4-Bromo-2-nitrobenzoic acid CAS 99277-71-1
4-Bromo-2-nitrobenzoic acid Basic information
| Product Name: | 4-Bromo-2-nitrobenzoic acid |
| Synonyms: | 4-BROMO-2-NITROBENZOIC ACID;4-Bromo-2-Nitrobenzoic Acid 2-Nitro-4-Bromobenzoic Acid;2-NITRO-4-BROMO BENZOIC ACID;2-Nitro-4-Bromine Benzoic Acids;4-bromo-2-nitrobenzoic;Bromonitrobenzoicacid 42---;5-Bromo-2-carboxynitrobenzene;2-Bromo-2-nitrobenzoic acid |
| CAS: | 99277-71-1 |
| MF: | C7H4BrNO4 |
| MW: | 246.01 |
| EINECS: | 627-797-3 |
| Product Categories: | intermediate;Multisubstituted Benzene;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;C7;Carbonyl Compounds;Carboxylic Acids;blocks;Bromides;Carboxes;NitroCompounds |
| Mol File: | 99277-71-1.mol |
4-Bromo-2-nitrobenzoic acid Chemical Properties
| Melting point | 165-169 °C |
| Boiling point | 368.6±32.0 °C(Predicted) |
| density | 1.892±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | soluble in Methanol |
| form | powder to crystal |
| pka | 1.97±0.25(Predicted) |
| color | White to Gray to Brown |
| InChI | 1S/C7H4BrNO4/c8-4-1-2-5(7(10)11)6(3-4)9(12)13/h1-3H,(H,10,11) |
| InChIKey | ZIRHHEZLJGORGU-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccc(Br)cc1[N+]([O-])=O |
| CAS DataBase Reference | 99277-71-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,N,Xi |
| Risk Statements | 22-36/37/38-43-50 |
| Safety Statements | 26-36/37-61 |
| RIDADR | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| HazardClass | IRRITANT |
| PackingGroup | III |
| HS Code | 29163990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Chemical Properties | Solid |
| Uses | 4-Bromo-2-nitrobenzoic acid is an intermediate in the synthesis of Lonafarnib (L469445), a potential anticancer agent. |
| Uses | Undergoes Negishi-type coupling with dimethylzinc in the presence of palladium-phosphine catalysis. |
| Synthesis | 610-36-6 99277-71-1 162046-38-0 Step 1: Synthesis of 4-bromo-2-nitrobenzoic acidThe reference method was modified as follows (Boojamra, C.G.; Burow, K.M.; Thompson, L.A.; Ellman, J.A. J. Org. Chem., 1997, 62, 1240-1256):1. An aqueous solution (65 mL) of NaNO2 (1.9 g, 27.4 mmol) was slowly added to a stirring solution of 4-amino-2-nitrobenzoic acid (1) (5 g, 27.4 mmol) dissolved in 48% aqueous HBr (40 mL) at 0 °C. After about 15 minutes, the turbid reaction mixture transformed into a clarified orange-yellow solution.2. After continued stirring for 25 minutes, the solution was added dropwise to a solution of CuBr (5.2 g, 36.3 mmol) dissolved in 48% aqueous HBr (90 mL) at 0°C. Yellow foam generation and gas release from the purple-brown mixture were observed during the reaction.3. After stirring at 0 °C for 1 h, the reaction mixture was concentrated under reduced pressure.4. The aqueous layer was extracted with EtOAc (4 x 300 mL), the organic phases were combined, dried over Na2SO4 and concentrated to dryness to give a dark solid crude product.5. The crude product was filtered through a column of Florisilica clay (~20 g) and washed with EtOAc.6. The combined organic fractions were evaporated to about 50 mL, 200 mL of water was added, washed sequentially with 1 M HCl (2 x 50 mL), brine (50 mL), then dried with Na2SO4, filtered and concentrated to dryness to give 6.1 g of light yellow solid product (2) in 91% yield and >90% HPLC purity. |
| References | [1] Patent: US2005/256157, 2005, A1 [2] Patent: US2005/261307, 2005, A1 |
4-Bromo-2-nitrobenzoic acid Preparation Products And Raw materials
| Raw materials | 4-Amino-2-nitrobenzoic acid-->4-Bromo-2-nitrotoluene-->Sodium nitrite-->Hydrogen bromide |
| Preparation Products | 1H-Indole-7-carboxylic acid, 4-broMo-, Methyl ester-->4-METHYL-2-NITROBENZOIC ACID-->2-AMINO-4-BROMOBENZALDEHYDE-->ethyl 4-bromo-2-nitrobenzoate |
