4-hydroxy-3-methylbenzonitrile
- Product Name
- 4-hydroxy-3-methylbenzonitrile
- CAS No.
- 15777-70-5
- Chemical Name
- 4-hydroxy-3-methylbenzonitrile
- Synonyms
- 2-Methyl-4-cyanophenol;4-hydroxy-3-methylbenzonitrile;Benzonitrile, 4-hydroxy-3-methyl-
- CBNumber
- CB41559556
- Molecular Formula
- C8H7NO
- Formula Weight
- 133.15
- MOL File
- 15777-70-5.mol
4-hydroxy-3-methylbenzonitrile Property
- Melting point:
- 93-95 °C
- Boiling point:
- 180-182 °C(Press: 12 Torr)
- Density
- 1.17±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- pka
- 8.19±0.18(Predicted)
- Appearance
- Light brown to yellow Solid
Safety
- HS Code
- 2926907090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- H972700
- Product name
- 4-Hydroxy-3-methylbenzonitrile
- Packaging
- 250mg
- Price
- $75
- Updated
- 2021/12/16
- Product number
- J96889
- Product name
- 4-Hydroxy-3-methylbenzonitrile
- Packaging
- 5g
- Price
- $330
- Updated
- 2021/12/16
- Product number
- J96889
- Product name
- 4-Hydroxy-3-methylbenzonitrile
- Packaging
- 10g
- Price
- $500
- Updated
- 2021/12/16
- Product number
- OR908148
- Product name
- 4-Hydroxy-3-methylbenzonitrile
- Purity
- 98%
- Packaging
- 5g
- Price
- $646
- Updated
- 2021/12/16
- Product number
- OR908148
- Product name
- 4-Hydroxy-3-methylbenzonitrile
- Purity
- 98%
- Packaging
- 1g
- Price
- $218
- Updated
- 2021/12/16
4-hydroxy-3-methylbenzonitrile Chemical Properties,Usage,Production
Synthesis
103264-03-5
15777-70-5
1. Dissolve 4-bromo-2-methylphenol (5.6 g, 30 mmol) and pyridine (6.1 mL, 75 mmol) in 50 mL of anhydrous dichloromethane in an ice bath, and slowly and dropwise add a dichloromethane solution (5 mL) of acetyl chloride (2.8 mL, 26 mmol). After 2 hours of reaction, the reaction mixture was concentrated under reduced pressure. The residue was treated with crushed ice, diluted with 150 mL of dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 6.9 g of 4-bromo-2-methylphenyl acetate as a light brown oil (quantitative yield). 2. 4-Bromo-2-methylphenyl acetate (6.9 g, 30 mmol) was dissolved in 75 mL of anhydrous dimethylacetamide, zinc cyanide (3 g, 25.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.5 g, 3.9 mmol) were added. The reaction mixture was heated at 100 °C for 2 h. After cooling to room temperature, 300 mL of cold water was added. The precipitate was filtered, washed with water and dried over air. Purification by silica gel column chromatography (100% dichloromethane) afforded 5.2 g of 4-cyano-2-methylphenyl acetate as a colorless oil (99% yield), which cured on standing. 3. 4-Cyano-2-methylphenyl acetate (5.2 g, 29.7 mmol) was dissolved in 75 mL of methanol and an aqueous solution (25 mL) of potassium carbonate (30 mmol, 4.15 g) was added. After stirring for 30 min at room temperature, the mixture was concentrated under reduced pressure and treated with 1N sulfuric acid. The precipitate was filtered, washed with water and dried to give 3.1 g of 4-hydroxy-3-methylbenzonitrile as a white solid (78% yield). 4. 4-Hydroxy-3-methylbenzonitrile (3.1 g, 23.3 mmol) was dissolved in 60 mL of anhydrous acetonitrile, cooled to -30 °C, and nitronium tetrafluoroborate (3.4 g, 25.6 mmol) was added in batches. After 60 min of reaction, 100 mL of water was added and diluted. The light yellow precipitate was filtered, washed with water and dried to give 3.9 g of 4-hydroxy-3-methyl-5-nitrobenzonitrile (94% yield). 5. Convert 4-hydroxy-3-methyl-5-nitrobenzonitrile to the target product according to the method for the preparation of 3-fluoro-2-nitrophenyl trifluoromethanesulfonate.
References
[1] Patent: WO2005/30213, 2005, A1. Location in patent: Page/Page column 184
[2] Chemische Berichte, 1891, vol. 24, p. 3671
4-hydroxy-3-methylbenzonitrile Preparation Products And Raw materials
Raw materials
Preparation Products
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