Basic information
- 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 properties
- 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
- color
- Clear colorless to slightly yellow
- Water Solubility
- immiscible
- Merck
- 14 · 14,1428
- BRN
- 1237590 · 1237590
- Henry's Law Constant
- 1.1 · 1.1×10-2 mol/(m3Pa) at 25℃, Pfeifer et al. (2001)
- Dielectric constant
- 7.4 · 7.4000000000000004
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- InChI
- 1S/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3
- InChIKey
- QJPJQTDYNZXKQF-UHFFFAOYSA-N
- SMILES
- COc1ccc(Br)cc1
- CAS DataBase Reference
- 104 · 104-92-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 430 F901J9 · U430F901J9
- NIST Chemistry Reference
- 1 · Benzene, 1-bromo-4-methoxy-(104-92-7)
- EPA Substance Registry System
- 1 · Benzene, 1-bromo-4-methoxy- (104-92-7)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 303 · H303-H315
- Precautionary statements
- 264 · P264-P280-P302+P352-P312-P362+P364-P332+P313
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Hazard Codes
- Xn
- Safety Statements
- 23 · 23-24/25
- WGK Germany
- 2 · 2
- RTECS
- 8501000 · BZ8501000
- F
- 8 · 8
- TSCA
- TSCA listed
- HS Code
- 29093038 · 29093038
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 OralSkin · Acute Tox. 4 OralSkin Irrit. 2
- Toxicity
- 50 orl-mus: · LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79
- REACH Registrations
- Active
Safety & regulation
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
- F
- 8
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- BZ8501000
- hs_code
- 29093038
- Toxicity
- LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H303-H315
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralSkin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P312-P362+P364-P332+P313
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
Downstream products
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Additional notes
DefinitionChEBI: 4-bromoanisole is a monomethoxybenzene carrying a bromo substituent at position 4. It is a monomethoxybenzene and an organobromine compound.
Related reactions
774 records
Linked notes
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