4-Cloromethyl-5-methyl-1,3-dioxol-2-one CAS 80841-78-7
Introduction：Basic information about 4-Cloromethyl-5-methyl-1,3-dioxol-2-one CAS 80841-78-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
4-Cloromethyl-5-methyl-1,3-dioxol-2-one Basic information
| Product Name: | 4-Cloromethyl-5-methyl-1,3-dioxol-2-one |
| Synonyms: | DMDO-CL;4-Cloromethyl-5-methyl-1,3-dioxol-2-one;Olmesartan Impurity 57;4-CloroMethyl-5-Methyl-1,3-dioxol-2-one (DMDO-Cl);OlMesartan IMpurity (4-(ChloroMethyl)-5-Methyl-1,3-Dioxol-2-one);4- chloroMethyl-5- Methyl-1,3- two oxygenheterocyclicpentadiene-2- ketone;-5--1,3- two4-chloroMethylMethylcyclopentene-2- ketoneheterocyclic oxygen;4-ChloroMethyl-5-Methyl-l,3-dioxocyclopenten-2–one |
| CAS: | 80841-78-7 |
| MF: | C5H5ClO3 |
| MW: | 148.54 |
| EINECS: | 617-178-6 |
| Product Categories: | Carbonates;Carbonyl Compounds;Organic Building Blocks;Pharmaceutical Intermediates;INTERMEDIATESOF;Chemical intermediate for Olmesartane |
| Mol File: | 80841-78-7.mol |
4-Cloromethyl-5-methyl-1,3-dioxol-2-one Chemical Properties
| Boiling point | >90℃/2mm |
| density | 1.362±0.06 g/cm3(Predicted) |
| refractive index | 1.4760-1.4820 |
| Fp | 129 °C |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | liquid |
| Specific Gravity | 1.36 |
| color | Colorless to Light yellow to Light orange |
| BRN | 4798926 |
| InChI | InChI=1S/C5H5ClO3/c1-3-4(2-6)9-5(7)8-3/h2H2,1H3 |
| InChIKey | QCLFSYYUWPUWQR-UHFFFAOYSA-N |
| SMILES | CC1=C(OC(=O)O1)CCl |
| CAS DataBase Reference | 80841-78-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 26 |
| WGK Germany | 3 |
| HS Code | 29329990 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Description | 4-Chloromethyl-5-methyl-1,3-dioxol-2-one is a useful branch side chain for synthetic penicillin esters such as Lenampicillin, Mecillinam, etc. It can improve the stability and absorption of drugs, increase biological activity, and reduce side effects. It is also used to prepare amine drugs, such as Norfloxacin prodrug. In the prior art, the primary method for synthesizing 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is a chlorination reaction of chlorine gas or N-chlorosuccinimide. |
| Chemical Properties | Colorless to Light yellow to Light orange clear liquid or Pale Yellow Oil. |
| Uses | 4-Chloromethyl-5-methyl-1,3-dioxol-2-one is an important reagent in the preparation of angiotensin II receptor antagonist such as Olmesratan Medoxomil (O550000). It is also used in the preparation of prodrugs of ampicillin. |
| Preparation | 4,5-dimethyl-1,3-dioxole-2-ketone (DMDO) is used as raw material, taking sulfonic acid chloride as a chlorinating agent. The reaction is reat under the effect of a catalyzer in organic solvent and reacts for 1-5 hours to obtain target product 4-Cloromethyl-5-methyl-1,3-dioxol-2-one. |
| Synthesis | 37830-90-3 80841-78-7 General procedure for the synthesis of 4-chloromethyl-5-methyl-1,3-dioxolan-2-one from 4,5-dimethyl-1,3-dioxolan-2-one: To a stirred solution of 4,5-dimethyl-1,3-dioxolan-2-one (DMDO) were added 4725 g of ethylene dichloride, 10.12.5 g of N-chlorosuccinimide (NCS) and 45 g of benzoyl peroxide (BPO), the reaction temperature was maintained at 90 °C, and the reaction lasted for 5.5 h. The crude product 4-chloromethyl-5-methyl-1,3-dioxolen-2-one (DMDO-Cl) was obtained as 382.5 g in 85.00% yield. Step 3: distillation: the crude product of DMDO-Cl was distilled under vacuum at -0.1 MPa at 110 °C to obtain 326 g of DMDO-Cl. Its purity was 99.06% as determined by gas chromatography (GC). |
| References | [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 6, p. 2241 - 2248 [2] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 1, p. 394 - 397 [3] Patent: US4554358, 1985, A [4] Patent: CN107892681, 2018, A. Location in patent: Paragraph 0015-0022 |
4-Cloromethyl-5-methyl-1,3-dioxol-2-one Preparation Products And Raw materials
| Raw materials | 4,5-Dimethyl-1,3-dioxol-2-one |
| Preparation Products | Trityl olmesartan-->Trityl Olmesartan Medoxomil |
