기본 정보
- 표준 SMILES
C1COCCOCCOCCOCCOCCO1- InChIKey
XEZNGIUYQVAUSS-UHFFFAOYSA-N- 분자식
- C12H24O6
- 평균 분자량
- 264.31 g/mol
- 단동위원소 질량
- 264.15728849
개요
18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms. It has a role as a phase-transfer catalyst. It is a saturated organic heteromonocyclic parent and a crown ether.
이름 및 식별자
- 우선 이름
- 18-Crown-6
- IUPAC
- 1,4,7,10,13,16-hexaoxacyclooctadecane
- 현지명
- 에틸렌 산화물 시클릭 헥사머
- 영어명
- 18-Crown-6
- 분자식
- C12H24O6
- 분자량
- 264.32
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
17455-13-9- PubChem CID
- 28557
- DTXSID
DTXSID7058626- ChEMBL
CHEMBL155204- ChEBI
CHEBI:32397- UNII
- 63J177NC5B
- EC Number
- 241-473-5
- Nikkaji
- J49.431C
물성
구조 계산 물성
- XLogP
- -0.7
- 극성 표면적
- 55.4 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 18
- 형식 전하
- 0
- 복잡도
- 108
실험 및 물리화학적 성질
Chemical Classes
Other Classes -> Other Organic Compounds
Industrial compound
물리화학적 성질
- 녹는점
- 42 · 42-45 °C(lit.)
- 끓는 점
- 116 °C · 116°C 0,2mm
- 밀도
- 1 · 1,175 g/cm3
- 굴절률
- 1.458 · 1.4580 (estimate)
- 인화점
- 230 °F · >230 °F
- 저장 조건
- 30 °C · Store below +30°C.
- 용해도
- 클로로포름(약간 용해됨), 메탄올(매우 소량)
- 물리적 상태
- 결정 또는 결정질 질량 또는 액체
- 색상
- 흰색 또는 투명한 무색
- 수용성
- 녹는
- Merck
- 14 · 14,2602
- BRN
- 1619616 · 1619616
- 안정성
- 안정적인. 강산, 강산화제와 호환되지 않습니다.
- InChI
- 1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2
- InChIKey
- XEZNGIUYQVAUSS-UHFFFAOYSA-N
- SMILES
- O1CCOCCOCCOCCOCCOCC1
- NIST
- 1 · 1,4,7,10,13,16-Hexaoxacyclooctadecane(17455-13-9)
- EPA
- 1 · 1,4,7,10,13,16-Hexaoxacyclooctadecane (17455-13-9)
화학적 성질
18-Crown-6 is a slightly yellow solid, it has a high affinity for the hydronium ion H3O+, as it can fit inside the crown ether. Thus, reaction of 18-crown-6 with strong acids gives the cation [H3O·18-crown-6]+.
안전 및 규제
GHS 분류
GHS Classification
Warning
H302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 314 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory Information
Chemical: 1,4,7,10,13,16-Hexaoxacyclooctadecane
Crown ether 18-crown-6: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
If absorbed, can cause electrolyte imbalance affecting the CNS; Signs of intoxication include hyperventilation, tremor, incoordination, and CNS depression; May damage the skin and eyes; LD50 (mouse) by ingestion is 0.7 g/kg; LD50 (rabbit) by skin absorption is 200 mg/kg; [Ullmann] Toxic by ingestion; A skin, eye, and respiratory tract irritant; Oral LD50 (rat) = 525 mg/kg; Dermal LDLo (rat) = 7000 mg/kg; High-dose feeding causes seizures, weight loss, and liver injury in experimental animals; [MSDSonline]
독성 정보
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- MP4500000
- ridadr
- 2811
- 독성
- LD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg
- HS 번호
- 29329995
- risk_code
- 22-36/37/38-36-20/22-20/21/22
- hazard_code
- Xn,Xi
- safety_code
- 26-36-39
- 포장분류
- III
- 위험 등급
- 6.1(b)
- 기존화학 물질
- KE-19820
- F 고인화성물질
- 10
- Hazard Classifications
- Acute Tox. 4 Oral
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
용도 및 제조
응용 분야
용도18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN).
일반 설명18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as a base. 18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst. It can also be used as a metal complexing agent to prepare a variety of molecular complexes.
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