Tetrahydrofuran-3-carboxylic acid

Base Information

• Chemical Name: Tetrahydrofuran-3-carboxylic acid
• CAS No.: 66838-42-4
• Molecular Formula: C5H8 O3
• 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: 66838-42-4.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
• Boiling Point: 252.1oC at 760 mmHg
• PKA: 4.33±0.20(Predicted)
• Flash Point: 113.2oC
• PSA: 46.53000
• Density: 1.262g/cm3
• LogP: 0.10750
• Storage Temp.: Sealed in dry,Room Temperature
• 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%,99%, ^*data from raw suppliers

(R)-Tetrahydrofuran-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 1281202
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1COCC1C(=O)O
• Uses: (R)-Tetrahydrofuran-3-carboxylic Acid is used in preparation of the zeste enhancer homolog 2 inhibitor and their medical applications.

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: 94.0%

2,5-dihydrofuran-3-carboxylic acid (1002728-73-5) → (3R,S)-tetrahydro-furan-3-carboxylic acid (66838-42-4) + (S)-tetrahydro-furan-3-carboxylic acid (168395-26-4)

Guidance literature:

With C₅₆H₇₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; caesium carbonate; In methanol; at 60 ℃; for 12h; under 4560.31 Torr; enantioselective reaction; Autoclave;

DOI:10.1002/anie.201301341

Reference yield:

tert-butyl 4-hydroxytetrahydrofuran-3-carboxylate (797038-33-6) → (3R,S)-tetrahydro-furan-3-carboxylic acid (66838-42-4) + (S)-tetrahydro-furan-3-carboxylic acid (168395-26-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

2: trifluoroacetic acid / dichloromethane / 20 h / 20 °C

3: C₅₆H₇₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); caesium carbonate; hydrogen / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave

With di-isopropyl azodicarboxylate; C₅₆H₇₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; caesium carbonate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/anie.201301341

Reference yield:

tert-butyl 2,5-dihydrofuran-3-carboxylate (797038-34-7) → (3R,S)-tetrahydro-furan-3-carboxylic acid (66838-42-4) + (S)-tetrahydro-furan-3-carboxylic acid (168395-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 20 h / 20 °C

2: C₅₆H₇₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); caesium carbonate; hydrogen / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave

With C₅₆H₇₂IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; caesium carbonate; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1002/anie.201301341

upstream raw materials:

(R)-tetrahydrofuran-3-carboxaldehyde

2,5-dihydrofuran-3-carboxylic acid

tert-butyl 4-hydroxytetrahydrofuran-3-carboxylate

tert-butyl 2,5-dihydrofuran-3-carboxylate

Downstream raw materials:

-(+)-3-hydroxymethyltetrahydrofuran

C₂₇H₃₄FN₅O₃*ClH

C₂₇H₃₄FN₅O₃

Refernces

• 1、 -. "Dihydro-Benzo-Oxazine and Dihydro-Pyrido-Oxazine Derivatives". . . Retrieved 2013/07/05.