2-Bromo-6-fluorobenzaldehyde Chemical Properties

Melting point:

43-47 °C

Boiling point:

100-102℃/8mm

Density 

1.70

Flash point:

>110°(230°F)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chlorofrom (Slightly), Ethyl Acetate (Slightly)

form 

Solid

Appearance

White to light brown Solid

Water Solubility 

Slightly soluble in water.

Sensitive 

Light Sensitive

InChI

InChI=1S/C7H4BrFO/c8-6-2-1-3-7(9)5(6)4-10/h1-4H

InChIKey

PJNILWKRAKKEQM-UHFFFAOYSA-N

SMILES

C(=O)C1=C(F)C=CC=C1Br

CAS DataBase Reference

360575-28-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

RIDADR 

UN 3335

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

9

HS Code 

29130000

2-Bromo-6-fluorobenzaldehyde Usage And Synthesis

Uses

It is a important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field.

Synthesis

To a stirred solution of iPr2NH (2.25 mL, 1.63 g, 16.1 mmol) in THF (20 mL) containing a 50 mL three-necked flask under the protection of dry argon gas was added dropwise nBuLi (6.3 mL, 2.35 M in hexane, 14.7 mmol). The reaction mixture was stirred at 0°C for 10 min. Subsequently, after continued stirring at 0°C for 20 min, the mixture was cooled to -78°C and a solution of 1-bromo-3-fluorobenzene (2.45 g, 14.0 mmol) in THF (10 mL) was added dropwise over a 12-minute period, maintaining the temperature in the range of -85 to -75°C, to give a deep red solution. After stirring at -78°C for 1 h, a THF (7 mL) solution of DMF (1.32 g, 18.2 mmol) was added dropwise over 5 min and stirring was continued for 1 h at -78°C. The reaction mixture was quenched with AcOH (2.5 mL) and slowly warmed to room temperature. The reaction mixture was poured into a mixture of 0.2 M HCl (40 mL) and MeOAc (50 mL) and the organic layer was separated. The aqueous layer was extracted with MeOAc (30 mL), and the combined organic phases were washed with brine (60 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give an orange colored oil. The oil was purified by recrystallization from hexane to afford the target product 2-bromo-6-fluorobenzaldehyde SI-1f (2.31 g, 11.4 mmol, 81% yield).

References

[1] Journal of Organic Chemistry, 2013, vol. 78, # 15, p. 7741 - 7748
[2] Tetrahedron Letters, 2016, vol. 57, # 1, p. 11 - 14
[3] Patent: US2017/158680, 2017, A1. Location in patent: Paragraph 0361; 0362; 0363
[4] Patent: WO2014/169167, 2014, A1. Location in patent: Page/Page column 57; 58
[5] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 2998 - 3001

2-Bromo-6-fluorobenzaldehyde(360575-28-6)Related Product Information

• 2-Bromo-6-fluorobenzaldehyde
• 2-Bromo-3,4,5,6-tetrafluorobenzoic acid
• 6-bromo-2-fluoro-3-methoxybenzaldehyde
• 2-Bromo-6-fluorobenzoic acid
• 2-BROMO-3,4,5,6-TETRAFLUOROBENZOYL CHLORIDE
• 2-BROMO-5-FLUOROBENZALDEHYDE
• 2-BROMO-3-FLUOROBENZALDEHYDE
• 3-Bromo-5-fluorobenzaldehyde 98%,3-Bromo-5-fluorobenzaldehyde98%,3-BROMO-5-FLUOROBENZALDEHYDE
• 4-Bromo-2-fluorobenzaldehyde98%,4-Bromo-2-fluorobenzaldehyde 98%,4-Bromo-2-Fluorobenzaldehyde 2-Fluoro-4-Bromobenzaldehyde,4-BROMO-2-FLUOROBENZALDEHYDE
• 2-BROMO-3-FLUOROBENZALDEHYDE
• 2-BROMO-4-FLUOROBENZALDEHYDE
• 3-BROMO-4-FLUOROBENZALDEHYDE,3-Bromo-4-fluorobenzaldehyde98%,3-Bromo-4-fluorobenzaldehyde 98%
• 4-Bromo-3-fluorobenzaldehyde98%,4-Bromo-3-fluorobenzaldehyde 98%,4-BROMO-3-FLUOROBENZALDEHYDE
• 5-BROMO-2-FLUOROBENZALDEHYDE,5-Bromo-2-Fluorobenzaldehyde 2-Fluoro-5-Bromobenzaldehyde,5-Bromo-2-fluorobenzaldehyde 98%,5-Bromo-2-fluorobenzaldehyde98%
• 3,6-dibromo-2-fluorobenzaldehyde
• 6-Bromo-2,3,4-Trifluorobenzoic Acid
• 2,3-DIFLUORO-6-BROMOBENZOIC ACID
• 2,4-DIBROMO-6-FLUOROBENZOYL CHLORIDE