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

(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

Product Name
(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
CAS No.
21461-84-7
Chemical Name
(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
Synonyms
TOF;5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID;(S)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID;(2S)-Tetrahydro-5-oxofuran-2-carboxylic Acid;TIMTEC-BB SBB006581;(S)-(+)-5-OXOTETRAHY;(s)-γ-carboxy-γ-butyrolactone;(2S)-5-oxo-2-oxolanecarboxylate;L-α-Hydroxyglutaric acid γ-lactone;(2S)-5-oxooxolane-2-carboxylic acid
CBNumber
CB4725592
Molecular Formula
C5H6O4
Formula Weight
130.1
MOL File
21461-84-7.mol
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(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Property

Melting point:
71-73 °C (lit.)
alpha 
+14°(20/D, c=5, CH3OH)
Boiling point:
150-155 °C/0.2 mmHg (lit.)
Density 
1.3985 (rough estimate)
refractive index 
1.5800 (estimate)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Acetone
form 
Solid
pka
3.11±0.20(Predicted)
color 
White
optical activity
[α]20/D +14°, c = 5 in methanol
BRN 
1424498
InChI
InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m0/s1
InChIKey
QVADRSWDTZDDGR-VKHMYHEASA-N
SMILES
O1C(=O)CC[C@H]1C(O)=O
CAS DataBase Reference
21461-84-7(CAS DataBase Reference)
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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

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
301469
Product name
(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
Purity
98%
Packaging
1g
Price
$94.3
Updated
2023/06/20
Sigma-Aldrich
Product number
301469
Product name
(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
Purity
98%
Packaging
5g
Price
$270
Updated
2023/06/20
TCI Chemical
Product number
O0276
Product name
(S)-(+)-5-Oxotetrahydrofuran-2-carboxylic Acid
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$83
Updated
2025/07/31
TCI Chemical
Product number
O0276
Product name
(S)-(+)-5-Oxotetrahydrofuran-2-carboxylic Acid
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$246
Updated
2025/07/31
TRC
Product number
O870435
Product name
(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
Packaging
100mg
Price
$55
Updated
2021/12/16
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(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Chemical Properties,Usage,Production

Chemical Properties

white to light yellow to beige crystalline powder

Uses

(S)-5-Oxo-2-tetrahydrofurancarboxylic Acid (cas# 21461-84-7) is a compound useful in organic synthesis.

Definition

ChEBI: (S)-alpha-hydroxyglutaric acid-gamma-lactone is a butan-4-olide obtained by formal intramolecular condensation between the 2-hydroxy and 4-carboxy groups of (S)-2-hydroxyglutaric acid It is a butan-4-olide and a monocarboxylic acid. It is functionally related to a (S)-2-hydroxyglutaric acid. It is a conjugate acid of a (S)-alpha-hydroxyglutarate-gamma-lactone.

General Description

(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid is a chiral derivatizing agent for alcohols.

Synthesis

56-86-0

21461-84-7

General procedure for the synthesis of (S)-5-oxo-2-tetrahydrofuran carboxylic acid from L-glutamic acid: L-glutamic acid (10.07 g, 0.068 mol, JK CHEMICA) was dissolved in 20 mL of water in a conical flask. A solution of NaNO2 (7.0 g, 0.102 mol, Shantou Xilong Chemical Factory) in 20 mL of water was slowly added to this solution at -5°C, along with HCl and 40 mL of water. The reaction mixture was stirred continuously at room temperature for 12 hours. Subsequently, the reaction mixture was subjected to vacuum evaporation at less than 50 °C to obtain a yellow oily substance. This oily substance was dissolved in EtOAc, filtered to remove the solid formed and the solid was washed with EtOAc. The filtrate and washings were combined and dried with Na2SO4. Finally, the solvent was removed by vacuum concentration to afford (S)-5-oxo-2-tetrahydrofuran carboxylic acid as a light yellow oil (8.1 g, 91.6% yield). The product was analyzed by mass spectrometry (ESI, cation mode), m/z: 130.9 (M+1); 1H NMR (400 MHz, CDCl3) data were as follows: δ 2.27-2.41 (m, 1H), 2.44-2.65 (m, 3H), 5.09 (m, 1H), 9.12-9.55 (m, 1H).

