Titanium isopropoxide

Last updated
Titanium isopropoxide
Sample of Titanium isopropoxide 01.jpg
IUPAC name
Titanium isopropoxide
Other names
Tetraisopropyl titanate
Titanium(IV) i-propoxide
Titanium tetraisopropoxide
Tetraisopropyl orthotitanate
3D model (JSmol)
ECHA InfoCard 100.008.100 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-909-6
PubChem CID
UN number 1993
  • InChI=1S/4C3H7O.Ti/c4*1-3(2)4;/h4*3H,1-2H3;/q4*-1;+4
  • CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C
Molar mass 284.219 g·mol−1
Appearancecolorless to light-yellow liquid
Density 0.96 g/cm3
Melting point 17 °C (63 °F; 290 K) approximation
Boiling point 232 °C (450 °F; 505 K)
Reacts to form TiO2
Solubility soluble in ethanol, ether, benzene, chloroform
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
H226, H318, H319, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
Lethal dose or concentration (LD, LC):
7600 mg/kg (rat, oral)
Related compounds
Other anions
Titanium methoxide; Titanium ethoxide; Titanium butoxide
Other cations
Aluminium isopropoxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Titanium isopropoxide, also commonly referred to as titanium tetraisopropoxide or TTIP, is a chemical compound with the formula Ti{OCH(CH3)2}4. This alkoxide of titanium(IV) is used in organic synthesis and materials science. It is a diamagnetic tetrahedral molecule. Titanium isopropoxide is a component of the Sharpless epoxidation, a method for the synthesis of chiral epoxides. [1] [2]


The structures of the titanium alkoxides are often complex. Crystalline titanium methoxide is tetrameric with the molecular formula Ti4(OCH3)16. [3] Alkoxides derived from bulkier alcohols such as isopropyl alcohol aggregate less. Titanium isopropoxide is mainly a monomer in nonpolar solvents. [4]


It is prepared by treating titanium tetrachloride with isopropanol. Hydrogen chloride is formed as a coproduct: [4]

TiCl4 + 4 (CH3)2CHOH → Ti{OCH(CH3)2}4 + 4 HCl


Titanium isopropoxide reacts with water to deposit titanium dioxide: [5]

Ti{OCH(CH3)2}4 + 2 H2O → TiO2 + 4 (CH3)2CHOH

This reaction is employed in the sol-gel synthesis of TiO2-based materials in the form of powders or thin films. Typically water is added in excess to a solution of the alkoxide in an alcohol. The composition, crystallinity and morphology of the inorganic product are determined by the presence of additives (e.g. acetic acid), the amount of water (hydrolysis ratio), and reaction conditions. [5]

The compound is also used as a catalyst in the preparation of certain cyclopropanes in the Kulinkovich reaction. Prochiral thioethers are oxidized enantioselectively using a catalyst derived from Ti(O-i-Pr)4. [6] [7]


Titanium(IV) isopropoxide is a widely used item of commerce and has acquired many names in addition to those listed in the table. A sampling of the names include: titanium(IV) i-propoxide, isopropyl titanate, tetraisopropyl titanate, tetraisopropyl orthotitanate, titanium tetraisopropylate, orthotitanic acid tetraisopropyl ester, Isopropyl titanate(IV), titanic acid tetraisopropyl ester, isopropyltitanate, titanium(IV) isopropoxide, titanium tetraisopropoxide, iso-propyl titanate, titanium tetraisopropanolate, tetraisopropoxytitanium(IV), tetraisopropanolatotitanium, tetrakis(isopropoxy) titanium, tetrakis(isopropanolato) titanium, titanic acid isopropyl ester, titanic acid tetraisopropyl ester, titanium isopropoxide, titanium isopropylate, tetrakis(1-methylethoxy)titanium.


TTIP can be used as a precursor for ambient conditions vapour phase deposition such as infiltration into polymer thin films. [8]

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Sharpless epoxidation</span> Chemical reaction

The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. The oxidizing agent is tert-butyl hydroperoxide. The method relies on a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate.

