Basic information
- Standard SMILES
Brc1ccc(-c2ccccc2)cc1- InChIKey
PKJBWOWQJHHAHG-UHFFFAOYSA-N- Molecular formula
- C12H9Br
- Average molar mass
- 233.1 g/mol
- Monoisotopic mass
- 231.98876239
Overview
4-bromobiphenyl appears as colorless crystals. Insoluble in water. (NTP, 1992)
Names & identifiers
- Preferred name
- 4-Bromobiphenyl
- IUPAC
- 1-bromo-4-phenylbenzene
- English name
- 4-Bromobiphenyl
- Molecular formula
- C12H9Br
- Molecular weight
- 233.1
Names & synonyms
Show more names
Database identifiers
- CAS
92-66-0- PubChem CID
- 7101
- DTXSID
DTXSID4024640- ChEMBL
CHEMBL1399688- UNII
- OE77OKH5BL
- EC Number
- 202-176-6
- Nikkaji
- J95.604J
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 141
Experimental & physicochemical properties
Physical Description
4-bromobiphenyl appears as colorless crystals. Insoluble in water. (NTP, 1992)
Colorless solid; [CAMEO] White crystalline solid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 82 · 82-86 °C(lit.)
- Boiling point
- 310 °C · 310 °C(lit.)
- Density
- 0.9327 · 0.9327
- refractive index
- 1.6565 · 1.6565 (estimate)
- Flash point
- 143 °C · 143 °C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 1 g/10 · dioxane: soluble1g/10 mL, clear, colorless to very faintly yellow
- form
- Crystalline Flakes
- color
- Almost white to slightly yellow
- Water Solubility
- Insoluble
- BRN
- 1907453 · 1907453
- Henry's Law Constant
- 6 · 6.0×10-2 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- Stability
- Stable. Incompatible with oxidizing agents.
- InChI
- 1S/C12H9Br/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H
- InChIKey
- PKJBWOWQJHHAHG-UHFFFAOYSA-N
- SMILES
- Brc1ccc(cc1)-c2ccccc2
- CAS DataBase Reference
- 92 · 92-66-0(CAS DataBase Reference)
- REACH Annex XVII Substances List
- 4 · 4-bromobiphenyl (92-66-0)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 77 OKH5BL · OE77OKH5BL
- NIST Chemistry Reference
- 1 · 1,1'-Biphenyl, 4-bromo-(92-66-0)
- EPA Substance Registry System
- 4 · 4-Bromobiphenyl (92-66-0)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS09
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H318-H335-H400
- Precautionary statements
- 273 · P273-P280-P301+P312+P330-P305+P351+P338+P310-P391
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,N,Xn
- Risk Statements
- 36 · 36/37/38-50/53-41-37/38-22
- Safety Statements
- 22 · 22-24/25-37/39-26-61-60-39
- RIDADR
- 3152 · UN 3152 9/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 1750100 · DV1750100
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- PackingGroup
- Ⅲ
- HS Code
- 29036990 · 29036990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Eye Dam. 1Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 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
This chemical does not meet GHS hazard criteria for 4% (2 of 50) of reports.
Danger
H302 (92%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Regulation (EC) No 178/2002 (amended)
S - indicates a substance that is identified in a final Significant New Use Rule.
Status: Active Update: 25-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32327
Restricted substance: 4-bromobiphenyl
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: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol 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
Treatment
EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Toxicity Summary
The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DV1750100
- ridadr
- UN 3152 9/PG 2
- hs_code
- 29036990
- risk_code
- 36/37/38-50/53-41-37/38-22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS09
- hazard_code
- Xi,N,Xn
- safety_code
- 22-24/25-37/39-26-61-60-39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- packing_group
- Ⅲ
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H318-H335-H400
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Eye Dam. 1Skin Irrit. 2STOT SE 3
- Precautionary statements
- P273-P280-P301+P312+P330-P305+P351+P338+P310-P391
Chemistry & industry
Pharmacology
Metabolism/Metabolites
PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)
Uses & manufacturing
Uses
Used in chemical synthesis; [NTP]
PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)
Applications
Uses4-Bromobiphenyl is used as halogenated hydrocarbon and Intermediates of Liquid Crystals. It is also used in used in the synthesis of 4-biphenylthiolate.
Uses4-Bromobiphenyl is used as a reagent in the synthesis of spirooxindole derivatives for use as AMPK activators. It is also used as a reagent in the preparation of indenoindole derivatives as organic electroluminescent device materials.
General DescriptionColorless crystals. Insoluble in water.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers1 total
Related reactions
Linked notes
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