2-Amino-4-methoxyphenol Chemical Properties

Melting point:

135-140 °C

Boiling point:

289.1±25.0 °C(Predicted)

Density 

1.219±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

10.24±0.18(Predicted)

form 

powder

color 

Black

Sensitive 

Air Sensitive

InChI

InChI=1S/C7H9NO2/c1-10-5-2-3-7(9)6(8)4-5/h2-4,9H,8H2,1H3

InChIKey

TUADYTFWZPZZTP-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(OC)C=C1N

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

22-52/53

Safety Statements 

61

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2922290090

2-Amino-4-methoxyphenol Usage And Synthesis

Uses

2-Amino-4-methoxyphenol is a volatile constituent in the aroma concentrate of Tieguanyin teas[1]. 2-Amino-4-methoxyphenol is used for the synthesis of pyridine analogues[2].

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1265, 1949 DOI: 10.1021/ja01172a036

Synthesis

The general procedure for the synthesis of 2-amino-4-methoxyphenol from 4-methoxy-2-nitrophenol was as follows: a suspension of 4-methoxy-2-nitrophenol (10 g, 59.17 mmol), methanol (500 mL), and 10% palladium-carbon-catalyst (500 mg) in methanol (5 mL) was added in a round bottom flask. Subsequently, hydrogen was passed through a balloon into the reaction system and the reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to afford 2-amino-4-methoxyphenol as a brown oil (7.9 g, 96% yield).

References

[1] Chen YJ, et al. Effects of baking and aging on the changes of phenolic and volatile compounds in the preparation of old Tieguanyin oolong teas. Food Research International (Ottawa, Ont.), 01 Oct 2013, 53(2):732-743.
[2] Sina Rezazadeh, et al. Synthesis of substituted 2-heteroarylbenzazol-5-ol derivatives as potential ligands for estrogen receptors. Tetrahedron 69(30):6076–6082.

2-Amino-4-methoxyphenol(20734-76-3)Related Product Information

• 4-Methoxyphenol
• Guaiacol
• 3-Methoxyphenol
• ALTRENOGEST
• p-(2-Methoxyethyl) phenol
• 3-Aminophenol
• 6-Aminocaproic acid
• Glycine
• 4-Aminophenol
• Acetaminophen
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane
• 4-Hydroxy-3-nitrobenzoic acid
• 4-HYDROXY-3-NITROPHENYLACETIC ACID
• 4-METHOXY-3-NITROBENZOTRIFLUORIDE
• 2-Nitro-p-cresol
• 2-(2-THIAZOLYLAZO)-P-CRESOL
• 6-AMINO-2,4-XYLENOL