16874-34-3

Basic information

• Product Name: Ethyl tetrahydro-2-furoate
• Synonyms: ETHYL TETRAHYDRO-2-FUROATE;Ethyl tetrahydro-2-f;2-Furancarboxylic acid,tetrahydro-, ethyl ester;Ethyl tetrahydrofuran-2-carboxylate
• CAS NO: 16874-34-3
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• Product Categories: Furan&Benzofuran
• Mol File: 16874-34-3.mol

Chemical Properties

• Boiling Point: 76-78°C
• Flash Point: 65.583 °C
• Appearance: colorless to light yellow liquid
• Density: 1.077 g/cm³
• Vapor Pressure: 0.879mmHg at 25°C
• Refractive Index: 1.445
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl tetrahydro-2-furoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl tetrahydro-2-furoate(16874-34-3)
• EPA Substance Registry System: Ethyl tetrahydro-2-furoate(16874-34-3)

Safety Data

• Hazardous Substances Data: 16874-34-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl tetrahydro-2-furoate is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its ability to form spiro/fused dihydrofurans and dihydropyrans makes it a valuable reactant in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
Ethyl tetrahydro-2-furoate is used as a versatile building block in the synthesis of a wide range of organic compounds. Its unique chemical properties allow it to be employed in the creation of complex molecular structures, which can be utilized in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Flavor and Fragrance Industry:
Ethyl tetrahydro-2-furoate is used as a component in the development of new fragrances and flavors. Its unique chemical structure contributes to the creation of novel scents and tastes, enhancing the sensory experience of various products in the market.
Used in Research and Development:
Ethyl tetrahydro-2-furoate is used as a research compound for exploring new synthetic pathways and understanding the reactivity of related molecules. Its application in academic and industrial research helps to advance the knowledge of organic chemistry and contribute to the development of innovative products and processes.

InChI:InChI=1/C7H12O3/c1-2-9-7(8)6-4-3-5-10-6/h6H,2-5H2,1H3

Upstream product

• 88-14-2 2-furanoic acid 
• 64-17-5 ethanol 
• 75-07-0 acetaldehyde 
• 614-99-3 Ethyl 2-furoate 
• 503-30-0 trimethylene oxide 
• 623-73-4 diazoacetic acid ethyl ester 
• 67-56-1 methanol 
• 52449-98-6 tetrahydrofuran-2-carbonyl chloride 
• 16874-33-2 tetrahydro-2-furancarboxylic acid 

Downstream Products

• 887411-85-0 ethyl 3-oxo-3-(tetrahydrofuran-2-yl)propanoate 
• 25330-02-3 2-(diphenylhydroxymethyl)-tetrahydrofuran 
• 103329-62-0 6-methoxy-5,7,8-triphenyl-1,2,3,4-tetrahydro-[1]naphthoic acid 
• 1191-99-7 2,3-dihydro-2H-furan 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 59293-11-7 tetrahydrofuran-2-carboxylic acid hydrazide 
• 91470-28-9 tetrahydrofuran-2-carboxamide 
• 1730-58-1 (5-ethyl-5,6,7,8-tetrahydro-[2]naphthyl)-methyl ether 
• 108-95-2 phenol 
• 87392-07-2 (S)-tetrahydro-2-furoic acid 
• 87392-05-0 (R)-tetrahydro-2-furoic acid 
• 375825-11-9 ethyl (S)-tetrahydrofuran-2-carboxylate 
• 375825-11-9 ethyl (R)-tetrahydrofuran-2-carboxylate 
• 784149-47-9 ethyl 2-({6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl}methyl)tetrahydrofuran-2-carboxylate 

Relevant articles and documents

Preparation method of tetrahydrofuranacetic acid and ester compounds thereof

The invention provides a preparation method of tetrahydrofuranacetic acid and ester compounds thereof. The preparation method comprises the following steps: in a proper solvent, in a reducing atmosphere and under the action of a hydrogenation catalyst, carrying out a reduction reaction on furanacetic acid and ester compounds thereof under the conditions that a pressure is 0.1-10MPa and a temperature is 30-250 DEG C for 0.1-72 hours, separating out the catalyst, and distilling out the solvent to obtain the target products, namely tetrahydrofuranacetic acid and the ester compounds thereof. Under relatively mild and environment-friendly conditions, efficient conversion of bio-based furanacetic acid and esters thereof is achieved, industrial production of the reaction is facilitated, platform molecules can be converted into various important intermediates or terminal products through chemical catalysis upgrading to replace existing petrochemical products, dependence on fossil resources is reduced, and the application range of biomass is expanded.

