3-Bromoaniline
3-Bromoaniline
CAS: 591-19-5
Molecular Formula: C6H6BrN
3-Bromoaniline - Names and Identifiers
| Name | 3-Bromoaniline |
| Synonyms | 3-BROMOANILINE 3-Bromoaniline m-Bromoaniline Aniline, m-bromo- Aniline, 3-bromo- 3-bromo-benzenamin 3-bromobenzenamine 3-BROMO-PHENYLAMINE m-bromochlorobenzene Benzenamine,3-bromo- Benzenamine, 3-bromo- 1-amino-3-bromobenzene |
| CAS | 591-19-5 |
| EINECS | 209-704-4 |
| InChI | InChI=1/C6H6BrN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2 |
3-Bromoaniline - Physico-chemical Properties
| Molecular Formula | C6H6BrN |
| Molar Mass | 172.02 |
| Density | 1.58g/mLat 25°C(lit.) |
| Melting Point | 16.8 °C |
| Boling Point | 251°C(lit.) |
| Flash Point | >230°F |
| Water Solubility | insoluble |
| Vapor Presure | 0.021mmHg at 25°C |
| Appearance | Powder |
| Specific Gravity | 1.580 |
| Color | White to beige |
| BRN | 742028 |
| pKa | 3.58(at 25℃) |
| Storage Condition | Store below +30°C. |
| Refractive Index | n20/D 1.625(lit.) |
| Physical and Chemical Properties | Yellowish crystals. Melting point 18.5 ℃, freezing point 16.7 ℃, boiling point 251 ℃,130 ℃(1.6kPa), relative density 1.5793(20.4/4 ℃), refractive index 1.6260(20.4 ℃). Soluble in alcohol, ether, slightly soluble in water. |
| Use | Used as raw materials for organic synthesis, pharmaceutical intermediates |
3-Bromoaniline - Risk and Safety
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R33 - Danger of cumulative effects R38 - Irritating to the skin R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R21/22 - Harmful in contact with skin and if swallowed. |
| Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2810 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | CX9855300 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | T |
| HS Code | 29214210 |
| Hazard Note | Harmful/Irritant |
| Hazard Class | 6.1 |
| Packing Group | III |
3-Bromoaniline - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | m-bromoaniline is a chemical intermediate with a very wide range of uses. It is widely used in the synthesis of medicines, dyes and other fine chemical products. In medicine, m-bromoaniline can prepare aminophenyl phosphate drugs, which are used to inhibit the formation of thrombus and prepare chloroquinolinothiazole diones as antibiotics. It is convenient for dyes, it is used to make a variety of azo dyes and polycyclic macromolecular dyes. In addition, it is also used to prepare polymerization inhibitors, various photosensitive materials, ion exchange resins, m-bromoaniline is a raw material for pesticides and medicines, which can be used to synthesize m-bromoanisole; It is also the main intermediate for the synthesis of anti-cancer, sedative and analgesic drugs, and can be used in other medicines, dyes and organic synthesis. |
| Application | m-bromoanisole is the main intermediate for the synthesis of anti-cancer, sedative and analgesic tramadol, and it is also the synthesis of rynoxicol intermediate methoxythiophenol The raw material of, and can be used in other medicines, dyes and organic synthesis. It is a chemical product urgently needed in the pharmaceutical industry. |
| preparation | step 1: diazotization reaction: in a reaction bottle equipped with a stirrer, a thermometer and a dropping funnel, 200-400mL of water, 130-260g of 98% concentrated sulfuric acid, 69-138g of m-bromoaniline under cooling, 100-150mL of water, the reaction solution is cooled below 5 ℃, and a solution prepared from sodium nitrite 32.2-64g dissolved in 90-180mL of water is added dropwise, control the diazotization temperature below 5 ℃, control the dropping time to be 25min, and then continue to stir for 10min, add 3-5g of urea to decompose excess sodium nitrite, stir for 10min, add 270mL of low-temperature water at 0 ℃, stir evenly for later use; Step 2: Hydrolysis reaction: 100-170g of catalyst is added to the reaction bottle equipped with stirrer, thermometer, dropping funnel and distillation device, 130-200g of concentrated sulfuric acid is 98%, and the temperature is heated to 110-130 ℃, the diazonium salt solution of step 1 is added dropwise, and the distillate is collected by the distillation device at the same time. The diazonium solution is controlled to be added at 3.5hr, and about 400mL of distillate is collected. Step 3: Extraction: After hydrolysis reaction, the mixture of hydrolysate and water is distilled, and halogenated with halogenated alkanes is used for extraction with 150-300mL of extraction solvent each time after cooling, extraction is carried out three times, extraction liquid is combined, and water washing is carried out, 200mL each time and, then use 10% sodium hydroxide to wash, use 100mL each time for two consecutive times, and wait for the next recycling. When PH = 2-3, neutralize these liquids with hydrochloric acid, then extract them with extraction solvent. After the extraction liquid is combined, the extraction solvent is evaporated, and then vacuum rectification is carried out. The vacuum degree is 1.6kPa. The fraction at 135-140 ℃ is collected to obtain m-bromophenol. |
| use | organic synthesis intermediate. Used as organic synthesis raw material and pharmaceutical intermediate |
| production method | is obtained by diazotization, bromination and reduction of m-nitroaniline. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | abdominal cavity-rat LDL0:140 mg/kg |
| flammability hazard characteristics | Combustible in case of open flame; Combustion produces toxic nitrogen oxides and bromide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants, acids and food additives |
| fire extinguishing agent | carbon dioxide, foam, sand, mist water |
Last Update：2024-04-09 02:00:05
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CAS: 591-19-5
Tel: 17505222756
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