2-Bromo-4,6-dinitroaniline

HCID 15752

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

2-BROMO-4,6-DINITROANILINE1817-73-8Benzenamine, 2-bromo-4,6-dinitro-6-Bromo-2,4-dinitroaniline2,4-Dinitro-6-bromoanilineBromo DNA2-Bromo-4,6-dinitroaminobenzeneAniline, 2-bromo-4,6-dinitro-NCI-C60844DTXSID40246462,4-Dinitro-6-bromoanilinBenzenamide, 2-bromo-4,6-dinitro-
Show more names
bromodna2-Bromo-4,6-dinitroa2-bromo-4,6-dinitro-anilin2-BROMO-4,6-DINITRONANILINE2,4-DINITRO-6-BROMO ANILINE2-Bromo-4,6-dinitroaniline,97%
NSC-16572DTXCID204646105X73C593RefChem:466406217-329-22,4-Dinitro-6-bromanilinAniline, 2,4-dinitro-6-bromo-MFCD00007146

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

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitroanilines
Color/FormYELLOW NEEDLES FROM ACETIC ACID OR ALCOHOL
Solubility · 2 items

less than 1 mg/mL at 70 °F (NTP, 1992)

SOL IN HOT ACETIC ACID; VERY SOL IN HOT ALCOHOL & ACETONE

Boiling PointSublimes (NTP, 1992)
Melting Point · 2 items

307 to 309 °F (NTP, 1992)

153 °C

Physical Description · 2 items

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)

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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

Fire HazardsFlash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms following exposure to this compound may include eye irritation.
Hazards SummaryA mutagen and mild eye irritant; Causes somnolence and weight loss in lethal-dose feeding studies of rats; [RTECS] Emergency treatment: Methemoglobinemia; [HSDB] An eye irritant; [CAMEO] An irritant; [MSDSonline]
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Reactivity Profile · 1 item

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

Fire FightingFires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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 · 1 item

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) · 1 item

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

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
TSCA Test Submissions · 5 items

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,

Chemistry & industry

Uses & manufacturing

Uses · 3 items

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 · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

(1979) 1.25X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1981) 4.54X10+7 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 2 items

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Methods of ManufacturingBROMINATION OF 2,4-DINITROANILINE SUSPENDED IN WATER
General Manufacturing InformationBenzenamine, 2-bromo-4,6-dinitro-: ACTIVE

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]
上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]

Related reactions

17 records

Compound notes

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