25308-82-1

Basic information

• Product Name: 1,1,1-trichloro-4-methylpent-4-en-2-ol
• Synonyms: 1,1,1-trichloro-4-methylpent-4-en-2-ol;4-Methyl-1,1,1-trichloropent-4-en-2-ol;1,1,1-Trichloro-4-methyl-4-penten-2-ol;4-Penten-2-ol, 1,1,1-trichloro-4-methyl-;Einecs 246-808-9
• CAS NO: 25308-82-1
• Molecular Formula: C₆H₉Cl₃O
• Molecular Weight: 203.49406
• EINECS: 246-808-9
• Mol File: 25308-82-1.mol

Chemical Properties

• Boiling Point: 241.2°Cat760mmHg
• Flash Point: 99.6°C
• Appearance: /
• Density: 1.316g/cm³
• Vapor Pressure: 0.0063mmHg at 25°C
• Refractive Index: 1.499
• CAS DataBase Reference: 1,1,1-trichloro-4-methylpent-4-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-trichloro-4-methylpent-4-en-2-ol(25308-82-1)
• EPA Substance Registry System: 1,1,1-trichloro-4-methylpent-4-en-2-ol(25308-82-1)

Safety Data

• Hazardous Substances Data: 25308-82-1(Hazardous Substances Data)

Usage

Chemical Class

Chlorinated alcohols

Molecular Weight

197.5 g/mol

Appearance

Colorless to pale yellow liquid

Boiling Point

220°C (428°F)

Melting Point

Not available

Density

1.3 g/cm3 (at 20°C)

Solubility

Soluble in water, organic solvents like ethanol, acetone, and diethyl ether

Uses

Biocidal and preservative in industrial applications
Water treatment
Wood preservation
Metalworking fluids
Intermediate in the production of other chemicals

Hazardous Classification

Classified as a hazardous substance

Health Risks

Exposure to high concentrations can be harmful to human health

Environmental Risks

Exposure can be harmful to the environment

Handling and Disposal

Proper handling and disposal procedures should be followed when using this compound

InChI:InChI=1/C6H9Cl3O/c1-4(2)3-5(10)6(7,8)9/h5,10H,1,3H2,2H3

Upstream product

• 75-87-6 chloral 
• 115-11-7 isobutene 
• 7446-70-0 aluminium trichloride 
• 110-54-3 hexane 

Downstream Products

• 134835-40-8 4-Methyl-2-p-tolyloxy-pent-4-enoic acid 
• 25308-83-2 1,1,1-trichloro-4-methyl-2-acetoxy-4-pentene 
• 130307-79-8 cis-2-Dichlormethyl-4-ethoxy-4-methyl-tetrahydrofuran 
• 130307-79-8 trans-2-Dichlormethyl-4-ethoxy-4-methyl-tetrahydrofuran 
• 65731-84-2 (+)-(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 134835-34-0 4-Methyl-2-phenoxy-pent-4-enoic acid methyl ester 
• 134835-39-5 2-(2,4-Dichloro-phenoxy)-4-methyl-pent-4-enoic acid methyl ester 
• 134847-04-4 2-(2,4-Dichloro-phenoxy)-4-methyl-pent-4-enoic acid 
• 134835-37-3 4-Methyl-2-o-tolyloxy-pent-4-enoic acid methyl ester 
• 134835-36-2 4-Methyl-2-m-tolyloxy-pent-4-enoic acid methyl ester 
• 134835-41-9 4-Methyl-2-m-tolyloxy-pent-4-enoic acid 
• 62836-20-8 1,1-Dichlor-4-methyl-pent-4-en-2-ol 
• 62434-98-4 1,1-dichloro-4-methyl-1,4-pentadiene 

Relevant articles and documents

Liebeskind-Srogl cross-coupling on γ-carboxyl-γ-butyrolactone derivatives: Application to the side chain of amphidinolides C and F

The synthetic approach for the C20-C29 and C20-C34 fragments of amphidinolide F and C was based on an original Liebeskind-Srogl cross-coupling reaction with a glutamic acid-derived building-block. Further highly diastereoselective reduction of the ketone was achieved by using an uncommon Ph3SiH/TBAF/HMPA system. The amphidinolide C side chain was built through a reductive elimination of chiral epoxide to install the stereogenic center at C29.

