Basic information
- CAS
1817-73-8- Standard SMILES
Nc1c(Br)cc([N+](=O)[O-])cc1[N+](=O)[O-]- InChIKey
KWMDHCLJYMVBNS-UHFFFAOYSA-N- Molecular formula
- C6H4BrN3O4
- Average molar mass
- 262.02 g/mol
- Monoisotopic mass
- 260.93851771
Overview
2-bromo-4,6-dinitroaniline is a bright yellow powder. (NTP, 1992)
Names & identifiers
- Preferred name
- 2-Bromo-4,6-dinitroaniline
- IUPAC
- 2-bromo-4,6-dinitroaniline
- English name
- 2-Bromo-4,6-dinitroaniline
- Molecular formula
- C6H4BrN3O4
- Molecular weight
- 262.02
Names & synonyms
Show more names
Database identifiers
- CAS
1817-73-8- PubChem CID
- 15752
- DTXSID
DTXSID4024646- ChEMBL
CHEMBL167513- UNII
- 105X73C593
- EC Number
- 217-329-2
- Nikkaji
- J38.265E
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 250
Experimental & physicochemical properties
Solubility
less than 1 mg/mL at 70 °F (NTP, 1992)
SOL IN HOT ACETIC ACID; VERY SOL IN HOT ALCOHOL & ACETONE
Melting Point
307 to 309 °F (NTP, 1992)
153 °C
Physical Description
2-bromo-4,6-dinitroaniline is a bright yellow powder. (NTP, 1992)
Yellow solid; [HSDB] Powder; [MSDSonline]
Physicochemical properties
- Melting point
- 151 · 151-153 °C (lit.)
- Boiling point
- 400.8 · 400.8±40.0 °C(Predicted)
- Density
- 2.1534 · 2.1534 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- Chloroform (Slightly), Methanol (Slightly, Sonicated)
- pka
- 1 · pK1: -6.94(+1) (25°C)
- form
- Solid
- color
- Pale Yellow to Light Yellow
- Henry's Law Constant
- 3.9 · 3.9×104 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- CAS DataBase Reference
- 1817 · 1817-73-8(CAS DataBase Reference)
- FDA UNII
- 105 X73C593 · 105X73C593
- EPA Substance Registry System
- 2 · 2-Bromo-4,6-dinitroaniline (1817-73-8)
- UNSPSC Code
- 12352100 · 12352100
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 303 · H303-H341-H228-H315-H319
- Precautionary statements
- 210 · P210-P240-P241-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P201-P202-P308+P313-P405-P501a
- Hazard Codes
- Xi,F
- Risk Statements
- 36 · 36/37/38-11
- Safety Statements
- 37 · 37/39-26-16
- RIDADR
- 1325 · 1325
- WGK Germany
- 2 · 2
- RTECS
- 9303000 · BW9303000
- TSCA
- TSCA listed
- HS Code
- 2921.42 · 2921.42.9000
- HazardClass
- 4.1 · 4.1
- PackingGroup
- III
- Hazardous Substances Data
- 1817 · 1817-73-8(Hazardous Substances Data)
- Toxicity
- 50 · rat,LD50,oral,4100mg/kg (4100mg/kg),BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNSBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Office of Toxic Substances Report. Vol. OTS,
- REACH Registrations
- Active
- Limited Quantities
- 5 Kg · 5.0 Kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H228 (16.7%): Flammable solid [Danger Flammable solids]
P203, P210, P240, P241, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 29-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33891
Benzenamine, 2-bromo-4,6-dinitro-: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
A halogenated and nitrated aryl amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
TSCA Test Submissions
The ability of 2-bromo-4,6-dinitroaniline (BDNA) to induce morphological transformation in the BALB/3T3 mouse cell line (Cell Transformation Assay) was evaluated in the absence of added metabolic activation. Based on preliminary clonal toxicity determinations (exposure time=24 hrs), BDNA, in 0.1% (v/v) aqueous acetone, was tested at 5, 15 and 50 ug/ml, with cell survival ranging from 89.6-36.9% relative to solvent control. None of the tested concentrations produced significantly greater transformation frequencies (p > 0.05, Modified Poisson Distribution) relative to the solvent control.
The ability of 2-bromo-4,6-dinitroaniline (BDNA) to induce morphological transformation in the BALB/3T3 mouse cell line (Cell Transformation Assay) was evaluated in the absence of added metabolic activation. Based on preliminary clonal toxicity determinations (exposure time=24 hrs), BDNA, in 0.1% (v/v) aqueous acetone, was tested at 5, 15 and 50 ug/ml, with cell survival ranging from 94.0-77.3% relative to solvent control. At 15 ug/ml, a statistically significant (P<0.05, Modified Poisson Distribution) increase in the number of transformed foci was observed relative to the solvent control.
The ability of 2-bromo-4,6-dinitroaniline (BDNA) to induce morphological transformation in the BALB/3T3 mouse cell line (Cell Transformation Assay) was evaluated in the presence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary clonal toxicity determinations (exposure time=2 hrs), BDNA, in 0.06% (v/v) aqueous acetone, was tested at 3, 10 and 30 ug/ml, with cell survival ranging from 94.8-94.5% relative to solvent control. None of the tested concentrations produced detectable transformation frequencies.
The mutagenicity of 2-bromo-4,6-dinitroaniline (BDNA) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. BDNA was tested for mutagenicity at concentrations ranging from 10-1000 ug/plate using the plate incorporation method. BDNA caused a positive response in all of the bacterial tester strains except TA1535, both in the presence and absence of metabolic activation.
The ability of trichlorobutylene oxide (TCBO) to cause unscheduled DNA synthesis in human lung fibroblast cells (WI-38) in vitro was evaluated both with and without metabolic activation by mouse liver S9 fraction. TCBO, dissolved in DMSO, was tested at concentrations of 0, 51, 128, 320, 800 or 2000 ug/ml in the absence of activation and at concentrations of 0, 1447, 1736, 2083, 2500 or 3000 ug/ml with activation. None of the tested concentrations caused an increase in unscheduled DNA synthesis as measured by the amount of tritiated thymidine incorporated into DNA of treated vs control cultures. Evidence of cytotoxicity was observed at each tested concentration.
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- BW9303000
- ridadr
- 1325
- hs_code
- 2921.42.9000
- Toxicity
- rat,LD50,oral,4100mg/kg (4100mg/kg),BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNSBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Office of Toxic Substances Report. Vol. OTS,
- risk_code
- 36/37/38-11
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07,GHS08
- hazard_code
- Xi,F
- safety_code
- 37/39-26-16
- hazard_class
- 4.1
- packing_group
- III
- Hazard statements
- H303-H341-H228-H315-H319
- Limited Quantities
- 5.0 Kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Precautionary statements
- P210-P240-P241-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P201-P202-P308+P313-P405-P501a
- Hazardous Substances Data
- 1817-73-8(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used in the synthesis of monoazo dyes; [ChemIDplus] Used as a chemical intermediate for azo derivatives; [HSDB]
CHEM INT FOR AZO DERIVS (PROBABLE AZO DYE INT)
CHEM INT FOR DISPERSE VIOLET 7 & 24-NO CURRENT U.S. PRODN
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) 1.25X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1981) 4.54X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS
Applications
Uses2-Bromo-4,6-dinitroaniline was used as a model chemical in the inter-laboratory evaluation of the bioluminescent Salmonella reverse mutation assay for detecting mutagenicity.
General DescriptionBright yellow powder.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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