1-Bromo-3-iodobenzene

1-Bromo-3-iodobenzene Property

Melting point:

−9.3-−9 °C(lit.)

Boiling point:

120 °C18 mm Hg(lit.)

Density 

2.219 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.66(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Oil

color 

Colourless

Specific Gravity

2.219

Water Solubility 

insoluble

Sensitive 

Light Sensitive

BRN 

1854384

InChIKey

CTPUUDQIXKUAMO-UHFFFAOYSA-N

CAS DataBase Reference

591-18-4(CAS DataBase Reference)

NIST Chemistry Reference

3-Bromoiodobenzene(591-18-4)

EPA Substance Registry System

Benzene, 1-bromo-3-iodo- (591-18-4)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Bromo-3-iodobenzene Chemical Properties,Usage,Production

Chemical Properties

Clear colourless to light yellow liquid

Chemical Properties

Light sensitive. Incompatible with strong oxidizing agents, strong bases and strong acids. Store in a cool place.

Uses

1-Bromo-3-iodobenzene is used in the preparation of 3'-bromo-2,3,4,5,6-pentaethyl-biphenyl by reacting with hex-3-yne. It is also used to prepare 1-(3'-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3'-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene. Further, it is involved in the preparation of oxygen-tethered 1,6-enynes.

Synthesis

Cesium carbonate (Cs2CO3, 0.6 mmol, 195 mg), m-bromobenzoic acid (1, 0.3 mmol), [Ir(dF(CF3)ppy]2(dtbbpy)]PF6 (D, 6 μmol, 6.7 mg), N-iodosuccinimide (NIS, 1.5 mmol, 337.5 mg) and iodine (I2, 60 μmol, 20 mol%). The tubes were evacuated and displaced three times with argon, followed by the addition of 3 mL of dry 1,2-dichloroethane (DCE) through a syringe under argon protection. The test tube was sealed with Parafilm? and placed in an oil bath equipped with a contact thermometer. The reaction system was irradiated with a 6 x 5 W blue LED lamp (λmax = 455 nm) at 50 °C for 24 to 36 hours. Upon completion of the reaction, the mixture was filtered through a 2 cm thick pad of silica gel and the silica gel was washed with dichloromethane (DCM, 50 mL). The filtrates were combined and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography on silica gel to afford the target product 1-bromo-3-iodobenzene (2). (Note: The reaction is extremely sensitive to moisture, and the product yield was significantly reduced to less than 5% when 0.01 equivalents of water was added to the system.)

References

[1] Synlett, 2018, vol. 29, # 12, p. 1572 - 1577
[2] Patent: WO2015/68159, 2015, A2. Location in patent: Paragraph 00215-00216