On the mechanism of ylide-mediated cyclopropanations: Evidence for a proton-transfer step and its effect on stereoselectivity

In this paper, we describe studies on the cyclopropanation of Michael acceptors with chiral sulfur ylides. It had previously been found that semi-stabilized sulfonium ylides (e.g., Ph-stabilized) reacted with cyclic and acyclic enones and substituted acrylates with high ee and that stabilized sulfonium ylides (e.g., ester-stabilized) reacted with cyclic enones again with high ee. The current study has focused on the reactions of stabilized sulfonium ylides with acyclic enones which unexpectedly gave low ee. Furthermore, a clear correlation of ee with ylide stability was observed in reactions with methyl vinyl ketone (MVK): ketone-stabilized ylide gave 25% ee, ester-stabilized ylide gave 46% ee, and amide-stabilized ylide gave 89% ee. It is believed that following betaine formation an unusual proton transfer step intervenes which compromises the enantioselectivity of the process. Thus, following addition of a stabilized ylide to the Michael acceptor, rapid and reversible intramolecular proton transfer within the betaine intermediate, prior to ring closure, results in an erosion of ee. Proton transfer occurred to the greatest extent with the most stabilized ylide (ketone). When the same reactions were carried out with deuterium-labeled sulfonium ylides, higher ees were observed in all cases since proton/deuteron transfer was slowed down. The competing proton transfer or direct ring-closure pathways that are open to the betaine intermediate apply not only to all sulfur ylides but potentially to all ylides. By applying this model to S-, N-, and P-ylides we have been able to rationalize the outcome of different ylide reactions bearing a variety of substituents in terms of chemo- and enantioselectivity.

Process for the preparation of trichloromethyl carbinols

The invention is directed to a new process for the preparation of carbinols of the general formula I STR1 by reaction chloral and olefins of the general formula STR2 and by optional acylation of the product comprising dissolving a catalyst of the general formula III in chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV STR3 from which a complex of the general formula V STR4 is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter (a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or (b) the product in the reaction mixture is acylated. The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.

Enantioselective preparation of substituted 2-hydroxypent-4-enes using optically-active catalysts

An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II STR1 wherein: X1, X2 and X3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C1 to C6 alkyl, C1 and C6 haloalkyl, and haloaryl; and R1, R2, R3 and R4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R3 and R4 is as hereinbefore defined and R1 and R2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. STR2 Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity. STR3

Process for the preparation of homoallyl alcohols

An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II wherein:, X1, X2 and X3 are independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C1 to C6 alkyl, C1 to C6 haloalkyl, and haloaryl; and, R1, R2, R3 and R4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R3 and R4 is as hereinbefore defined and R1 and R2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene of formula IV in the presence of an optically-active organometallic catalyst. Furthermore, the compound of formula II can be isomerised to the allylic alcohol of formula I with retention of optical purity.

Electrochemical Reduction of Trichloroacetaldehyde-Olefin-Addition-Products

Trichloroacetaldehyde reacts with different olefins forming addition products.In most cases this reaction results in 1,1,1-trichloro-2-hydroxy compounds (2a-d).But also a different route of reaction is possible.Thus 2,3-dimethylbut-1-ene (1e) forms 4-trichloro-1,1,2-tetrahydroxyfurane (2e) and cyclohexene (1f) forms 3-trichloromethyl-2-oxabicyclo-2,2,2-octane (2f).All addition products are suitable starting materials for electrochemical conversions.In acidic electrolytes, on lead cathodes the electrochemical reduction results in a simultaneous cleavage of a C-Cl and a C-O bond to form the CH=CCl2-group (3a-f).In neutral electrolytes, on mercury cathodes, however, a reductive conversion of a CCl3-group to a CHCl2-group takes place (4c, 4f).

Alkyl 6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylates

Lactones of the formula STR1 wherein R is hydrogen or a CX3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.

Reactions of a Technical Fraction of Butene with Trichloroacetaldehyde

In pyrolysis plants for gasoline production a C4-fraction is formed containing isobutene, but-1-ene and but-2-ene as main products.The reactive separation of this fraction represents an industrial problem.On way to solve this problem is the reaction of trichloroacetaldehyde with these components to form addition products.The favoured reaction is the formation of 1,1,1-trichloro-4-methyl-pent-4-en-2-ol (1) and 1,1,1-trichloro-4-methyl-pent-3-en-2-ol (2) from iso-butene.The other isomers react very slowly.The influence of different reaction parameters was investigated to find a method for a reactive separation of the C4-fraction.

Lewis Acid Catalysis of Ene Addition of Chloral and Bromal to Olefins; Product Studies

The addition of chloral and bromal to a variety of alkyl-substituted alkenes has been investigated.The effect of the reaction of varying the Lewis acid catalyst and the structure of substrate have been studied.Anhydrous AlCl3 was found to be most effective catalyst, and ene-type adducts were the major products in most cases.Side reactions were observed with the less reactive systems leading, variously, to the formation of trihalogenoketones, hydrohalogenated ene adducts, and cyclic ethers.Conditions for optimising the yield of ene adducts were established in some cases.The trihalogenoketone by-products can be conveniently removed by a Grignard-type reaction.

Process for preparing cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Lactones of the formula STR1 wherein R is hydrogen or a CX3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.