4-(4-Nitrophenyl)azoresorcinol Chemical Properties

Melting point:

195-200 °C (dec.)(lit.)

Boiling point:

402.47°C (rough estimate)

Density 

1.3450 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

Store below +30°C.

form 

Powder

pka

8.05±0.35(Predicted)

color 

Orange-red to red

Odor

Odorless

Appearance

Red, Orange or Red-Orange Powder

Water Solubility 

Soluble in dilute sodium hydroxide. Insoluble in water.

λmax

432 nm

Merck 

14,5695

BRN 

674709

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

Major Application

diagnostic assay manufacturing
hematology
histology

InChI

1S/C12H9N3O4/c16-10-5-6-11(12(17)7-10)14-13-8-1-3-9(4-2-8)15(18)19/h1-7,16-17H/b14-13+

InChIKey

NGPGYVQZGRJHFJ-BUHFOSPRSA-N

SMILES

Oc1ccc(\N=N\c2ccc(cc2)[N+]([O-])=O)c(O)c1

CAS DataBase Reference

74-39-5(CAS DataBase Reference)

EPA Substance Registry System

1,3-Benzenediol, 4-[(4-nitrophenyl)azo]- (74-39-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

VH2810000

TSCA 

TSCA listed

HS Code 

29270000

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-(4-Nitrophenyl)azoresorcinol Usage And Synthesis

Description

Oxygen violet can be prepared by one-step reaction of p-nitroaniline and 1,3-benzenediol. Azo violet can be used to prepare an azobenzene photochromic liquid crystal compound. Photochromic liquid crystal compounds have both photochromic properties and liquid crystallinity, which has become a research hotspot in the field of information storage. Azobenzene-based liquid crystals are the most interesting photochromic liquid crystal materials in recent years due to their unique photoinduced cis-trans isomerism. Azobenzene compounds undergo reversible cis-trans isomerization under the action of light, which makes them have great potential applications in many aspects such as optical storage, photo-holography and optical information processing.

Chemical Properties

dark red to brown crystalline powder

Uses

It is a derivitized resorcinol dye compound with an absorption maximum of 432 nm. Used as a pH indicator.

Uses

4-(4-Nitrophenyl)azoresorcinol is used for the detection of magnesium with which it yields a bright blue color in alkaline solution and it also used to determine molybdenum with which it forms a red-violet complex: Nikitina, Andrianova, C.A. 75, 136789v (1971).

Definition

ChEBI: 4-(4-nitrophenylazo)resorcinol is an azobenzene in which the phenyl rings are 4-nitro- and 2,4-dihydroxy-substituted respectively. It is a member of resorcinols, a C-nitro compound and a member of azobenzenes.

Biochem/physiol Actions

4-(4-Nitrophenylazo)resorcinol is a pH indicator.

Synthesis

A solution of NaNO2 (1.035 g) in deionized water (15 mL) is slowly added to a solution of p-nitroaniline (2.07 g) in hydrochloric acid (2.5 mol/L, ) 10 mL) in hydrochloric acid (2.5 mol/L, ). The solution is held at 0??C for 1 hour under vigorous mechanical stirring. The solution was then washed with ammonia and deionized water until the pH of the filtrate reached 7. The diazonium salt was then washed with ammonia and deionized water until the pH of the filtrate reached 7. The diazonium salt solution is then added to a solution of 1,3-benzenediol (1.65 g) and sodium hydroxide (1.2 g) in deionized water (60 mL) at 0??C and held under stirring for 1 hour. 1 hour. The solid precipitate was washed with ammonia and deionized water until the pH of the filtrate reached 7. The resulting precipitate was filtered and the crude product was recrystallized twice with ethanol. The orange-red compound apoxidized violet was obtained in 73.8% yield.

Purification Methods

Crystallise the dye from EtOH. [Beilstein 16 H 181, 16 IV 1266.]

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