4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Product Name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- CAS No.
- 91526-18-0
- Chemical Name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Synonyms
- DMDO-OH;4-(HydroxyMethyl)-5-Methyl-[1,3]dioxol-2-one;AZATMint-D;Azilsartan Impurity 55;Azilasartan medoximil(HPLC-98.2%);4-(hidroximetil)-5-metil-1,3-dioxol-2-ona;4-(hidroxiMetil)-5-Metil-1,3-dioxol-2-one;4-(hydroxymethyl)-5-methyl-l,3-dioxol-2-one;4-(HydroxyMethyl)-5-Methyl-?,3]dioxol-2-one;4-(hydroxymethyl)-5-methyl-1,3-Diaxole-2-one
- CBNumber
- CB82515847
- Molecular Formula
- C5H6O4
- Formula Weight
- 130.1
- MOL File
- 91526-18-0.mol
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Property
- Boiling point:
- 214℃
- Density
- 1.367
- Flash point:
- 93℃
- storage temp.
- Inert atmosphere,Store in freezer, under -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- liquid
- pka
- 14.54±0.10(Predicted)
- color
- Pale yellow
- InChI
- InChI=1S/C5H6O4/c1-3-4(2-6)9-5(7)8-3/h6H,2H2,1H3
- InChIKey
- JEQSUJXHFAXJOW-UHFFFAOYSA-N
- SMILES
- O1C(C)=C(CO)OC1=O
Safety
- HS Code
- 2932990090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- H1447
- Product name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Purity
- min. 93.0 %
- Packaging
- 1G
- Price
- $53
- Updated
- 2025/07/31
- Product number
- H1447
- Product name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Purity
- min. 93.0 %
- Packaging
- 5G
- Price
- $160
- Updated
- 2025/07/31
- Product number
- H939928
- Product name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Packaging
- 50mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- OR927927
- Product name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Purity
- 96%
- Packaging
- 1g
- Price
- $30
- Updated
- 2021/12/16
- Product number
- 2H25-1-2V
- Product name
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one
- Purity
- 97%
- Packaging
- 5G
- Price
- $176
- Updated
- 2021/12/16
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Chemical Properties,Usage,Production
Description
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is a reagent used in organic synthesis, particularly for the introduction of the non-chiral (oxodioxolenyl)methyl carbamate group to active pharmaceutical ingredients (APIs) to afford the corresponding pro-drug.
Definition
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one can be reacted with oxalyl chloride to afford (5-methyl-2-oxo-1,3-dioxol-4-yl) methylglyoxal chloride, which provides for an alternative approach to introduce the (oxodioxolenyl) methylcarbamate group.
Uses
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is used in preparation method of key intermediate of olmesartan medoxomil.
Preparation
At 20-25°C, 50 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one and 45 g of formic acid were added to 500 mL of acetonitrile. The reaction was cooled to 10-15°C followed by 95 g of triethylamine added. The mixture was heated to 60-65°C and stirred for approximately 5-6 h. The reaction system was subsequently cooled to 15-20°C, filtered, and washed with acetonitrile. Collecting filtrate, and the acetonitrile was removed under vacuum to concentrate the solution. The reaction system was again cooled to 25-30°C, and ethyl acetate and water were added. The mixture was then stirred for approximately 15-20 minutes at 25-30°C. Finally, 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one was obtained after further purification.
Synthesis
80841-78-7
91526-18-0
Example 4 Preparation of 4-hydroxymethyl-5-methyl-1,3-dioxolan-2-one: 4-chloromethyl-5-methyl-1,3-dioxolan-2-one (50 g) was dissolved in acetonitrile (500 ml), and formic acid (45 g) was slowly added at 20-25 °C. The reaction mixture was then cooled to 10-15 °C and triethylamine (95 g) was added. The reaction system was heated to 60-65°C and the reaction was kept at this temperature with stirring for 5-6 hours. After completion of the reaction, the mixture was cooled to 15-20 °C, filtered and the filter cake was washed with acetonitrile. The filtrates were combined and the acetonitrile was removed by distillation under reduced pressure to concentrate the solution. The concentrated reaction was cooled to 25-30 °C, ethyl acetate and water were added and stirred at 25-30 °C for 15-20 minutes. The aqueous layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined and washed with brine. The organic layer was separated and evaporated to dryness at 35-40°C under reduced pressure. Methanol was added to the residual oil and heated to reflux temperature. Isopropanol solution of HCl was added dropwise and the reaction was refluxed for 60-75 minutes. At the end of the reaction, it was cooled to 30-35 °C and distilled under reduced pressure to remove all solvent to give 4-(hydroxymethyl)-5-methyl-[1,3]dioxolen-2-one as an oily product (yield: 34.6 g; yield: 79%).
References
[1] Patent: WO2012/107814, 2012, A1. Location in patent: Page/Page column 14-15
[2] Patent: CN105492423, 2016, A. Location in patent: Paragraph 0741; 0742; 0743; 0744
[3] Patent: TW2016/2093, 2016, A. Location in patent: Paragraph 0323
[4] Patent: US2016/194302, 2016, A1. Location in patent: Paragraph 0413; 0414
4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Preparation Products And Raw materials
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View Lastest Price from 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one manufacturers
- Product
- 4-(hidroximetil)-5-metil-1,3-dioxol-2-ona 91526-18-0
- Price
- US $0.00-0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 1000kg
- Release date
- 2021-11-19
- Product
- 4-(hidroximetil)-5-metil-1,3-dioxol-2-one 91526-18-0
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-29
- Product
- 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one 91526-18-0
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-03-18