24019-66-7

Basic information

• Product Name: 3-ALLYLSALICYLALDEHYDE
• Synonyms: Salicylaldehyde, 3-allyl-;TIMTEC-BB SBB010096;3-ALLYL-2-HYDROXY-BENZALDEHYDE;3-ALLYL SALCYLALDEHYDE;3-ALLYLSALICYLALDEHYDE;AKOS BBS-00003205;2-HYDROXY-3-(2-PROPENYL)-BENZALDEHYDE;ASINEX-REAG BAS 02801117
• CAS NO: 24019-66-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);pharmacetical;aldehydes;Aromatics;C10 to C21;Carbonyl Compounds;Intermediate;Pyridines
• Mol File: 24019-66-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 248.88°C (rough estimate)
• Flash Point: 224 °F
• Appearance: light yellow liquid
• Density: 1.099 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0208mmHg at 25°C
• Refractive Index: n20/D 1.5645
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in chloroform.
• PKA: 8.50±0.10(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 3-ALLYLSALICYLALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ALLYLSALICYLALDEHYDE(24019-66-7)
• EPA Substance Registry System: 3-ALLYLSALICYLALDEHYDE(24019-66-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 24019-66-7(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Liquid

Uses

Different sources of media describe the Uses of 24019-66-7 differently. You can refer to the following data:
1. 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.
2. 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.

InChI:InChI=1/C10H10O2/c1-2-4-8-5-3-6-9(7-11)10(8)12/h2-3,5-7,12H,1,4H2

Upstream product

• 28752-82-1 2-(allyloxy)benzaldehyde 
• 90-02-8 salicylaldehyde 
• 106-95-6 allyl bromide 
• 1746-13-0 allyl phenyl ether 
• 108-95-2 phenol 
• 1745-81-9 o-Allylphenol 
• 89-95-2 2-methyl-benzyl alcohol 
• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 114279-46-8 4-(3-allyl-2-hydroxy-benzylidene)-1,2-diphenyl-pyrazolidine-3,5-dione 
• 24019-59-8 3-Allyl-2-hydroxy-benzaldehyd-phenylimin 
• 872304-61-5 3-allyl-2,5-dihydroxy-benzaldehyde 
• 249515-81-9 1,2-bis(6-allyl-2-formylphenoxy)ethane 
• 249515-82-0 1,3-bis(6-allyl-2-formylphenoxy)propane 
• 249515-83-1 1,4-bis(6-allyl-2-formylphenoxy)butane 
• 84682-15-5 3-allyl-2-(allyloxy)benzaldehyde 
• 1027381-97-0 1-allyl-2-(tert-butyldimethylsilanyloxy)-3-[1-(tert-butyldimethylsilanyloxy)-2,2,2-trichloroethyl]benzene 
• 98652-20-1 bis[N-(2-(benzylamino)ethyl)-3-allyl-salicylaldiminato]iron(III) nitrate 
• 633290-49-0 7-allyl-4-nitro-2-(p-toluenesulfonyl)-1,2-dihydrobenz[6,7]oxepino[4,3,2-cd]indole 

Relevant articles and documents

Semicarbazone derivatives and use thereof

The invention belongs to the technical field of medicine, and relates to semicarbazone derivatives disclosed as general formula I, and geometrical isomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein the substituent groups M, R1, R2, R and n are defined in the specification. The invention also relates to a method for preparing compounds disclosed as Formula I, a pharmaceutical composition containing the compounds and application of the compounds and pharmaceutical composition in preparing drugs for treating and/or preventing cancers and other hyperplastic diseases.

Design, synthesis and biological evaluation of novel 4-phenoxy-6,7-disubstituted quinolines possessing (thio)semicarbazones as c-Met kinase inhibitors

In continuing our efforts to identify small molecules able to inhibit c-Met kinase, three series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives (23a-w, 26a-d and 30a-d) bearing (thio)semicarbazone scaffold were designed, synthesized and evaluated for their cytotoxicity. The biological data revealed that most compounds exhibited moderate-to-excellent activity against HT-29, MKN-45, A549 cancer cell lines and relative poor potency toward MDA-MB-231 cell as well as hardly any cytotoxicity in normal PBL cell. Eleven compounds were further examined for their inhibitory activity against c-Met kinase and three compounds (23h, 23n and 26a) demonstrated good inhibitory activity. This work resulted in the discovery of a potent c-Met inhibitor 23n, bearing 2-hydroxy-3-allylphenyl group at R2 moiety, as a valuable lead molecule, which possessed remarkable cytotoxicity and high selectivity against A549 and HT-29 cell lines with IC50 values of 11 nM and 27 nM. Besides, it displayed excellent c-Met kinase inhibition on a single-digital nanomolar level (IC50 = 1.54 nM). Meanwhile, the results from preliminarily in vivo study reflected that compound 23n showed promising overall PK profiles, consistent with the efficacy in both MKN-45 and HT-29 tumor xenograft mice model. These results clearly indicated that compound 23n is a potent and highly selective c-Met inhibitor and its favorable in vitro and in vivo profiles warrant further investigation.

Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: A facile approach for the synthesis of substituted 2H-chromene-3-carboxylates

A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a-v by the condensation of salicylaldehydes 1a-v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather than ester carbonyl due to a strong electron withdrawing effect and produced coumarin derivative 3a with the elimination of CHCl3.