| Identification | More | [Name]
4-ISOPROPOXYBENZALDEHYDE | [CAS]
18962-05-5 | [Synonyms]
4-ISOPROPOXYBENZALDEHYDE
AKOS 226-45
AKOS B000275
AKOS BC-2523
ASISCHEM R42745
BUTTPARK 32\08-27
4-ISOPROPOXY-1-FORMYLBENZENE | [EINECS(EC#)]
606-183-9 | [Molecular Formula]
C10H12O2 | [MDL Number]
MFCD00052357 | [Molecular Weight]
164.2 | [MOL File]
18962-05-5.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to yellow liquid | [Melting point ]
167 °C | [Boiling point ]
108-110 °C (5 mmHg)
| [density ]
1.036 | [refractive index ]
1.545-1.547
| [Fp ]
108-110°C/5mm | [storage temp. ]
Inert atmosphere,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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2912490090 |
| Hazard Information | Back Directory | [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 |
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