87392-07-2

Basic information

• Product Name: (S)-(-)-Tetrahydro-2-furoic acid
• Synonyms: RARECHEM AL BO 2358;(S)-(-)-2-TETRAHYDROFUROIC ACID;(S)-2-TETRAHYDROFUROIC ACID;(S)-2-CARBOXY-TETRAHYDROFUROIC-ACID;S-(-)-2-CARBOXY-TETRAHYDROFUROIC-ACID;TETRAHYDROFURANCARBOXYLIC(S-(-)-) ACID;(S)-(-)-TETRAHYDRO-2-FURANCARBOXYLIC ACID;(S)-(-)-TETRAHYDRO-2-FUROIC ACID
• CAS NO: 87392-07-2
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.12
• EINECS: 618-003-6
• Product Categories: CARBOXYLICACID;Carbonic Acid;Chiral Compounds;chiral;Tetrahydrofuran Series;Furans;Carboxylic Acids & Deriv.;CHIRAL CHEMICALS;Chiral Compound;Chiral Building Blocks;Heterocyclic Building Blocks
• Mol File: 87392-07-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 244-251 °C(lit.)
• Flash Point: 230 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.2 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.60±0.20(Predicted)
• BRN: 4658738
• CAS DataBase Reference: (S)-(-)-Tetrahydro-2-furoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Tetrahydro-2-furoic acid(87392-07-2)
• EPA Substance Registry System: (S)-(-)-Tetrahydro-2-furoic acid(87392-07-2)

Safety Data

• Hazard Codes: C,Xi
• Statements: 22-34-36/37/38
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 87392-07-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

InChI:InChI=1/C6H8O5/c7-4(8)6(5(9)10)2-1-3-11-6/h1-3H2,(H,7,8)(H,9,10)

Upstream product

• 16874-33-2 tetrahydro-2-furancarboxylic acid 
• 37443-42-8 methyl tetrahydrofuran-2-carboxylate 
• 16874-34-3 ethyl tetrahydrofurancarboxylate 
• 83867-83-8 butyl (+/-)-tetrahydrofuran-2-carboxylate 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 78277-21-1 benzyl (+/-)-tetrahydrofuran-2-carboxylate 

Downstream Products

• 97-99-4 (S)-(tetrahydrofuran-2-yl)methanol 
• 1073263-57-6 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[(3S,4R)-4-phenyl-1-((S)-tetrahydro-furan-2-carbonyl)-pyrrolidin-3-yl]-isobutyramide 
• 1185280-32-3 (S)-1,7-dimethyl-3-(2-methyl-5-(5-(tetrahydrofuran-2-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one 
• 1206791-17-4 (S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-((S)-1-{4-[1-((S)-tetrahydro-furan-2-carbonyl)-piperidin-4-yl]-phenyl}-ethyl)-[1,3]oxazinan-2-one 
• 1314127-73-5 N-(2-{[(2-methylpropyl)amino]methyl}-3,7-dimethyl-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-74-6 N-(3,7-dimethyl-2-{[(tetrahydro-2H-pyran-4-ylmethyl)amino]methyl}-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-75-7 N-(2-{[(2,2-dimethylpropyl)amino]methyl}-3,7-dimethyl-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-77-9 N-{2-[(cyclopentylamino)methyl]-3,7-dimethyl-1H-indol-6-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-78-0 2-fluoro-N-(2-{[(2-hydroxy-2-methylpropyl)amino]methyl}-3,7-dimethyl-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-80-4 N-(2-{[(2,2-dimethylpropyl)amino]methyl}-7-fluoro-3-methyl-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-81-5 N-(7-fluoro-2-{[(2-methylpropyl)amino]methyl}-3-methyl-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-82-6 N-(7-fluoro-3-methyl-2-{[(tetrahydro-2H-pyran-4-ylmethyl)amino]methyl}-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-83-7 N-(2-{[(2-methylpropyl)amino]methyl}-1,3,7-trimethyl-1H-indol-6-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 
• 1314127-84-8 4-[(2S)-tetrahydrofuran-2-ylmethoxy]-N-(1,3,7-trimethyl-2-{[(tetrahydro-2H-pyran-4-ylmethyl)amino]methyl}-1H-indol-6-yl)benzamide 

Relevant articles and documents

Preparation process of optically pure 2-tetrahydrofuroic acid

The invention discloses a preparation process of optically pure 2-tetrahydrofuroic acid. The preparation process comprises the following steps: carrying out a splitting reaction on L-phenylalaninol with (RS)-2-tetrahydrofuroic acid in a first organic solvent to obtain a diastereoisomer salt, carrying out recrystallization to obtain an (S)-2-tetrahydrofuroic acid crude product, and carrying out post-treatment on the crude product to obtain high-optical purity (S)-2-tetrahydrofuroic acid with an enantiomeric excess (ee) value larger than 99%; and combining the mother liquor with the recrystallization mother liquor to obtain a mixed solution containing (R)-2-tetrahydrofuroic acid, then carrying out a reaction on the (R)-2-tetrahydrofuroic acid in the mixed solution with D-phenylalaninol for saltifying, recrystallizing the obtained salt to obtain an (R)-2-tetrahydrofuroic acid crude product, and carrying out post-treatment on the crude product to obtain high-optical purity (R)-2-tetrahydrofuroic acid with an ee value larger than 99%. According to the invention, the 2-tetrahydrofuroic acid is effectively split by using the two configurations of optically pure phenylalaninol, and the twooptical isomers of the 2-tetrahydrofuroic acid are separately obtained, and the ee values of the two optical isomers are both larger than 99%; secondly, the solvents, such as acetone, ethyl acetate and the like which are low in price and low in boiling point are used as solvents for the splitting reaction and recrystallization, the solvents are easy to recycle, and the recovery rate is high.

Process for resolving chiral acids with 1-aminoindan-2-ols

A process for the full or partial resolution of a mixture of enantiomers of a genus of chiral carboxylic acids is disclosed. The process uses a pure enantiomer of 1-aminoindan-2-ol as the resolving agent and achieves separation of the diastereomeric salts by fractional crystallization followed by liberation of the chiral acid from the salt by treatment with mineral acid. Diastereomeric salts and solyates of those salts are disclosed. The production of ketoprofen, flurbiprofen and other chiral medicaments and precursors thereto is disclosed.

Synthesis and Chromatographic Separation of the Stereoisomers of Furnidipine

The four stereoisomers of methyl tetrahydrofuran-2-ylmethyl 2,6-dimethyl-4-(o-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (furnidipine), have been synthesized and separated by chiral chromatography using D-phenylglycine as chiral stationary phase.Enantiomeric purity of stereoisomers is determined by HPLC-CSP technique and configurations deduced via X-ray crystallography.