4-HYDROXY-3-NITROPHENYLACETIC ACID Chemical Properties

Melting point:

146-148 °C (lit.)

Boiling point:

334.23°C (rough estimate)

Density 

1.5023 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

ethanol: soluble5%, clear, yellow to orange

form 

crystalline

pka

4.25±0.10(Predicted)

color 

yellow

BRN 

2696044

CAS DataBase Reference

10463-20-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29182900

MSDS

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

4-HYDROXY-3-NITROPHENYLACETIC ACID Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

4-Hydroxy-3-nitrophenylacetic acid was used in the synthesis of 4-hydroxy-3-nitrophenylacetyl caproic acid.

Uses

A metabolite of Nitrotyrosine (N597000), which is excreted in the urine.

Definition

ChEBI: (4-hydroxy-3-nitrophenyl)acetic acid is a monocarboxylic acid that is acetic acid carrying a 2-hydroxy-3-nitrophenyl substituent at C-2. It has a role as a hapten. It is a conjugate acid of a (4-hydroxy-3-nitrophenyl)acetate.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 30, p. 1166, 1987 DOI: 10.1021/jm00390a009

General Description

4-Hydroxy-3-nitrophenylacetic acid enhances the ice-nucleation activity of Xanthomonas campestris.

Synthesis

General procedure for the synthesis of 4-hydroxy-3-nitrophenylacetic acid from p-hydroxyphenylacetic acid: (a) Nitration reaction: fuming nitric acid (1.36 mL) was slowly added dropwise to a solution of 4-hydroxyphenylacetic acid (4.00 g, 26.3 mmol) in acetic acid (25 mL) under cooling in an ice bath. After the dropwise addition was completed, the reaction mixture was slowly warmed up to room temperature and reacted for 1 hour, during which time the solution gradually changed from yellow to brown color, accompanied by the formation of a precipitate. After completion of the reaction, the solid product was collected by filtration and recrystallized from ethyl acetate/hexane mixed solvent to obtain yellow needle-like crystals of 4-hydroxy-3-nitrophenylacetic acid (3.61 g, 70% yield). The structure of the product was confirmed by 1H-NMR: δ (CDCl3-d4/DMSO, 4:1) 3.50 (2H, s), 7.04 (1H, d, J = 9 Hz), 7.46 (1H, dd, J = 9, 3 Hz), 7.94 (1H, d, J = 3 Hz).

References

[1] Synthetic Communications, 1985, vol. 15, # 12, p. 1075 - 1080
[2] Patent: US5229510, 1993, A
[3] Journal of Medicinal Chemistry, 1987, vol. 30, # 7, p. 1166 - 1176
[4] Patent: US9995679, 2018, B2. Location in patent: Page/Page column 52
[5] Patent: US5852191, 1998, A

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