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1,4-Dibromobenzene

HCID 7804
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Basic information

CAS
106-37-6
Standard SMILES
Brc1ccc(Br)cc1
InChIKey
SWJPEBQEEAHIGZ-UHFFFAOYSA-N
Molecular formula
C6H4Br2
Average molar mass
235.9 g/mol
Monoisotopic mass
233.86798

Overview

1,4-dibromobenzene is a dibromobenzene.

Names & identifiers

Preferred name
1,4-Dibromobenzene
IUPAC
1,4-dibromobenzene
English name
1,4-Dibromobenzene
Molecular formula
C6H4Br2
Molecular weight
235.9

Names & synonyms

1,4-Dibromobenzene106-37-6P-DIBROMOBENZENEBenzene, 1,4-dibromo-p-Bromophenyl bromideBenzene, p-dibromo-DTXSID40240129991W3M5HZNSC-33942DTXCID504012CHEBI:37150RefChem:73210
Show more names
dibromobenzene1,4-DibrombenzolNSC 339421.4-DibroMobendibromobenzene.p-dibromo-benzen4-DibroMobenzeneOf DibroMobenzene
203-390-21,4-dibromo benzeneDIBROMOBENZENE, 1,4-1,4-dibromo-benzeneMFCD000000891.4-dibromobenzene2,5-dibromobenzeneCHEMBL195407

Database identifiers

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

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
8
Formal charge
0
Complexity
54.9

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Halogenated Monoaromatics
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 2 items

Log Kow= 3.79

3.89

OdorODOR OF XYLENE
Density0.9641 @ 99.6 °C
Color/Form · 2 items

PLATES

COLORLESS CRYSTALS

Solubility · 5 items

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H315 (98.5%): Causes skin irritation [Warning Skin corrosion/irritation]

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.

Danger

H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Hazard information

Regulatory Information · 4 items

Chemical: Benzene, 1,4-dibromo-

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

REACH registered substance: 1,4-dibromobenzene (EC: 203-390-2)

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 items

/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/

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

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.

Uses & manufacturing

Uses · 2 items

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
Applications · 2 items

UsesSolvent for oils; ore flotation; motor fuels; organic synthesis.

Uses1,4-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.

Upstream & downstream products

Downstream products

L-Phenylalanine

Related reactions

340 records
New reaction record
HRID 475 reaction equation
HRID 475As reactant750 AstraZeneca ELN dataset
HRID 506 reaction equation
HRID 506As reactant750 AstraZeneca ELN dataset
HRID 518 reaction equation
HRID 518As reactant750 AstraZeneca ELN dataset
HRID 519 reaction equation
HRID 519As reactant750 AstraZeneca ELN dataset
HRID 520 reaction equation
HRID 520As reactant750 AstraZeneca ELN dataset
HRID 9233 reaction equation
HRID 9233As reactantuspto-grants-2006_08
HRID 12952 reaction equation
HRID 12952As reactantuspto-grants-2010_06
HRID 12969 reaction equation
HRID 12969As reactantuspto-grants-2010_06
Page 1 of 43

Compound notes

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DecompositionMODERATELY DANGEROUS; WHEN HEATED TO DECOMPOSITION, IT EMITS TOXIC FUMES OF /HYDROGEN BROMIDE/.
Melting Point87.3 °C
Vapor Density8.1 (Air= 1)

Physicochemical properties

Melting point
83 · 83-87 °C (lit.)
Boiling point
219 °C · 219 °C (lit.)
Density
1.841 g/mL · 1.841 g/mL at 25 °C (lit.)
vapor pressure
0.134 at · 0.134 at 35 °C (Hine et al., 1963)
refractive index
1.5742 · 1.5742
Flash point
219 · 219-220°C
storage temp.
Inert atmosphere,Room Temperature
solubility
Soluble in alcohol, benzene, chloroform, toluene and carbon tetrachloride. Insoluble in ether.
form
Crystals
color
Colorless to almost white
Water Solubility
practically insoluble
λmax
282 nm · 282nm(EtOH)(lit.)
Merck
14 · 14,3019
BRN
1904543 · 1904543
Henry's Law Constant
5 x · 5.0 x 10-4 atmm3/mol at 25 °C (Hine and Mookerjee, 1975)
Dielectric constant
8.8 · 8.8(20℃)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
InChI
1S/C6H4Br2/c7-5-1-2-6(8)4-3-5/h1-4H
InChIKey
SWJPEBQEEAHIGZ-UHFFFAOYSA-N
SMILES
Brc1ccc(Br)cc1
CAS DataBase Reference
106 · 106-37-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
9991 W3M5HZ · 9991W3M5HZ
NIST Chemistry Reference
1 · Benzene, 1,4-dibromo-(106-37-6)
EPA Substance Registry System
p-Dibromobenzene (106-37-6)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
315 · H315-H319-H335-H411
Precautionary statements
273 · P273-P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
24 · 24/25-36-26
RIDADR
2711 · UN 2711
WGK Germany
2 · 2
RTECS
1791000 · CZ1791000
TSCA
TSCA listed
HazardClass
9 · 9
PackingGroup
III
HS Code
29036990 · 29036990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Eye · Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
106 · 106-37-6(Hazardous Substances Data)
Toxicity
50 for · Acute oral LD50 for mice 120 mg/kg (quoted, RTECS, 1985).
REACH Registrations
Active

