| Identification | More | [Name]
3-Bromo-5-nitrobenzoic acid | [CAS]
6307-83-1 | [Synonyms]
3-BROMO-5-NITROBENZOIC ACID
3-Bromo-5-nitrobenzoic aci | [Molecular Formula]
C7H4BrNO4 | [MDL Number]
MFCD00100098 | [Molecular Weight]
246.01 | [MOL File]
6307-83-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellow crystalline needles | [Melting point ]
159-161°C | [Boiling point ]
376.8±32.0 °C(Predicted) | [density ]
1.892±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
3.09±0.10(Predicted) | [color ]
White to Light yellow to Light orange | [BRN ]
2051365 | [InChIKey]
AXRKIZCFYZBBPX-UHFFFAOYSA-N | [CAS DataBase Reference]
6307-83-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to slightly yellow crystalline needles | [Uses]
3-Bromo-5-nitrobenzoic acid serves as a precursor for synthesizing substituted benzamides via amidation with primary or secondary amines promoted by thionyl chloride under solvent- and catalyst-free conditions, and for producing methyl 3-bromo-5-nitrobenzoate through esterification in acidic methanol[6-7]. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 72, p. 5867, 2007 DOI: 10.1021/jo070477u | [Synthesis]
Part G: Preparation of 3-bromo-5-nitrobenzoic acid
3-Nitrobenzoic acid (16.7 g, 100 mmol) was dissolved in a mixed solution of trifluoroacetic acid (50 mL) and sulfuric acid (20 mL) at 50 °C. Subsequently, N-bromosuccinimide (26.7 g, 150 mmol) was added in three batches over 3 hours. The reaction mixture was stirred at 50 °C for 16 h and then cooled to room temperature. The reaction mixture was slowly poured into ice water (200 mL) and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized by dichloromethane to give the white solid product 3-bromo-5-nitrobenzoic acid (17.7 g, 72% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 13.8 (broad peak, 1H, carboxylic acid proton), 8.60 (single peak, 1H, aromatic proton), 8.55 (single peak, 1H, aromatic proton), 8.37 (single peak, 1H, aromatic proton). | [References]
[1] ChemMedChem, 2014, vol. 9, # 5, p. 973 - 983
[2] Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12579 - 12590
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
[4] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[5] Chemistry - A European Journal, 2011, vol. 17, # 10, p. 2987 - 2995 |
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