| Identification | More | [Name]
4-Bromo-3-nitrobenzoic acid | [CAS]
6319-40-0 | [Synonyms]
4-BROMO-3-NITROBENZOIC ACID
RARECHEM AH CK 0042
4-BROMO-3-NITRO-BENZOIC ACID >97%
3-Nitro-4-bromobenzoic acid | [Molecular Formula]
C7H4BrNO4 | [MDL Number]
MFCD00272137 | [Molecular Weight]
246.01 | [MOL File]
6319-40-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
202-204°C | [Boiling point ]
340.9±32.0 °C(Predicted) | [density ]
2.0176 (rough estimate) | [refractive index ]
1.6200 (estimate) | [storage temp. ]
2-8°C | [solubility ]
soluble in Methanol | [form ]
Solid | [pka]
3.35±0.10(Predicted) | [color ]
White to yellow | [InChI]
1S/C7H4BrNO4/c8-5-2-1-4(7(10)11)3-6(5)9(12)13/h1-3H,(H,10,11) | [InChIKey]
RVCTZJVBWNFYRU-UHFFFAOYSA-N | [SMILES]
OC(=O)c1ccc(Br)c(c1)[N+]([O-])=O | [CAS DataBase Reference]
6319-40-0(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 . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29163990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow powder | [Uses]
4-Bromo-3-nitrobenzoic acid serves as a synthesis precursor that is treated with thionyl chloride and subsequently reacted with chlorobenzene under aluminum chloride promotion to yield benzophenone derivatives such as 4-bromo-3-nitro-4'-chlorobenzophenone[6]. | [Synthesis]
The general procedure for the synthesis of 4-bromo-3-nitrobenzoic acid from 4-bromobenzoic acid is as follows:
1. prepare a nitration mixture by slowly adding fuming nitric acid (12.4 mL, 0.3 mol) to concentrated hydrochloric acid followed by sulfuric acid (30.1 mL, 0.6 mol) at 0-5 °C.
2. the cooled nitrification mixture was transferred to a beaker fitted with a mechanical stirrer and a charging funnel.
3. 4-Bromobenzoic acid (40 g, 0.2 mol) was slowly added to the nitrification mixture in batches while maintaining a temperature of 0-5°C. The dosing process lasted for 5 hours.
4. After completion of the addition, the reaction mixture was continued to be stirred at room temperature for 2 hours.
5. The reaction mixture was slowly poured into ice water to precipitate the solid product.
6. The solid product was separated by filtration, washed with water to neutrality and subsequently air dried to constant weight to give the pure 4-bromo-3-nitrobenzoic acid (white solid, 47.2 g, 96% yield).
Product characterization data:
1H NMR (300 MHz, CDCl3): δ 7.85 (d, J = 12.0 Hz, 1H), 8.09 (d, J = 12.0 Hz, 1H), 8.48 (s, 1H).
13C NMR (75 MHz, CDCl3): δ 124.2, 132.1, 135.2, 138.0, 139.8, 159.8, 171.0. | [References]
[1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[2] Patent: US2008/293736, 2008, A1. Location in patent: Page/Page column 32
[3] Patent: WO2017/7634, 2017, A1. Location in patent: Paragraph 0730; 0731; 0732
[4] Patent: WO2005/16882, 2005, A1. Location in patent: Page/Page column 13
[5] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 178 Anm. 1 |
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