2-Bromo-4-methylphenol
- Iupac Name：2-bromo-4-methylphenol
- CAS No.: 6627-55-0
- Molecular Weight：187.03388
- Modify Date.: 2022-11-29 02:45
- Introduction:
2-Bromo-4-methylphenol, with the chemical formula C7H7BrO and CAS registry number 6627-55-0, is a compound known for its applications in various chemical processes. This white crystalline solid, also referred to as 2-Bromo-4-methylphenol, is characterized by its bromine and methyl functional groups. It is commonly used as an antimicrobial agent and preservative in personal care products, such as soaps and cosmetics. Additionally, 2-Bromo-4-methylphenol has been found to exhibit antioxidant and anti-inflammatory properties, making it a potential candidate for pharmaceutical applications. Further research is being conducted to explore its potential uses in the field of medicine.
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1. Names and Identifiers
- 1.1 Name
- 2-Bromo-4-methylphenol
- 1.2 Synonyms
2-Bromo-4-cresol 2-BROMO-4-METHYLPHENOL 2-Bromo-4-methylphenoll)ethyl]-1H-imidazole monohydrochloride 2-bromo-p-creso 2-BROMO-P-CRESOL 2-Bromo-p-cresol, 3-Bromo-4-hydroxytoluene 3-BROMO-4-HYDROXY-BENZYLIC ALCOHOL 3-Bromo-4-hydroxytoluene AKOS BBB/368 NSC 60115 p-Cresol, 2-bromo- Phenol, 2-bromo-4-methyl-
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- 1.3 CAS No.
- 6627-55-0
- 1.4 CID
- 23109
- 1.5 EINECS(EC#)
- 229-595-7
- 1.6 Molecular Formula
- C7H7BrO (isomer)
- 1.7 Inchi
- InChI=1S/C7H7BrO/c1-5-2-3-7(9)6(8)4-5/h2-4,9H,1H3
- 1.8 InChIkey
- MTIDYGLTAOZOGU-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC1=CC(=C(C=C1)O)Br
- 1.10 Isomers Smiles
- CC1=CC(=C(C=C1)O)Br
2. Properties
- 2.1 Density
- 1.547
- 2.1 Melting point
- 213-214℃
- 2.1 Boiling point
- 213-214℃
- 2.1 Refractive index
- 1.576-1.579
- 2.1 Flash Point
- 82.9 °C
- 2.1 Precise Quality
- 185.96800
- 2.1 PSA
- 20.23000
- 2.1 logP
- 2.46310
- 2.1 Appearance
- clear colourless to pale yellow liquid
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- clear colourless to pale yellow liquid 2-Bromo-4-methylphenol Preparation Products And Raw materials Raw materials
- 2.4 pKa
- 8.73±0.18(Predicted)
- 2.5 Water Solubility
- Slightly soluble in water.
- 2.6 Stability
- Stable at room temperature in closed containers under normal storage and handling conditions.
