| Identification | More | [Name]
2,7-Dibromofluorene | [CAS]
16433-88-8 | [Synonyms]
2,7-DIBROMOFLUORENE
TIMTEC-BB SBB007691
2,7-Dibromo-9H-fluorene
Fluorene, 2,7-dibromo-
Aluminum oxide, fused, #325 mesh, 99+%
Dibromofluorene
2,7-Dibromofluorene, 98+% | [EINECS(EC#)]
629-430-2 | [Molecular Formula]
C13H8Br2 | [MDL Number]
MFCD00019048 | [Molecular Weight]
324.01 | [MOL File]
16433-88-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystalline powder | [Melting point ]
164-166 °C (lit.) | [Boiling point ]
329.77°C (rough estimate) | [density ]
1.7203 (estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly) | [form ]
Crystalline Powder | [color ]
White to off-white | [BRN ]
2049205 | [InChI]
InChI=1S/C13H8Br2/c14-10-1-3-12-8(6-10)5-9-7-11(15)2-4-13(9)12/h1-4,6-7H,5H2 | [InChIKey]
AVXFJPFSWLMKSG-UHFFFAOYSA-N | [SMILES]
C1C2=C(C=CC(Br)=C2)C2=C1C=C(Br)C=C2 | [CAS DataBase Reference]
16433-88-8(CAS DataBase Reference) | [NIST Chemistry Reference]
9H-fluorene, 2,7-dibromo-(16433-88-8) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [TSCA ]
T | [HazardClass ]
IRRITANT | [HS Code ]
29039900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Fluorene-->Aluminum-->o-Phenetidine-->Cuprous bromide-->Carbon tetrachloride | [Preparation Products]
2,7-Dibromo-9H-fluoren-9-one-->2,7-Dibromo-9,9'-spiro-bifluorene-->2,7-Dibromo-9,9-dimethylfluorene-->3,3'-(2,7-DibroMo-9H-fluorene-9,9-diyl)bis(N,N-diMethylpropan- 1-aMine)-->(2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene)-->2,2'-(9H-fluorene-2,6-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-->Spiro[9H-fluorene-9,4'-piperidine]-1'-carboxylic acid, 2,7-dibromo-, 1,1-dimethylethyl ester-->9,9-Di-n-octylfluorene-2,7-dicarboxaldehyde |
| Hazard Information | Back Directory | [Description]
2,7-Dibromofluorene is a halogenated polycyclic aromatic compound and its vapour pressure has been measured using the Knudsen effusion method. | [Chemical Properties]
white to off-white crystalline powder | [Uses]
2,7-Dibromofluorene was used as a template for the N-carbazole capped oligofluorenes which show potential as hole-transporting materials for organic light emitting devices (OLEDs). It may be used in the synthesis of conjugated polymer, poly[9,9′-bis(6′′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT), used in label-free DNA microarrays. It was used in the preparartion of blue photoluminescent unsymmetrically substituted polyfluorene. It was also used in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2 and 3) in the 9,9′-position of the fluorene ring, such as:
9,9-bis[(3,5-bis(benzyloxy)benzyloxy)methyl]-2,7-dibromofluorene
9,9-bis[(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy)-methyl] 2,7-dibromo-fluorene
9,9-bis[(3,5-bis(3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzyloxy) benzyloxy)-methyl]-2,7-dibromofluorene | [General Description]
2,7-Dibromofluorene is a halogenated polycyclic aromatic compound and its vapour pressure has been measured using the Knudsen effusion method. | [Synthesis]
General procedure for the synthesis of 2,7-dibromofluorene from fluorene: Fluorene (1.5 g, 9.0 mmol) was dissolved in carbon tetrachloride (80 mL), followed by the addition of 30 g of copper(II) bromide loaded on aluminum oxide. The reaction mixture was stirred under reflux conditions for 5 hours. Upon completion of the reaction, the solution was cooled to room temperature, filtered to remove solid impurities, and the filter cake was washed with carbon tetrachloride (50 mL). The combined organic phases were dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give 2.87 g (98% yield) of 2,7-dibromofluorene as a yellow solid. Recrystallization by ethyl acetate/hexane (5:95, v/v) mixed solvent gave pure 2,7-dibromofluorene as light yellow crystals. | [References]
[1] Tetrahedron, 2003, vol. 59, # 17, p. 3131 - 3156
[2] Dyes and Pigments, 2015, vol. 113, p. 682 - 691
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 22, p. 4071 - 4075
[4] Chemistry Letters, 2013, vol. 42, # 11, p. 1355 - 1357
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443 |
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