1,4-Dibrombenzol

1,4-Dibromobenzene

HCID 7804CAS 106-37-6

Grundinformationen

Standard-SMILES
Brc1ccc(Br)cc1
InChIKey
SWJPEBQEEAHIGZ-UHFFFAOYSA-N
Summenformel
C6H4Br2
Durchschnittliche Molmasse
235,9 g/mol
Monoisotopische Masse
233,86798

Namen und Bezeichner

Bevorzugter Name
1,4-Dibromobenzene
IUPAC
1,4-dibromobenzene
Lokaler Name
1,4-Dibrombenzol
Englischer Name
1,4-Dibromobenzene
Summenformel
C6H4Br2
Molmasse
235.9

Namen und Synonyme

1,4-Dibromobenzene106-37-6P-DIBROMOBENZENEBenzene, 1,4-dibromo-p-Bromophenyl bromideBenzene, p-dibromo-DTXSID40240129991W3M5HZNSC-33942DTXCID504012CHEBI:37150RefChem:73210
Weitere Namen anzeigen
dibromobenzene1,4-DibrombenzolNSC 339421.4-DibroMobendibromobenzene.p-dibromo-benzen4-DibroMobenzeneOf DibroMobenzene
203-390-21,4-dibromo benzene1,4-dibromo-benzeneMFCD000000891.4-dibromobenzeneCHEMBL195407DIBROMOBENZENE, 1,4-27815-07-2

Datenbank-Bezeichner

CAS
106-37-6
PubChem CID
7804
DTXSID
DTXSID4024012
ChEMBL
CHEMBL195407
ChEBI
CHEBI:37150
UNII
9991W3M5HZ
EC Number
203-390-2
Nikkaji
J3.607B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

LogPLog Kow= 3.79
OdorODOR OF XYLENE
Density0.9641 @ 99.6 °C
Color/Form · 2 Einträge

PLATES

COLORLESS CRYSTALS

Solubility · 5 Einträge

SOLUBLE IN TOLUENE, VERY SOL IN HOT TOLUENE; VERY SOLUBLE IN CARBON DISULFIDE

Pratically insoluble in water; sol in about 70 parts alcohol; sol in benzene, chloroform; very sol in ether

> 10% in acetone

> 10% in benzene

For more Solubility (Complete) data for P-DIBROMOBENZENE (8 total), please visit the HSDB record page.

Boiling Point220.40 °C

Physikochemische Eigenschaften

Schmelzpunkt
83 · 83-87 °C (lit.)
Siedepunkt
219 °C · 219 °C (lit.)
Dichte
1.841 g/mL · 1.841 g/mL at 25 °C (lit.)
Dampfdruck
0.134 at · 0.134 at 35 °C (Hine et al., 1963)
Brechungsindex
1.5742 · 1.5742
Flammpunkt
219 · 219-220°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H315 (98.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (98.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (95.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H400 (68.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H411 (21.2%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 66 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Benzene, 1,4-dibromo-

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 30-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25812

1,4-Dibromobenzene: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and eye irritant; [eChemPortal: ERMA] An irritant; May cause kidney and liver injury; [MSDSonline] See Bromobenzene. See p-Dichlorobenzene.
DOT Emergency Guidelines · 5 Einträge

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Dibromobenzene/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Dibromobenzene/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Dibromobenzene/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Dibromobenzene/

For more DOT Emergency Guidelines (Complete) data for P-DIBROMOBENZENE (8 total), please visit the HSDB record page.

Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (98.5%);Eye Irrit. 2 (98.5%);STOT SE 3 (95.5%);Aquatic Acute 1 (68.2%);Aquatic Chronic 2 (21.2%)

Specific target organ toxicity - Repeated exposure - Category 1 (kidney)_x000D_ Category 2 (liver);Hazardous to the aquatic environment (Acute) - Category 1;Hazardous to the aquatic environment (Long-term) - Category 1

Shipment Methods and Regulations · 2 Einträge

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 2 Einträge

UN 2711; Dibromobenzene

IMO 3.3; Dibromobenzene

Sicherheit und Schutzausrüstung

Fire Fighting Procedures · 1 Eintrag

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Dibromobenzene/

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 2 Einträge

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Dibromobenzene/

Personnel protection: Keep upwind. Avoid breathing vapors. ... /Dibromobenzene/

Personal Protective Equipment (PPE)Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. Wear positive pressure self-contained breathing apparatus. /Dibromobenzene/