References

[1] Journal of Organic Chemistry, 2010, vol. 75, # 2, p. 390 - 398
[2] Patent: WO2010/45095, 2010, A1. Location in patent: Page/Page column 69; 70
[3] Synthesis, 2007, # 15, p. 2279 - 2286
[4] Tetrahedron, 2009, vol. 65, # 48, p. 9997 - 10001
[5] Carbohydrate Research, 1983, vol. 124, p. 35 - 42

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

Raw materials

L-Glutamic acid Sodium nitrite Tetrahydrofuran Benzene Ethyl acetate Hydrochloric acid PETROLEUM ETHER

Preparation Products

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(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Suppliers

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

Henan Fengda Chemical Co., Ltd
Product
(2S)-5-Oxotetrahydro-2-furancarboxylic acid 21461-84-7
Price
US $200.00-1.00/KG
Min. Order
1KG
Purity
99%, 99.5% Sublimated
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-30
Career Henan Chemical Co
Product
(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 21461-84-7
Price
US $8.80/KG
Min. Order
1KG
Purity
97%-99%
Supply Ability
100kg
Release date
2019-08-08
Career Henan Chemical Co
Product
(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 21461-84-7
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg,5kg,100kg
Release date
2019-07-04

21461-84-7, (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACIDRelated Search:

(1S)-(-)-Camphanic acid (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 2-(2-METHOXYPHENYL)-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID (R)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID 2,2-DIMETHYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID 2-Tetrahydrofuroic acid (-)-Galanthaminyl (-)-Camphanate (S)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID (R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE HYDROXYCITRIC ACID LACTONE, (-)-(P) 2-(1-Carboxyundecyl)-5-oxotetrahydrofuran-2-carboxylic acid (3S)-2-(2-METHOXYPHENYL)-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID 4-METHYLENE-2-OCTYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID 2-[[(4S)-4-[[(2,6-Difluorophenyl)acetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt 3-Methyl-4-methylene-2-oxotetrahydrofuran-3-carboxylic acid ethyl ester 4-Isopropenyl-3-methyl-2-oxotetrahydrofuran-3-carboxylic acid ethyl ester 2-[[(4S)-4-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt 2-[[(4S)-4-[[(4-Pyridinylthio)acetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt

  • 5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID (S-)
  • 5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
  • (S)-(+)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE
  • (S)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE
  • (S)-(+)-TETRAHYDRO-5-OXO-2-FURANCARBOXYLIC ACID
  • (S)-(+)-TETRAHYDRO-5-OXO-2-FURANECARBOXYLIC ACID
  • TIMTEC-BB SBB006581
  • (S)-(+)-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID
  • (S)-(+)-5-OXO-2-TETRAHYDROFUROIC ACID
  • (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
  • (S)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
  • TOF
  • (S)-(+)-5-OXO-2-TETRAHYDROFURANCARBOXYLI C ACID, 98% (99% EE/GLC)
  • (S)-5-Oxotetrahydro-2-furancarboxylic acid
  • 2-Furancarboxylic acid, tetrahydro-5-oxo-, (2S)-
  • (s)-γ-carboxy-γ-butyrolactone
  • (2S)-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID
  • (S)-γ-Carboxy-γ-butyrolactone, (S)-5-Oxotetrahydro-2-furancarboxylic acid
  • (S)-(+)-5-OXO-2-TETRAHYDROFURANCARBOXILIC ACID, 98%
  • (2S)-5-Oxotetrahydrofuran-2-carboxylic acid
  • (2S)-5-Oxotetrahydrofuran-2α-carboxylic acid
  • (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid,98%
  • (R)-5-Oxotetrahydro-2-furancarboxylic acid
  • (S)-(+)-5-OXOTETRAHY
  • (2S)-(+)-2-Carboxy-5-oxotetrahydrofuran, (S)-gamma-Carboxy-gamma-butyrolactone
  • (2S)-Tetrahydro-5-oxo-2-furancarboxylic Acid
  • (2S)-Tetrahydro-5-oxofuran-2-carboxylic Acid
  • 5S-(+)-Butyrolactone Carboxylic Acid
  • (S)-(+)-gamma-Carboxy-gamma-butyrolactone (S)-(+)-5-Oxo-2-tetrahydrofuroic Acid
  • (<i>S</i>)-(+)-5-Oxotetrahydrofuran-2-carboxylic Acid
  • L-α-Hydroxyglutaric acid γ-lactone
  • (2S)-5-oxooxolane-2-carboxylic acid
  • (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid 98%
  • (2S)-5-oxo-2-oxolanecarboxylate
  • (S)-(+)-5-Oxotetrahydrofuran-2-carboxylicAcid&gt
  • (<i>S</i>)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
  • 21461-84-7
  • Carboxylic Acids (Chiral)
  • Chiral Building Blocks
  • Asymmetric Synthesis
  • Chiral Resolution Reagents
  • Chiral Resolving Reagents
  • Furans
  • Heterocyclic Building Blocks
  • Carboxylic Acids (Chiral)
  • Chiral Building Blocks
  • Synthetic Organic Chemistry
  • Chiral Reagents
  • Miscellaneous Reagents