84459-32-5

Basic information

• Product Name: 2-bromo-5-nitrobenzaldehyde
• Synonyms: 2-bromo-5-nitrobenzaldehyde;2-Bromo-5-nitrobenzenecarbaldehyde;4-Bromo-3-formylnitrobenzene;2-Bromo-5-nitrobenzadehyde;Benzaldehyde, 2-bromo-5-nitro-
• CAS NO: 84459-32-5
• Molecular Formula: C₇H₄BrNO₃
• Molecular Weight: 230.017
• EINECS: 200-002-4
• Mol File: 84459-32-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 105-107 °C
• Boiling Point: 307.174 °C at 760 mmHg
• Flash Point: 139.574 °C
• Appearance: /
• Density: 1.781
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-bromo-5-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-5-nitrobenzaldehyde(84459-32-5)
• EPA Substance Registry System: 2-bromo-5-nitrobenzaldehyde(84459-32-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 84459-32-5(Hazardous Substances Data)

Usage

Uses

2-Bromo-5-nitrobenzaldehyde is a cholesteryl ester transfer protein (CETP) inhibitor. 2-Bromo-5-nitrobenzaldehyde is a commonly used reactant for the synthesis of (-)-Linarinic acid derivatives as neuroprotective agents against oxygen glucose deprivation (OGD)-?induced cell damage.

InChI:InChI=1/C7H4BrNO3/c8-7-2-1-6(9(11)12)3-5(7)4-10/h1-4H

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 373622-95-8 2-bromo-N-methoxy-N-methyl-5-nitrobenzamide 
• 68-12-2 N,N-dimethyl-formamide 
• 586-78-7 para-nitrophenyl bromide 
• 80887-01-0 2-bromo-5-nitrobenzoyl chloride 
• 99-61-6 3-nitro-benzaldehyde 
• 33499-33-1 3-nitrobenzaldoxime O-methyl ether 
• 332883-48-4 (2-bromo-5-nitro-phenyl)methanol 
• 943-14-6 2-bromo-5-nitrobenzoic acid 

Downstream Products

• 90987-43-2 10-(2,4-Dimethyl-phenyl)-7-nitro-10H-pyrimido[4,5-b]quinoline-2,4-dione 
• 313696-22-9 isopropyl 4-(2-bromo-5-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate 
• 1037082-28-2 1-(2-bromo-5-nitrophenyl)-N-methylmethanamine 

Relevant articles and documents

Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.

Sequential Assembly of Morita-Baylis-Hillman Carbonates and Activated ortho-Vinylbenzaldehydes to Construct Chiral Methanobenzo[7]annulenone Frameworks

The α-regioselective asymmetric [3 + 2] annulation reaction of Morita-Baylis-Hillman carbonates from isatins and activated ortho-vinylbenzaldehyses was developed by the catalysis of a chiral tertiary amine. The sequential N-heterocyclic carbene-mediated intramolecular Stetter reaction was conducted to finally furnish the bridged 5,8-methanobenzo[7]annulen-9-one architectures incorporating a spirooxindole motif with excellent stereoselectivity.

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

The enantioselective, catalytic vicinal difluorination of alkenes is reported by II/IIII catalysis using a novel, C2-symmetric resorcinol derivative. Catalyst turnover via in situ generation of an ArIIIIF2 species is enabled by Selectfluor oxidation and addition of an inexpensive HF–amine complex. The HF:amine ratio employed in this process provides a handle for regioselective orthogonality as a function of Br?nsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) is disclosed (>20:1 in both directions). Validation with electron deficient styrenes facilitates generation of chiral bioisosteres of the venerable CF3 unit that is pervasive in drug discovery (20 examples, up to 94:06 e.r.). An achiral variant of the reaction is also presented using p-TolI (up to >95 % yield).