In chemistry, titanate usually refers to inorganic compounds composed of titanium oxides. Together with niobate, titanate salts form the Perovskite group.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

<span class="mw-page-title-main">Transition metal alkoxide complex</span> Conjugate base of an alcohol

A transition metal alkoxide complex is a kind of coordination complex containing one or more alkoxide ligands, written as RO, where R is the organic substituent. Metal alkoxides are used for coatings and as catalysts.

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4" due to the phonetic resemblance of its molecular formula to the word.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

Xanthate usually refers to a salt of xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]M+ ,. Xanthate also refers to the anion [R−O−CS2]. Xanthate also may refer to an ester of xanthic acid. The formula of xanthic acid is R−O−C(=S)−S−H, while the formula of the esters of xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός xanthos, meaning “yellowish, golden”, and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain sulphide bearing ores. They are also versatile intermediates in organic synthesis.

<span class="mw-page-title-main">Aluminium isopropoxide</span> Chemical compound

Aluminium isopropoxide is the chemical compound usually described with the formula Al(O-i-Pr)3, where i-Pr is the isopropyl group (–CH(CH3)2). This colourless solid is a useful reagent in organic synthesis.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, which contain the hydroperoxy functional group (–OOH). The hydroperoxide anion and the neutral hydroperoxyl radical (HOO·) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular H2. It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular H2 used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis. It uses hydrogen donor compounds such as formic acid, isopropanol or dihydroanthracene, dehydrogenating them to CO2, acetone, or anthracene respectively. Often, the donor molecules also function as solvents for the reaction. A large scale application of transfer hydrogenation is coal liquefaction using "donor solvents" such as tetralin.

Asymmetric catalytic oxidation is a technique of oxidizing various substrates to give an enantio-enriched product using a catalyst. Typically, but not necessarily, asymmetry is induced by the chirality of the catalyst. Typically, but again not necessarily, the methodology applies to organic substrates. Functional groups that can be prochiral and readily susceptible to oxidation include certain alkenes and thioethers. Challenging but pervasive prochiral substrates are C-H bonds of alkanes. Instead of introducing oxygen, some catalysts, biological and otherwise, enantioselectively introduce halogens, another form of oxidation.

The Kulinkovich reaction describes the organic synthesis of substituted cyclopropanols through reaction of esters with dialkyl­dialkoxy­titanium reagents, which are generated in situ from Grignard reagents containing a hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. This reaction was first reported by Oleg Kulinkovich and coworkers in 1989.

<span class="mw-page-title-main">Diethyl tartrate</span> Chemical compound

Diethyl tartrate is an organic compound with the formula (HOCHCO2Et)2 (Et = ethyl). Three stereoisomers exist, R,R-, S,S-, and R,S (=S,R-). They are the ethyl esters of the respective R,R-, S,S-, and R,S-tartaric acids. The R,R- and S,S- isomers are enantiomeric, being mirror images. The meso stereoisomer is not chiral. The chiral isomer is far more common.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether. They all have the formula C3H8O.

<span class="mw-page-title-main">Titanium ethoxide</span> Chemical compound

Titanium ethoxide is a chemical compound with the formula Ti4(OCH2CH3)16. It is a commercially available colorless liquid that is soluble in organic solvents but hydrolyzes readily. Alkoxides of titanium(IV) and zirconium(IV) are used in organic synthesis and materials science. They adopt more complex structures than suggested by their empirical formulas.

<span class="mw-page-title-main">Nickel(II) titanate</span> Chemical compound

Nickel(II) titanate is an inorganic compound with the chemical formula NiTiO3 nickel(II) titanate, also known as nickel titanium oxide, is a coordination compound between nickel(II), titanium(IV) and oxide ions. It has the appearance of a yellow powder. There are several methods of synthesis for nickel(II) titanate. The first method involves nickel(II) titanate's melting temperature of over 500 °C at which its precursor decomposes to give nickel(II) titanate as a residue. Nickel(II) titanate has been used as a catalyst for toluene oxidation. The second method involved using enthalpy and entropy on the reaction to synthesize nickel(II) titanate through its phase transition.

