2-Bromo-9,9-dimethylfluorene

Name: 2-Bromo-9,9-dimethylfluorene
Brand: ChemScene
Availability: InStock
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CAS No. 28320-31-2
Cat. No. CS-W003603
Purity≥98%
MDL No.MFCD09261272

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 28320-31-2

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General Information

CAS No. 28320-31-2
Cat. No. CS-W003603
Purity ≥98%
MDL No. MFCD09261272
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₃Br
Molecular Weight 273.17
Synonym(s) None
SMILES CC1(C2=CC=CC=C2C3=C1C=C(Br)C=C3)C

Description

2-Bromo-9,9-dimethylfluorene features a sterically hindered fluorene core with a bromine substituent at the 2-position, enabling reliable coupling in palladium-catalyzed cross-coupling reactions. The dimethyl groups at the 9,9-positions enhance stability and reduce unwanted side reactions, making this compound well-suited for synthetic applications requiring robustness under standard conditions.

Application

2-Bromo-9,9-dimethylfluorene serves as a versatile building block in transition-metal-catalyzed coupling reactions, particularly in Suzuki and Stille couplings. Its sterically encumbered fluorenyl framework enhances stability and minimizes side reactions, while the bromo substituent enables reliable cross-coupling under standard conditions. The compound exhibits excellent bench stability and facilitates efficient purification, making it well-suited for applications in synthetic organic chemistry and materials science.

Synthesis

Route1
- In-stock
  
  4569-45-3
- ~20%
- In-stock
  
  28320-31-2
References
- Idemitsu Kosan Co., Ltd. Patent: EP1533289 A1, 2005 ; Location in patent: Page/Page column 22 ;
Route2
- In-stock
  
  1133-80-8
- 74-88-4
- ~10%
- In-stock
  
  28320-31-2
References
- Kobin, Bjoern; Grubert, Lutz; Blumstengel, Sylke; Henneberger, Fritz; Hecht, Stefan Journal of Materials Chemistry, 2012 , vol. 22, # 10 p. 4383 - 4390

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 0
LogP 4.7554
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Fluorenes, Fluorenones

Key Words

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2-Bromo-9,9-dimethylfluorene

CAS No. 28320-31-2

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