4-Nitro-o-phenylenediamine synthesis

10synthesis methods

Product Name:4-Nitro-o-phenylenediamine
CAS Number:99-56-9
Molecular formula:C6H7N3O2
Molecular Weight:153.14

Commercial production of 4-nitro-o-PDA was first reported in the United States in 1946. Two U.S. companies were reported to produce undisclosed amounts of the chemical in 1975. U.S. imports of 4-nitro-o-PDA were reported to be about 1900 kg in 1973 and 1100 kg in 1975. 4-Nitro-o-PDAis used in fur dyes, inks, and semipermanent yellow hair coloring formulations requiring a yellow color component that does not involve the use of hydrogen peroxide in the color development.
Occupational exposure to 4-nitro-o-PDA may occur through inhalation and dermal contact with this compound at workplaces where p-PDA is produced or used. The general population may be exposed to the compound via dermal contact, primarily through the use of hair dyes containing this compound.

97-02-9
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99-56-9
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Yield:99-56-9 72%

Reaction Conditions:

with hydrazine hydrate;palladium on activated charcoal in ethanol at 20; for 1 h;

Steps:

1
Step 1: To a solution of 2,4-dinitroaniline (500 mg, 2.7 mmol) in EtOH (5 mL) was added Pd/C (25 mg) and hydrazine hydrate (860 mg, 13.7 mmol) in turn at RT. The reaction mixture was stirred at room temperature for 1 h and filtered through Celite. The filtrate was treated with a saturated aq. solution of NaHCC and extracted with ethyl acetate. The organic phase was dried over Na2SC>4 and concentrated in vacuo to provide a residue, which was purified by silica gel column (Hex/EA from 20: 1 to 2: 1) to provide 4-nitrobenzene-1,2-diamine (300 mg, 72%) as a brown solid. LC/MS (ES⁺) calcd.for C6H7N3O2: 153.05; found: 154.1 [M+H] *H NMR (400 MHz, DMSO-

References:

KINETA, INC.;GOLDBERG, Daniel R.;PROBST, Peter;BEDARD, Kristin M. WO2020/36574, 2020, A1 Location in patent:Page/Page column 55

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97-02-9
30 suppliers
$10.00/25g

5307-14-2 Synthesis