Prime in substituted benzene

Question

I was sent data for a molecule referred to as 1,2'-bis(4-aminophenoxy)benzene. I haven't been able to figure out if that is a real molecule.

If I drop the prime, I know 1,2-bis(4-aminophenoxy)benzene should look like that:

and Google agrees. But with the prime, I have no idea what the molecule could be. Is there such a molecule, or is it a typo?

Answer 1

I believe the prime in the name, 1,2'-bis(4-aminophenoxy)benzene, is a typo as you originally suspected. However, the compound in your picture you thought is the correct one is neither 1,2-bis(4-aminophenoxy)benzene. The compound in the picture is 1,4-bis(4-aminophenoxy)benzene (CAS#: 3491-12-1).

Nonetheless, 1,2-bis(4-aminophenoxy)benzene exists (CAS#: 49860-97-1; Ref.1). It was synthesized and used to make ortho‐linked aromatic polyimides with aromatic dicarboxylic acids (Ref.1).

Reference:

1. Chin‐Ping Yang, Jeng‐Jieh Cherng, "Synthesis and properties of aromatic polyamides derived from 1,2‐bis(4‐aminophenoxy)benzene and aromatic dicarboxylic acids," Polymer Chemistry 1995, 33(13), 2209-2220 (https://doi.org/10.1002/pola.1995.080331315).

Answer 2

This is a typo. The prime 2' would refer to position 2 in a separate ring, but you are only numbering the central ring.

Note that you have drawn the structure of 1,4-bis(4-aminophenoxy)benzene.

You can test the names of chemicals and their structures using a tool such as OPSIN.