- 2.7 StorageTemp
- Inert atmosphere,Room Temperature
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBrGeneral procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBrGeneral procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of NaGeneral procedure: To a solution of 4-alkylphenol (20 mmol) in chloroform (20 mL), sodium hydrogencarbonate (2 g, 24 mmol) was added. The resulting suspension was cooled to 0°C. While a solution of elementary bromine (1.12 mL, 22 mmol) in chloroform (8 mL) was slowly added, the suspension was vigorously stirred. After completion of the reaction, monitored by TLC the suspension was filtered. The filter with the solid residue was rinsed once with 50 mL of chloroform. The combined organic solutions were evaporated under reduced pressure. The final workup of the product was done either by distillation or by column chromatography (petroleum ether : ethyl acetate, 9 : 1).General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines, or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4–5 h at 50–60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5percent sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure productGeneral procedure: NHA solution of the starting material (~10 mmol) and pTsOH (10 mol percent) in MeOH (1.0 mL per mmol starting material) was stirred for 10 min, then a solution of NBS (100 mol percent; recrystallized from HGeneral procedure: Complex 2a (6 mg, 0.015 mmol) and p-cresol (198 mg, 1.8 mmol) were dissolved in CH3CN (10 mL). To this mixture, KBr (440mg, 3.7 mmol)dissolved in water (2 mL) was added, followed by 30percent H2O2 (1 mL) added dropwise with constant stirring. The pH of the solution wasadjusted to approximately 3 by dropwise addition of 2N HCl solution.The reaction mixture was stirred for 20 h at room temperature. Theproduct was extracted with diethyl ether and concentrated to about1 mL. Two products, 2-bromo-4-methylphenol and 2, 6-dibromo-4-methylphenol, were separated by TLC and characterised byspectroscopic techniques. The isolated yields were 79 mg and 60 mg, respectively. The results of the conversions are given in Table 3. Thesame reaction was carried out keeping all other components andconditions the same but not adding the catalyst.General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na
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4. Safety and Handling
- 4.1 Hazard Codes
- Xn
- 4.1 Risk Statements
- R21/22;R36/37/38
- 4.1 Safety Statements
- S26;S36/37/39
- 4.1 Hazard Class
- IRRITANT
- 4.1 Hazard Declaration
- H315-H319-H335
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P261-P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- GO6868200
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
6627-55-0Total: 21 Synthesis Route
9. Other Information
- 9.0 Usage
- It is applied as a compound responsible for iodine off-flavor in wines.
- 9.1 Storage Conditions
- General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBrGeneral procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBrGeneral procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of NaGeneral procedure: To a solution of 4-alkylphenol (20 mmol) in chloroform (20 mL), sodium hydrogencarbonate (2 g, 24 mmol) was added. The resulting suspension was cooled to 0°C. While a solution of elementary bromine (1.12 mL, 22 mmol) in chloroform (8 mL) was slowly added, the suspension was vigorously stirred. After completion of the reaction, monitored by TLC the suspension was filtered. The filter with the solid residue was rinsed once with 50 mL of chloroform. The combined organic solutions were evaporated under reduced pressure. The final workup of the product was done either by distillation or by column chromatography (petroleum ether : ethyl acetate, 9 : 1).General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines, or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4–5 h at 50–60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5percent sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure productGeneral procedure: NHA solution of the starting material (~10 mmol) and pTsOH (10 mol percent) in MeOH (1.0 mL per mmol starting material) was stirred for 10 min, then a solution of NBS (100 mol percent; recrystallized from HGeneral procedure: Complex 2a (6 mg, 0.015 mmol) and p-cresol (198 mg, 1.8 mmol) were dissolved in CH3CN (10 mL). To this mixture, KBr (440mg, 3.7 mmol)dissolved in water (2 mL) was added, followed by 30percent H2O2 (1 mL) added dropwise with constant stirring. The pH of the solution wasadjusted to approximately 3 by dropwise addition of 2N HCl solution.The reaction mixture was stirred for 20 h at room temperature. Theproduct was extracted with diethyl ether and concentrated to about1 mL. Two products, 2-bromo-4-methylphenol and 2, 6-dibromo-4-methylphenol, were separated by TLC and characterised byspectroscopic techniques. The isolated yields were 79 mg and 60 mg, respectively. The results of the conversions are given in Table 3. Thesame reaction was carried out keeping all other components andconditions the same but not adding the catalyst.General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na
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- 9.2 Manufacturing Info
- Phenol, 2-bromo-4-methyl-: ACTIVE|PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
10. Computational chemical data
- Molecular Weight: 187.03388g/mol
- Molecular Formula: C7H7BrO
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 185.96803
- Monoisotopic Mass: 185.96803
- Complexity: 94.9
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 20.2
- Heavy Atom Count: 9
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBgIAAAEAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgBACAABrASAmAAyBoAAAgCAAiBCAAACAAAgIAQIiAAGCKgIJiKCERKAcAAkwBEImheAwAAOIAAAEAAABABAAAAgAAAIAAAAAAAAAA==
11. Question & Answer
-
2-Bromo-4-methylphenol is a colorless to pale yellow liquid that serves as an important intermediate for drugs and broad-spectrum fragrances like vanillin. Preparation Method A method for preparing 2-..
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13. Realated Product Infomation
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