Description Synthesis
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3,5-Dibromobenzaldehyde

Description Synthesis
3,5-Dibromobenzaldehyde Structure
3,5-Dibromobenzaldehyde
  • CAS No.56990-02-4
  • Chemical Name:3,5-Dibromobenzaldehyde
  • CBNumber:CB4253350
  • Molecular Formula:C7H4Br2O
  • Formula Weight:263.91
  • MOL File:56990-02-4.mol
3,5-Dibromobenzaldehyde Property
  • Melting point 84-88 °C (lit.)
  • Boiling point 287.2±20.0 °C(Predicted)
  • Density 1.977±0.06 g/cm3(Predicted)
  • storage temp. Keep in dark place,Inert atmosphere,Room temperature
  • solubility soluble in DMSO, Ethyl Acetate, Methanol
  • form Powder or Crystals
  • color White to light beige
  • Water Solubility insoluble
  • Sensitive Air Sensitive
  • BRN 2573432
  • InChI InChI=1S/C7H4Br2O/c8-6-1-5(4-10)2-7(9)3-6/h1-4H
  • InChIKey ZLDMZIXUGCGKMB-UHFFFAOYSA-N
  • SMILES C(=O)C1=CC(Br)=CC(Br)=C1
  • CAS DataBase Reference 56990-02-4(CAS DataBase Reference)
  • UNSPSC Code 12352100
  • NACRES NA.22
Safety
  • Hazard Codes  :C
  • Risk Statements  :34
  • Safety Statements  :26-36/37/39-45
  • RIDADR  :UN 3261 8/PG 2
  • WGK Germany  :3
  • HazardClass  :8
  • PackingGroup  :Ⅱ
  • HS Code  :29130000
  • NFPA 704:
    1
    2 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H314
  • Precautionary statements P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
3,5-Dibromobenzaldehyde Price More Price(6)
  • Brand: Sigma-Aldrich(India)
  • Product number: 515396
  • Product name : 3,5-Dibromobenzaldehyde
  • Purity: 
  • Packaging: 5G
  • Price: ₹6062
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: ALFA India
  • Product number: ALF-B25495-14
  • Product name : 3,5-Dibromobenzaldehyde, 98%
  • Purity: 
  • Packaging: 25g
  • Price: ₹25875
  • Updated: 2022/05/26
  • Buy: Buy
  • Brand: ALFA India
  • Product number: ALF-B25495-06
  • Product name : 3,5-Dibromobenzaldehyde, 98%
  • Purity: 
  • Packaging: 5g
  • Price: ₹7526
  • Updated: 2022/05/26
  • Buy: Buy
  • Brand: ALFA India
  • Product number: ALF-B25495-03
  • Product name : 3,5-Dibromobenzaldehyde, 98%
  • Purity: 
  • Packaging: 1g
  • Price: ₹1210
  • Updated: 2022/05/26
  • Buy: Buy
  • Brand: TCI Chemicals (India)
  • Product number: D2832
  • Product name : 3,5-Dibromobenzaldehyde
  • Purity: min. 97.0 %
  • Packaging: 5G
  • Price: ₹7500
  • Updated: 2022/05/26
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3,5-Dibromobenzaldehyde Chemical Properties,Usage,Production

  • Description 3,5-Dibromobenzaldehyde is a white or beige solid with a melting point of 84-88 °C. Its boiling point and density are estimated to be 287.2±20.0 °C and 1.977±0.06 g/cm3, respectively. It is insoluble in water.
  • Synthesis 1,3,5-tribromobenzene (3.01 g, 9.6 mmol) in diethyl ether (80 mL) was cooled to -78°C followed by the addition of one equivalent of n-BuLi dropwise (2.5 M, 3.8 mL). The reaction was stirred for 30 minutes then DMF (740 µL, 9.6 mmol) was added dropwise to the reaction and stirred at -78°C for one hour. The vessel was then placed in an ice bath and stirred for 30 minutes. A 10% HCl solution (100 mL) was added to quench the reaction followed by CHCl3 (150 mL). The organic layer was collected and the aqueous layer washed with CHCl3 (80 mL). The organic layers where combined and dried over MgSO4 and the solvent removed. The crude product was purified by column chromatography eluting with 10% EtOAc in hexanes. Spectral data for the title compound was not reported in the literature reference. Yield: 1.93 g of the title compound (77%). 1H NMR (CDCl3, 300 MHz): δ = 9.90 (s, 1H), 7.92 (d, 2H), 7.60 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ = 189.3, 139.7, 139.0, 131.37, 124.1; GC-MS [M+H]+ 262.8709, calcd 262.8707
    3,5-Dibromobenzaldehyde
  • Uses 3,5-Dibromobenzaldehyde is a dibrominated benzaldehyde that is a very useful building block for the preparation of a wide range of biologically active compounds such as a antibacterials. The non-AIE active compound 3,5-dibromobenzaldehyde (DBB) could be used as the core to synthesize AIE luminogens, which differs from the traditional synthetic methods that are heavily dependent on the AIE active core. The three obtained DBB derivatives (S1, S2 and S3) displayed typical AIE features in which the quantum efficiencies of the solid film state were much higher than their solution state. The emission of these DBB derivatives could be fine-tuned by varying the substituents on the DBB rings[1].
  • Application Reactant involved in:
    Suzuki-Miyaura cross-coupling reactions
    Synthesis of blue fluorescent dye derivatives for organic light emitting diodes
    Sharpless kinetic resolution for the formation of Baylis-Hillman enal adducts
    Synthesis of podophyllotoxin mimetic pyridopyrazoles as anticancer agents
    Allylic alkylation
    Synthesis of C2-symmetric biphosphine ligand I
  • References [1] Kuang, Yunsuo et al. “Novel AIEgens with a 3,5-dibromobenzaldehyde skeleton: molecular design, synthesis, tunable emission and detection application?.” Analytical Methods 46 (2018): 5486–5492.
3,5-Dibromobenzaldehyde Preparation Products And Raw materials
Raw materials
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