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

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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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 515396
Product name: 3,5-Dibromobenzaldehyde
Packaging: 5g
Price: $47.7
Updated: 2024/03/01

TCI Chemical

Product number: D2832
Product name: 3,5-Dibromobenzaldehyde
Purity: >97.0%(GC)
Packaging: 5g
Price: $63
Updated: 2024/03/01

TCI Chemical

Product number: D2832
Product name: 3,5-Dibromobenzaldehyde
Purity: >97.0%(GC)
Packaging: 25g
Price: $252
Updated: 2024/03/01

Alfa Aesar

Product number: B25495
Product name: 3,5-Dibromobenzaldehyde, 98%
Packaging: 5g
Price: $90.65
Updated: 2024/03/01

Alfa Aesar

Product number: B25495
Product name: 3,5-Dibromobenzaldehyde, 98%
Packaging: 1g
Price: $28.3
Updated: 2021/12/16

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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

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

N,N-Dimethylformamide Chloroform 1,3,5-Tribromobenzene Diethyl ether Hydrochloric acid Magnesium sulfate n-Butyllithium

Preparation Products

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View Lastest Price from 3,5-Dibromobenzaldehyde manufacturers

Shaanxi Dideu Medichem Co. Ltd

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

Suzhou Nordica Biopharma CO.,LTD

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

Hebei Weibang Biotechnology Co., Ltd

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

56990-02-4, 3,5-DibromobenzaldehydeRelated Search:

2,3-Dibromopropionic acid p-Anisaldehyde 2-Nitrobenzaldehyde Benzaldehyde 4-Hydroxybenzaldehyde 3-(Trifluoromethyl)benzaldehyde 3-Methoxybenzaldehyde 4-Dimethylaminobenzaldehyde 3,4-DIBROMOBENZALDEHYDE,3,4-Dibromobenzaldehyde 99% 4-Hydroxy-3,5-dibromobenzaldehyde 2-Hydroxy-3,5-dibromobenzaldehyde 2-AMINO-3,5-DIBROMOBENZALDEHYDE 98+%,2-AMINO-3,5-DIBROMOBENZALDEHYDE=3,5-DIBROMOANTHRANILALDEHYDE,2-AMINO-3,5-DIBROMOBENZALDEHYDE 2,5-DIBROMOBENZALDEHYDE 3,5-Dibromobenzaldehyde dimethyl acetal 2,6-DIBROMOBENZALDEHYDE 2,4-Dibromobenzaldehyde dimethyl acetal 3,4-Dibromobenzaldehyde dimethyl acetal 2,3-DIBROMOBENZALDEHYDE

3,5-Dibromobenzaldehyde97%MinByG.C

3,5-Dibromobenzaldehyde,98%

3,5-DIBROMOBENZALDEHYDE

3,5-DIBROMOBENZALDEHYDE 98%

METHYL3,5-DIBROMOPHENYLACETATE

DBBA

3,5-Dibromobenzaldehyde&gt

Benzaldehyde, 3,5-dibromo-

3,5-dibromophenylformaldehyde

3,5-Dibromobenzaldehyde//DBBA

56990-02-4

52990-02-4

56880-02-4

Br2C6H3CHO

Building Blocks for Dendrimers

C7

Carbonyl Compounds

Building Blocks

Aldehydes

Organic Building Blocks

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