HYDRAZINE.
Think of it as a versatile tool for forming heterocycles, too. Lately, research chemists have been doing quite a bit of work with hydrazine and its derivatives as synthesizers of heterocyclic rings. A glance at the chart we've prepared will give you a pretty good idea of what types of rings they've been working on. And what kinds of appli cations they've been looking at. Why hydrazine? Hydrazine is a difunctional molecule, with two active N-sites.
Agnc. Chem.
Anti oxidants, Corros. Inhib.
Dyes& Pigments
Drugs
Optic. Br., Light Stab., U.V. Screeners , Photog.
Polymers
& Fibers
Pyrazoles Pyrazolines Pyrazolones
K"
Thiadiazoles
V
•
Oxadiazoles
\S
V
Triazoles •
| Tetrazoles
V
\S
*
\S
Pyridazines Pyndazine-ones
\S
Triazines
\S
Triazine-ones
"
Tetrazines
sugar cane cultivation, is synthesized with a hydrazine derivative, methylthiosemicarbazide. Each end of the molecule can thus react to form heterocycles. (Which makes it a good polymer former and chain extender, too.) With hydrazine or its deriva tives you can synthesize heterocycles of three to seven members. One to four of these may be nitrogens. (Compounds with fewer members tend to be more reactive. Those with more members are more stable.) You can construct rings in corporating oxygen, sulfur, phospho rus or the reactive N-amino group. You can change one heterocyclic ring into another. You can expand the rings, or form polycyclic molecules. You can form heterocycles by reacting hydrazine or its derivatives with unsaturated heteromolecuies, such as nitriles or thiocyanates. Or, you can use hydrazine derivatives in 1,3-dipolar additions to form new derivatives. The ring of the cash register Above all, you can make hydrazine-based heterocycles pay off commercially. For example, Spike*, a highly successful herbicide used in
CH3HNCNHNH2 Ο Ν_ ChLNHCNC
I ^S
Ν
II CC(CH3)3 x
CH 3 Hydralazine, a drug widely used for control of hypertension, is a phthalazine made with hydrazine. NHNhL
These chemicals are only two examples of how hydrazine can help change a heterocycle from just an interesting possibility to a commer cially important product. Maybe you have a few interesting possibilities of your own that hydrazine could help make even more interesting.
You, too, can be a ring leader We've prepared a brochure, "The Chemistry of Hydrazine," which will give you more details about this remarkably versatile chemical. Not just about its use in heterocyclic synthesis, but also in reductions, oxidations, olefinic additions, epoxidations and other applications. When you're ready to do more than read, we'll give you technical assistance. Or, if you'd rather do it yourself, we'll send you samples — 64, 54.4 or 35% solutions, hydrazine salts or anhy drous hydrazine — to do it with. By the way, we're also see ing to it there'll be plenty of hydrazine for you when you make your big breakthrough. Our ability to meet your needs will be strengthened with a plant expansion that will triple our capacity when it comes on stream in 1979. You supply the inspiration. We'll supply whatever else you need — literature, technical service, sample quantities. Just ask on your company letterhead. Write: Hydrazine Market Manager, Olin Chemicals, Dept. 31, 120 Long Ridge Road, Stamford, Connecticut 06904.
Olin
CHEMICALS
"Spike" is a registered trademark of Eli Lilly & Co.
Dec. 18, 1978 C&EN
15
