Water-soluble tetrazolium salts
View Patent ↗Thiazolyl tetrazolium salts with increased solubility in aqueous solutions have alkylammonium alkoxy substituents, preferably trimethyl ammonium propoxy groups substituents, on phenyl rings attached to the tetrazolium ring. Thiazolyl tetrazolium salts with increased solubility in aqueous solutions have alkyl ammonium alkoxy substituents, preferably trimethyl ammonium propoxy groups substituents, on phenyl rings attached to the tetrazolium ring, e.g. the compounds of the general formula shown below. Formula (A-) a .
1. A compound having the formula
wherein:
A =counter-ion
a =1-3
b =0-3
X =1-6C alkyl or heteroalkyl
R 1 =1-6C alkyl
one of R 2 and R 3 is alkyl and the other is XN+H b (R 1) 3 - b , or R 2 and R 3 form a methylene dioxy group
one of R 4 and R 5 is halogen and the other is halogen substituted 1-6C alkyl, both of R 4 and R 5 being XN+H b (R 1) 3 - b , or R 4 and R 5 are joined to form an aromatic ring or a substituted aromatic ring.
2. The compound of claim 1 having the formula
wherein:
A =counter-ion
X =1-6C alkyl
a =1-3
b =0-3
R 1 =1-3C alkyl
one of R 2 and R 3 is 1-4C alkyl and the other is XN+H b (R 1) 3 - b , or R 2 and R 3 form a methylene dioxy group
R 4 =CHF 2
R 5 =Halogen.
3. The compound of claim 2 , wherein
X is propyl
b is zero
R 1 is methyl
R 2 and R 3 form a methylene dioxy group
R 4 is CHF 2
R 5 is Cl.
4. The compound of claim 2 , wherein
X is propyl
b is 1
R 1 is methyl
R 2 and R 3 form a methylene dioxy group
R 4 is CHF 2
R 5 is Cl.
5. The compound of claim 2 , wherein
X is propyl
b is zero
R 1 is methyl
R 2 is trimethylammonium propyl
R 3 is methyl;
R 4 is CHF 2
R 5 is Cl.
6. The compound of claim 1 having the formula
wherein:
a =1-3
A =counter-ion
X =1-6C alkyl
b =0-3
R 1 =1-3C alkyl
one of R 2 and R 3 is alkyl and the other is XN+H b (R 1 ) 3-b , or R 2 and R 3
form a methylene dioxy group
one of R 4 and R 5 is halogen and the other is a halogen substituted 1-6C alkyl, or R 4 and R 5 are hydrogen
R 6 =1-4C alkoxy, hydrogen, or halogen.
7. The compound of claim 6 , wherein
X is propyl
b is zero
R 1 is methyl
R 2 is trimethylammonium propyl
R 3 is methyl
R 4 , R 5 , and R 6 are hydrogen.
8. The compound of claim 6 , wherein
X is propyl
R 1 is methyl
b is zero
R 2 is trimethylammonium propyl
R 3 is methyl
R 4 and R 5 form an aromatic ring
R 6 is methoxy.
9. The compound of claim 6 , wherein
X is propyl
b is zero
R 1 is methyl
R 2 is trimethylammonium propyl
R 3 is methyl
R 4 and R 5 are hydrogen
R 6 is ethoxy.
10. The compound of claim 6 , wherein
X is propyl
b is zero
R 1 is methyl
R 2 is trimethylammonium propyl
R 3 is methyl
R 4 and R 5 are hydrogen
R 6 is bromine.
11. The compound of claim 1 , wherein said at least one counter-ion is nitrite, phosphate, hydrogenphosphate, dihydrogen phosphate, hydrogen sulfate, sulfate, hydrogen carbonate, carbonate, methane sulfonate, fluoroborate, bromide, chloride, iodide, or combinations thereof.
12. The compound of claim 1 , wherein one of R 4 and R 5 is halogen and the other is a halogen substituted 1-6C alkyl.
13. The compound of claim 1 , wherein R 4 and R 5 are joined to form an aromatic ring.
14. The compound of claim 13 , wherein R 4 and R 5 are joined to form a 6-membered aromatic ring.