What is the simplest way to connect PEX to a Vintage Radiator?

Use these with reducing adaptors as needed.

 
make sure when you spin that nipple off with the piece of coupling left on it to hold the nut that is against the radiator or you will have a problem AKA Leak
 
I'm not sure I want to spin that nipple off... seems like it should be part of what holds the sections together. At the bottom of the picture you can see what the other side looks like. The bushing is somehow attached to the nut on the opposite side, compressing the four sections together.

Also, it's been on there for 100 years, and the nipple might crush easily. I'd be screwed then...

So if I could make up to it without removing it, that would be best. I want to find the other half of that steam coupling, two of them, one for the top and one for the bottom, then I can go from iron pipe to pex.
 
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Seems like what you need might be called a cast iron face bushing
This looks to be machined to mate with the bushing on your radiator; tighten the captured nut on this and then screw on a standard pipe connector and a reducing adapter with a hose barb?
 
No, Red, that's just a cast version of what Ronn47 posted. I need to find t'other half of the two steam couplings, on a short piece of iron pipe...

...or I need that nipple out of there and insert a bushing that goes to PEX.

I just don't know if the nipple is really part of the clamp that holds the 4 pieces together.
 
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The piece you have looks like part of a radiator union elbow.

You can look on supplyhouse or similar online sites for an example.

The other end generally ends in NPT of various sizes.

You could buy a couple of those, use the side you need, and then use a NPT x PEX adapter.

EDIT: You could also buy the appropriate straight union and use half of it.
 
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Enlightenment from @elirab.
I think the part numbered 2 is in your radiator, and you need the part numbered 3 – to which you can cobble up an adapter to Pex
 
Yep. Get the other half of that radiator union. Then you can transition to PEX.

Just did this for a friend of mine last year.

He put one in his basement garage (bi-level house). Tapped into the supply and return from his boiler before the zone valves.

No matter what zone was calling for heat, the garage would get heat.

10° outside, two car garage stayed at 70°. And the upstairs bedrooms stayed warm.
 
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