2,4,6-trinitrobenzene-1,3,5-triamine

Water solubility

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

key study

Study period:

October 20th to November 1st, 2017

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study with acceptable restrictions

Qualifier:

according to guideline

Guideline:

OECD Guideline 105 (Water Solubility)

GLP compliance:

no

Type of method:

column elution method

Key result

Water solubility:

< 0.5 µg/L

Conc. based on:

test mat.

Temp.:

20 °C

Remarks on result:

not determinable

Remarks:

below LOQ

Executive summary:

Determination of the water solubility of the test substance was conducted according to OECD 105 guideline, column elution method.

Samples were analysed with validated HPLC/MS/MS method, but no peak was detected in the solutions, so the result was set as below the LOQ of 0.5 µg/L.

Reference 2

Endpoint:

water solubility

Type of information:

not specified

Adequacy of study:

supporting study

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

secondary literature

Remarks:

Data comes from a review publication, as a secondary source citing various references. Test conditions are not specified. The substance is adequately identified, but without purity. Therefore validity cannot be granted.

Principles of method if other than guideline:

(no data)

Water solubility:

0.16 other: unit not specified

Temp.:

25 °C

Remarks on result:

other: pH not specified

Water solubility:

0.197 other: unit not specified

Temp.:

25 °C

Remarks on result:

other: pH not specified

Water solubility:

2.5 other: unit not specified

Temp.:

25 °C

Remarks on result:

other: pH not specified

Aqueous solubility @ 25°C: 0.16; 0.197; 2.5

Toghiani et al reported three different values from three different literature sources.

Reference 3

Endpoint:

water solubility

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

results derived from a (Q)SAR model, with limited documentation / justification

Remarks:

The publication provides results from calculation methods/QSAR without QMRF/QPRF or other validation parameters available. Therefore validity cannot be granted.

Justification for type of information:

1. SOFTWARE
COSMOtherm
2. MODEL (incl. version number)
Version 1.06
3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
Electrostatic potential surface

Principles of method if other than guideline:

QSAR calculation

Water solubility:

0.16 g/L

Temp.:

25 °C

Remarks on result:

other: pH n/a for QSAR

Water solubility:

0.197 g/L

Temp.:

25 °C

Remarks on result:

other: pH n/a for QSAR

Water solubility:

2.5 g/L

Temp.:

25 °C

Remarks on result:

other: pH n/a for QSAR

Comparison of predictive methods for aqueous solubility (g/L) at 298.15 K for TATB:

Method of Klopman et al. (1992)       0.16

COSMOtherm prediction                   0.197

Ideal Solubility Equation                      2.5

Reference 4

Endpoint:

water solubility

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

results derived from a (Q)SAR model, with limited documentation / justification

Remarks:

The publication prov ides results from calculation methods/QSAR without QMRF/QPRF or other validation parameters available. Therefore validity cannot be granted.

Justification for type of information:

1. SOFTWARE
EPI Suite

Principles of method if other than guideline:

QSAR calculation

Water solubility:

ca. 0.16 - 2 544 000 mg/L

Remarks on result:

other: T and pH not specified

Sw (mg/L) for TATB:

2.626 E5

663.95 (Boethling 1999)

2.544 E6

0.16 (method of Klopman) (Toghiani 2008)

0.197 (COSMOtherm) (Toghiani 2008)

2.5 (ideal solubility equation) (Toghiani 2008)

The comparison with literature values shows that the predicted values differ substantially with experimental values.

In the case of solubility, none of the predicted values developed so far are close to the values measured in the laboratory at ERDC-CERL.

Description of key information

Experimental water solubility < 0.5 µg/L at 20°C (< LOQ).

Additional information

First, several literature sources were identified, providing solubility data from various experiment and QSARs. Values ranged from 0.16 mg/L to 2.5 g/L, so were considered inconsistent and not suitable for a WoE approach.

The variability may be explained by the very particular structure of the substance, with strong intra- and inter-molecular hydrogen bonds.

Therefore, an attempt was made to measure the solubility with the column elution method. A HPLC/MS/MS method was developed and validated for the analysis, but all samples were found below the LOQ of 0.5 µg/L. Therefore the result is expressed as a limit value.