2-Nitroresorcinol Chemical Properties

Melting point:

81-83 °C (lit.)

Boiling point:

234 °C

Density 

1.5553 (rough estimate)

refractive index 

1.5423 (estimate)

storage temp. 

RT, stored under nitrogen

form 

Crystalline Powder

pka

4.88±0.10(Predicted)

color 

Orange

Water Solubility 

Slightly soluble in water. Solubility in methanol is almost transparent.

BRN 

2048819

InChI

InChI=1S/C6H5NO4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H

InChIKey

ZLCPKMIJYMHZMJ-UHFFFAOYSA-N

SMILES

C1(O)=CC=CC(O)=C1[N+]([O-])=O

CAS DataBase Reference

601-89-8(CAS DataBase Reference)

NIST Chemistry Reference

2-Nitro-1,3-dihydroxybenzene(601-89-8)

EPA Substance Registry System

1,3-Benzenediol, 2-nitro- (601-89-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-24/25

RIDADR 

2811

WGK Germany 

3

Autoignition Temperature

800 °F

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29089990

MSDS

• Language:English Provider:2-Nitroresorcinol
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Nitroresorcinol Usage And Synthesis

Chemical Properties

orange crystalline powder

Uses

2-Nitroresorcinol is a good subject for detecting intramolecular hydrogen bonding. 2-Nitroresorcinol can be used as a starting material to prepare 4-Hydroxy-2-benzoxazolone, HBOA.

Synthesis

At room temperature, 1 mmol of resorcinol was dissolved in 40 mL of phosphate buffer solution of pH=7, followed by the addition of 60 mmol of sodium nitrite. 4 mmol of hydrogen peroxide was dissolved in 10 mL of phosphate buffer solution and added to the reaction system after 15 min. Subsequently, 0.06 g of Fe-Al-MCM-41 molecular sieves was added to initiate the reaction, and the reaction was stirred for 80 min at room temperature. After completion of the reaction, the filtrate was extracted with ethyl acetate (2 x 80 mL), and the organic phases were combined and concentrated under reduced pressure. The target products 2-nitroresorcinol (27.4% yield) and 4-nitroresorcinol (23.5% yield) were isolated by column chromatography purification (silica gel column, eluent was a mixture of petroleum ether and acetone, 1:1, v/v/v/v/v), and the total yield was 50.9%. Under the same reaction conditions, when 0.06 g of water-soluble tetrakis(sodium sulfonate) iron porphyrin was used as the catalyst instead of molecular sieves, the yields of 2-nitroresorcinol were 9.9%, 4-nitroresorcinol were 11.8%, and the total yield was 21.7%.

Purification Methods

Recrystallise 2-nitroresorcinol from aqueous EtOH. [Beilstein 6 H 823.]

References

[1] Patent: CN106045803, 2016, A. Location in patent: Paragraph 0045-0046
[2] Patent: CN104987293, 2017, B. Location in patent: Paragraph 0052; 0053; 0054; 0055; 0556; 0057; 0058; 0059
[3] Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999

2-Nitroresorcinol(601-89-8)Related Product Information

• 4-Chlororesorcinol
• Resorcinol
• 2-Methylresorcinol
• 4-METHYLRESORCINOL
• 1,3,5-TRIMETHOXY-2-NITROBENZENE
• 2-NITROPHLOROGLUCINOL
• 7-HYDROXY-4-METHYL-8-NITROCOUMARIN
• 4',5'-DINITROFLUORESCEIN
• 2,4,6-TRINITRORESORCINOL
• 2,6-Dimethoxynitrobenzene 98%
• 3,5-DIHYDROXY-4-NITROBENZOIC ACID
• Lead styphnate
• 4-Amino-6-nitroresorcinol hydrochloride
• 4-Nitroresorcinol dimethyl ether
• 2，4-Dinitro-1，3-benzene diol
• 4-nitroresorcinol
• 2,4-DINITROSORESORCINOL
• 4,6-DINITRORESORCINOL