5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Product Name
- 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- CAS No.
- 85920-63-4
- Chemical Name
- 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Synonyms
- idene)-2,2-dimethyL;Acetyl Meldrum's acid;Acetyl Michaelis Acid;Acetyl Michaelic Acid;Sitagliptin Impurity 155;Acetyl Meldrum’s Acid (AMA);5-(1-hydroxyethylidene) acetyl meldrum;5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione;1,3-Dioxane-4,6-dione, 5-(1-hydroxyethylidene)-2,2-dimethyl-
- CBNumber
- CB51073673
- Molecular Formula
- C8H10O5
- Formula Weight
- 186.16
- MOL File
- 85920-63-4.mol
5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Property
- Melting point:
- 83-84 °C
- Boiling point:
- 385.9±42.0 °C(Predicted)
- Density
- 1.303
- storage temp.
- 2-8°C
- pka
- 4.50±1.00(Predicted)
- Appearance
- Light yellow to yellow Solid
- InChI
- InChI=1S/C8H10O5/c1-4(9)5-6(10)12-8(2,3)13-7(5)11/h9H,1-3H3
- InChIKey
- WIIDJHLROTYVRD-UHFFFAOYSA-N
- SMILES
- O1C(=O)/C(=C(\O)/C)/C(=O)OC1(C)C
Safety
- HS Code
- 2932990090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H332Harmful if inhaled
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 3394AC
- Product name
- 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Packaging
- 250mg
- Price
- $104
- Updated
- 2021/12/16
- Product number
- OR900528
- Product name
- 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Purity
- 95%
- Packaging
- 250mg
- Price
- $167
- Updated
- 2021/12/16
- Product number
- 2H29-1-0C
- Product name
- 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Purity
- 95%
- Packaging
- 250mg
- Price
- $184
- Updated
- 2021/12/16
- Product number
- OR900528
- Product name
- 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Purity
- 95%
- Packaging
- 1g
- Price
- $348
- Updated
- 2021/12/16
- Product number
- 2H29-1-0C
- Product name
- 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
- Purity
- 95%
- Packaging
- 1g
- Price
- $384
- Updated
- 2021/12/16
5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical Properties,Usage,Production
Description
5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Acetyl Meldrum's acid) is a pharmaceutical intermediate compound used in the preparation of Vinaxanthone. Vinaxanthone is a selective inhibitor of signal transduction factor 3A, phospholipase C (PLC), and FabI, and exhibits antibacterial activity.
Uses
Acetyl Meldrum''s Acid is used in preparation of Bicyclic β-Lactams/Oxazinones via Cycloaddition and metathesis starting from Acyl/Carbamoyl-dimethyl-dioxa-diones.
Synthesis
2033-24-1
75-36-5
85920-63-4
The general procedure for the synthesis of 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxo-4,6-dione from cyclic (sub)isopropyl malonate and acetyl chloride is as follows: GENERAL METHOD: Method A (adapted from Srensen et al:) 1. To a dichloromethane solution of Meldrum acid (1 eq.) was added dropwise pyridine (2 eq.) at 0 °C and stirred for 15 min. 2. to the reaction mixture was added the corresponding acyl chloride (1 eq.). 3. The reaction mixture was stirred at 0 °C for 1.5 hours, followed by continued stirring at room temperature for 1.5 hours. 4. Upon completion of the reaction, the reaction was quenched with 2M hydrochloric acid and extracted with dichloromethane. 5. The organic layers were combined, dried with sodium sulfate, filtered and concentrated in vacuum. 6. the residue is purified by silica gel chromatography using a hexane solution of 5% to 10% ethyl acetate (containing 1% acetic acid) as eluent to afford the target product 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxo-4,6-dione (acyl Meldrum acid derivatives, nos. 11a-e, j, l, p).
References
[1] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1003 - 1007
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1321 - 1340
[3] Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 403 - 410
[4] Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1427 - 1445
[5] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 10, p. 1303 - 1306
5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Preparation Products And Raw materials
Raw materials
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View Lastest Price from 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione manufacturers
- Product
- acetyl-Meldrum's acid 85920-63-4
- Price
- US $2100.00/kg
- Min. Order
- 1kg
- Purity
- 99
- Supply Ability
- 20tons
- Release date
- 2025-08-07
- Product
- 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 85920-63-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-22
- Product
- Acetyl Michaelis Acid 85920-63-4
- Price
- US $30.00-28.00/Kg
- Min. Order
- 1Kg
- Purity
- 99.0% up
- Supply Ability
- 50 tons per month
- Release date
- 2022-09-29