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HomeProduct name list4-Bromoanisole

4-Bromoanisole

Synonym(s):1-Bromo-4-methoxybenzene

  • CAS NO.:104-92-7
  • Empirical Formula: C7H7BrO
  • Molecular Weight: 187.03
  • MDL number: MFCD00000097
  • EINECS: 203-252-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:07:02
4-Bromoanisole Structural

What is 4-Bromoanisole?

Chemical properties

4-Bromoanisole is a colourless to pale yellow oily liquid with a pleasant smell similar to that of anise seed. Insoluble in water, soluble in ethanol, ether and chloroform. It is one of three isomers of bromoanisole, the others being 3-bromoanisole and 2-bromoanisole. It is the precursor to many 4-anisyl derivatives.

The Uses of 4-Bromoanisole

4-Bromoanisole finds application as an intermediate in synthetic chemistry. It is used in the preparation of aryl 1,3-diketones and ethyl 4-methoxycinnamate. It is a used as a brominating reagent. Further, it is used in Suzuki coupling reaction with phenylboronic acid as well as in Heck reaction.

Definition

ChEBI: 4-bromoanisole is a monomethoxybenzene carrying a bromo substituent at position 4. It is a monomethoxybenzene and an organobromine compound.

Preparation

4-Bromoanisole is obtained by reacting p-bromophenol with dimethyl sulfate.

Biological Functions

4-Bromoanisole is compound sometimes used in RNA extraction which serves to further eliminate DNA contamination. It interacts with genomic DNA(gDNA) and through a separation phase, it will be located in the organic layer instead of the aqueous layer (upper layer) containing the RNA extract.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7429, 1994 DOI: 10.1016/0040-4039(94)85333-9
Synthesis, p. 868, 1986 DOI: 10.1055/s-1986-31813

General Description

4-Bromoanisole is a useful brominating reagent. It is formed as reaction product in the reaction between HOBr and anisole. Suzuki coupling of 4-bromoanisole with phenylboronic acid catalyzed by palladium pincer complexes has been studied. Heck Reaction of 4-bromoanisole with ethyl acrylates in room-temperature ionic liquids is reported to afford ethyl 4-methoxycinnamate.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic vapors of Br-.

Purification Methods

Crystallise the anisole by repeated partial freezing, then distil it under reduced pressure. [Beilstein 6 III 741, 6 IV 1044.]

Properties of 4-Bromoanisole

Melting point: 9-10 °C (lit.)
Boiling point: 223 °C (lit.)
Density  1.494 g/mL at 25 °C (lit.)
refractive index  n20/D 1.564(lit.)
Flash point: 202 °F
storage temp.  Store below +30°C.
solubility  Chloroform (Sparingly), Ethyl Acetate (Slightly)
form  Liquid
color  Clear colorless to slightly yellow
Water Solubility  immiscible
Merck  14,1428
BRN  1237590
Dielectric constant 7.4000000000000004
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference 104-92-7(CAS DataBase Reference)
NIST Chemistry Reference Benzene, 1-bromo-4-methoxy-(104-92-7)
EPA Substance Registry System Benzene, 1-bromo-4-methoxy- (104-92-7)

Safety information for 4-Bromoanisole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.

Computed Descriptors for 4-Bromoanisole

InChIKey QJPJQTDYNZXKQF-UHFFFAOYSA-N

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