| Identification | More | [Name]
3-ALLYLSALICYLALDEHYDE | [CAS]
24019-66-7 | [Synonyms]
AKOS BBS-00003205
TIMTEC-BB SBB010096
3-Allylsalicyladehyde
3-ALLYL SALCYLALDEHYDE
3-ALLYLSALICYLALDEHYDE
ASINEX-REAG BAS 02801117
Salicylaldehyde, 3-allyl-
3-Allylsalicylaldehyde 97%
3-Allylsalicylaldehyde, 96.5%
2-Hydroxy-3-allylbenzaldehyde
3-ALLYL-2-HYDROXY-BENZALDEHYDE
2-hydroxy-3-prop-2-enylbenzaldehyde
2-hydroxy-3-prop-2-enyl-benzaldehyde
2-HYDROXY-3-(2-PROPENYL)-BENZALDEHYDE
Benzaldehyde, 2-hydroxy-3-(2-propenyl)-
2-Hydroxy-3-(2-propen-1-yl)benzaldehyde
2-hydroxy-3-(prop-2-en-1-yl)benzaldehyde
Benzaldehyde, 2-hydroxy-3-(2-propen-1-yl)- | [Molecular Formula]
C10H10O2 | [MDL Number]
MFCD00037364 | [Molecular Weight]
162.19 | [MOL File]
24019-66-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Liquid | [Melting point ]
45 °C | [Boiling point ]
248.88°C (rough estimate) | [density ]
1.099 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5645
| [Fp ]
224 °F
| [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Soluble in chloroform. | [form ]
Oil | [pka]
8.50±0.10(Predicted) | [color ]
Light Yellow to Yellow | [Sensitive ]
Air Sensitive | [Usage]
A synthetic intermediate for the sythesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity | [InChI]
InChI=1S/C10H10O2/c1-2-4-8-5-3-6-9(7-11)10(8)12/h2-3,5-7,12H,1,4H2 | [InChIKey]
INLWEXRRMUMHKB-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=CC(CC=C)=C1O | [CAS DataBase Reference]
24019-66-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29124990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Liquid | [Uses]
3-Allyl Salicylaldehyde is a synthetic intermediate for the sythesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. Used in the prepar
ation of oxazole derivatives. Used in the preparation of imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. Also a reagent in the synthesis of antioxida
nt and antimicrobial novel chalcones. | [Uses]
3-Allylsalicylaldehyde is a synthetic intermediate for the synthesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. It is used in the preparation of oxazole derivatives and also imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. It is a reagent in the synthesis of antioxidant and antimicrobial novel chalcones. | [Synthesis]
The general procedure for the synthesis of 3-allyl-2-hydroxybenzaldehyde from formaldehyde and 2-allylphenol was as follows: 13.5 g (0.1 mol) of 2-allylphenol and 100 mL of acetonitrile were added to a three-necked flask, and 6.5 g of paraformaldehyde, 22 g (0.39 mol) of anhydrous magnesium chloride, and 0.02 mol of triethylamine were added sequentially under stirring conditions. The reaction mixture was refluxed for 4 h. The reaction solution was poured into ice water and the pH was adjusted with aqueous hydrochloric acid to 5. It was extracted twice with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 11 g of solid product was obtained in 68% yield. Mass spectrometry analysis showed a molecular ion peak of 163 (M + 1). | [References]
[1] Patent: US2012/142921, 2012, A1. Location in patent: Page/Page column 13
[2] Patent: EP2468730, 2012, A1. Location in patent: Page/Page column 14
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 8, p. 1525 - 1532
[4] Organic Letters, 2012, vol. 14, # 12, p. 3226 - 3229 |
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