/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 items

Skin Irrit. 2 (98.5%)

Specific target organ toxicity - Repeated exposure - Category 1 (kidney)_x000D_ Category 2 (liver)

Shipment Methods and Regulations · 2 items

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 items

UN 2711; Dibromobenzene

IMO 3.3; Dibromobenzene

Safety & protection

Fire Fighting Procedures · 1 item

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 item

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 items

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/

Toxicology

Interactions · 1 item

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 items

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
EPA IRIS Information · 3 items

1,4-Dibromobenzene

Hepatic

1 x 10 ^-2 mg/kg-day

Soil Adsorption/Mobility · 1 item

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).

Artificial Pollution Sourcesp-Dibromobenzene's production and use in the organic synthesis of dyestuffs and drugs, the manufacture of intermediates and as a fumigant(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationUsing the MITI test, 100 mg/l of p-dibromobenzene was innoculated with activated sludge(1). After an incubation period of two weeks, a theoretical BOD of 0 percent was obtained.
Environmental Bioconcentration · 1 item

An experimental BCF value of 1,413 was determined for p-dibromobenzene(2,SRC) in the guppy (Poecilia reticulata). Studies also showed a depuration rate constant of 1.41 /d(2). When exposed to 10 ug/l p-dibromobenzene, the experimental BCF in carp ranged from 42.9 to 313. When exposed to 1 ug/l p-dibromobenzene, the experimental BCF ranged from 44.2 to 279(1). According to a classification scheme(3), these BCF values suggest that bioconcentration in aquatic organisms is moderate to very high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for p-dibromobenzene is estimated as 8.93X10-4 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.0575 mm Hg(1), and water solubility, 20.0 mg/l(2). This value indicates that p-dibromobenzene will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 5.9 hours(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 157 days(3,SRC). p-Dibromobenzene's values for vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces may occur(SRC).

Non-Human Toxicity Excerpts · 3 items

LIMITED EXPERIMENTS WITH ANIMALS SUGGEST MODERATE TOXICITY.

ADMIN ORALLY TO MALE RATS FOR 45 & 90 DAYS @ 10 & 20 MG/KG 1,4-DIBROMOBENZENE INCR LIVER TO BODY WT RATIOS, CYTOCHROME p450 CONTENT, EPN DETOXIFICATION & AZOREDUCTASE ACTIVITY.

1,4-Dibromobenzene was covalently bound to DNA from liver, kidney, lung, and stomach of mice after intraperitoneal administration. The covalent binding index value (23 in mouse liver) was typical of weak initiators. On the contrary, no interaction with DNA from rat organs was observed (covalent binding index detection limit: 1.3-2.6). The in vitro interaction of 1,4-dibromobenzene with calf thymus DNA was mediated mainly by microsomes, especially those from liver of both species and from mouse lung. Mouse subcellular fractions were more active then rat subcellular fractions. Both cytochrome p450 and glutathione-transferases are involved in 1,4-dibromobenzene bioactivation.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of p-dibromobenzene with photochemically produced hydroxyl radicals has been estimated as 0.35X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 46 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
CZ1791000
ridadr
UN 2711
hs_code
29036990
Toxicity
Acute oral LD50 for mice 120 mg/kg (quoted, RTECS, 1985).
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xi
safety_code
24/25-36-26
hazard_class
9
Storage Class
11 - Combustible Solids
packing_group
III
target organs
Respiratory system
Hazard statements
H315-H319-H335-H411
REACH Registrations
Active
Hazard Classifications
Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P273-P302+P352-P305+P351+P338
Hazardous Substances Data
106-37-6(Hazardous Substances Data)
1,4-Phenylenebisboronic acid
4-Morpholinophenylboronic acid
Vat Black 8
4-Chloromandelic acid
Ambroxol
4-Bromophenoxybenzene
1-(4-Bromophenyl)hexane
N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine
1,4-Bis(dimethylsilyl)benzene
1-(4-Bromophenyl)-naphthlene
4-(Naphthalen-2-yl)phenylboronic acid
4-Bromo-4'-methoxybenzophenone
1-Bromo-4-propylbenzene
2,5-Dibromobiphenyl
4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carbonitrile
1 4-Bis(diphenylamino)benzene

Additional notes

DefinitionChEBI: 1,4-dibromobenzene is a dibromobenzene.