SUBSTITUTED PYRAZOLE COMPOUNDS AS SERINE PROTEASE INHIBITORS

There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of thrombin and/or kallikrein, which compounds include substituted pyrazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing certain diseases or disorders, which diseases or disorders are amenable to treatment or prevention by the inhibition of thrombin and/or kallikrein.

TETRAHYDROFURAN DERIVATIVES AS FRAGRANCES

What is proposed are specific tetrahydrofuran derivatives of the formula (I), fragrance and aroma substance mixtures comprising these tetrahydrofuran derivatives, their use in fragrance or aroma substance (mixture) and corresponding perfumed products.

NOVEL CARBOXAMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to carboxamide derivatives of Formula (I), where B1, B2, X, L, n, R, R1, R2, Z1, Z2, Rx and Ry are as defined in the claims, as compounds and compositions for inhibiting Human Immunodeficiency Virus (HIV) and process for making the compounds.

Alpha substituted carboxylic acids

Alpha substituted carboxylic acids of formula (I):

ALPHA SUBSTITUTED CARBOXYLIC ACID AS PPAR MODULATORS

Alpha substituted carboxylic acids of formula (I): wherein R' and R2 are as defined in the specification and R3 is A) formula (II); B) formula (III); C) formula (IV); and D) formula (V); wherein Y, Art, Are, AP, R4, R5, R6, R7, R6, R9, R9a, R10, R", R12, R17, ring A, and p are as defined in the specification; pharmaceutical compositions containing effective amounts of said compounds or their salts are useful for treating PPAR, specifically PPAR α/y related disorders, such as diabetes, dyslipidemia, obesity and inflammatory disorders.

A scalable chemoenzymatic preparation of (R)-tetrahydrofuran-2-carboxylic acid

To develop a practical scalable approach to (R)-tetrahydrofuran-2-carboxylic acid (THFC) 1, a chiral building block for furopenem 2, enantioselective hydrolysis of its esters is explored: When ethyl (±)-tetrahydrofuran-2-carboxylate 3d (2 M, 288 g/L) is digested by an Aspergillus melleus protease {0.2% (w/v)} in a 1.5 M potassium phosphate buffer (pH 8) for 20 h, enantioselective hydrolysis proceeds with E=60 to give (R)-THFC 1 in 94.4% ee. On separation from the left-over antipodal ester (S)-3d by partition, (R)-THFC 1 is treated with N,N-dicyclohexylamine (DCHA) in methyl ethyl ketone/methanol (5:1) to precipitate the crystalline salt 4 that contains (R)-THFC 1 of >99% ee in 22% overall yield from (±)-3d.

Reactions of Carbenes with Oxetane and with Oxetane/ Methanol Mixtures

Ethoxycarbonylcarbene, bis(methoxycarbonyl)carbene, phenylcarbene (17a), diphenylcarbene (17b), fluorenylidene (17c), 2-furylcarbene (31a), 2-furyl(phenyl)carbene (31b), 4-oxo-2,5-cyclohexadienylidene (40), and 4,4-dimethyl-2,5-cyclohexadienylidene (53) were generated by photolysis of the appropriate diazo compounds.With neat oxetane, most of these carbenes react by competitive C-H insertion (B -> A, Scheme 1) and ylide formation (B -> C). 31a and 40 do not insert into C-H bonds; 31b does not attack oxetane but rearranges exclusively with formation of 26.The ylides undergo Stevens rearrangement to give tetrahydrofurans (C -> D) and α',β-elimination, leading to allyl ethers (C -> E).With oxetane/ methanol mixtures, the intervention of oxonium ions (H) is indicated by the formation of 1,3-dialkoxypropanes (I).The oxonium ions arise either by protonation of the ylides (C -> H) or by protonation of the carbenes (B -> G), followed by electrophilic attack of the carbocations (G) at oxetane (G -> H).The former route is followed by the alkoxycarbonylcarbenes and by 40; the ylides derived from the remaining carbenes do not react with methanol, owing to their rapid Stevens rearrangements.Protonation of the carbenes 17b, 31, and 53 is clearly indicated by their product ratios and, for 31, by the formation of isomeric ethers (33, 36).The more electrophilic carbenes discriminate but slightly between oxetane and methanol while the more nucleophilic carbenes (17b, 31, 53) prefer the protic methanol strongly over the aprotic oxetane. Key Words: Carbenes/ Oxygen ylides/ Stevens rearrangement/ Oxonium ions/ Insertion, O-H/ Ylides

OXYGEN YLIDES-I. REACTIONS OF CARBENES WITH OXETANE

The ylides generated from carbenes (:CH2, :CHCO2Et, :CHPh) and oxetane in the presence of methanol undergo Stevens rearrangement and protonation competitively, yielding tetrahydrofurans and 1,3-dialkoxycyclopropanes as major products.