(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
(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)
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.
N-Bromosuccinimide Price
- Product number
- 301469
- Product name
- (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
- Purity
- 98%
- Packaging
- 1g
- Price
- $94.3
- Updated
- 2023/06/20
- Product number
- 301469
- Product name
- (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
- Purity
- 98%
- Packaging
- 5g
- Price
- $270
- Updated
- 2023/06/20
- Product number
- O0276
- Product name
- (S)-(+)-5-Oxotetrahydrofuran-2-carboxylic Acid
- Purity
- >98.0%(GC)(T)
- Packaging
- 1g
- Price
- $83
- Updated
- 2025/07/31
- Product number
- O0276
- Product name
- (S)-(+)-5-Oxotetrahydrofuran-2-carboxylic Acid
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $246
- Updated
- 2025/07/31
- Product number
- O870435
- Product name
- (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
- Packaging
- 100mg
- Price
- $55
- Updated
- 2021/12/16
(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
Preparation Products
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View Lastest Price from (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID manufacturers
- 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
- 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
- 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