3,5-Dibromobenzaldehyde
Description Synthesis- Product Name
- 3,5-Dibromobenzaldehyde
- CAS No.
- 56990-02-4
- Chemical Name
- 3,5-Dibromobenzaldehyde
- Synonyms
- DBBA;3,5-DIBROMOBENZALDEHYDE;Benzaldehyde, 3,5-dibromo-;3,5-Dibromobenzaldehyde>3,5-DIBROMOBENZALDEHYDE 98%;3,5-Dibromobenzaldehyde,98%;3,5-Dibromobenzaldehyde//DBBA;3,5-dibromophenylformaldehyde;METHYL3,5-DIBROMOPHENYLACETATE;3,5-Dibromobenzaldehyde97%MinByG.C
- 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)
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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
N-Bromosuccinimide Price
- Product number
- 515396
- Product name
- 3,5-Dibromobenzaldehyde
- Packaging
- 5g
- Price
- $47.7
- Updated
- 2024/03/01
- Product number
- D2832
- Product name
- 3,5-Dibromobenzaldehyde
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $63
- Updated
- 2024/03/01
- Product number
- D2832
- Product name
- 3,5-Dibromobenzaldehyde
- Purity
- >97.0%(GC)
- Packaging
- 25g
- Price
- $252
- Updated
- 2024/03/01
- Product number
- B25495
- Product name
- 3,5-Dibromobenzaldehyde, 98%
- Packaging
- 5g
- Price
- $90.65
- Updated
- 2024/03/01
- Product number
- B25495
- Product name
- 3,5-Dibromobenzaldehyde, 98%
- Packaging
- 1g
- Price
- $28.3
- Updated
- 2021/12/16
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
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
Preparation Products
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View Lastest Price from 3,5-Dibromobenzaldehyde manufacturers
- Product
- 3,5-dibromobenzaldehyde 56990-02-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 0.98
- Supply Ability
- 1 tons
- Release date
- 2024-11-15
- Product
- 3,5-Dibromobenzaldehyde 56990-02-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 10mg
- Purity
- 99%HPLC
- Supply Ability
- 2000tons
- Release date
- 2020-01-15
- Product
- 3,5-Dibromobenzaldehyde 56990-02-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 mt
- Release date
- 2024-10-24