dimethyl[[2,2'''-[1,3-propanediylbis(oxy-kO)]bis[3'',5,5''-tris(1,1-dimethylethyl)-5'-methyl[1,1':3',1''-terphenyl]-2'-olato-kO]](2-)]-zirconium

Hydrolysis

Link to relevant study record(s)

Reference

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

abstract

Qualifier:

no guideline followed

Principles of method if other than guideline:

To identify the hydrolysis product is by adding water to the neat metallocene DOC-6114 (white powder) followed by addition of CH2Cl2 or CDCl3.
In a 10 mL glass vial, 5,0066 g demi water was poured and 4.4 mg neat DOC-6114 was added. The resulting mixture (containing white solids) was stirred for 30 min at 20ºC. To this mixture, 3.0467 g CDCl3 was added and the mixture was further stirred for 30 min at 20ºC. A crimp cap was placed on the vial (no hermetically sealed) to avoid solvent evaporation.
Samples from the organic layer (bottom layer) and the aqueous layer (upper layer) were taken and analyzed by 1H NMR spectroscopy. The white solids present were not isolated neither analyzed.
In addition, a sample of the CDCl3 employed was analyzed by 1H NMR spectroscopy.

GLP compliance:

no

Radiolabelling:

no

Analytical monitoring:

yes

Buffers:

Deionized water.

Duration:

30 min

Temp.:

20 °C

Initial conc. measured:

ca. 880 mg/L

Remarks:

test substance was added to deionized water.

Number of replicates:

no information.

Positive controls:

not specified

Negative controls:

not specified

Transformation products:

yes

Details on hydrolysis and appearance of transformation product(s):

Identitiy of transformation product: [1,1':3',1''-Terphenyl]-2'-ol, 2,2'''-[1,3-propanediylbis(oxy)]bis[3'',5,5''-tris(1,1-dimethylethyl)-5'-methyl-

Details on results:

The test substance and its transformation product are not soluble in water.

Half-lives cannot be determined due to the low water solubility of DOC-6114 as well as Ligand 6114. When in contact with water DOC-6114 hydrolyzes instantly to Ligand 6114.

Validity criteria fulfilled:

not applicable

Conclusions:

It was clearly demonstrated that hydrolysis of DOC-6114 with water leads to the formation of free Ligand 6114, as determined by1H NMR spectroscopy.
All DOC-6114 employed is completely hydrolyzed and free Ligand 6114 is obtained.

Half-lives cannot be determined due to the low water solubility of DOC-6114 as well as Ligand 6114. When in contact with water DOC-6114 hydrolyzes instantly to Ligand 6114.

Executive summary:

The hydrolysis of DOC-6114 with water in the presence of organic solvents such as dimethyl sulfoxide (DMSO), methanol (MeOH), dichloromethane (CH₂Cl₂) and deuterated chloroform (CDCl₃) was investigated at 20°C. The hydrolysis products were analyzed by¹H NMR spectroscopy. Based on these experiments, the best procedure to identify the hydrolysis product is by adding water to the neat metallocene DOC-6114 (white powder) followed by addition of CH₂Cl₂or CDCl₃. The latest was employed to further characterize the hydrolysis product by¹H NMR spectroscopy.

 

The organics are easily extracted with CH₂Cl₂or CDCl₃and analyzed by¹H NMR spectroscopy. Mainly, free ligand 6114 was identified by¹H NMR spectroscopy. The aqueous solution did not contain any trace of ligand 6114. The presence of ligand 6114 was not detected by¹H NMR spectroscopy. 

From these experiments, it was clearly demonstrated that hydrolysis of DOC-6114 with water leads to the formation of free ligand 6114, as determined by¹H NMR spectroscopy. The hydrolysis procedure is reproducible.

Half-lives cannot be determined due to the low water solubility of DOC-6114 as well as Ligand 6114. When in contact with water DOC-6114 hydrolyzes instantly to Ligand 6114.

Description of key information

In an adapted hydrolysis study it was clearly demonstrated that hydrolysis of DOC-6114 with water leads to the formation of free Ligand 6114 (CAS 1042662 -40 -7), as determined by 1H NMR spectroscopy.

All DOC-6114 employed is completely hydrolyzed and free Ligand 6114 is obtained.

Half-lives cannot be determined due to the low water solubility of DOC-6114 as well as Ligand 6114. When in contact with water DOC-6114 hydrolyzes instantly to Ligand 6114.