ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon halides 1-Bromo-3-iodobenzene

1-Bromo-3-iodobenzene

Product Name1-Bromo-3-iodobenzene
CAS591-18-4
MFC6H4BrI
MW282.9
EINECS209-703-9
MOL File591-18-4.mol

Chemical Properties

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
InChI	1S/C6H4BrI/c7-5-2-1-3-6(8)4-5/h1-4H
InChIKey	CTPUUDQIXKUAMO-UHFFFAOYSA-N
SMILES	Brc1cccc(I)c1
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 Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39-24/25
WGK Germany	3
Hazard Note	Irritant
TSCA	TSCA listed
HazardClass	IRRITANT, LIGHT SENSITIVE
HS Code	29039990
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
1-Bromo-3-iodobenzene	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

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

585-76-2

591-18-4

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

1-Bromo-3-iodobenzene

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

1-Bromo-3-iodobenzene Supplier

1-Bromo-3-iodobenzene manufacturers

Related Product Information