5443-49-2 Usage
Description
2-Bromocinnamaldehyde is a light yellow to ochre crystalline powder that is commonly employed as an anti-mildew agent in commercial products. It is a chemical compound with the molecular formula C9H7BrO, which is derived from cinnamaldehyde by the substitution of a bromine atom at the 2nd carbon position.
Uses
Used in Pharmaceutical Industry:
2-Bromocinnamaldehyde is used as a synthetic intermediate for the development of various pharmaceutical compounds, particularly in the synthesis of 3,4-diaryl 1H-pyrazoles. These pyrazoles have potential applications in the treatment of various diseases due to their diverse biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Bromocinnamaldehyde is utilized in the preparation of spiro imidazolidine-oxazolidine intermediates. This is achieved through a guanidinium ylide mediated aziridination process, which allows for the creation of complex molecular structures with potential applications in various industries.
Used as an Anti-Mildew Agent:
2-Bromocinnamaldehyde is widely used as an anti-mildew agent in commercial products, such as paints, coatings, and textiles. Its anti-fungal properties help prevent the growth of mold and mildew, thereby enhancing the durability and longevity of these products.
Hazard
Causes somnolence in oral, intraperitoneal, and subcutaneous lethal-dose
studies of rats; A skin and strong eye irritant; Toxic by
ingestion;
Synthesis
The synthesis of α-Bromocinnamaldehyde is as follows:The cinnamaldehyde and glacial acetic acid were stirred and bromine was added after cooling. Then add anhydrous potassium carbonate, reactants heated reflux for half an hour, cooling, precipitation coarse product. The crude product is dissolved by ethanol and recrystallized to obtain the finished product with a yield of about 80%.
Check Digit Verification of cas no
The CAS Registry Mumber 5443-49-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,4 and 3 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5443-49:
(6*5)+(5*4)+(4*4)+(3*3)+(2*4)+(1*9)=92
92 % 10 = 2
So 5443-49-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H7BrO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-7H/b9-6-
5443-49-2Relevant articles and documents
Synthesis, X-ray crystal structure, electrochemical and antibacterial activity of a silver(I) complex with α-bromo-cinnamaldehyde salicylhydrazone
Liu, Jun An,Li, Qing,Wang, Ming Ming,Wang, Hui,Gan, Guo Qing,Qu, Yang,Lin, Zhi Dong
, p. 507 - 511 (2010)
The mononuclear silver(I) complex [AgL(HL)· DMF] (I) (HL = C 6H13O2N2Br) has been prepared and characterized by physicochemical and spectroscopic methods, single crystal X-ray diffraction, cyclic voltammetry, and antibacterial activity tests. The complex crystallized in the triclinic system, and each Ag(I) is six-coordinate with a distorted octahedral geometry. The ligands chelate the metal center with N, O, and Br atoms from two different Schiff base ligands. O- H···O intermolecular hydrogen bonds connect adjacent complex molecules to form zigzag one-dimensional linear chains along the b axis. Cyclic voltammetry showed that the complex displays an irreversible reduction process at -0.41 V. The data from antibacterial activity tests indicate that the complex inhibits the growth of Staphyloccus aureus and Bacillus subtilis Cohn. Springer Science+Business Media B.V. 2010.
Enantioselective NHC-Catalyzed [3+3] Annulation of α-Bromoenals with 2-Aminobenzimidazoles
Xie, Yangxi,Li, Luoyuan,Sun, Shaofa,Wu, Zijun,Lang, Ming,Jiang, Di,Wang, Jian
supporting information, p. 391 - 394 (2020/01/31)
A chiral carbene-catalyzed [3+3] annulation of α-bromoenals with 2-aminobenzimidazoles providing pyrimido[1,2-a]benzimidazoles has been described. This protocol features a broad scope and good functional group tolerance. Biological studies indicated that the formed pyrimido[1,2-a]benzimidazole exhibited moderate cytotoxic activity against tumor cells.
NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones
Meng, Di,Xie, Yangxi,Peng, Qiupeng,Wang, Jian
supporting information, p. 7635 - 7639 (2020/10/09)
The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of α-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities.