| Identification | Back Directory | [Name]
2,6-DICHLORO-3-NITROBENZOIC ACID | [CAS]
55775-97-8 | [Synonyms]
RARECHEM AL BO 2381
TIMTEC-BB SBB003247
2,6-DICHLORO-3-NITROBENZOIC ACID
Benzoic acid, 2,6-dichloro-3-nitro-
2,6-Dichloro-3-nitrobenzoic acid 98% | [Molecular Formula]
C7H3Cl2NO4 | [MDL Number]
MFCD00075422 | [MOL File]
55775-97-8.mol | [Molecular Weight]
236.01 |
| Chemical Properties | Back Directory | [Melting point ]
152-158 °C(lit.)
| [Boiling point ]
374.4±42.0 °C(Predicted) | [density ]
1.713±0.06 g/cm3(Predicted) | [Fp ]
152-158°C | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
0.76±0.29(Predicted) | [color ]
White to Orange to Green | [InChI]
1S/C7H3Cl2NO4/c8-3-1-2-4(10(13)14)6(9)5(3)7(11)12/h1-2H,(H,11,12) | [InChIKey]
PCIHIUCCINHORT-UHFFFAOYSA-N | [SMILES]
OC(=O)c1c(Cl)ccc(c1Cl)[N+]([O-])=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-37/39 | [WGK Germany ]
3
| [HS Code ]
2916399090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
2,6-Dichloro-3-nitrobenzoic acid may be used in the preparation of 9-chloro-2-methoxy-6-nitro-5,10-dihydrobenzo[b][1,5]naphthyridin-10-one, required for the synthesis of potential DNA-binding antitumor agents. It may be used in the preparation of 2-(aminoalkyl)-5-nitropyrazolo [3,4,5-kl] acridines. | [General Description]
FT-IR and Raman spectra of 2, 6-dichloro-3-nitrobenzoic acid (DCNBA) have been investigated. | [Synthesis]
Step a: Synthesis of 2,6-dichloro-3-nitrobenzoic acid
2,6-Dichlorobenzoic acid (10 g, 52 mmol) was added to a pre-stirred mixture of nitric acid (15 mL) and sulfuric acid (30 mL) and reacted at 55 °C for 30 min, followed by continued stirring at room temperature for 30 min. Upon completion of the reaction, the reaction mixture was slowly poured into ice-cold water (1 L) and the precipitated solid was filtered and dried to afford 2,6-dichloro-3-nitrobenzoic acid (9 g). The filtrate was extracted with ethyl acetate (2 x 200 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to dryness to give the additional product (2 g). The total yield was 11 g in 88% yield.
1H NMR (400 MHz, MeOH-d4): δ 7.98 (d, J=8.8 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H). | [References]
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6597 - 6611
[2] Patent: WO2012/160464, 2012, A1. Location in patent: Page/Page column 79
[3] Patent: US2014/155398, 2014, A1. Location in patent: Paragraph 0474
[4] Chemische Berichte, 1987, vol. 120, p. 803 - 810
[5] Chemische Berichte, 1937, vol. 70, p. 1526,1531 |
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