170941-14-7

Basic information

• Product Name: 1H-Indene,5-fluoro-1-methyl-,(1S)-(9CI)
• Synonyms: 1H-Indene,5-fluoro-1-methyl-,(1S)-(9CI)
• CAS NO: 170941-14-7
• Molecular Formula: C10H9F
• Molecular Weight: 148.18
• Product Categories: HALIDE
• Mol File: 170941-14-7.mol

Chemical Properties

• Boiling Point: 212.6±29.0 °C(Predicted)
• Appearance: /
• Density: 1.089±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Indene,5-fluoro-1-methyl-,(1S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indene,5-fluoro-1-methyl-,(1S)-(9CI)(170941-14-7)
• EPA Substance Registry System: 1H-Indene,5-fluoro-1-methyl-,(1S)-(9CI)(170941-14-7)

Safety Data

• Hazardous Substances Data: 170941-14-7(Hazardous Substances Data)

Upstream product

• 935-77-3 (S)-3-methyl-1-indanone 
• 210759-89-0 (S)-3-methyl-6-nitroindan-1-one 
• 210760-03-5 (S)-6-fluoro-3-methylindan-1-one 
• 210759-96-9 (S)-6-amino-3-methylindan-1-one 
• 170941-17-0 5-fluoro-1-methylindene 

Relevant articles and documents

1,3-HYDRON TRANSFER IN SOME 5- AND 7-SUBSTITUTED 1-METHYLINDENES. ENANTIOSELECTIVITIES AND ENANTIOMER-DEPENDENT KINETIC ISOTOPE EFFECTS

Base-catalysed substrate-enantioselective 1,3-hydron transfer (kinetic resolution) was studied in the indene system.A series of 1-methylindenes substituted in the aromatic ring and 1-methylindene (1) were employed as substrates.The rate constants, the enantioselectivities and the kinetic isotope effects (KIEs) for the enantioselective reactions H/kD)+ and (kH/kD)-> were determined at 20 deg C using (+)-(8R,9S)-dihydroquinidine as chiral catalyst in the solvent o-dichlorobenzene.The rate constants vary according to the electronic effects of the substituents.The primary deuterium KIE, ranging from 4.73 to 11.3 , is correlated with the rate constants as expected on the basis of the Melander-Westheimer postulate.The introduction of a substituent in the aromatic ring decreases the enantioselectivity.All compounds except 5 show the same sense of the enantioselectivity +/k- > 1; all substrates used are (+)-(S)/(-)-(R)>.The enantiomer dependence of the KIE is most pronounced for 1 H/kD)+ = 5.71 and (kH/kD)- = 6.46> and vanishes for the most acidic substrates (4 and 5).

1,3-Hydron transfer in some 5- or 7-substituted 1-methylindenes. Reaction rates and kinetic isotope effects

Rate constants and primary deuterium kinetic isotope effects (KIEs) have been determined for the base-catalysed 1,3-hydrotropic rearrangements of 1-methyl-5-nitroindene (12), 1-methyl-7-nitroindene (13), 5-methoxy-1-methylindene (14) and 5-fluoro-1-methylindene (15) in o-dichlorobenzene at 20°C. The tertiary amine 1,4-diazabicyclo[2.2.2]octane (DABCO) was used as catalyst. The kinetics were followed by polarimetry using the isotopic quasi-racemate method. The rearrangement of 13 was also investigated by 1H NMR kinetic experiments. The reaction rate correlates, as expected, with the electronic effect of the substituent ranging from a large increase for the 5-nitro substrate to a small decrease for the methoxy compound as compared with the unsubstituted 1-methylindene. The KIEs vary as predicted from the Melander Westheimer postulate showing an increase with reaction rate from 5.57 to 8.56. The syntheses of the (+)-(5)-form of the 5- or 7-substituted indenes and the (-)-(R)-form of the deuteriated analogues are also reported. Acta Chemica Scandinavica 1998.