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.

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.