4-ISOPROPOXYBENZALDEHYDE Chemical Properties

Melting point:

167 °C

Boiling point:

108-110 °C (5 mmHg)

Density 

1.036

refractive index 

1.545-1.547

Flash point:

108-110°C/5mm

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Light orange to Yellow

Sensitive 

Air Sensitive

BRN 

742921

InChI

InChI=1S/C10H12O2/c1-8(2)12-10-5-3-9(7-11)4-6-10/h3-8H,1-2H3

InChIKey

WDANSDASCKBVKH-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(OC(C)C)C=C1

CAS DataBase Reference

18962-05-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

HazardClass 

IRRITANT

HS Code 

2912490090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-ISOPROPOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

clear colorless to yellow liquid

Uses

ALDH1A3-IN-3 (compound 16) is a potent inhibitor of ALDH1A3, with an IC50 of 0.26 μM. ALDH1A3-IN-3 is also a good ALDH3A1 substrate. ALDH1A3-IN-3 can be used for the research of prostate cancer[1].

Synthesis

General procedure for the synthesis of 4-isopropoxybenzaldehyde from 2-iodopropane and p-hydroxybenzaldehyde: Referring to Example 3, to a 100 mL DMF solution containing 2 g (16.38 mmol) of p-hydroxybenzaldehyde was added sequentially 2.72 g (19.69 mmol) of K2CO3, 2.74 g (16.52 mmol) of KI, and 3.94 mL ( 39.38 mmol) 2-iodopropane and the reaction was carried out under argon protection. The reaction mixture was stirred at 80 °C overnight and subsequently concentrated. The concentrated residue was partitioned between CHCl3 and H2O to separate the organic and aqueous phases. The aqueous phase was further extracted with CHCl3 and after combining all the organic phases was dried and concentrated with MgSO4. The crude product was purified by silica gel column chromatography using a gradient polarity EtOAc/hexane mixed solvent as eluent, resulting in 2.08 g of oily 4-isopropoxybenzaldehyde in 77% yield. The structure of the product was confirmed by 1H-NMR (300 MHz, CDCl3, δTMS): 1.39 (d, J=6Hz, 6H), 4.67 (m, 1H), 6.96 (d, J=8.7Hz, 2H), 7.81 (d, J=8.7Hz, 2H), 9.87 (s, 1H).

IC 50

ALDH3; ALDH1

References

[1] Ibrahim AIM, et, al. Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer. J Med Chem. 2022 Mar 10;65(5):3833-3848. DOI:10.1021/acs.jmedchem.1c01367

4-ISOPROPOXYBENZALDEHYDE(18962-05-5)Related Product Information

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