HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Bromoanisole
1-BROMO-4-METHOXYBENZENE · P-BROMOANISOLE · 2-Bromoanisole,98% · 4-Bromoanisole,98% · 1-bromo-4-methoxy-benzen · 4-Bromoanisole,1-Bromo-4-methoxybenzene · p-Bromanisole · p-bromoanisol
Identifiers & Physical Properties
| CAS No. | 104-92-7 |
|---|---|
| Molecular formula | C7H7BrO |
| Average molar mass | 187.03 g/mol |
| Monoisotopic mass | 185.96802694 g/mol |
| SMILES | COc1ccc(Br)cc1 |
| InChIKey | QJPJQTDYNZXKQF-UHFFFAOYSA-N |
| PubChem CID | 7730 |
| ChEBI | CHEBI:47257 |
| EC No. | 203-252-1 |
| DTXSID | DTXSID2059308 |
Chemical & Physical Properties
| XLogP | 2.8 |
|---|---|
| Topological polar surface area | 9.2 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 77 |
| Chemical classes | Other Classes -> Halogenated Anisoles |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | 3.15 |
| Physical Description | Clear light yellow liquidmp = 9-10 deg C[Sigma-Aldrich MSDS] |
| 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 conditions | Store below +30°C. |
| Solubility | Chloroform (Sparingly), Ethyl Acetate (Slightly)immiscible |
| Physical state | Liquid |
| Color | Clear colorless to slightly yellow |
| Merck | 14,1428 |
| BRN | 1237590 |
| Henry's law constant | 1.1×10-2 mol/(m3Pa) at 25℃, Pfeifer et al. (2001) |
| Dielectric constant | 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 | 104-92-7(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | U430F901J9 |
| NIST Chemistry Reference | Benzene, 1-bromo-4-methoxy-(104-92-7) |
| EPA Substance Registry System | Benzene, 1-bromo-4-methoxy- (104-92-7) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H303-H315 |
| GHS precautionary statements | P264-P280-P302+P352-P312-P362+P364-P332+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
| Hazard symbols | Xn |
| Safety statements (S) | 23-24/25 |
| Water hazard class (WGK) | 2 |
| RTECS number | BZ8501000 |
| F | 8 |
| TSCA inventory status | TSCA listed |
| Customs code | 29093038 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Acute Tox. 4 OralSkin Irrit. 2 |
| Toxicity | LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 3.3% (4 of 123) of reports.WarningH315 (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. |
|---|---|
| Regulatory information | Chemical: Benzene, 1-bromo-4-methoxy-Status: Active Update: 23-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11455Benzene, 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 miceCauses tetany in oral lethal-dose studies of mice and rats[RTECS] A skin irritantHarmful by ingestion[ECHA REACH Registrations] May cause irritation[Sigma-Aldrich MSDS] See Anisole. |
| Hazard Classes and Categories | Skin Irrit. 2 (12.2%) |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Toxicity Data | LC50 (mouse) = 20 mg/m3 |
| F | 8 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | BZ8501000 |
| Customs code | 29093038 |
| Toxicity | LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 23-24/25 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H303-H315 |
| REACH registrations | Active |
| Hazard class | Acute Tox. 4 OralSkin Irrit. 2 |
| GHS precautionary statements | P264-P280-P302+P352-P312-P362+P364-P332+P313 |
Applications & Uses
Uses
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.
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.
Preparation & Synthesis
Preparation
4-Bromoanisole is obtained by reacting p-bromophenol with dimethyl sulfate.