ChemicalBook > CAS DataBase List > (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

Product Name: (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
CAS No.: 53558-93-3
Chemical Name: (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
Synonyms: (R)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID;5-oxo-2-tetrahydrofurancarboxylic acid;(theta)-2-furancarboxylicaci;(r)-γ-carboxy-γ-butyrolactone;5-Oxo-tetrahydro-furan-2-carboxylic;(2R)-5-Oxooxolane-2β-carboxylic acid;(R)-(-)-5-OXO-2-TETRAHYDROFUROIC ACID;(R)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE;(2R)-Tetrahydro-5-Oxo-2-Furan Carboxy;(R)-(-)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE
CBNumber: CB6492559
Molecular Formula: C5H6O4
Formula Weight: 130.1
MOL File: 53558-93-3.mol

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(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Property

Melting point:: 71-73 °C (lit.)
Boiling point:: 165-167 °C/0.3 mmHg (lit.)
alpha: -14°(D/20℃) (c=5, メタノール)
Density: 1.3985 (rough estimate)
refractive index: 1.5800 (estimate)
storage temp.: Inert atmosphere,Room Temperature
form: solid
pka: 3.11±0.20(Predicted)
Appearance: White to light yellow Solid
optical activity: [α]20/D 14°, c = 5 in methanol
BRN: 1424499
InChI: InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m1/s1
InChIKey: QVADRSWDTZDDGR-GSVOUGTGSA-N
SMILES: O1C(=O)CC[C@@H]1C(O)=O
CAS DataBase Reference: 53558-93-3(CAS DataBase Reference)
EPA Substance Registry System: 2-Furancarboxylic acid, tetrahydro-5-oxo-, (2R)- (53558-93-3)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 29321900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 310476
Product name: (R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid
Purity: 98%
Packaging: 1g
Price: $52
Updated: 2025/07/31

Sigma-Aldrich

Product number: 310476
Product name: (R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid
Purity: 98%
Packaging: 5g
Price: $210
Updated: 2025/07/31

TCI Chemical

Product number: O0281
Product name: (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid
Purity: >98.0%(GC)(T)
Packaging: 1g
Price: $35
Updated: 2025/07/31

TCI Chemical

Product number: O0281
Product name: (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid
Purity: >98.0%(GC)(T)
Packaging: 5g
Price: $116
Updated: 2025/07/31

TRC

Product number: O870405
Product name: (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid
Packaging: 1g
Price: $65
Updated: 2021/12/16

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(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Chemical Properties,Usage,Production

Chemical Properties

white crystalline powder

Uses

(R)-5-Oxotetrahydrofuran-2-carboxylic Acid is an intermediate used to synthesize 2'',3''-dideoxy-4''-selenonucleosides as potential antiviral agents.

General Description

(R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid belongs to the class of furans, considered as heterocyclic building blocks. It is used as an HPLC derivatization reagent for UV/Vis detection.

Synthesis

6893-26-1

53558-93-3

Example 1: Synthesis of (R)-(-)-5-oxo-2-tetrahydrofuran carboxylic acid (2) 1. To a mixed solution of D-glutamic acid (1 , 25 g, 170 mmol) in water (67 mL) and concentrated hydrochloric acid (35 mL) was slowly added a solution of NaNO2 (17.5 g, 253.6 mmol) in water (37.5 mL) at 0 °C for 4 hours. 2. After the addition was completed, the reaction mixture was stirred overnight at room temperature to obtain a clarified solution. 3. The solvent was removed by vacuum evaporation and the residue was treated with ethyl acetate (EtOAc, 80 mL) and filtered. 4. The filtrate was dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated. 5. The concentrated residue was crystallized from a solvent mixture of ethyl acetate/benzene/hexane to afford (R)-(-)-5-oxo-2-tetrahydrofuran carboxylic acid (2) as a white crystalline solid (12.63 g, 57% yield). Product Characterization: - Melting point: 71-73°C - 1H NMR (400 MHz, CD3OD): δ 4.20 (m, 1H, CHO), 1.8-2.3 (m, 4H, CH2CH2).

