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

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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

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Safety

HS Code: 2932990090

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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.

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N-Bromosuccinimide Price

AK Scientific

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

Apolloscientific

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

SynQuest Laboratories

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

Apolloscientific

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

SynQuest Laboratories

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

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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

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Preparation Products

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5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Suppliers

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View Lastest Price from 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione manufacturers

Xinxiang Juyuan Biological Technology Co., Ltd.

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

Henan Aochuang Chemical Co.,Ltd.

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

Xinxiang Hongqi District Houyuan Trading Co.,Ltd

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

85920-63-4, 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneRelated Search:

2-Methoxyethyl acetoacetate Acetyl bromide INDIUM ACETYLACETONATE 2-Acetyloxy-2-phenyl-acetic acid Ethyl acetoacetate

5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Acetyl Meldrum's acid

idene)-2,2-dimethyL

1,3-Dioxane-4,6-dione, 5-(1-hydroxyethylidene)-2,2-dimethyl-

5-(1-hydroxyethylidene) acetyl meldrum

Acetyl Michaelis Acid

Sitagliptin Impurity 155

Acetyl Michaelic Acid

Acetyl Meldrum’s Acid (AMA)

85920-63-4