2190-48-9

Basic information

• Product Name: 3-CHLORO-3-METHYL-1-BUTENE
• Synonyms: 1-butene,3-chloro-3-methyl-;2-chloro-2-methyl-3-butene;3-Chloro-3-methyl-1-butene;3-chloro-3-methyl-but-1-ene;3-Methyl-3-chloro-1-butene
• CAS NO: 2190-48-9
• Molecular Formula: C₅H₉Cl
• Molecular Weight: 104.58
• Mol File: 2190-48-9.mol

Chemical Properties

• Boiling Point: 103.83°C (estimate)
• Appearance: /
• Density: 0.8786
• Vapor Pressure: 73.1mmHg at 25°C
• Refractive Index: 1.4167
• CAS DataBase Reference: 3-CHLORO-3-METHYL-1-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-3-METHYL-1-BUTENE(2190-48-9)
• EPA Substance Registry System: 3-CHLORO-3-METHYL-1-BUTENE(2190-48-9)

Safety Data

• Hazardous Substances Data: 2190-48-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Chloro-3-methyl-1-butene is employed as a key intermediate in organic synthesis for the creation of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure allows it to participate in various chemical reactions, such as alkylation, reduction, and addition reactions, which are crucial for the synthesis of complex organic molecules.
Used in Specialty Polymer Production:
3-CHLORO-3-METHYL-1-BUTENE also finds application in the production of specialty polymers, where its reactive nature and ability to undergo specific chemical transformations contribute to the development of polymers with unique properties and applications.
Used as a Solvent in Industrial Processes:
In some industrial processes, 3-chloro-3-methyl-1-butene is utilized as a solvent due to its ability to dissolve certain substances and facilitate chemical reactions. Its solvent properties can be beneficial in specific manufacturing operations.
However, it is important to note that due to its flammable nature and potential health hazards, proper safety measures and handling procedures should be strictly followed when working with 3-chloro-3-methyl-1-butene to ensure the safety of personnel and the environment.

InChI:InChI=1/C5H9Cl/c1-4-5(2,3)6/h4H,1H2,2-3H3

Upstream product

• 78-79-5 isoprene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 7647-01-0 hydrogenchloride 
• 556-82-1 3-methyl-2-buten-1-ol 
• 7719-12-2 phosphorus trichloride 
• 2568-33-4 3-methyl-butane-1,3-diol 

Downstream Products

• 4489-84-3 3-methyl-1-phenylbut-2-ene 
• 10276-04-7 3-methyl-1-phenylsulfanylbut-2-ene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 24509-88-4 2-methyl-3-buten-2-yl acetate 
• 60173-64-0 N-(1,1-dimethylprop-2-en-1-yl)aniline 
• 109733-42-8 S-(3-methyl-but-2-enyl)-N,N'-diphenyl-isothiourea; hydrochloride 
• 627-97-4 2-methyl-2-heptene 
• 3404-77-1 3,3-dimethylhex-1-ene 
• 16736-42-8 2,7-dimethyl-octa-2,6-diene 
• 4490-10-2 geranyl chloride 
• 53477-48-8 3-Chlormethyl-2,6-dimethyl-hepta-1,5-dien 

Relevant articles and documents

Design, total synthesis, and evaluation of novel open-chain epothilone analogues

The design, total synthesis, and biological evaluation of two open-chain analogues of epothilone incorporating the critical C1-C8 fragment and the aromatic side chain held together by a small molecular scaffold have been achieved. Biological evaluation revealed that further restraint between the flexible C1-C8 region and the molecular scaffold may be necessary for potent inhibition of cell proliferation.

Selective formation of chloroethane by the hydrochlorination of ethene using zinc catalysts

A detailed study of the hydrochlorination of ethene and higher alkenes using ZnCl2/SiO2 and ZnCl2/Al2O3 catalysts is described and discussed. Based on earlier observations that supported gold can be an active catalyst for both ethyne hydrochlorination and oxidation reactions, we initially investigated using supported gold as catalysts for the oxychlorination of ethene. However, we found that oxychlorination did not occur in the presence of oxygen and, furthermore, that the gold acted as a poison/inhibitor during the initial reaction period, with the underlying reaction being ethene hydrochlorination. Supported Zn2+ was found to be a very effective catalyst for this reaction. The hydrochlorination of higher alkenes occurred, with high selectivity to a range of relatively complex chlorinated hydrocarbon products at rates of ca. 10-13 mol/(kgcat h).

