5443-49-2

Usage

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%.

InChI:InChI=1/C9H7BrO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-7H/b9-6-

Upstream product

• 60-29-7 diethyl ether 
• 66894-04-0 2,3-dibromo-3-phenyl propanal 
• 94579-37-0 Triphenylphosphin-brom-formyl-methylen 
• 100-52-7 benzaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 104-55-2 3-phenyl-propenal 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 

Downstream Products

• 4364-05-0 (Z)-(2-bromo-3,3-diethoxyprop-1-en-1-yl)benzene 
• 13301-83-2 p-nitro-α-bromocinnamaldehyde 
• 37524-13-3 (Z)-2-bromo-3-(2-nitrophenyl)acrylaldehyde 
• 3463-27-2 1-methyl-5-phenyl-1H-pyrazole 
• 67565-85-9 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (2-bromo-3-phenyl-allylidene)-hydrazide 
• 82304-48-1 ethyl bis(2-bromo-1-hydroxy-3-phenylallyl)phosphinate 
• 111492-90-1 2-((Z)-1-Bromo-2-phenyl-vinyl)-oxirane 
• 82304-51-6 isobutyl bis(2-bromo-1-hydroxy-3-phenylallyl)phosphinate 
• 82304-49-2 propyl bis(2-bromo-1-hydroxy-3-phenylallyl)phosphinate 
• 82304-50-5 n-butyl bis(2-bromo-1-hydroxy-3-phenylallyl)phosphinate 
• 130366-30-2 (1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylsulfanyl)-acetic acid [(Z)-2-bromo-3-phenyl-prop-2-en-(E)-ylidene]-hydrazide 
• 140421-91-6 3-((2E,4Z)-4-Bromo-5-phenyl-penta-2,4-dienoyl)-chromen-2-one 
• 143212-87-7 (7-Amino-[1,2,4]triazolo[1,5-c]pyrimidin-5-ylsulfanyl)-acetic acid [(Z)-2-bromo-3-phenyl-prop-2-en-(E)-ylidene]-hydrazide 

Relevant academic research and scientific papers

Synthesis, X-ray crystal structure, electrochemical and antibacterial activity of a silver(I) complex with α-bromo-cinnamaldehyde salicylhydrazone

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.

Preparation method for catalytic synthesis of dihydropyrone compound containing 1, 3-enyne functional group by N-heterocyclic carbene

The invention discloses a preparation method for catalytic synthesis of dihydropyrone compound containing 1, 3-enyne functional group by N-heterocyclic carbene, which is characterized in that the derivative is shown as a general formula (1), in the formula, R1 is phenyl, substituted benzene, naphthalene, furan, thiophene or alkyl; R2 is phenyl, substituted benzene, furan or thiophene; and R3 is phenyl, substituted benzene, thiophene or alkyl. The dihydropyrone compound containing 1,3-enyne functional group can be effectively and efficiently prepared from reactant molecules alpha, beta-unsaturated aldehyde and 1,3-enyne aldehyde with simple structural units under the catalysis of N-heterocyclic carbene, and the dihydropyrone derivative has the advantages of good substrate universality, excellent yield, high enantioselectivity and the like.

Enantioselective NHC-Catalyzed [3+3] Annulation of α-Bromoenals with 2-Aminobenzimidazoles

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.

Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization–[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils

This work reports gold-catalyzed [4+3]-annulations of 2-(1-alkynyl)-2-alken-1-ones with anthranils to yield epoxybenzoazepine products with excellent exo-diastereoselectivity (dr>25:1). The utility of this new gold catalysis is manifested by applicable substrates over a broad scope. More importantly, the enantioselective versions of these [4+3]-cycloadditions have been developed satisfactorily with chiral gold catalysts under ambient conditions (DCM, 0 °C); the ee levels range from 88.0–99.9 %. With DFT calculations, we postulate a stepwise pathway to rationalize the preferable exo-stereoselection.

NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones

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.

Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N-versus C-Attack Paths

Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.

Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds

In this study, propane 3-bromo-1- (triphenyl phosphonium) bromide, I, and propane 3-bromo-1- (triphenyl phosphonium) tribromide, II, (II as a new brominating agent) were synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT-IR, spectroscopy, Thermogravimetric Analysis, Differential thermal analysis, Differential scanning calorimetry and single crystal X-ray analysis. Density functional theory calculations (energy, structural optimization and frequencies, Natural Bond Orbital, absorption energy and binding energy) were performed by using B3LYP/6-311 G++ (d, p) level of theory. Hirshfeld surface analysis and fingerprint plots were utilized to investigate the role of bromide and tribromide anions on the crystal packing structures of title compounds. The results revealed that the change of accompanying anionic moiety can affect the directional interactions of C-H?Br hydrogen bonds between anionic and cationic units in which the H?Br with a proportion of 53.8% and 40.9% have the major contribution in the stabilization of crystal structures of I and II, respectively. Furthermore, the thermal stability of new brominating agent II with tribromide anion was compared with compound I with bromide anion. Nontoxicity, short reaction time, thermal stability, simple working up and high yield are some of the advantages of these salts.

Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles

A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.

N-Heterocyclic Carbene-Catalyzed β-Indolylation of α-Bromoenals with Indoles

An unprecedented example of NHC-catalyzed β-indolylation of α-bromoenals with indoles has been developed. This concise protocol features several advantages (mild reaction conditions, broad substrate scope) and constructs synthetically useful building blocks, namely β-biaryl methylene esters. Notably, the β-biaryl methylene-type fragment is widely found in natural products or pharmaceuticals. (Figure presented.).

A method for synthesis of α - bromo cinnamic aldehyde

The invention discloses a method for synthesis of α - bromo cinnamic aldehyde, the first is the preparation of silica gel supported bromine; then to carbon tetrachloride as solvent, cinnamic aldehyde with silica gel supported bromine addition reaction for the synthesis of 2, 3 - dibromo - 3 - phenyl propanal; finally 2, 3 - dibromo - 3 - phenyl-propionaldehyde in phase transfer catalyst under the effect of the elimination reaction with the sodium carbonate in the synthetic α - bromo cinnamic aldehyde. The invention has the high reaction yield, the product quality is good, the after-treatment process is simple.