| Identification | More | [Name]
2-Bromo-3-methylbenzoic acid | [CAS]
53663-39-1 | [Synonyms]
2-BROMO-3-METHYLBENZOIC ACID
3-methyl-2-bromobenzoic acid
2-Bromo-m-toluic acid
2-Bromo-3-methyl
2-Bromo-m-toluic acid (COOH=1) | [Molecular Formula]
C8H7BrO2 | [MDL Number]
MFCD00079721 | [Molecular Weight]
215.04 | [MOL File]
53663-39-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white powder | [Melting point ]
135-138 °C (lit.) | [Boiling point ]
308.3±30.0 °C(Predicted) | [density ]
1.599±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Powder | [pka]
2.92±0.10(Predicted) | [color ]
Off-white | [InChI]
1S/C8H7BrO2/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4H,1H3,(H,10,11) | [InChIKey]
LSRTWJCYIWGKCQ-UHFFFAOYSA-N | [SMILES]
Cc1cccc(C(O)=O)c1Br | [CAS DataBase Reference]
53663-39-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29163990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white powder | [Uses]
2-Bromo-3-methylbenzoic acid may be used to synthesize N-phenyl-3-methylanthranilic acid via copper-catalyzed amination reaction with aniline. | [General Description]
2-Bromo-4-nitrotoluene is formed as an intermediate during the synthesis of 2-bromo-3-methylbenzoic acid. 2-Bromo-3-methylbenzoic acid can be obtained from 2-bromo-4-nitrotoluene via Von-Richter reaction. | [Synthesis]
The general procedure for synthesizing 2-bromo-3-methylbenzoic acid from 2-amino-3-methylbenzoic acid was as follows: referring to Example 1 (0142), 1.00 g of 2-amino-3-methylbenzoic acid, 8 mL of acetic acid, 4 mL of 50% hydrobromic acid, and 16 mL of water were mixed, followed by the addition of 0.46 g of sodium nitrite and 3 mL of water chilled on ice. After stirring the mixture in an ice bath for 10 minutes, the complete reaction of 2-amino-3-methylbenzoic acid was confirmed by silica gel thin layer chromatography (Spreader: hexane/ethyl acetate = 1/1, Rf value of 0.67 for 2-amino-3-methylbenzoic acid). Next, 1.42 g of copper bromide and 5 mL of water were added and the mixture was heated and reacted at 50 °C for 3 hours. Upon completion of the reaction, water was added to the mixture and the precipitate was collected by filtration to give 1.0 g of 2-bromo-3-methylbenzoic acid. (0143) 1H-NMR (CDCl3) δ (ppm): 2.49 (3H, s), 7.29 (1H, t, J=7.6Hz), 7.42 (1H, d, J=7.2Hz), 7.70 (1H, t, J=3.9Hz). | [References]
[1] Patent: US2017/57935, 2017, A1. Location in patent: Paragraph 0142; 0143 |
|
|