4-Bromoanisole
Completing data — refresh the page later to see the latest
Basic information
- CAS
104-92-7- Standard SMILES
COc1ccc(Br)cc1- InChIKey
QJPJQTDYNZXKQF-UHFFFAOYSA-N- Molecular formula
- C7H7BrO
- Average molar mass
- 187.03 g/mol
- Monoisotopic mass
- 185.96802694
Overview
4-bromoanisole is a monomethoxybenzene carrying a bromo substituent at position 4. It is a monomethoxybenzene and an organobromine compound.
Names & identifiers
- Preferred name
- 4-Bromoanisole
- IUPAC
- 1-bromo-4-methoxybenzene
- English name
- 4-Bromoanisole
- Molecular formula
- C7H7BrO
- Molecular weight
- 187.03
Names & synonyms
4-BROMOANISOLE1-Bromo-4-methoxybenzene104-92-7p-Bromoanisole4-MethoxybromobenzeneBenzene, 1-bromo-4-methoxy-Anisyl bromidep-Anisyl bromide4-Methoxyphenyl bromidep-Bromanisolep-Methoxyphenyl bromideAnisole, p-bromo-
Show more names
2-Bromoanisole,98%4-Bromoanisole,98%1-bromo-4-methoxy-benzen4-Bromoanisole,1-Bromo-4-methoxybenzenep-bromoanisolp-bromo-anisol
p-Methoxybromobenzene4-Methoxy-1-bromobenzenep-Bromophenyl methyl ether4-Bromoanisolpara-bromoanisole4-bromo-1-methoxybenzene4-anisyl bromidep-Bromomethoxybenzene
Database identifiers
- CAS
104-92-7- PubChem CID
- 7730
- DTXSID
DTXSID2059308- ChEBI
CHEBI:47257- UNII
- U430F901J9
- EC Number
- 203-252-1
- Nikkaji
- J5.038E
Properties
Computed structural propertiesFilling in
- XLogP
- 2.8
- Topological polar surface area
- 9.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 77
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Halogenated Anisoles
SpringerMaterials PropertiesBoiling point
LogP3.15
Physical DescriptionClear light yellow liquid; mp = 9-10 deg C; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 9 · 9-10 °C (lit.)
- Boiling point
- 223 °C · 223 °C (lit.)
- Density
- 1.494 g/mL · 1.494 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.564(lit.)
- Flash point
- 202 °F · 202 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Chloroform (Sparingly), Ethyl Acetate (Slightly)
- form
- Liquid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.3% (4 of 123) of reports.
Warning
H315 (12.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P260, P264, P273, P280, P302+P352, P319, P321, P332+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 123 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzene, 1-bromo-4-methoxy-
Status: Active Update: 23-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11455
Benzene, 1-bromo-4-methoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards Summary
Causes ataxia, coma, and cough in inhalation lethal-concentration studies of mice; Causes tetany in oral lethal-dose studies of mice and rats; [RTECS] A skin irritant; Harmful by ingestion; [ECHA REACH Registrations] May cause irritation; [Sigma-Aldrich MSDS] See Anisole.
Hazard Classes and CategoriesSkin Irrit. 2 (12.2%)
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity DataLC50 (mouse) = 20 mg/m3
Safety data
Chemistry & industry
Uses & manufacturing
UsesUsed in closed process manufacturing; [ECHA REACH Registrations]
General Manufacturing InformationBenzene, 1-bromo-4-methoxy-: ACTIVE
Applications
Uses4-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.
General Description4-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.
Preparation methods
Preparation4-Bromoanisole is obtained by reacting p-bromophenol with dimethyl sulfate.
Upstream & downstream products
Upstream raw materials
Related reactions
774 records
Compound notes
Loading…