References

[1] Tetrahedron, 2006, vol. 62, # 37, p. 8687 - 8695
[2] Tetrahedron: Asymmetry, 1993, vol. 4, # 6, p. 1391 - 1396
[3] Organic Letters, 2014, vol. 16, # 16, p. 4336 - 4339
[4] Pharmazie, 1995, vol. 50, # 1, p. 15 - 21
[5] Patent: US2004/67877, 2004, A1

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Suppliers

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View Lastest Price from (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID manufacturers

Career Henan Chemical Co

Product: (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 53558-93-3
Price: US $1.00/KG
Min. Order: 1KG
Purity: 95-99%
Supply Ability: 500kg
Release date: 2019-09-02

53558-93-3, (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACIDRelated Search:

2-(2-METHOXYPHENYL)-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 2,2-DIMETHYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID 2-Tetrahydrofuroic acid (1R)-(+)-CAMPHANIC ACID (S)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 2-(1-Carboxyundecyl)-5-oxotetrahydrofuran-2-carboxylic acid (R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE (3S)-2-(2-METHOXYPHENYL)-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID 4-METHYLENE-2-OCTYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID 3,4,4-Trimethyl-2-oxotetrahydrofuran-3-carboxylic acid ethyl ester 2-[[(4S)-4-[[Cyanoacetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt 2-[[(4S)-4-[[Phenyl-sodiosulfoacetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt D-CAMPHANIC ACID ANHYDRIDE CAMPHANIC ACID 2-[[(4S)-4-[[2-Thienylacetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt 2-[[(4S)-4-[[2-Pyridinylthioacetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt

(R)-(-)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE

(R)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

(R)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

(R)-(-)-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID

(R)-(-)-5-OXO-2-TETRAHYDROFUROIC ACID

(R)-(-)-TETRAHYDRO-5-OXO-2-FURANECARBOXYLIC ACID

(R)-(-)-5-OXO-2-TETRAHYDROFURANCARBOXYLI C ACID, 98% (97% EE/GLC)

(R)-5-OXOTETRAHYDRO-2-FURANCARBOXYLIC ACID 98+%

(R)-(-)-5-Oxo-2-tetrahydrofurancarboxylic acid, 99% (99% ee)

(<i>R</i>)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid

(theta)-2-furancarboxylicaci

D-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID (R-)

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC

(r)-γ-carboxy-γ-butyrolactone

(R)-5-Oxotetrahydro-2-furancarboxylic acid,(R)-γ-Carboxy-γ-butyrolactone

(R)-()-5-Oxo-2-tetrahydrofurancarboxylic acid,(R)-γ-Carboxy-γ-butyrolactone, (R)-5-Oxotetrahydro-2-furancarboxylic acid

2-Furancarboxylic acid,tetrahydro-5-oxo-, (2R)

(R)-(-)-5-Oxo-2-tetrahydrofurancarboxylic acid, 99% (99% ee) 1GR

(R)-(-)-gamma-Carboxy-gamma-butyrolactone (R)-(-)-5-Oxo-2-tetrahydrofuroic Acid

5-Oxo-tetrahydro-furan-2-carboxylic

2-Furancarboxylic acid, tetrahydro-5-oxo-,(S)-

5-oxo-2-tetrahydrofurancarboxylic acid

(R)-γ-Carboxy-γ-butyrolactone, (R)-5-Oxotetrahydro-2-furancarboxylic acid

(R)-(-)-5-Oxo-2-tetrahydrofurancarboxylic acid, 99%, ee:.99%

(2R)-5-Oxooxolane-2β-carboxylic acid

(R)-Tetrahydro-5-oxo-2β-furancarboxylic acid

(R)-(-)-5-Oxo-2-tetrahydrofurancarboxylic acid 98%

(2R)-Tetrahydro-5-oxo-2-furancarboxylic Acid

(R)-(-)-5-Oxotetrahydrofuran-2-carboxylicAcid&gt

(2R)-Tetrahydro-5-Oxo-2-Furan Carboxy

(2R)-5-oxotetrahydrofuran-2-carboxylic acid

(<i>R</i>)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid

(2R)-5-Oxotetrahydro-2-furancarboxylic acid

53558-93-3

CARBOXYLIC ACID

Chiral Building Blocks

Carboxylic Acids (Chiral)

Asymmetric Synthesis

Chiral Resolution Reagents

Chiral Resolving Reagents

Heterocyclic Building Blocks

Furans

Carboxylic Acids (Chiral)

Chiral Building Blocks

Synthetic Organic Chemistry