoxy)benzaldehyde Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 2267, 1995 DOI: 10.1021/jo00112a059

Synthesis

GENERAL METHODS: A mixture of 4-hydroxybenzaldehyde (1 mmol), 2-chloroethanol (1 mmol) and potassium carbonate (3 mmol) in dimethylsulfoxide (DMSO) was heated and refluxed for 6 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with water and extracted with dichloromethane. The organic phases were combined and concentrated under reduced pressure to remove the solvent, and the resulting residue was purified by column chromatography to afford the target product 4-(2-hydroxyethoxy)benzaldehyde (3m). 4.3.1. 4-(2-Hydroxyethoxy)benzaldehyde (3m) was a yellow oil in 80% yield; 1H NMR (400 MHz, CDCl3): δ 3.03 (1H, s, OH), 3.98 (2H, t, J = 4.4 Hz, -CH2-), 4.14 (2H, t, J = 4.4 Hz, -OCH2-), 6.98 (2H , d, J = 8.4 Hz, Ar-H), 7.80 (2H, d, J = 8.4 Hz, Ar-H), 9.84 (1H, s, CHO) ppm.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6519 - 6522
[2] Journal of the American Chemical Society, 2008, vol. 130, # 50, p. 16996 - 17003
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 10, p. 4235 - 4243
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 639 - 646
[5] Journal of Organometallic Chemistry, 2018, vol. 870, p. 38 - 50

4-(2-Hydroxyethoxy)benzaldehyde(22042-73-5)Related Product Information

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• L-PICEIN
• 4-CARBOXYPHENOXYACETIC ACID
• 4-ACETYLPHENOXYACETIC ACID
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• Robinin
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• MARITIMEIN
• 1,4-BENZODIOXAN-6-CARBOXALDEHYDE
• Diosmin
• RHOIFOLIN
• Hesperidin methylchalcone
• 3',5'-Dimethoxytricetin 7-O-β-D-glucopypranoside