9,10-Dibromoanthracene (HCID 68226)

Names & identifiers

Preferred name: 9,10-Dibromoanthracene
IUPAC: 9,10-dibromoanthracene
English name: 9,10-Dibromoanthracene
Molecular formula: C14H8Br2
Molecular weight: 336.02

Names & synonyms

9,10-Dibromoanthracene523-27-3Anthracene, 9,10-dibromo-DTXSID5049312UNII-61CP7C5Y8261CP7C5Y82NSC 6263NSC-6263EINECS 208-342-4DTXCID00292689,10-DIBROMOANTHRACENE [MI]RefChem:107475

Show more names

9,10-Dibromoanthracene99%9,10-anthracenems-Dibromoanthracene9, 10-Dibromoanthrac10-Dibromoanthracene9,I O-Dibromanthracen9,1-Dibromoanthracene9,1O-dibromoanthracene9,10-DIRBOMOANTHRACENE

Anthracene, 9,10dibromo52f3-27-3208-342-4BRUOAURMAFDGLP-UHFFFAOYSA-NInChI=1/C14H8Br2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-89,10-Dibromo-anthraceneMFCD00001244NSC 6263;

Database identifiers

CAS: 523-27-3
PubChem CID: 68226
DTXSID: DTXSID5049312
ChEMBL: CHEMBL3183379
UNII: 61CP7C5Y82
EC Number: 208-342-4
Nikkaji: J6.630C

Properties

Computed structural properties

XLogP: 5.8
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 0
Heavy atoms: 16
Formal charge: 0
Complexity: 203

Physicochemical properties

Melting point: 223 · 223-224 °C (lit.)
Boiling point: 342.21 °C · 342.21°C (rough estimate)
Density: 1.7167 · 1.7167 (estimate)
refractive index: 1.63 · 1.6300 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform
form: Fluffy Powder
color: Yellow to yellow-green
Water Solubility: Soluble in water.
Merck: 14 · 14,3018
BRN: 1912109 · 1912109
InChI: 1S/C14H8Br2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
InChIKey: BRUOAURMAFDGLP-UHFFFAOYSA-N
SMILES: Brc1c2ccccc2c(Br)c3ccccc13
CAS DataBase Reference: 523 · 523-27-3(CAS DataBase Reference)
FDA UNII: 61 CP7C5Y82 · 61CP7C5Y82
NIST Chemistry Reference: 9 · Anthracene, 9,10-dibromo-(523-27-3)
EPA Substance Registry System: 9 · Anthracene, 9,10-dibromo- (523-27-3)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 9 · GHS09
Signal word: Warning
Hazard statements: 410 · H410
Precautionary statements: 273 · P273-P501
PPE: Eyeshields, Gloves
Hazard Codes: Xi,N
Risk Statements: 36 · 36/37/38-50/53
Safety Statements: 37 · 37/39-26-61-60-36
RIDADR: 3077 · UN 3077
WGK Germany: 3 · 3
TSCA: TSCA listed
HazardClass: 9 · 9
HS Code: 29039990 · 29039990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1
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

Safety data

PPE: Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
ridadr: UN 3077
hs_code: 29039990
risk_code: 36/37/38-50/53
Signal word: Warning
Symbol(GHS): GHS09
hazard_code: Xi,N
safety_code: 37/39-26-61-60-36
hazard_class: 9
Storage Class: 11 - Combustible Solids
Hazard statements: H410
Limited Quantities: 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1
Precautionary statements: P273-P501

Chemistry & industry

Applications · 2 items

Description9,10-Dibromoanthracene is an organic chemical compound containing anthracene with two bromine atoms substituted on its central ring. As a symmetrically brominated anthracene derivative, it is bearing functional groups to extend its conjugation further mainly via C-C bond forming i.e. Stille and Suzuki coupling reactions. It is notable in that it was the first single molecule to have a chemical reaction observed by an atomic force microscope and scanning tunneling microscopy. It is a low-molecular-weight organic semiconductor. It can used as an initiator in visible-spectrum solar-light-mediated benzylic C–H oxygenation through solar light or the blue LED activate[1-2].

Uses9,10-Dibromoanthracene is a dibrominated polycyclic aromatic hydrocarbon (PAH). 9,10-Dibromoanthracene is often used as an energy acceptor and activator in reactions that produce chemiluminescence.

Preparation methods · 1 item

Preparation9,10-Dibromoanthracene is synthesized by the bromination of anthracene. The bromination reaction is carried out at room temperature using carbon tetrachloride as a solvent. Using 80-85% anthracene as raw material, adding bromine to react for half an hour, the yield is 83-88%.