138555-58-5

Basic information

• Product Name: 2-BROMOCINNAMALDEHYDE
• Synonyms: 2-PROPENAL, 3-(2-BROMOPHENYL)-,(2E);(E)-3-(2-Bromophenyl)-2-propenal;trans-2-Bromocinnamaldehyde;2-Bromocinnamaldehyde;3-(2-BroMophenyl)acrylaldehyde;2-BROMOCINMALDEHYDE
• CAS NO: 138555-58-5
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• EINECS: 226-637-6
• Mol File: 138555-58-5.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 305.751 °C at 760 mmHg
• Flash Point: 111.167 °C
• Appearance: /
• Density: 1.467 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-BROMOCINNAMALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOCINNAMALDEHYDE(138555-58-5)
• EPA Substance Registry System: 2-BROMOCINNAMALDEHYDE(138555-58-5)

Safety Data

• Hazardous Substances Data: 138555-58-5(Hazardous Substances Data)

Usage

General Description

2-Bromocinnamaldehyde is a chemical compound with the molecular formula C9H7BrO. It is a yellow crystalline solid with a sweet, floral odor. 2-BROMOCINNAMALDEHYDE is commonly used in the production of various pharmaceuticals, as well as in the synthesis of other organic compounds. It is also used as a flavor and fragrance ingredient in the manufacturing of perfumes, soaps, and cosmetics. Additionally, 2-Bromocinnamaldehyde has been researched for its potential biological and pharmacological properties, including its antiproliferative and anti-inflammatory effects. However, it is important to handle this compound with caution due to its potential health hazards, including skin and eye irritation.

InChI:InChI=1/C9H7BrO/c10-9-6-2-1-4-8(9)5-3-7-11/h1-7H/b5-3+

Upstream product

• 64-17-5 ethanol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 75-07-0 acetaldehyde 
• 108-05-4 vinyl acetate 
• 56984-71-5 (E:Z)-3-(2-bromophenyl)prop-2-en-1-ol 
• 222713-56-6 1-(2-bromophenyl)-2-propyn-1-ol 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 125643-35-8 1-bromo-2-(buta-1,3-dien-1-yl)benzene 
• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 583-55-1 1-Bromo-2-iodobenzene 
• 91047-77-7 ethyl (2E)-3-(2-bromophenyl)prop-2-enoate 
• 42918-20-7 1-allyl-2-bromobenzene 
• 114837-50-2 2-bromo-α-(ethenyl)benzenemethanol 

Downstream Products

• 7345-79-1 2-bromocinnamic acid 
• 167367-47-7 (E)-1-bromo-2-(3'-hydroxy-3'-phenylprop-1'-enyl)benzene 
• 1345157-50-7 (3S,4R,6R)-ethyl 1-benzyl-4-(2-bromophenyl)-6-hydroxy-2-oxopiperidine-3-carboxylate 
• 1182719-39-6 C₁₆H₁₈BrFO₅ 
• 223576-76-9 C₉H₆BrNO 
• 1213268-41-7 C₉H₈BrNO₂ 
• 1253858-23-9 C₁₈H₂₀BrNO₄ 
• 1290540-49-6 (R)-3-(2-bromophenyl)-3-(10-oxo-9,10-dihydro-anthracen-9-yl)-propanal 
• 1292323-41-1 (E)-tert-butyl 2-(3-(2-bromophenyl)allylamino)ethylcarbamate 
• 1292323-85-3 tert-butyl 2-(7-acetyl-9-(2-bromophenyl)-3-oxo-1H-pyrrolo[3,4-β]indolizin-2(3H)-yl)ethylcarbamate 

Relevant articles and documents

A simple route to 9-fluorenylidenes by domino Suzuki/Heck coupling reactions

A palladium catalyzed domino intermolecular Suzuki followed by intramolecular Heck coupling is described. This strategy afforded a novel and convenient synthesis of various 9-fluorenylidene derivatives in one-pot under relatively mild reaction condition.

Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion

Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.

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.