CAS 141-05-9 Diethyl Maleate (HCID 5271566)

기본 정보

CAS: 141-05-9
표준 SMILES: CCOC(=O)/C=C\C(=O)OCC
InChIKey: IEPRKVQEAMIZSS-WAYWQWQTSA-N
분자식: C8H12O4
평균 분자량: 172.18 g/mol
단동위원소 질량: 172.07355886

개요

Diethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10C) with boiling point 220C at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It has a role as a glutathione depleting agent. It is an ethyl ester and a maleate ester. It is functionally related to an ethanol.

이름 및 식별자

우선 이름: Diethyl Maleate
IUPAC: diethyl (Z)-but-2-enedioate
현지명: 디에틸말산
영어명: Diethyl maleate
분자식: C8H12O4
분자량: 172.18

이름 및 동의어

DIETHYL MALEATE141-05-9DiethylmaleateMaleic acid, diethyl ester2-Butenedioic acid (2Z)-, diethyl esterDiethylester kyseliny maleinoveDTXSID8020464G81WQB56OLSTAFLEX DEMNSC-8394DTXCID80464CHEBI:68508

이름 더 보기

디에틸말산말레산다이에틸디에틸말산다이에틸말리에이트디에틸말레에이트DEMETHYL MALEATEiethylmaleateDiethyl malcateDiethylMaleate>DiethylbutenedioateMaleic acid diethyl

RefChem:133422diethyl maleic acid diester205-451-9Maleic acid diethyl esterdiethyl (Z)-but-2-enedioate2-Butenedioic acid (Z)-, diethyl esterDiethyl (Z)-2-butenedioatediethyl (2Z)-but-2-enedioate

데이터베이스 식별자

CAS: 141-05-9、623-91-6
PubChem CID: 5271566
DTXSID: DTXSID8020464
ChEMBL: CHEMBL2037000

물성

구조 계산 물성

XLogP: 0.9
극성 표면적: 52.6 Å²
수소 결합 공여자 수: 0
수소 결합 수용자 수: 4
회전 가능 결합 수: 6
무거운 원자 수: 12
형식 전하: 0
복잡도: 163

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Esters, Other

SpringerMaterials PropertiesBoiling point

FragrancesFragrance substance (Diethyl maleate) -> IFRA amendment 40

Flavoring AgentsEU Flavoring substances

Solubility1.40E+04 mg/L @ 30 °C (exp)

Boiling Point218.00 °C. @ 760.00 mm Hg

물리화학적 성질

녹는점: -10 °C · -10 °C (lit.)
끓는 점: 225 °C · 225 °C (lit.)
밀도: 1.064 g/mL · 1.064 g/mL at 25 °C (lit.)
증기 밀도: 5.93 · 5.93 (vs air)

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 1.8% (5 of 281) of reports.

Warning

H317 (97.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 281 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

유해성 정보

Regulatory Information · 5건

Chemical: 2-Butenedioic acid, (Z)-, diethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Butenedioic acid (2Z)-, 1,4-diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butenedioic acid (2Z)-, 1,4-diethyl 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: 27-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10052

Diethyl maleate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Maleic acid esters (short chain)

Hazards SummaryA skin and eye irritant; [Hawley] A mild skin irritant based an animal studies; [MSDSonline]

Hazard Classes and Categories · 2건

Skin Sens. 1 (97.5%)

Flammable liquids - Category 4

안전 데이터

wgk: 2
tsca: TSCA listed

화학 및 산업

약리 정보

Cellular LocationsCytoplasm

용도 및 제조

UsesUsed in organic synthesis and as a flavoring agent; [Hawley]

U.S. Production2023: 250,000 - <400,000 lb

Consumer UsesNot Known or Reasonably Ascertainable

Industry UsesNot Known or Reasonably Ascertainable

IFRA Fragrance Standards · 6건

Diethyl maleate

2-Butenedioic acid (2Z)-, diethyl ester; Ethyl maleate; Maleic acid, diethyl ester

IFRA_STD_130.pdf

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient

General Manufacturing Information · 2건

Not Known or Reasonably Ascertainable

2-Butenedioic acid (2Z)-, 1,4-diethyl ester: ACTIVE

응용 분야 · 3건

출처Has apparently not been reported to occur in nature.

용도Diethyl maleate can be used for the preparation of organophosphorus insecticide malathion. It is unsaturated polyester resins that are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc., and as protective coatings, finishes, and lacquers.

일반 설명Diethyl maleate is reported to occur in the cabernet sauvignon wine.

제조 방법

Diethyl maleate is synthesized by the direct esterification of maleic anhydride and ethanol in the presence of sulfuric acid. Esterification is a commonly used reaction in organic synthesis.

화합물 노트

불러오는 중…

디에틸말산