| Identification | More | [Name]
4-Bromo-2-nitrobenzoic acid | [CAS]
99277-71-1 | [Synonyms]
2-NITRO-4-BROMO BENZOIC ACID
4-BROMO-2-NITROBENZOIC ACID
4-Bromo-2-Nitrobenzoic Acid 2-Nitro-4-Bromobenzoic Acid
4-bromo-2-nitrobenzoic | [EINECS(EC#)]
627-797-3 | [Molecular Formula]
C7H4BrNO4 | [MDL Number]
MFCD01013599 | [Molecular Weight]
246.01 | [MOL File]
99277-71-1.mol |
| Chemical Properties | Back Directory | [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 | [CAS DataBase Reference]
99277-71-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
R50:Very Toxic to aquatic organisms. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [PackingGroup ]
III | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
Solid | [Uses]
Undergoes Negishi-type coupling with dimethylzinc in the presence of palladium-phosphine catalysis. | [Uses]
4-Bromo-2-nitrobenzoic acid is an intermediate in the synthesis of Lonafarnib (L469445), a potential anticancer agent. | [Synthesis]
Step 1: Synthesis of 4-bromo-2-nitrobenzoic acid
The 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 |
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