49678-04-8

Basic information

• Product Name: 4-Bromocinnamaldehyde
• Synonyms: 4-BROMOCINNAMALDEHYDE;2-PROPENAL, 3-(4-BROMOPHENYL)-,(2E);TRANS-4-BROMOCINNAMALDEHYDE;E-3-(4-Bromophenyl)-2-propenal;(E)-3-(4-Bromophenyl)propenal;(E)-4-Bromocinnamaldehyde;4-Bromo-trans-cinnamaldehyde;3-(4-broMophenyl)acrylaldehyde
• CAS NO: 49678-04-8
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• Product Categories: Miscellaneous Reagents;aldehydes
• Mol File: 49678-04-8.mol

Chemical Properties

• Melting Point: 70-74°C
• Boiling Point: 310.5 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: Light Yellow Solid
• Density: 1.466 g/cm³
• Vapor Pressure: 0.000598mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Hexane
• CAS DataBase Reference: 4-Bromocinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromocinnamaldehyde(49678-04-8)
• EPA Substance Registry System: 4-Bromocinnamaldehyde(49678-04-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 49678-04-8(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Solid

InChI:InChI=1/C9H7BrO/c10-9-5-3-8(4-6-9)2-1-7-11/h1-7H/b2-1+

Upstream product

• 105515-33-1 3-(4-bromophenyl)prop-2-en-1-ol 
• 3650-78-0 methyl 4-bromocinnamate 
• 13565-09-8 4-bromocinnamoyl chloride 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 75-07-0 acetaldehyde 
• 80793-25-5 3-(4-bromophenyl)propanal 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 589-87-7 1,4-bromoiodobenzene 
• 1124-14-7 1-bromo-4-cyclopropylbenzene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 75-27-4 bromodichloromethane 
• 64-17-5 ethanol 

Downstream Products

• 36382-37-3 p-Bromzimtaldehyd-diethylacetal 
• 1013984-77-4 1-(4-bromo-phenyl)-4-methyl-penta-1,4-dien-3-ol 
• 898822-61-2 (E)-1-(4-bromophenyl)-4-methylpenta-1,4-dien-3-one 
• 1020746-20-6 (2S,3R)-3-(4-bromophenyl)oxirane-2-carbaldehyde 
• 1095532-18-5 (2R,3R)-2-(benzylthio)-3-(4-bromophenyl)-3-(2,5-dioxopyrrolidin-1-yl)propanal 
• 1095532-17-4 (2S,3R)-2-(benzylthio)-3-(4-bromophenyl)-3-(2,5-dioxopyrrolidin-1-yl)propanal 
• 1119040-15-1 (2S,3R,4S)-2-(4-bromophenyl)-4-hydroxy-4-methyl-3,4-dihydro-2H-thiochromene-3-carbaldehyde 
• 1032816-34-4 C₁₅H₁₅BrO₂ 
• 1032816-30-0 C₁₄H₁₃BrO₂ 
• 1062118-01-7 (4S)-4-(4-bromophenyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one 
• 1142043-02-4 C₂₁H₁₅BrN₂O₂ 
• 1111644-55-3 (1S,2R,3R,5R)-ethyl-2-(4-bromophenyl)-5-(2-hydroxypropan-2-yl)-7-oxo-6-oxabicyclo[3.2.0]heptane-3-carboxylate 
• 1111644-57-5 (1S,2S,3R,5R)-ethyl-2-(4-bromophenyl)-5-(2-hydroxypropan-2-yl)-7-oxo-6-oxabicyclo[3.2.0]heptane-3-carboxylate 

Relevant articles and documents

Synthesis and biological evaluation of novel radioiodinated benzimidazole derivatives for imaging α-synuclein aggregates

α-Synuclein (α-syn) aggregates are commonly found in the brains of patients with Parkinson's disease (PD), dementia with Lewy bodies (DLB), and some other diseases. Therefore, in vivo imaging of α-syn aggregates would aid in drug development, early diagno

A structural study of Troger's base scaffold-based dyes for DSSC applications

Three Troger's base scaffold-based metal-free sensitizers TD1, TD2 and TD3 with triphenylamine donor and rhodanine-3-acetic acid as an acceptor/anchoring group were designed and synthesized for dye-sensitized solar cells. The sensitizer series was designed to investigate the influence of the poly[n]enic (from n?=?0 to 2) backbones and their anchoring effect in DSSCs. Optical, electrochemical and photovoltaic properties were compared with analogues dyes D1-D3 possessing one anchoring group. It has been proven that the extended polymethine chains ensure flexibility of these units and inspire the interaction between two chromophores promoting aggregate formation in these Troger's base-based dyes.

Cis-Enals in N-heterocyclic carbene-catalyzed reactions: Distinct stereoselectivity and reactivity

The first successful generation of cis-homoenolate equivalents from cis-enals under the catalysis of N-heterocyclic carbenes (NHCs) has been realized. The cis-homoenolate intermediates undergo effective reactions with α,β-unsaturated imines to afford chir

An efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones

An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% ? 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the obove characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Substrate-Controlled Chemo-/Enantioselective Synthesis of α-Benzylated Enals and Chiral Cyclopropane-Fused 2-Chromanone Derivatives

Substrate-controlled cascade reactions between α,β-unsaturated aldehydes or their analogues and 2,4-dinitrobenzyl chloride in the presence of a chiral secondary amine as the catalyst and base were developed, to obtain a broad spectrum of α-benzylated enals and enantioenriched cyclopropane-fused chroman-2-one derivatives. The cyclopropane-tethered iminium ion clearly served as a key intermediate in these reactions to trigger stereochemical outcomes, one of which was supported by a control experiment. (Figure presented.).

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.

Asymmetric Synthesis of Functionalized 9-Methyldecalins Using a Diphenylprolinol-Silyl-Ether-Mediated Domino Michael/Aldol Reaction

Substituted 9-methyldecalin derivatives containing an all carbon quaternary chiral center were synthesized with excellent enantioselectivity via an organocatalyst-mediated domino reaction. The first reaction is a diphenylprolinol silyl ether-mediated Michael reaction, and the second reaction is an intramolecular aldol reaction. The enantiomerically pure catalyst is involved in both reactions.

Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method

The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.

Enantioselective Organocatalytic Synthesis of 1,2,3-Trisubstituted Cyclopentanes

An organocatalytic asymmetric domino Michael/α-alkylation reaction between enals and non-stabilized alkyl halides has been developed. Chiral secondary amine catalyzed cyclization reaction of 1-bromo-3-nitropropane with α,β-unsaturated aldehydes provides 1,2,3-trisubstituted cyclopentane carbaldehydes with high diastereo- (dr up to 8 : 1) and enantioselectivities (ee up to 96 %).