Tetrahydrofuran-3-carboxylic acid

Base Information

• Chemical Name: Tetrahydrofuran-3-carboxylic acid
• CAS No.: 89364-31-8
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 2932190090
• European Community (EC) Number: 629-382-2,663-296-6
• ChEMBL ID: CHEMBL2228306
• DSSTox Substance ID: DTXSID00405339
• Nikkaji Number: J667.535B
• Mol file: 89364-31-8.mol

Synonyms:tetrahydrofuran-3-carboxylic acid;89364-31-8;Tetrahydro-3-furoic acid;Oxolane-3-carboxylic Acid;Tetrahydro-3-furancarboxylic acid;Tetrahydro-furan-3-carboxylic acid;CHEMBL2228306;MFCD00075173;3-Furancarboxylic acid, tetrahydro-;(R)-Tetrahydro-3-furoic acid;MFCD07369984;3-tetrahydrofuroic acid;3-oxolanecarboxylic acid;rac-tetrahydro-3-furoic acid;SCHEMBL226904;(RS)-3-Tetrahydrofuroic acid;tetrahydrofuran-3-carboxylicacid;3-tetrahydrofuranecarboxylic acid;3-tetrahydrofuran-carboxylic acid;tetrahydrofuran-3-carboxylic?acid;DTXSID00405339;BOTREHHXSQGWTR-UHFFFAOYSA-N;(+/-) tetrahydro-3-furoic acid;(+/-)-tetrahydro-3-furoic acid;tetrahydro-furan-4-carboxylic acid;BCP08172;STR05208;BDBM50486227;GEO-02247;rac-tetrahydrofuran-3-carboxylic acid;AKOS005256738;CS-W004096;PB15879;PB26265;PS-3907;(RS)-tetrahydro-furan-3-carboxylic acid;SY016390;SY016391;SY031543;racemic tetrahydro-furan-3-carboxylic acid;AM20120290;FT-0647964;FT-0649342;FT-0772043;EN300-53423;A26924;A843148;J-502295;J-502551;J-640086;J-800087;W-200520;F2196-0154;Z381356480;Tetrahydro-3-furoic acid, contains 250 ppm BHT as inhibitor, 99%;Tetrahydro-furan-3-carboxylic acid, stabilized with 250 ppm BHT;3-Tetrahydrofuroic;tetrahydro-3-furancarboxylic acid;Tetrahydrofuran-3-carboxylic acid

Chemical Property of Tetrahydrofuran-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.00618mmHg at 25°C
• Melting Point: 129-130 °C
• Refractive Index: n20/D 1.4605(lit.)
• Boiling Point: 252.1 °C at 760 mmHg
• PKA: 4.33±0.20(Predicted)
• Flash Point: 113.2 °C
• PSA: 46.53000
• Density: 1.262 g/cm³
• LogP: 0.10750
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Acetone, Chloroform (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

98%, ^*data from raw suppliers

Tetrahydro-3-furoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCC1C(=O)O
• Uses: Tetrahydro-3-furoic Acid can be used in the synthesis of anti-tumor compounds comprising of hydroxyisovalerylshikonin analogs. Furthermore, the compound is a reagent in the synthesis of class II c-Met inhibitors, in the treatment of c-Met dependant tumors. Tetrahydro-3-furoic acid was used in synthesis of o-ethylphenyl tetrahydro-3-furanyl ketone.

Technology Process of Tetrahydrofuran-3-carboxylic acid

There total 8 articles about Tetrahydrofuran-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-tetrahydrofuranmethanol (124391-75-9,124506-31-6,15833-61-1) → 3-tetrahydrofuroic acid (89364-31-8)

Guidance literature:

With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; In aq. buffer; at 20 ℃; for 3h; pH=9.8 - 10.1; Electrolysis;

DOI:10.1021/acscatal.8b01640

Reference yield: 95.0%

3-Furoic acid (488-93-7) → 3-tetrahydrofuroic acid (89364-31-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 20 ℃; for 24h; under 2660 Torr;

DOI:10.1002/hlca.200390124

Reference yield:

tetrahydrofuran-3-carboxaldehyde (79710-86-4) → 3-tetrahydrofuroic acid (89364-31-8)

Guidance literature:

With oxygen; In water; at 68 - 125 ℃; for 0 - 6.53333h; under 6464.52 Torr;

upstream raw materials:

3-Furoic acid

3-tetrahydrofuranmethanol

tetrahydrofuran-3-carboxaldehyde

tetrahydro-furan-3-carboxylic acid benzyl ester

Downstream raw materials:

3-tetrahydrofuranmethanol

(3S,3'S)-3-phenyl-3-[(tetrahydro-furan-3-carbonyl)-amino]-propionic acid ethyl ester

3-[(benzyloxycarbonyl)amino]tetrahydrofuran

N-(2'-anilino-4,4'-bipyridin-2-yl)tetrahydrofuran-3-carboxamide

Refernces

• 1、 Ahmed, Maaz S.,Mannel, David S.,Root, Thatcher W.,Stahl, Shannon S.. "Aerobic Oxidation of Diverse Primary Alcohols to Carboxylic Acids with a Heterogeneous Pd-Bi-Te/C (PBT/C) Catalyst". supporting information. p. 1388 - 1393. Retrieved 2017/09/22.
• 2、 Gual, Aitor,Godard, Cyril,Castillon, Sergio,Claver, Carmen. "Highly efficient rhodium catalysts for the asymmetric hydroformylation of vinyl and allyl ethers using C1-symmetrical diphosphite ligands". experimental part. p. 463 - 477. Retrieved 2010/06/13.