| Identification | More | [Name]
4-Fluoro-7-nitrobenzofurazan | [CAS]
29270-56-2 | [Synonyms]
4-FLUORO-7-NITRO-2,1,3-BENZOXADIAZOLE
4-FLUORO-7-NITROBENZ-2-OXA-1,3-DIAZOLE
4-FLUORO-7-NITROBENZOFURAZAN
4-FLUORO-7-NITROBENZOFUROZAN
7-FLUORO-4-NITROBENZO-2-OXA-1,3-DIAZOLE
NBD-F
NBD FLUORIDE
NITROBENZOFURAZAN, 4-FLUORO-7-
4-FLUORO-7-NITROBENZOFURAZAN, FOR FLUORE SCENCE
NBD-F (=4-FLUORO-7-NITRO-2,1,3-BENZOXADIAZOLE)
4-Fluoro-7-nitrobenzofurazane
2,1,3-BENZOXADIAZOLE, 4-FLUORO-7-NITRO-
NBD-F (=4-Fluoro-7-nitro-2,1,3-benzoxadiazole) [for HPLC Labeling]
7-Fluoro-4-nitro-2,1,3-benzoxadiazole
7-Nitro-4-fluoro-2,1,3-benzoxadiazole | [Molecular Formula]
C6H2FN3O3 | [MDL Number]
MFCD00010196 | [Molecular Weight]
183.1 | [MOL File]
29270-56-2.mol |
| Chemical Properties | Back Directory | [Appearance]
BROWN CRYSTALLINE CHUNKS | [Melting point ]
52-54 °C(lit.) | [Boiling point ]
308.6±45.0 °C(Predicted) | [density ]
1.6753 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
It is soluble in DMSO, DMF, CH3OH, CH3CN and CHCl3. | [form ]
Crystalline Chunks | [pka]
-5.59±0.50(Predicted) | [color ]
Brown | [BRN ]
1077571 | [InChI]
InChI=1S/C6H2FN3O3/c7-3-1-2-4(10(11)12)6-5(3)8-13-9-6/h1-2H | [InChIKey]
PGZIDERTDJHJFY-UHFFFAOYSA-N | [SMILES]
N1=C2C([N+]([O-])=O)=CC=C(F)C2=NO1 | [CAS DataBase Reference]
29270-56-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S39:Wear eye/face protection . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
BROWN CRYSTALLINE CHUNKS | [Uses]
4-Chloro-7-nitrobenzofurazan (NBD-chloride) was used in the following studies, Synthesis of fluorescent phospholipid-derivative, NBD-didecanoylphosphatidylethanolamine, Synthesis of functionalized hydroxynaphthofurazan, Spectrophotometric and spectrofluorometric determination of clemastine hydrogen fumarate, loratadine, losartan potassium and ramipril in pharmaceutical formulations. Synthesis of 7-nitrobenzofurazan (NBD)-labeled maleimide, via Diels-Alder reaction. NBD-Cl is widely used to label peptides, proteins, drugs and other biomolecules. It is also a popular derivatizing reagent for HPLC analysis | [Uses]
A fluorescence reagent | [Synthesis]
General procedure for the synthesis of 4-fluoro-7-nitro-2,1,3-benzoxadiazole from 4-fluoro-2,1,3-benzoxadiazole: 4-fluoro-2,1,3-benzoxadiazole (1.00 g, 7.24 mmol) was dissolved in concentrated H2SO4 (8 mL) and cooled to -10 °C. The nitration mixture (H2SO4:HNO3, 3:1, 2.40 mL) was added slowly and dropwise with stirring. The reaction temperature was maintained at -10 °C and stirring was continued for 1 hour. The progress of the reaction was monitored by TLC and LCMS. Upon completion of the reaction, the reaction mixture was quenched with H2O (250 mL) and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: 0 to 10% EtOAc gradient in hexane) to afford 4-fluoro-7-nitro-2,1,3-benzoxadiazole (0.39 g, yellow solid) in 30% yield.1H NMR (400 MHz, DMSO-d6) δ 7.70 (d, J=8.40 Hz, 1H), 8.77-8.80 (m 1H). | [Purification Methods]
Purify it by repeated recrystallisation from pet ether (b 40-60o). On treatment with MeONa in MeOH it gives 4-methoxy-7-nitrobenzo-2-oxa-1,3-diazole m 115-116o. [Nunno et al. J Chem Soc (C) 1433 1970.] It is a very good fluorophore for amino acids [Imai & Watanabe Analyt Chim Acta 130 377 1981], as it reacts with primary and secondary amines to form fluorescent adducts with 470nm and 530nm. It gives a glycine derivative with m 185-187o [Miyano et al. Anal Chim ex em Acta 170 81 1985]. 5-Fluorouracil (5 -fluoropyrimidinedi -2,4 -[1 H ,3 H ]-one) [51 -21 -8] M 130.1, m 282 -2 8 3o(dec), 282-286o(dec), pK 1 8.04, pK 2 13.0. Recrystallise it from H2O or MeOH/Et2O and sublime it at 190-200o/0.1mm or 210-230o/0.5mm. UV: at 265-266nm ( 7070). [Barton et al. J Org max Chem 37 329 1972, Duschinsky & Pleven J Am Chem Soc 79 4559 1957, Beilstein 24 III/IV 1229.] | [References]
[1] Journal of the American Chemical Society, 2016, vol. 138, # 48, p. 15596 - 15604
[2] Patent: WO2018/122232, 2018, A1. Location in patent: Page/Page column 213
[3] Tetrahedron Letters, 2011, vol. 52, # 20, p. 2533 - 2535 |
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