3,5-Dibromobenzaldehyde

3,5-Dibromobenzaldehyde Basic information
Description Synthesis
Product Name:3,5-Dibromobenzaldehyde
Synonyms:3,5-Dibromobenzaldehyde97%MinByG.C;3,5-Dibromobenzaldehyde,98%;3,5-DIBROMOBENZALDEHYDE;3,5-DIBROMOBENZALDEHYDE 98%;METHYL3,5-DIBROMOPHENYLACETATE;DBBA;3,5-Dibromobenzaldehyde>;Benzaldehyde, 3,5-dibromo-
CAS:56990-02-4
MF:C7H4Br2O
MW:263.91
EINECS:611-441-9
Product Categories:intermediate;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials, Aromatic Aldehydes;OLED;Functional Materials;Aldehydes;C7;Carbonyl Compounds;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Adehydes, Acetals & Ketones;Bromine Compounds;Building Blocks for Dendrimers
Mol File:56990-02-4.mol
3,5-Dibromobenzaldehyde Structure
3,5-Dibromobenzaldehyde Chemical Properties
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
InChIKeyZLDMZIXUGCGKMB-UHFFFAOYSA-N
CAS DataBase Reference56990-02-4(CAS DataBase Reference)
Safety Information
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 
HS Code 29130000
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
3,5-Dibromobenzaldehyde Usage And Synthesis
Description3,5-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.
Synthesis1,3,5-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
Uses3,5-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
ApplicationReactant 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
3,5-Dibromobenzaldehyde Preparation Products And Raw materials
Raw materialsHydrochloric acid-->Diethyl ether-->N,N-Dimethylformamide-->Chloroform-->Magnesium sulfate-->n-Butyllithium-->Tribromobenzene
Preparation Products3,5-DIBROMOBENZONITRILE
3,4-Dibromobenzaldehyde dimethyl acetal 2-AMINO-3-5-DIBROMOBENZALDEHYD 2-AMINO-3,5-DIBROMOBENZALDEHYDE 98+%,2-AMINO-3,5-DIBROMOBENZALDEHYDE=3,5-DIBROMOANTHRANILALDEHYDE,2-AMINO-3,5-DIBROMOBENZALDEHYDE 2,4-dibromobenzaldehyde 2,3-DIBROMOBENZALDEHYDE 2-Hydroxy-3,5-dibromobenzaldehyde 3-(Trifluoromethyl)benzaldehyde 2,6-DIBROMOBENZALDEHYDE 3,5-Dibromobenzaldehyde dimethyl acetal 2-(benzyloxy)-3,5-dibromobenzaldehyde oxime AMBROXOL HYDROCHLORIDE IMP.E (EP): 2-AMINO-3,5-DIBROMOBENZALDEHYDE 2,4-Dibromobenzaldehyde dimethyl acetal 2,6-Dibromobenzaldehyde thiosemicarbazone 2,3-Dibromopropionic acid 4-Hydroxy-3,5-dibromobenzaldehyde 4-[(2-Chlorobenzyl)oxy]-3,5-dibromobenzaldehyde BROMHEXINE HYDROCHLORIDE IMP.B (EP): 2-AMINO-3,5-DIBROMOBENZALDEHYDE 3-Methoxybenzaldehyde

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