503-60-6

Usage

Uses

1. Used in the Synthesis of Geraniol:
1-Chloro-3-methyl-2-butene is used as a key intermediate in the synthesis of geraniol, which is an important compound in the fragrance and flavor industries due to its pleasant rose-like scent.
2. Used as an Alkylating Agent:
1-Chloro-3-methyl-2-butene serves as an alkylating agent, which is a substance that donates an alkyl group to another molecule in a chemical reaction. Alkylating agents are widely used in the chemical industry for various applications, including the production of pharmaceuticals and other organic compounds.
3. Used as a Reagent in Hyperforin:
1-Chloro-3-methyl-2-butene is utilized as a reagent in the production of hyperforin, a polyprenylated acylphloroglucinol (PA) compound found in the plant Hypericum perforatum (St. John's wort). Hyperforin has been studied for its potential therapeutic effects, particularly in the context of depression.
4. Used as an Antibiotic:
1-Chloro-3-methyl-2-butene is also used as an antibiotic to inhibit the growth of tumor cells. Its application in the medical field highlights its potential as a therapeutic agent in cancer treatment.
5. Used in the Chemical Industry:
1-Chloro-3-methyl-2-butene is employed in the chemical industry for various purposes, including the synthesis of different organic compounds and pharmaceuticals, thanks to its reactivity and versatility as a chemical building block.

InChI:InChI=1/C5H9Cl/c1-5(2)3-4-6/h3H,4H2,1-2H3

Upstream product

• 2190-48-9 3-chloro-3-methyl-1-butene 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 563-45-1 3-Methyl-1-butene 
• 78-79-5 isoprene 
• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 763-32-6 2-methyl-1-buten-4-ol 
• 98-88-4 benzoyl chloride 
• 115-18-4 2-methyl-3-buten-2-ol 
• 75-36-5 acetyl chloride 
• 69065-31-2 4-Octen-3-one 
• 870-63-3 prenyl bromide 
• 14309-15-0 phenyl prenyl ether 

Downstream Products

• 109733-42-8 S-(3-methyl-but-2-enyl)-N,N'-diphenyl-isothiourea; hydrochloride 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 23446-47-1 1-methyl-2-(3-methylbut-2-enyloxy)benzene 
• 6800-76-6 2-Methyl-4-<3-methyl-buten-(2)-yl>-phenol 
• 103483-02-9 1-(4',5'-dihydrothiazol-2'-yl)thio-3-methylbut-2-ene 
• 73290-83-2 6,7-Dihydro-4,8,8,10-tetramethyl-2H,8H-benzo<1,2-b:5,4-b'>dipyran-2-one 
• 478-67-1 mammea B/AA 
• 704-99-4 2-(3-methylbut-2-en-1-yl)cyclohexanone 
• 62894-04-6 phenyl prenyl ketone 
• 63972-14-5 1-(dimethylphenylsilyl)-3-methyl-2-butene 
• 81195-14-4 [(Diphenylphosphanyl)-methyl]-(3-methyl-but-2-enyl)-diphenyl-phosphonium; chloride 
• 81194-90-3 C₃₆H₄₂P₂⁽²⁺⁾*2Cl^(1-) 
• 56506-81-1 (2E,6E)-1-(benzyloxy)-3,7,11-trimethyl-2,6,10-dodecatriene 
• 34600-27-6 3,3-dimethyl-5-phenylpent-1-en-4-yne 

Relevant academic research and scientific papers

Surface-mediated hydrohalogenation of isoprene: A facile preparation of prenyl halides

The reaction of isoprene with SOCl2 (0.5 mol equiv.) or PBr3 (0.4 mol equiv.) or PI3 (0.4 mol equiv.) in the presence of SiO2 at -10°C produced prenyl chloride (82%), or bromide (70%) or iodide (65%), respectively, in less than 30 min reaction time.

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.

Synthesis method of 5,5,5-trichloro-2-methyl-2-pentene

The invention provides a synthetic method of 5,5,5-trichloro-2-methyl-2-pentene. The synthetic method comprises the following steps: taking 2-methyl-3-butene-2-ol as an initial compound of a reaction;adding a haloid acid into the reaction system, and conducting distilling to obtain an intermediate product 1-halo-3-methyl-2-butene; adding the intermediate product and chloroform into a reaction kettle, conducting stirring at a low temperature, and adding an inorganic base into the system in batches; wherein the reaction temperature is 0-40 DEG C, the reaction time is 2-10 hours, the mass ratioof the 2-methyl-3-butene-2-ol to the haloid acid in the reaction is (0.3-1):1, the weight ratio of the chloroform to the 1-halo-3-methyl-2-butene is (1-10):1, and the weight ratio of the inorganic base to the 1-halo-3-methyl-2-butene is (0.1-2.0):1. The method is high in reaction yield and low in environmental pollution degree, and the corrosion degree of equipment is reduced.

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.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

α-Selective Allylation of Isatin Imines Using Metallic Barium

The Barbier-type allylation of isatin imines with allylic chlorides was achieved by using metallic barium as the promoter. Various α-allylated 3-amino-2-oxindoles were synthesized from the corresponding allylic chlorides and isatin imines. The double-bond geometry of allylic chlorides was retained throughout the reaction. An arylic bromide or iodide functionality of the products was robust to metalation under the optimum reaction conditions.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE

The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):

Efficient organic transformations mediated by ZrOCl28H 2O in Water

Operationally simple and environmentally benign methods for some organic transformations comprising reductive coupling of sulfonyl chlorides, chemoselective deoxygenation of sulfoxides, and halogenation of alcohols mediated by ZrOCl28H2O/MX in water have been developed.