기본 정보
- CAS
67719-69-1- 표준 SMILES
[CH3-].[CH3][Al][CH3].[Cl-].[Ti+4].c1cc[cH-]c1.c1cc[cH-]c1- InChIKey
JJNHBFYGCSOONU-UHFFFAOYSA-M- 분자식
- C13H19AlClTi
- 평균 분자량
- 285.59 g/mol
개요
Tebbe's reagent is the organometallic compound and titanium and aluminum. It is used in the methylenation of carbonyl compounds. Aluminum is the most abundant metal in the earth's crust and is always found combined with other elements such as oxygen, silicon, and fluorine. (L739, L740, L780)
이름 및 식별자
- 우선 이름
- mu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titanium
- 영어명
- TEBBE REAGENT
- 분자식
- C13H4AlClTi
- 분자량
- 270.47
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
67719-69-1- PubChem CID
- 91617563
- UNII
- V040SDB67S
물성
구조 계산 물성
- 극성 표면적
- 0 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 16
- 형식 전하
- 0
- 복잡도
- 14.9
물리화학적 성질
- 밀도
- 0.96 g/mL · 0.96 g/mL at 20 °C
- 인화점
- 34 °F · 34 °F
- 저장 조건
- Refrigerator
- 물리적 상태
- 액체
- 색상
- 진한 빨간색에서 보라색까지
- 수용성
- 톨루엔, 벤젠, 디클로로메탄에 용해됩니다. 물에 불용성.
- Merck
- 9091 · 9091
- InChI
- InChI=1S/2C5.2CH2.C.Al.ClH.Ti/c2*1-2-4-5-3-1;;;;;;/h;;2*1H2;;;1H;/q4*-1;-2;+3;;+4/p-1
- InChIKey
- QEJAQNUJXFLWSP-UHFFFAOYSA-M
- SMILES
- [CH2-][Al+3]1([Cl-][Ti+4]23456789(C%10[C-]2C3=C4C5=%10)(C2[C-]6C7=C8C9=2)[C-2]1)[CH2-]
화학적 성질
The Tebbe reagent is the organometallic compound with the formula (CH)TiCHClAl(CH). It is used in the methylenation of carbonyl compounds, that is it converts organic compounds containing the RC=O group into the related RC=CH derivative.It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research. Tebbe's reagent contains two tetrahedral metal centers linked by a pair of bridging ligands. The titanium has two cyclopentadienyl ([CH]-, or Cp) rings and aluminium has two methyl groups. The titanium and aluminium atoms are linked together by both a methylene bridge (-CH-) and a chloride atom in a nearly square-planar (Ti–CH–Al–Cl) geometry.The Tebbe reagent was the first reported compound where a methylene bridge connects a transition metal (Ti) and a main group metal (Al).Preparation The Tebbe reagent is synthesized from titanocene dichloride and trimethylaluminium in toluene solution.
안전 및 규제
유해성 정보
Regulatory Information
Titanium, .mu.-chlorobis(.eta.5-2,4-cyclopentadien-1-yl)(dimethylaluminum)-.mu.-methylene-: 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.
안전 및 보호
독성 정보
Health Effects
Aluminum targets the nervous system and causes decreased nervous system performance and is associated with altered function of the blood-brain barrier. The accumulation of aluminum in the body may cause bone or brain diseases. High levels of aluminum have been linked to Alzheimer's disease. A small percentage of people are allergic to aluminium and experience contact dermatitis, digestive disorders, vomiting or other symptoms upon contact or ingestion of products containing aluminium. (L739, L740)
Toxicity Summary
The main target organs of aluminum are the central nervous system and bone. Aluminum binds with dietary phosphorus and impairs gastrointestinal absorption of phosphorus. The decreased phosphate body burden results in osteomalacia (softening of the bones due to defective bone mineralization) and rickets. Aluminum's neurotoxicity is believed to involve several mechanisms. Changes in cytoskeletal protein functions as a results of altered phosphorylation, proteolysis, transport, and synthesis are believed to be one cause. Aluminum may induce neurobehavioral effects by affecting permeability of the blood-brain barrier, cholinergic activity, signal transduction pathways, lipid peroxidation, and impair neuronal glutamate nitric oxide-cyclic GMP pathway, as well as interfere with metabolism of essential trace elements because of similar coordination chemistries and consequent competitive interactions. It has been suggested that aluminum's interaction with estrogen receptors increases the expression of estrogen-related genes and thereby contributes to the progression of breast cancer (A235), but studies have not been able to establish a clear link between aluminum and increased risk of breast cancer (A15468). Certain aluminum salts induce immune responses by activating inflammasomes. (L739, A235, A236)
Signs and Symptoms
Inhalating aluminum dust causes coughing and abnormal chest X-rays. A small percentage of people are allergic to aluminium and experience contact dermatitis, digestive disorders, vomiting or other symptoms upon contact or ingestion of products containing aluminium. (L739, L740)
Carcinogen Classification
Not listed by IARC. IARC classified aluminum production as carcinogenic to humans (Group 1), but did not implicate aluminum itself as a human carcinogen. (L135) A link between use of aluminum-containing antiperspirants and increased risk of breast cancer has been proposed (A235), but studies have not been able to establish a clear link (A15468).
안전 데이터
- wgk
- 2
- ridadr
- UN 2924 3/PG 2
- HS 번호
- 29310099
- risk_code
- 11-34-48/20-63-65-67
- hazard_code
- F,C
- safety_code
- 26-36/37/39-45-62-16
- 포장분류
- II
- 위험 등급
- 4.3
- F 고인화성물질
- 1-10
- Hazard Classifications
- Aquatic Chronic 3Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Repr. 2Skin Corr. 1BSTOT RE 2STOT SE 3
- 스토리지 클래스
- 3 - Flammable liquids
화학 및 산업
약리 정보
Metabolism/Metabolites
Aluminum is poorly absorbed following either oral or inhalation exposure and is essentially not absorbed dermally. The bioavailability of aluminum is strongly influenced by the aluminum compound and the presence of dietary constituents which can complex with aluminum and enhance or inhibit its absorption. Aluminum binds to various ligands in the blood and distributes to every organ, with highest concentrations found in bone and lung tissues. In living organisms, aluminum is believed to exist in four different forms: as free ions, as low-molecular-weight complexes, as physically bound macromolecular complexes, and as covalently bound macromolecular complexes. Absorbed aluminum is excreted principally in the urine and, to a lesser extent, in the bile, while unabsorbed aluminum is excreted in the faeces. (L739)
용도 및 제조
응용 분야
용도μ-Chloro-μ-methylenebis(cyclopentadienyl)titaniumdimethylaluminum is used in organic synthesis for carbonyl methylenation, A versatile methylenation reagent for the conversion of ketones and aldehydes to olefins, it offers facile reaction with hindered ketones and allows the conversion of esters to vinyl ethers. Tebbe reagent can be used to olefinate aldehydes, to methylenate a chiral polyhydroxyketone with high diasteroselctivity.
일반 설명Tebbe reagent is a Lewis acid stabilized organometallic compound, which is used to transform carbonyl groups into β-substituted methylenes. It also reacts with a wide range of carbonyl compounds, including esters, amides, and lactones to yield corresponding olefins.
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