Toxikologische Informationen

Interactions · 1 Eintrag

The halogenated benzenes, inducers of xenobiotic metabolism, were studied for their effects on the metabolism of malathion, malaoxon (lindane), and paraoxon and on the toxicity and lethality of these organophosphorus insecticides and parathion. One mmol/kg of 1,4-dichlorobenzene (p-dichlorobenzene), 1,2,4-trichlorobenzene, 1,4-dibromobenzene, 1,2,4-tribromobenzene, or hexabromobenzene or 0.1 mmol/kg hexachlorobenzene was administered po to male mice daily for 7 days. In general, the trihalogenated benzenes increased the LD50 of all 4 insecticides 2- to 6-fold. These increases were larger than those observed with the di- or hexahalogenated isomers. The bromide-substituted benzenes were usually more active than the chlorinated ones with the exception being hexabromobenzene. There was a good correlation between their effects on lethality and increases in in vitro carboxylesterase activity with either-malathion or malaoxon as the substrate. The trihalogenated benzenes decreased the inhibitory effect of malathion on cholinesterase activity in the brain and to a lesser degree in the red blood cells, but not in 1iver or plasma.

Target OrgansHepatic
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2,700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that p-dibromobenzene will have slight mobility in soil(SRC). Volatilization of p-dibromobenzene will be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 8.93X10-4 atm-cu m/mole(SRC), calculated using experimental vapor pressure(4) and water solubility(5). Volatilization from dry soil surfaces(SRC) should not be important based on an experimental vapor pressure of 0.0575 mm Hg(4,SRC). Based on limited screening data, p-dibromobenzene is resistant to biodegradation; after a period of two weeks, 0% biodegradation occurred(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(1), indicates that p-dibromobenzene may adsorb to suspended solids and sediment in water(SRC). p-Dibromobenzene will volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 8.33X10-4 atm-cu m/mole(SRC), calculated using experimental vapor pressure(3) and water solubility(4). Estimated half-lives for a model river and model lake are 6 and 157 hrs, respectively(1,SRC). According to a classification scheme(5), experimental BCF values ranging from 42.9 to 1,413(6,7,SRC) suggests that bioconcentration in aquatic organisms is moderate to very high(SRC). Based on limited screening data, this compound is resistant to biodegradation; 0 biodegradation occurred after a period of two weeks(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-dibromobenzene, which has an experimental vapor pressure of 0.0575 mm Hg at 25 °C(2,SRC), will exist solely as a vapor in the ambient atmosphere. Vapor-phase p-dibromobenzene is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 46 days(3,SRC). Particulate-phase p-dibromobenzene may be physically removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
EPA IRIS Information · 3 Einträge

1,4-Dibromobenzene

Hepatic

1 x 10 ^-2 mg/kg-day

Soil Adsorption/Mobility · 1 Eintrag

The Koc of p-dibromobenzene is estimated as approximately 2,700(SRC), using an experimental log Kow of 3.79(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that p-dibromobenzene has slight mobility in soil(SRC).

Regulatorische Informationen

Regulatory Information · 4 Einträge

Chemical: Benzene, 1,4-dibromo-

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 30-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25812

1,4-Dibromobenzene: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 2711
hs_code
29036990
RTECS-Nr.
CZ1791000
risk_code
36/37/38

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

FOLLOWING IP ADMIN OF P-DIBROMOBENZENE TO RABBITS, BOTH 2,4- & 2,5-DIBROMO PHENOL WERE RECOVERED IN THE URINE SUGGESTING THE FORMATION OF AN ARENE OXIDE AS AN INTERMEDIARY METABOLITE.

FOLLOWING IP ADMIN OF P-DIBROMOBENZENE TO PIGS, BOTH 2,4- & 2,5-DIBROMOPHENOL WERE RECOVERED IN THE URINE SUGGESTING THE FORMATION OF AN ARENE OXIDE AS AN INTERMEDIARY METABOLITE.

Verwendung und Herstellung

Uses · 2 Einträge

Used for organic synthesis of dyestuffs and drugs; Has been used as a fumigant; [Hawley]

ORGANIC SYNTHESIS OF DYESTUFFS & DRUGS; MANUFACTURE OF INTERMEDIATES; FUMIGANT

U.S. Imports(1983) 9.65X10+3 lb
Methods of ManufacturingPREPARED FROM DIAZOTIZED P-BROMOANILINE; BY CATALYTIC BROMINATION OF BROMOBENZENE.
General Manufacturing InformationBenzene, 1,4-dibromo-: ACTIVE
Anwendungen · 1 Eintrag

Verwenden1,4-Dibromobenzene is used in the synthesis of 2,5-dibromoacetophenone, triarylamines and trans- stilbenes. It is widely used as a heavy liquid solvent as well as a motor oil additive. It finds application as an intermediate in the manufacture of organic chemicals such as dyes, pharmaceuticals and flame retardants for polymeric materials.

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