말론산 디메틸
디메틸말로네이트 · 말론산디메틸 · 말론산메틸 · 디메틸말론산 · 프로판디오익산,디메틸에스테르 · 2-메틸프로판디오에이트 · 다이메틸말로네이트 · DMM
식별자 및 물리적 특성
| CAS No. | 108-59-8 |
|---|---|
| 분자식 | C5H8O4 |
| 평균 분자량 | 132.11 g/mol |
| 단동위원소 질량 | 132.04225874 g/mol |
| SMILES | COC(=O)CC(=O)OC |
| InChIKey | BEPAFCGSDWSTEL-UHFFFAOYSA-N |
| PubChem CID | 7943 |
| ChEMBL | CHEMBL1986332 |
| EC No. | 203-597-8 |
| DTXSID | DTXSID4029145 |
| 현지명 | 말론산 디메틸 |
화학 및 물리적 성질
| XLogP | 0 |
|---|---|
| 극성 표면적 | 52.6 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 4 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 104 |
| 물질 분류 | Other Classes -> Esters, Other |
| SpringerMaterials Properties | Boiling point |
| LogP(분배 계수) | -0.05 |
| 향미제 | EU Flavoring substances |
| 증기압 | 14.7 [mmHg]0.15 hPa (20 °C) |
| Physical Description | Liquid[Merck Index] Colorless liquid with an ester-like odor[OECD SIDS: Malonic Acid Diesters - 2005] |
| Ionization Efficiency | Positive1.582.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| 녹는점 | -62 °C (lit.) |
| 끓는 점 | 180-181 °C (lit.) |
| 밀도 | 1.156 g/mL at 25 °C (lit.) |
| 증기 밀도 | >1 (vs air) |
| 굴절률 | n20/D 1.413(lit.) |
| 인화점 | 194 °F |
| 저장 조건 | Store below +30°C. |
| 용해도 | 알코올: 혼합 가능 |
| pKa(산도 계수) | 11.80±0.46(Predicted) |
| 물리적 상태 | 액체 |
| 색상 | 무색의 |
| 냄새 | 과일 같은 |
| 폭발한계 | 1.3-17.4%(V) |
| 용해도 | 무시할 만한 |
| Merck | 14,6096 |
| BRN | 774261 |
| 헨리 상수 | 3.8×101 mol/(m3Pa) at 25℃, Katrib et al. (2003) |
| 유전율 | 10.4(20℃) |
| 안정성 | 안정적인. 강한 산화제와 호환되지 않습니다. 가연성. |
| InChI | 1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3 |
| InChIKey | BEPAFCGSDWSTEL-UHFFFAOYSA-N |
| SMILES | COC(=O)CC(=O)OC |
| LogP(분배 계수) | -0.05 at 20-25℃ and pH6.4 |
| NIST | Propanedioic acid, dimethyl ester(108-59-8) |
| EPA | Dimethyl malonate (108-59-8) |
화학적 성질
Dimethyl malonate is soluble in alcohol and ether and very slightly soluble in water. It may slowly decompose.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 86.3% (1530 of 1773) of all reports.WarningH319 (13.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 1773 reports by companies from 16 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: Propanedioic acid, dimethyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Propanedioic acid, 1,3-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanedioic acid, 1,3-dimethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 04-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20020Dimethyl malonate: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| 유해성 요약 | Causes no skin irritation and mild to moderate eye irritation in rabbitsNo adverse effects observed in oral or dermal lethal-dose studies of rats (LD50s > 2,000 mg/kg)Reversible hepatocellular hypertrophy (considered indicative of liver metabolism rather than systemic toxicity) observed in an oral repeated-dose study of rats at the highest tested dose (1,000 mg/kg/day)No evidence of reproductive toxicity, developmental toxicity, or mutagenicity[OECD SIDS: Malonic Acid Diesters - 2005] May cause irritation[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Eye Irrit. 2 (13.6%) |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | OO0950000 |
| 운송 번호(UN) | NA1993 |
| 독성 | LD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| 관세 코드 | 29171910 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36 |
| 위험 등급 | CBLEye Irrit. 2 |
| 기존화학 물질 | KE-24322 |
| 위험 참고 사항 | Irritant |
| 자연 발화 온도 | 440 °C |
| 저장 분류 | 10 - Combustible liquids |
용도
개요
Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.
용도
Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.
일반 설명
Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines.
제조 및 합성 방법
생산 방법
Dimethyl malonate is produced via direct esterification of methanol with malonic acid under azeotropic conditions.