2,2-디메틸-1,3-디옥산-4,6-디온
2,2-디메틸-1,3-디옥산-4,6-디온 · MELDRUM'S ACID · Meldrum’s acid · MELDRUMS ACID · CYCL-ISOPROPYLIDENE MALONATE · ISOPROPYLIDENE MALONATE · Isopropyl Malonate · MALONIC ACID CYCLIC ISOPROPYLIDENE ESTER
식별자 및 물리적 특성
| CAS No. | 2033-24-1 |
|---|---|
| 분자식 | C6H8O4 |
| 평균 분자량 | 144.12 g/mol |
| 단동위원소 질량 | 144.04225874 g/mol |
| SMILES | CC1(C)OC(=O)CC(=O)O1 |
| InChIKey | GXHFUVWIGNLZSC-UHFFFAOYSA-N |
| PubChem CID | 16249 |
| EC No. | 217-992-8 |
| DTXSID | DTXSID7051846 |
| 현지명 | 2,2-디메틸-1,3-디옥산-4,6-디온 |
화학 및 물리적 성질
| XLogP | 0.6 |
|---|---|
| 극성 표면적 | 52.6 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 164 |
| 물질 분류 | Other Classes -> Other Organic Compounds |
| SpringerMaterials Properties | Chemical shift |
| Physical Description | Solid[Merck Index] White powder[Alfa Aesar MSDS] |
| 녹는점 | 92-96 °C(lit.) |
| 끓는 점 | 182.71°C (rough estimate) |
| 밀도 | 1.1311 (rough estimate) |
| 증기압 | 0.044-133Pa at 25℃ |
| 굴절률 | 1.4434 (estimate) |
| 저장 조건 | 2-8°C |
| 용해도 | 디옥산: 용해성 5%, 투명하거나 매우 약간 흐릿함, 무색 내지 희미한 노란색 |
| pKa(산도 계수) | 5.1(at 25℃) |
| 물리적 상태 | 결정 또는 분말 |
| 색상 | 갈색을 띤 흰색에서 베이지색 갈색 |
| 용해도 | 2.5g/100mL(20℃) |
| Merck | 14,5817 |
| BRN | 117310 |
| InChI | 1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3 |
| InChIKey | GXHFUVWIGNLZSC-UHFFFAOYSA-N |
| SMILES | CC1(C)OC(=O)CC(=O)O1 |
| LogP(분배 계수) | -1.58-4.786 at 25℃ |
| NIST | 1,3-Dioxane-4,6-dione, 2,2-dimethyl-(2033-24-1) |
| EPA | 1,3-Dioxane-4,6-dione, 2,2-dimethyl- (2033-24-1) |
화학적 성질
The compound appears as white to beige crystals. It has a melting point of 94-95℃ (decomposition), is insoluble in water, and is soluble in ethanol and acetone.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 26.1% (12 of 46) of reports.WarningH315 (39.1%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: 1,3-Dioxane-4,6-dione, 2,2-dimethyl-Status: Active Update: 09-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/186351,3-Dioxane-4,6-dione, 2,2-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| 유해성 요약 | A skin and strong eye irritant[Alfa Aesar MSDS] See 1,3-Dioxane. |
| Hazard Classes and Categories | Skin Irrit. 2 (39.1%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | JH0800000 |
| 관세 코드 | 29322090 |
| 위험 문구(R) | 36/37/38-45 |
| 위험 표시 | Xi,T |
| 안전 문구(S) | 37/39-24/25-53-45-36-26 |
| 위험 등급 | IRRITANT |
| 기존화학 물질 | KE-11336 |
| F 고인화성물질 | 10-21 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Meldrum's acid, also known as 2,2-dimethyl-1,3-dioxane-4,6-dione, is an organic compound with the formula C6H8O4. The compound was first made in 1908 by Andrew Norman Meldrum by a condensation reaction of malonic acid with acetone in acetic anhydride and sulfuric acid. Meldrum misidentified the structure as a β-lactone of β-hydroxyisopropylmalonic acid. Yet Meldrum's acid has a high acidity with a pKa of 4.97, because like ascorbic acid, deprotonation at the methylene next to the carbonyls produces a stable enolate. Because of this property Meldrum's acid like malonic acid is a reactant in Knoevenagel condensations.
용도
Meldrum's acid serves as an intermediate in a variety of organic synthesis reactions. It is commonly used as an alternative to acyclic malonic esters and generally acts as a C3O2 synthon in organic synthesis.
일반 설명
2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pKa 4.83) and steric rigidity. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.
제조 및 합성 방법
제조 방법
2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid)is usually prepared by condensation of malonic acid with acetone in acetic anhydride in the presence of sulfuric acid. Excellent yield of the product was achieved when acetic anhydride was added in a slow, controlled manner to a mixture of acetone, malonic acid and an acid catalyst.