380611-49-4

Basic information

• Product Name: [2-chloro-6-(trifluoromethyl)benzene]lithium
• CAS NO: 380611-49-4
• Molecular Weight: 186.49
• Mol File: 380611-49-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [2-chloro-6-(trifluoromethyl)benzene]lithium(CAS DataBase Reference)
• NIST Chemistry Reference: [2-chloro-6-(trifluoromethyl)benzene]lithium(380611-49-4)
• EPA Substance Registry System: [2-chloro-6-(trifluoromethyl)benzene]lithium(380611-49-4)

Safety Data

• Hazardous Substances Data: 380611-49-4(Hazardous Substances Data)

Upstream product

• 98-15-7 3-chlorotrifluoromethylbenzene 
• 135227-01-9 1-lithio-2-chloro-5-(trifluoromethyl)benzene 
• 1289519-62-5 2-deutero-1-chloro-3-(trifluoromethyl)benzene 
• 2417-95-0 p-tolyllithium 

Downstream Products

• 2376-00-3 2-chloro-6-(trifluoromethyl)benzoic acid 

Relevant articles and documents

Regioselective lithium diisopropylamide-mediated ortholithiation of 1-CHLORO-3-(trifluoromethyl)benzene: Role of autocatalysis, lithium chloride catalysis, and reversibility

Ortholithiation of 1-chloro-3-(trifluoromethyl) benzene with lithium diisopropylamide (LDA) in tetrahydrofuran at -78 °C displays characteristics of reactions in which aggregation events are rate limiting. Metalation with lithium-chloride-free LDA involves a rate-limiting deaggregation via dimer-based transition structures. The post-rate-limiting proton transfers are suggested to involve highly solvated triple ions. Autocatalysis by the resulting aryllithiums or catalysis by traces (100 ppm) of LiCl diverts the reaction through di- and trisolvated monomer-based pathways for metalation at the 2 and 6 positions, respectively. The regiochemistry is dictated by a combination of kinetically controlledmetalations overlaid by an equilibration involving diisopropylamine that is shown to occur by the microscopic reverse of the monomer-based metalations.

METHOD FOR METAL-ORGANIC PRODUCTION OF ORGANIC INTERMEDIATE PRODUCTS BY MEANS OF ARYL LITHIUM-BASES

The invention relates to a method for the production of substituted aromatic compounds by producing lithium arylene and by reacting it with suitable electrophiles. The method comprises the following steps (step 1); an aryl lithium compound ( auxiliary base'') is initially produced by reacting a halogen aromatic compound with lithium metal; said compound is subsequently (step 2) reacted for deprotonation of the aromatic substrate in order to form the corresponding lithium aromatic compound which is subsequently (step 3) reacted with a corresponding electrophile to form the desired substituted aromatic compound, see page 2 of the description.