Registration Dossier
Registration Dossier
Data platform availability banner - registered substances factsheets
Please be aware that this old REACH registration data factsheet is no longer maintained; it remains frozen as of 19th May 2023.
The new ECHA CHEM database has been released by ECHA, and it now contains all REACH registration data. There are more details on the transition of ECHA's published data to ECHA CHEM here.
Diss Factsheets
Use of this information is subject to copyright laws and may require the permission of the owner of the information, as described in the ECHA Legal Notice.
EC number: 248-284-7 | CAS number: 27165-25-9
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Hydrolysis
Administrative data
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Study period:
- 11-2017
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- comparable to guideline study with acceptable restrictions
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 017
Materials and methods
Test guideline
- Qualifier:
- equivalent or similar to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- Deviations:
- yes
- Remarks:
- substance prepared in situ in acidic solution. At t0 the solution was neutralized to pH 7 and test was started
- Principles of method if other than guideline:
- The study was performed according to the principles described in the guideline, i.e. preliminary screening at 50°C and assessment of hydrolysis at 20°C and neutral pH. Unlike the OECD guideline, only pH 7 was tested. Moreover, due to the instability of the substance, the substance was made in situ by a diazotization reaction. The resulting acidic solution containing the newly formed diazonium salt was neutralized to pH 7 on t0 and the test was started.
- GLP compliance:
- no
Test material
- Reference substance name:
- 5-(N,N-diethylaminosulphonyl)-2-methoxybenzenediazonium chloride
- EC Number:
- 248-543-4
- EC Name:
- 5-(N,N-diethylaminosulphonyl)-2-methoxybenzenediazonium chloride
- Cas Number:
- 27580-14-9
- Molecular formula:
- C11H16ClN3O3S
- IUPAC Name:
- 5-(diethylsulfamoyl)-2-methoxybenzenediazonium chloride
Constituent 1
- Specific details on test material used for the study:
- IN SITU SYNTHESIS OF THE DIAZONIUM SALT
2-nitro-p-anisidine (CAS 96-96-8) was converted in a diazotisation reaction to its corresponding diazonium salt.
1) 2-nitro-p-anisidine (13.5 g) was suspended in mixture of 25 mL water and 21.3 mL 30 % HCl at 0°C.
2) The mixture was cooled in an ice bath to 0°C and stirred for 30 min
3) A pre-cooled 30 % aq. solution of NaNO2 (80 mmol) was added dropwise over 2h to induce the diazotisation reaction. This reaction is highly exothermic and needs to be carried out carefully. The internal temperature was continuously monitored and maintained below 5°C.
4) Afterwards, the reaction mixture was diluted with water (100 mL) and stirred for another 30 minutes and kept at 0°C.
5) The products were not isolated, but kept in this aqueous solution in an ice bath. The hydrolysis experiments were immediately started. - Radiolabelling:
- no
Study design
- Analytical monitoring:
- yes
- Remarks:
- LC-UV-MS
- Details on sampling:
- Pre-test at 50°C:
- Sampling intervals: 5 days
Main test at 20°C:
- Sampling intervals: 0, 3, 6, 12, 24, 48, 72, 96, 120 h
- Sampling method: vials from which sample was taken were not used anymore after sampling
- Sampling intervals/times for pH measurements: pH measurement at test start
- Sampling intervals/times for sterility check: not performed
- Sample treatment: filtered in case of precipitation or diluted in 1:5 methanol
- Sample storage conditions before analysis: direct analysis - Buffers:
- phosphate buffer 0.1M at pH 7
- Details on test conditions:
- TEST SYSTEM
- Type, material: glass test flasks and vials
- Sterilisation method: none
- Lighting: none
- Measures taken to avoid photolytic effects: incubation in the dark
- Temperature: pre-test at 50°C and main test at 20°C in thermostated oven
TEST MEDIUM
- Preparation of test medium: synthesis solution with concentration 60 mg/mL dissolved 1:30 in 0.1 M phosphate buffer of pH 7
- For main test at 20°C: synthesis solution divided over 20 separate vials
- Renewal of test solution: samples were not disturbed during hydrolysis period
OTHER TEST CONDITIONS
- Adjustment of pH: after dissolution, pH was checked
Duration of test
- Duration:
- 120 h
- pH:
- 7
- Temp.:
- 20 °C
Results and discussion
- Preliminary study:
- After 5 days, significant amount of precipitation, which is removed by filtering. Dilution of 1:10 in MeOH dissolved precipitation.
