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(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
Molecular Weight:
130.1
MDL Number:
MFCD00011567
MOL File:
53558-93-3.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-04-24 14:58:44
Product description Number Pack Size Price
(R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid 98% 310476 1g $111
(R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid 98% 310476 5g $320
(R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid >98.0%(GC)(T) O0281 1g $28
(R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid >98.0%(GC)(T) O0281 5g $93
(R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid O870405 1g $65

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

Melting point 71-73 °C (lit.)
alpha -14°(D/20℃) (c=5, メタノール)
Boiling point 165-167 °C/0.3 mmHg (lit.)
Density 1.3985 (rough estimate)
refractive index 1.5800 (estimate)
storage temp. Inert atmosphere,Room Temperature
pka 3.11±0.20(Predicted)
form solid
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)
UNSPSC Code 12352005
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs Respiratory system
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
TSCA  TSCA listed
HS Code  29321900
Storage Class 11 - Combustible Solids
Hazard Classifications Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
NFPA 704
0
2 0

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID price More Price(25)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 310476 (R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid 98% 53558-93-3 1g $111 2026-04-30 Buy
Sigma-Aldrich 310476 (R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid 98% 53558-93-3 5g $320 2026-04-30 Buy
TCI Chemical O0281 (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid >98.0%(GC)(T) 53558-93-3 1g $28 2026-04-30 Buy
TCI Chemical O0281 (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid >98.0%(GC)(T) 53558-93-3 5g $93 2026-04-30 Buy
TRC O870405 (R)-(-)-5-Oxotetrahydrofuran-2-carboxylic Acid 53558-93-3 1g $65 2021-12-16 Buy
Product number Packaging Price Buy
310476 1g $111 Buy
310476 5g $320 Buy
O0281 1g $28 Buy
O0281 5g $93 Buy
O870405 1g $65 Buy

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

D(-)-Glutamic acid

6893-26-1

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

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

328-50-7
21461-84-7
53558-93-3
Synthesis of (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID from 2-Ketoglutaric acid

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

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

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

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID pictures 2019-09-03 (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
53558-93-3
US $1.00 / KG 1KG 95-99% 500kg Career Henan Chemical Co
(R)-(-)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE (R)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE (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) (R)-(-)-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> (2R)-Tetrahydro-5-Oxo-2-Furan Carboxy (2R)-5-oxotetrahydrofuran-2-carboxylic acid (R)-(?)-5-Oxo-2-tetrahydrofurancarboxylic acid (2R)-5-Oxotetrahydro-2-furancarboxylic acid (R)-tetrahydro-5-oxo-2-furancarboxylic acid (R)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC 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