7-Benzylamino-4-nitrobenz-2-oxa-1,3-diazole

Product Name7-Benzylamino-4-nitrobenz-2-oxa-1,3-diazole
CAS18378-20-6
MFC13H10N4O3
MW270.24
EINECS242-261-5
MOL File18378-20-6.mol

Chemical Properties

Melting point	206-209 °C
Boiling point	413.36°C (rough estimate)
Density	1.2858 (rough estimate)
refractive index	1.6120 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
solubility	Acetonitrile: Slightly Soluble: 0.1-1 mg/ml DMSO: Slightly Soluble: 0.1-1 mg/ml
form	Solid
pka	-3.78±0.45(Predicted)
color	Brown to orange
CAS DataBase Reference	18378-20-6

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	24/25-36-26
HS Code	29349990

MSDS

Provider	Language
4-Benzylamino-7-nitrobenzofurazan	English
ACROS	English

Usage And Synthesis

Chemical Properties

BROWN FINE POWDER

Uses

BBD (NSC240867) is a biochemical reagent/chromogenic reagent.

Definition

ChEBI: 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole is a benzoxadiazole. It has a role as a fluorochrome.

Synthesis

10199-89-0

100-46-9

7-Benzylamino-4-nitrobenz-2-oxa-1,3-diazole

18378-20-6

GENERAL METHOD: To a solution of 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl, 1 eq.) in acetonitrile (0.1 M) was added benzylamine (1.1 eq.) followed by triethylamine (2 eq.). The reaction mixture was stirred at reflux for 16 hours under nitrogen protection. Upon completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residue was redissolved in ethyl acetate, washed sequentially with 1 M hydrochloric acid, water and saturated saline, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with gradient elution using ethyl acetate/hexane mixed solvent.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 370 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 3, p. 487 - 504
[3] Journal of Medicinal Chemistry, 1968, vol. 11, # 2, p. 305 - 311
[4] R. A. KENNER A. A A. New fluorescent probe for protein and nucleoprotein conformation. Binding of 7-(p-methoxybenzylamino)-4-nitrobenzoxadiazole to bovine trypsinogen and bacterial ribosomes[J]. Biochemistry Biochemistry, 1971, 10 24: 4433-4440. DOI: 10.1021/bi00800a013
[5] SARAH A. STEVENSON G. J B. Dynamics of 4-Benzylamino-7-nitrobenzofurazan in the 1-Propanol/Water Binary Solvent System. Evidence for Composition-Dependent Solvent Organization[J]. The Journal of Physical Chemistry A, 2006, 110 10: 3426-3431. DOI: 10.1021/jp057039g
[6] Y MATSUSHITA I M M Takahashi. Binding of fluorescent 7-amino-4-nitrobenzoxadiazole derivatives to bovine serum albumin.[J]. Chemical & pharmaceutical bulletin, 1986, 34 1: 333-339. DOI: 10.1248/cpb.34.333

7-Benzylamino-4-nitrobenz-2-oxa-1,3-diazole

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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