Degradation after 5 days at 50°C was complete. - Transformation products:
- yes
Identity of transformation products
- No.:
- #1
Reference
- Reference substance name:
- Unnamed
Dissipation DT50 of parent compoundopen allclose all
- Key result
- pH:
- 7
- Temp.:
- 20 °C
- DT50:
- < 24 h
- Remarks on result:
- other: final test
- pH:
- 7
- Temp.:
- 50 °C
- DT50:
- < 5 d
- Remarks on result:
- other: preliminary test
- Details on results:
- see any other information on results incl.tables
Any other information on results incl. tables
The concentration of the diazonium salt was found to drop to ca. 22% of the starting concentration after 24 hours. After 48 hours, none of the parent diazonium salt is left in the reaction mixture. These findings demonstrate that the diazonium salt is hydrolytically unstable, and its DT50 is < 24 hours. Hence, the identification of any relevant hydrolysis products was attempted.
The main degradation product that is formed during the hydrolysis experiment is 4-methoxy- benzenediazonium chloride. Unexpectedly, this hydrolysis product is in itself again a diazonium salt, in which the nitro group present in the parent substance has been replaced by a hydrogen atom.
Furthermore, the analysis of the sample at t0 shows that the diazotization reaction does not proceed very cleanly, and many side products are already visible before the start of the hydrolysis experiment. The main side product formed during the generation of the diazonium salt is 2-nitroanisole, i.e. the diazonium salt from which the N2 group was lost. Its concentration drops over time during the hydrolysis experiment.
Furthermore, also the aniline used for the synthesis of the diazonium salt is present in the t0 sample. Its concentration increases slightly during the hydrolysis experiment, but does not reach more than 15% of the starting concentration of the parent diazonium salt after 5 days.
Many other degradation and/or transformation products are found in the hydrolysis solution. However, it was not possible to (fully) identify most of them, and none of them reaches a concentration >5% of the parent diazonium salt.
Applicant's summary and conclusion
- Validity criteria fulfilled:
- not applicable
- Conclusions:
- The 4-methoxy-2-nitrobenzenediazonium chloride was found to rapidly hydrolyse. The half-life at 20°C and pH 7 is < 24h. The main degradation product formed is another diazonium salt: 4-methoxybenzenediazonium chloride.
- Executive summary:
The hydrolysis of the diazonium salt 4-methoxy-2-nitrobenzenediazonium chloride was investigated in a study based on the principles of OECD 111. Deviation compared to the guideline was needed since the diazonium salt had to be generated in situ due to it's reactivity and explosive properties when isolated.
First, 2-nitro-p-anisidine (CAS 96-96-8) was converted in a diazotisation reaction to its corresponding diazonium salt, 4-methoxy-2-nitrobenzenediazonium chloride. This acidic cooled solution was neutralized to pH 7 in a phosphate buffer. This was considered to be t0 of the experiment.
In the main study at 20°C, the hydrolysis was followed by sampling after 0, 3, 6, 12, 24, 48, 72, 96 and 120h. Samples were filtered or diluted in methanol (1:5) and directly measured by LC-UV-MS. This analysis allowed a semi-quantitative analysis of the degradation products.
The concentration of diazonium salt was found to drop rapidly to 25 % of the starting concentration after 24h. After 48h, complete hydrolysis is assumed as no parent diazonium salt is left in the reaction mixture. The main degradation product that is formed during the hydrolysis experiment is another diazonium salt 4-methoxy- benzenediazonium chloride. Many other degradation and/or transformation products are found in the hydrolysis solution. However, it was not possible to (fully) identify most of them, and none of them reaches a concentration >5% of the parent diazonium salt.
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.