| Identification | More | [Name]
5-(4-NITRO-PHENYL)-2H-TETRAZOLE | [CAS]
16687-60-8 | [Synonyms]
5-(4-NITROPHENYL)-1H-TETRAZOLE
5-(4-NITRO-PHENYL)-2H-TETRAZOLE
5-(4-NITROPHENYL)TETRAZOLE
BUTTPARK 2\01-81 | [Molecular Formula]
C7H5N5O2 | [MDL Number]
MFCD00268795 | [Molecular Weight]
191.15 | [MOL File]
16687-60-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
223°C (dec.) | [Boiling point ]
435.3±47.0 °C(Predicted) | [density ]
1.534±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT. | [pka]
3.38±0.10(Predicted) | [Appearance]
Yellow to brown Solid | [Water Solubility ]
Insoluble in water. Soluble in DMSO. | [BRN ]
192840 | [CAS DataBase Reference]
16687-60-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Danger | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280a-P304+P340-P305+P351+P338-P405-P501a | [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:Wear suitable protective clothing . | [Hazard Note ]
Irritant | [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [Uses]
It is used as a reagent used as activator for both solution- and solid-phase synthesis of oligonucleotides using the phosphoramidite method. | [Synthesis]
The general procedure for the synthesis of 5-(4-nitrophenyl)-1H-tetrazole from 4-nitrophenyl aldoxime was as follows: InCl3 (3 mol%) was added to a stirred solution of DMF (5 mL) containing appropriate amounts of aldoxime (1 mmol) and NaN3 (1.5 mmol). The reaction mixture was heated to 120 °C. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature. H2O (5 mL), 2M HCl aqueous solution (10 mL) and EtOAc (10 mL) were added sequentially with vigorous stirring for 15 minutes. The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 15 mL). The organic extracts were combined, washed with H2O, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography [eluent: EtOAc-hexane (9:1)]. | [References]
[1] Synlett, 2016, vol. 27, # 8, p. 1241 - 1244
[2] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3706 - 3709
[3] Synthesis (Germany), 2018, vol. 50, # 6, p. 1293 - 1300
[4] Synlett, 2016, vol. 27, # 15, p. 2225 - 2228
[5] Tetrahedron Letters, 2016, vol. 57, # 5, p. 523 - 524 |
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