mu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titanium

HCID 91617563

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

Tebbe reagent [MI]V040SDB67Smu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titanium(mu-Chloro)(mu-methylene)bis(cyclopentadienyl)(dimethylaluminum)titaniumTitanium, mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)-mu-methylene-(.MU.-CHLORO)(.MU.-METHYLENE)BIS(CYCLOPENTADIENYL)(DIMETHYLALUMINUM)TITANIUM.MU.-METHYLENE-.MU.-CHLOROBIS(.ETA.5-2,4-CYCLOPENTADIEN-1-YL)(DIMETHYLALUMINUM)TITANIUMTITANIUM, .MU.-CHLOROBIS(.ETA.5-2,4-CYCLOPENTADIEN-1-YL)(DIMETHYLALUMINUM)-.MU.-METHYLENE-RefChem:819575Tebbe reagentUNII-V040SDB67SQ27291363
이름 더 보기
tebbeTebbe's reagentTebbe reagtebbe reagent solutionca.0.5mol/lToluenesolutionTebbe Reagent 0.5 M in TolueneTEBBE REAGENT ISO 9001:2015 REACHTEBBE REAGENT, 0.5M SOLUTION IN TOLUENETebbe Reagent (ca. 0.5mol/L in Toluene)

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

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.
화학적 성질 · 1건

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 · 1건

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

Minimum Risk LevelIntermediate Oral: 1.0 mg/kg/day (L134) Chronic Oral: 1.0 mg/kg/day (L134)

독성 정보

Health Effects · 1건

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)

Exposure RoutesOral (L739) ; inhalation (L739)
Toxicity Summary · 1건

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 · 1건

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 · 1건

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

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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

UsesTebbe's reagent is used in the methylenation of carbonyl compounds. (L780)
응용 분야 · 2건

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.

공급사41 곳

阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
广东方信生物科技有限公司0751-2838688 13376594225 · [email protected]

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