ContaminantDB: Tebbe's reagent

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-06-19 21:58:55 UTC

Update Date

2016-11-09 01:08:30 UTC

Accession Number

CHEM001302

Identification

Common Name

Tebbe's reagent

Class

Small Molecule

Description

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. (6, 7, 8)

Contaminant Sources

T3DB toxins

Contaminant Type

Aluminum Compound
Aromatic Hydrocarbon
Industrial/Workplace Toxin
Organic Compound
Organometallic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₃H₂₁AlClTi

Average Molecular Mass

287.607 g/mol

Monoisotopic Mass

287.063 g/mol

CAS Registry Number

67719-69-1

IUPAC Name

titanium(3+) ion λ¹-alumanylium bis(cyclopenta-2,4-dien-1-ide) bis(methane) chloride methanide

Traditional Name

titanium(3+) ion λ¹-alumanylium bis(cyclopentadienide) bis(methane) chloride methanide

SMILES

C.C.[CH3-].[Al+].[Cl-].[Ti+3].[CH-]1C=CC=C1.[CH-]1C=CC=C1

InChI Identifier

InChI=1S/2C5H5.2CH4.CH3.Al.ClH.Ti/c2*1-2-4-5-3-1;;;;;;/h2*1-5H;2*1H4;1H3;;1H;/q2*-1;;;-1;+1;;+3/p-1

InChI Key

DAACJUOBIIIHLU-UHFFFAOYSA-M

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aromatic hydrocarbons. These are aromatic compounds that are made up of carbon and hydrogen atoms only.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Aromatic hydrocarbons

Sub Class

Not Available

Direct Parent

Aromatic hydrocarbons

Alternative Parents

Substituents

Aromatic hydrocarbon
Organic metal halide
Organic transition metal salt
Unsaturated hydrocarbon
Hydrocarbon derivative
Organic aluminium salt
Organic chloride salt
Organic salt
Saturated hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.73	ALOGPS
logP	2.25	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.72 m³·mol⁻¹	ChemAxon
Polarizability	7.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Toxicity Profile

Route of Exposure

Oral (6) ; inhalation (6)

Mechanism of Toxicity

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 (1), but studies have not been able to establish a clear link between aluminum and increased risk of breast cancer (3). Certain aluminum salts induce immune responses by activating inflammasomes. (6, 1, 2)

Metabolism

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. (6)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC 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. (5) A link between use of aluminum-containing antiperspirants and increased risk of breast cancer has been proposed (1), but studies have not been able to establish a clear link (3).

Uses/Sources

Tebbe's reagent is used in the methylenation of carbonyl compounds. (8)

Minimum Risk Level

Intermediate Oral: 1.0 mg/kg/day (4) Chronic Oral: 1.0 mg/kg/day (4)

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. (6, 7)

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. (6, 7)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Tebbe's reagent

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Tebbe's reagent (CHEM001302)

Structure for CHEM001302: Tebbe's reagent