4-METHOXY-O-PHENYLENEDIAMINE Chemical Properties

Melting point:

46-48°C

Boiling point:

253.57°C (rough estimate)

Density 

1.1315 (rough estimate)

refractive index 

1.5200 (estimate)

RTECS 

ST2690000

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in dimethyl sulfoxide and methanol.

form 

Solid

color 

Dark Brown to Black Oil

Sensitive 

Air Sensitive

InChI

InChI=1S/C7H10N2O/c1-10-5-2-3-6(8)7(9)4-5/h2-4H,8-9H2,1H3

InChIKey

AGAHETWGCFCMDK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

102-51-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

23/24/25-36/37/38

Safety Statements 

26-36/37/39-45

RIDADR 

2811

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

2922190090

MSDS

• Language:English Provider:ALFA

4-METHOXY-O-PHENYLENEDIAMINE Usage And Synthesis

Chemical Properties

Dark Brownish Black Solid

Uses

4-Methoxy-o-phenylenediamine is widely used as an intermediate in organic synthesis and pharmaceuticals. It is an important precursor for the synthesis of other heterocyclic compounds. It is used in the determination of glyoxal, methylglyoxal, and diacetyl in urine using 4-methoxy-o-phenylenediamine as a derivatizing reagent by High-performance liquid chromatography (HPLC).

Synthesis

General procedure for the synthesis of 4-methoxy-o-phenylenediamine from 4-methoxy-2-nitroaniline: 360 mg (2.14 mmol) of 4-methoxy-2-nitroaniline was placed in a hydrogenation reactor and 65 mL of ethanol was added. Subsequently, a small amount of 10% palladium/activated carbon catalyst was added and the reaction mixture was hydrogenated at room temperature under 50 Psi hydrogen pressure for 24 hours. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated on a rotary evaporator to afford 4-methoxyphthalimide (294 mg, 2.12 mmol, 99% yield) as a dark purple oil. The product was characterized by 1HNMR (CDCl3): δ 6.64 (d, J = 8.7 Hz, 1H), 6.35-6.30 (m, 1H), 6.26 (d, J = 8.7 Hz, 1H), 3.52 (s br, 2H), 3.07 (s br, 2H).

References

[1] Patent: US2013/315825, 2013, A1. Location in patent: Paragraph 0220
[2] Patent: WO2010/84152, 2010, A1. Location in patent: Page/Page column 109-110
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 7, p. 1756 - 1758
[4] RSC Advances, 2015, vol. 5, # 78, p. 63421 - 63428
[5] Patent: WO2017/37604, 2017, A1. Location in patent: Page/Page column 25

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