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EC number: 204-310-9 | CAS number: 119-27-7
Partition coefficient
Administrative data
Link to relevant study record(s)
- Endpoint:
- partition coefficient
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Study period:
- June 2011
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- guideline study without detailed documentation
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 107 (Partition Coefficient (n-octanol / water), Shake Flask Method)
- GLP compliance:
- not specified
- Type of method:
- flask method
- Partition coefficient type:
- octanol-water
- Specific details on test material used for the study:
- DNAN, a light yellow powder, provided by Defense Research and Development Canada (Valcartier, QC) and used as received.
- Analytical method:
- high-performance liquid chromatography
- Key result
- Type:
- Pow
- Partition coefficient:
- ca. 38.02
- Temp.:
- 22 °C
- pH:
- 6.7
- Conclusions:
- Kow of 2,4-dinitroanisole is 38.02.
- Executive summary:
The report summarizes findings on the environmental fate and ecological impact of DNAN. Aqueous solubility (Sw), octanol/water partition coefficients (Kow), sorption and stability of DNAN in two soils (DRDC-08 and DRDC-09 as provided by DRDC) were measured.
The study followed OECD Guideline 107 (Partition Coefficient (n-octanol / water), Shake Flask Method), and found Kow of DNAN to be 38.02.
- Endpoint:
- partition coefficient
- Type of information:
- experimental study
- Adequacy of study:
- weight of evidence
- Study period:
- 2014
- Reliability:
- 4 (not assignable)
- Rationale for reliability incl. deficiencies:
- secondary literature
- Qualifier:
- equivalent or similar to guideline
- Guideline:
- OECD Guideline 107 (Partition Coefficient (n-octanol / water), Shake Flask Method)
- GLP compliance:
- not specified
- Type of method:
- flask method
- Partition coefficient type:
- octanol-water
- Specific details on test material used for the study:
- DNAN (98.4%) was provided by Defense Research and Development Canada (Valcartier, QC).
- Analytical method:
- high-performance liquid chromatography
- Key result
- Type:
- log Pow
- Partition coefficient:
- ca. 1.58
- Temp.:
- 58 °C
- pH:
- ca. 5.5
- Details on results:
- The octanol/water partition coefficient, logKow, for DNAN and its reduced products followed the order: DNAN > 2-ANAN > 4-ANAN > DAAN (Table 2), which is the exact opposite of the observed solubility trend. Successive replacement of the ANO2 groups by ANH2 groups in DNAN therefore reduces the hydrophobicity. The precursor, DNAN, which is less soluble than any of its amine derivatives, exhibited a higher logKow value (1.58). The fully reduced DAAN, which partially ionizes in water, is very polar and has a marked preference for water over organic solvents (logKow < 1).
- Conclusions:
- Log Kow of 2,4-dinitroanisole is 1.58 at 25°C, pH 5.5
- Executive summary:
Reduction of DNAN with either zero valent iron or bacteria regioselectively produced 2-amino-4-nitroanisole (2-ANAN) which, under strict anaerobic conditions, gave 2,4-diaminoanisole (DAAN). Hydrolysis under environmental conditions was insignificant whereas photolysis gave photodegradable intermediates 2-hydroxy-4-nitroanisole and 2,4-dinitrophenol. Physicochemical properties of DNAN and its amino products drastically depended on the type and position of substituent(s) on the aromatic ring.
Sw followed the order (TNT < DNAN < 2-ANAN < 4-ANAN < DAAN), whereas logKow followed the order (DAAN < 4-ANAN < 2-ANAN < DNAN < TNT). In soil, successive replacement of ANO2 by ANH2 in DNAN enhanced irreversible sorption and reduced bioavailability under oxic conditions.
The study followed OECD Guideline 107 (Partition Coefficient (n-octanol / water), Shake Flask Method). Log Kow of 2,4-dinitroanisole was determined to be 1.58 at 25°C, pH 5.5
Referenceopen allclose all
Description of key information
For this endpoint 2 different independent sources of data were provided. Every information provided is relevant for this endpoint, even if the information from each single source alone could be judged insufficient, as these studies did not followed strictly established guidelines, under GLP conditions.
Despite, a strong consistency in the results presented in both studies used for this endpoint was noticed, leading to conclude that combined weight is substantial for allowing an expert judgement.
In fact, every studies presented for this endpoint, not following strictly established guidelines, but these studies all concluded on the same key value: log Kow of the substance (i.e. 2,4 -dinitroanisole) is 1.58.
Key value for chemical safety assessment
- Log Kow (Log Pow):
- 1.58
- at the temperature of:
- 25 °C
Additional information
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