Registration Dossier

Administrative data

Endpoint:
oxidising properties
Type of information:
other: Result of semiempirical SCF MO calculations in combination with testing on structurally related compounds
Adequacy of study:
key study
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
other: acceptable, well documented study report

Data source

Referenceopen allclose all

Reference Type:
study report
Title:
Unnamed
Year:
2009
Report Date:
2009
Reference Type:
study report
Title:
Unnamed
Year:
2009
Report Date:
2009

Materials and methods

Principles of method if other than guideline:
A series of semiempirical SCF-MO calculations was performed using the MOPAC program package with the PM3 Hamiltonian in combination with testing on structurally related compounds.
GLP compliance:
no

Test material

Reference
Name:
Unnamed
Type:
Constituent
Details on test material:
- Name of test material (as cited in study report): 2,3-Dichloronitrobenzene
- Analytical purity: no data (not relevant because it is a calculation)

Results and discussion

Any other information on results incl. tables

In report 2009/01371, m-Nitrotoluene (liquid at room temperature) was found to have no oxidising properties in the EC A.21 test. Similarly 2, 4-Dichloronitrobenzene (solid at room temperature) did not exhibit any oxidising behaviour in the UN O.2 test (see report 2009/01427).

 

A redox reaction means the transfer of electrons from the reducing to the oxidising agent. Therefore, electron-with drawing substituents should increase a molecules oxidation potential. For nitro compounds, the net atomic charge on the Nitrogen atom of the NO2group should be a simple indicator of this effect.

 

Therefore, a series of semiempirical SCF-MO calculations was performed using the MOPAC program package with the PM3 Hamiltonian. The results are shown in the table below:

 

Compound

Net atomic charge (calculated)

Rank

m-Nitrotoluene

(CAS: 99-08-1)

1,3060

5

o-Chloronitrobenzene

(CAS: 88-73-3)

1,3089

2

2, 3-Dichloronitrobenezene

(CAS: 3209-22-1)

1,3083

3

2, 4-Dichloronitrobenezene

(CAS: 611-06-3)

1,3104

1

3, 4-Dichloronitrobenezene

(CAS: 99-54-7)

1,3066

4

Table 1: Net atomic charges and rank of oxidation potential

 

The rank describes the relative oxidation potential which is totally in agreement with chemical intuition. Since m-Nitrotoluene (rank 5) as well as 2, 4-Dichloronitrobenzene (rank 1) have been found to be not an oxidizer in testing, the substances with intermediate ranks should not be classified as such either.

 

Therefore 2, 3-Dichloronitrobenzene is not to be classified as an oxidising solid.

Applicant's summary and conclusion

Interpretation of results:
other: no oxidising properties
Remarks:
Migrated information
Executive summary:

Heitkamp D and Keldenich H-P (Currenta), 2009

A test conducted according to the Guideline EC A.21 showed that the mean pressure rise time for 3-nitrotoluene (m-nitrotoluene) (6850 ms; five run tests) was longer than the pressure rise time for the reference substance (65% nitric acid, 2550 ms; single value). Furthermore, no spontaneous ignition was observed. Therefore, 3-nitrotoluene was found to have no oxidising properties.

Similarly 2,4-Dichloronitrobenzene (CAS: 611-06-3) did not exhibit any oxidising behaviour in the UN O.2 test.

A series of semiempirical SCF-MO calculations resulted a rank.

The rank describes the relative oxidation potential which is totally in agreement with chemical intuition.Since m-Nitrotoluene (99-08-1) (rank 5) as well as 2,4 -Dichloronitrobenzene (rank 1) have been found to be not an oxidizer in testing, the substances with intermediate ranks should not be classified as such either.

Therefore 1,2-dichloro-3-nitrobenzene (2,3-Dichloronitrobenzene) is not to be classified as an oxidising solid.