<span class="mw-page-title-main">Titanium butoxide</span> Chemical compound

Titanium butoxide is an metal-organic chemical compound with the formula Ti(OBu)4 (Bu = CH2CH2CH2CH3). It is a colorless odorless liquid, although aged samples are yellowish with a weak alcohol-like odor. It is soluble in many organic solvents. It hydrolyzes to give titanium dioxide, which allows deposition of TiO2 coatings of various shapes and sizes down to the nanoscale.

Titanium(IV) acetate or titanium tetraacetate is a hypothetical coordination complex with the formula Ti(C2H3O2)4. It is discussed in archaic literature, well before the advent of X-ray crystallography and an appreciation of the structural trends in metal carboxylate complexes.

The +4 oxidation state dominates titanium chemistry, but compounds in the +3 oxidation state are also numerous. Commonly, titanium adopts an octahedral coordination geometry in its complexes, but tetrahedral TiCl4 is a notable exception. Because of its high oxidation state, titanium(IV) compounds exhibit a high degree of covalent bonding.


  1. Katsuki, T.; K. Barry Sharpless (1980). "The first practical method for asymmetric epoxidation". J. Am. Chem. Soc. 102 (18): 5974. doi:10.1021/ja00538a077.
  2. Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. (1985). "Enantioselective Epoxidation Of Allylic Alcohols: (2s,3s)-3-propyloxiranemethanol". Org. Synth. 63: 66. doi:10.15227/orgsyn.063.0066.
  3. Wright, D. A.; Williams, D. A. (1968). "The Crystal and Molecular Structure of Titanium Tetramethoxide". Acta Crystallographica B . 24 (8): 1107–1114. doi:10.1107/S0567740868003766.
  4. 1 2 Donald Charlton Bradley; Ram C. Mehrotra; Rothwell, Ian P.; Singh, A. (2001). Alkoxo and Aryloxo Derivatives of Metals. San Diego: Academic Press. ISBN   978-0-08-048832-5.
  5. 1 2 Hanaor, Dorian A. H.; Chironi, Ilkay; Karatchevtseva, Inna; Triani, Gerry; Sorrell, Charles C. (2012). "Single and Mixed Phase TiO2 Powders Prepared by Excess Hydrolysis of Titanium Alkoxide". Advances in Applied Ceramics . 111 (3): 149–158. arXiv: 1410.8255 . Bibcode:2012AdApC.111..149H. doi:10.1179/1743676111Y.0000000059. S2CID   98265180.
  6. Zhao, S. H.; Samuel, O.; Kagan, H. B. (1987). "Asymmetric Oxidation of Sulfides Mediated by Chiral Titanium Complexes: Mechanistic and Synthetic Aspects". Tetrahedron . 43 (21): 5135–5144. doi:10.1016/S0040-4020(01)87689-4.
  7. Zhao, S. H.; Samuel, O.; Kagan, H. B. (1990). "Enantioelective Oxidation of a Sulfide: (S)-(−)-Methyl p-Tolyl Sulfoxide". Organic Syntheses . 68: 49. doi:10.15227/orgsyn.068.0049.; Collective Volume, vol. 8, p. 464
  8. Giraud, Elsa C.; Mokarian-Tabari, Parvaneh; Toolan, Daniel T. W.; Arnold, Thomas; Smith, Andrew J.; Howse, Jonathan R.; Topham, Paul D.; Morris, Michael A. (2018-07-27). "Highly Ordered Titanium Dioxide Nanostructures via a Simple One-Step Vapor-Inclusion Method in Block Copolymer Films" (PDF). ACS Applied Nano Materials. 1 (7): 3426–3434. doi:10.1021/acsanm.8b00632. S2CID   139474500.