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

Method for synthesizing methyl heptenone from isopentenyl alcohol

The invention provides a method for synthesizing methyl heptenone from isopentenyl alcohol. The method comprises the following steps: (1) reacting isopentenyl alcohol with concentrated hydrochloric acid in the presence of a catalyst A, splitting phase for the reacting liquid, washing and distilling the organic phase to obtain a chloro mixture of 1-chloro-3-methyl-2-butene and 3-chloro-3-methyl-1-butene; (2) directly condensing the chloro mixture with acetone in the presence of a catalyst B to obtain a single product methyl heptenone. According to the method, isopentenyl alcohol is efficientlychlorinated in the presence of metal inorganic salt functioning as a catalyst and concentrated hydrochloric acid functioning as a chlorinating agent; the chlorinating reaction liquid is split and simply distilled to obtain the chlorinated mixture, operation steps of isomerization, rectification and the like are not required; alkali solution is promoted by using N,N-dimethyl formamide as a condensation solvent, and a phase transfer catalyst is not required to be added, the condensation time is reduced, and the reaction yield is improved.

Preparation method of 1-chloro-3-methyl-2-butene

The invention discloses a preparation method of 1-chloro-3-methyl-2-butene. The preparation method is characterized by comprising the following steps: adding 3-methyl-2-butene-1-ol into a closed reaction device, and introducing hydrogen chloride gas under the condition of -30 to 25 DEG C for carrying out reaction; after the reaction is finished, separating and removing the water layer to obtain the 1-chloro-3-methyl-2-butene product. The preparation method takes the 3-methyl-2-butene-1-ol and the hydrogen chloride as raw materials, and an organic solvent and a catalyst do not need to be used in a preparation process, so that an aftertreatment process is simplified, the environmental pollution is reduced, and the production efficiency and safety are improved.

EPOTHILONE ANALOGUES

Epothilone analogues include a molecular scaffold which holds at least one segment of epothilone in a predetermined orientation and which rigidities a region between the macrolactone ring and the aromatic side-chain.

Synthesis and application of quinazoline-oxazoline-containing (Quinazox) ligands

(Chemical Equation Presented) A practical synthesis of potentially tridentate P,N,N-ligands containing two stereogenic elements incorporated into the axially chiral Quinazolinap and centrally chiral 2-oxazoline subunits is reported. The application of these novel hybrid ligands in Pd(0)-catalyzed asymmetric allylic alkylation revealed the matched and mismatched diastereomer, dominant stereogenic element, as well as the effect of the oxazoline R substituent on the level of enantioselectivity (ee's up to 81%).

Tailor-made silylating agents for efficient surface modification

N-Silyldimethylamines are efficient silylating agents for the chemical surface modification of hydroxylated silicon dioxide preparations. The synthesis of chloro(5-X-3,3-dimethylpentyl)-dimethyl-silanes and their conversion to the corresponding (dimethylamino) silanes are described, where X is a methoxy, methoxymethoxy, cyano or dimethylamino group. The bulky substituent forms a two stage protecting layer at the surface. The second stage hinders the access of nucleophiles to the silicon atom resulting an enhanced hydrolytic stability.

(Dialkyl-1,1 propene-2-yl)-2 thiazolidines: synthese regioselective et hydrolyse en aldehydes β-ethyleniques α,α-disubstitues

We describe a convenient method leading to α,α-disubstituted β-ethylenic aldehydes by hydrolysis of 2-(1,1-dialkyl 2-propenyl) thiazolidines, which are easily prepared by reaction between gem-disubstituted allylic Grignard reagents and 4,5-dihydrothiazoles.

Synthesis of 1,2,3,3,6,6-Hexamethyl-1-cyclohexene - A Cascade of C12H23+ Carbenium Ion Rearrangements

6-Chloro-2,6,7,7-tetramethyl-2-octene (4), prepared via prenyl chloride addition to 2,3,3-trimethyl-1-butene, at room temperature undergoes a zinc chloride/hydrogen chloride-catalysed cyclocondensation to yield 1,2,3,3,6,6-hexamethyl-1-cyclohexene (1).The reaction mechanism is elucidated by isolation of intermediate five-membered carbocycles and by force field calculations.