186315-85-5

Basic information

• Product Name: 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE
• Synonyms: 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE;2,4-Difluoro-3-(trimethylsilyl)nitrobenzene;1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE 97%
• CAS NO: 186315-85-5
• Molecular Formula: C9H11F2NO2Si
• Molecular Weight: 231.27
• Mol File: 186315-85-5.mol

Chemical Properties

• Boiling Point: 263.136 °C at 760 mmHg
• Flash Point: 112.941 °C
• Appearance: /
• Density: 1.177 g/cm³
• Vapor Pressure: 0.017mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE(186315-85-5)
• EPA Substance Registry System: 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE(186315-85-5)

Safety Data

• Statements: R36/38:Irritating to eyes and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• Hazardous Substances Data: 186315-85-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE is used as a reagent or building block in organic synthesis for creating more complex molecules. Its unique structure allows for selective reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Protective Group Chemistry:
In the field of organic chemistry, 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE is used as a protective group for reactive functional groups. The trimethylsilyl group can be selectively removed when needed, enabling chemists to carry out reactions on specific parts of a molecule without affecting other functional groups.
Used in Materials Science:
The presence of fluorine atoms in 1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE makes it potentially useful in materials science. Its unique properties can be exploited to develop new materials with specific characteristics, such as improved stability or enhanced performance in certain applications.
Used in Pharmaceutical Research:
1,3-DIFLUORO-4-NITRO-2-(TRIMETHYLSILYL)BENZENE is also utilized in pharmaceutical research. Its structural features can be incorporated into drug molecules to modulate their properties, such as solubility, bioavailability, or binding affinity to target proteins. This can lead to the development of new drugs with improved therapeutic effects and reduced side effects.

InChI:InChI=1/C9H11F2NO2Si/c1-15(2,3)9-6(10)4-5-7(8(9)11)12(13)14/h4-5H,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 446-35-5 2,4-Difluoronitrobenzene 
• 133117-48-3 1,3-difluoro-2-trimethylsilylbenzene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Relevant articles and documents

Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride

A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.

Electrophilic ipso substitution of trimethylsilyl groups in fluorobenzenes

Using variants of literature methods 2,4- and 2,6- difluorophenyltrimethylsilanes have been bromodesilylated to the corresponding bromodifluorobenzenes in moderate to good yields, 3-bromo-2,6-difluorophenyltrimethylsilane afforded 1,3-dibromo-2,4-difluorobenzene whilst 1,3-difluoro-2,4-bis(trimethylsilyl)benzene yielded 3-bromo-2,6-difluorophenyltrimethylsilane. Application of either the Eaborn or Chvalovsky methods of nitrodesilylation to 4-fluorophenyltrimethylsilane, 2,4-difluorophenyltrimethylsilane and 2,6-difluorophenyltrimethylsilane afforded largely the corresponding desilylated products together with products associated with initial protodesilylation, followed by nitration of the resulting fluorobenzenes. The results obtained show that ipso desilylation in the fluoroaromatic series does follow the expected pattern previously obtained in the hydrocarbon analogues. They also show that in some cases the formation of unusually substituted fluoroarenes can be achieved more readily than by the methods previously used.