28314-01-4

Usage

Uses

Used in Chemical Synthesis:
METHYL 1-FLUORENECARBOXYLATE is used as an intermediate in the synthesis of Fluoren-1-ol (F462450), a metabolite of the PAH micropollutant Fluorene (F462002). It plays a crucial role in the production of various chemicals and compounds.
Used in Environmental and Health Studies:
METHYL 1-FLUORENECARBOXYLATE is used as a biomarker to evaluate exposure to PAHs (polycyclic aromatic hydrocarbons) and environmental tobacco smoke in the general population. This helps in understanding the potential health risks associated with exposure to these pollutants and contributes to the development of strategies for mitigating their effects.

InChI:InChI=1/C15H12O2/c1-17-15(16)13-8-4-7-12-11-6-3-2-5-10(11)9-14(12)13/h2-8H,9H2,1H3

Upstream product

• 67-56-1 methanol 
• 6276-03-5 9H-fluorene-1-carboxylic acid 
• 1573-92-8 9-oxo-9H-fluorene-1-carboxylic acid 
• 206-44-0 fluoranthene 
• 84989-67-3 methyl 9,9-bis(ethylthio)fluorene-1-carboxylate 
• 84966-02-9 methyl 9-(ethylthio)fluorene-1-carboxylate 
• 84966-05-2 methyl 9-propylfluorene-1-carboxylate 

Downstream Products

• 73728-55-9 fluoren-1-yl-methanol 
• 1730-37-6 1-methylfluorene 
• 88909-93-7 fluorene-1-carbonyl azide 

Relevant academic research and scientific papers

Chemical Consequences of the Intramolecular Interaction between a Sulphur Atom and a Methoxycarbonyl Group in Fluorene Systems

The intramolecular interaction between a sulphur atom and a methoxycarbonyl group was found to affect their chemical reactivity.The rates of C-S bond cleavage in methyl-9,9-bis(ethylthio)fluorene-x-carboxylate, where x is 1, 2, or 3, with sodium ethanethiolate show that the rate is minimal, though comparable with the others, when x=1, because of steric effects.In contrast, methyl 9-(ethylthio)fluorene-x-carboxylates, where x=1, 2, or 3, exhibit the maximum rate when x=1.The rates of ester exchange in the presence of toluene-p-sulphonic acid indicate that the reaction is accelerated by the presence of two ethylthio groups at the 9 position of methyl fluorene-1-carboxylate but no significant effect is detected if there is only one ethylthio group.The hydrolysis of the thioketal group in 9,9-bis(ethylthio)fluorene is also accelerated by the presence of a 1-methoxycarbonyl group.The implication of these results are discussed with the use of a model compound.

THE EFFECTS OF THE NEIGHBORING METHOXYCARBONYL GROUP AND SULFUR ATOM(S) IN THE CARBON-SULFUR BOND CLEAVAGE AND THE ESTER EXCHANGE IN FLUORENE SYSTEMS

9,9-bis(ethylthio)fluorene (1a) reacted with sodium ethanethiolate in methanol ro give 9-ethylthiofluorene and diethyl disulfide suggesting that a C-S bond cleavage occurs by attack of a nucleophile at sulfur if a leaving group is sufficiently stable.The pseudo-first-order rate constans for the reaction of 1a and methoxycarbonyl-substituted 9-ethylthiofluorenes have suggested that the methoxycarbonyl group at 1-position exerts through space interaction eith sulfur atoms(s).The rate constants for ester exchange in 1-methoxycarbonylfluorene and its derivatives have been discussed on the ground of neighboring sulfur participation.