| Identification | More | [Name]
4-Cloromethyl-5-methyl-1,3-dioxol-2-one | [CAS]
80841-78-7 | [Synonyms]
4-CHLOROMETHYL-5-METHYL-1,3-DIOXOL-2-ONE
4-CHLOROMETHYL-5-METHYL-1,3-DIOXOLEN-2-ONE
4-CHLOROMETHYL-5-METHYL-2-OXO-1,3-DIOXOLE
4-Cloromethyl-5-methyl-1,3-dioxol-2-one
DMDO-CL
DMDO CL (4-METHYL-5-CHLOROMETHYL-1,3-DIOXOL-2-ONE)
4-Chloromethyl-5-Methyl-1,3-Dioxol-2-One(Dmdo-Cl)
4-Chloromethyl-5-Methyl-1,3-Dioxocyclopenten-2-one
4-Chloromethyl-5-methyl-2H-1,3-dioxol-2-one
4-Choromethyl-5-methyl-2-oxo-1,3-dioxole
4-Chloromethyl-5-Methyl-1,3-Di
4-CHLOROMETHYL-5-METHYL-1,3-DIOXOL-3-ONE
4-methyl-5-chloro methyl-1,3-dioxol-2-one
4-CHLOROMETHYL-5-METHYL-1,3-DIOXOL-2-ONE (INTERMEDIATE OF OLMESARTAN MEDOXOMIL)
4-CHLOROMETHYL-5-METHYL-1,3-DIOXOL-2-ONE HPLC 95%
4-Chloromethyl-5-methyl-1,3-dioxol-2-on
4-Methyl-5-(chloromethyl)-1,3-dioxole-2-one | [EINECS(EC#)]
617-178-6 | [Molecular Formula]
C5H5ClO3 | [MDL Number]
MFCD07787494 | [Molecular Weight]
148.54 | [MOL File]
80841-78-7.mol |
| Chemical Properties | Back Directory | [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 ]
Oil | [color ]
Light Yellow to Very Dark Brown | [Specific Gravity]
1.36 | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [HS Code ]
29329990 |
| Hazard Information | Back Directory | [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]
4-Cloromethyl-5-methyl-1,3-dioxol-2-one is 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). 4-Chloromethyl-5-methyl-1,3-dioxol-2-o
ne 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]
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 |
|
|