503-60-6

Basic information

• Product Name: 1-Chloro-3-methyl-2-butene
• Synonyms: 1-Chloro-3-methyl-2-butene,95%,stab.withpotassiumcarbonate;1-CHLORO-3-METHYL-2-BUTENE , STABILIZED WITH POTASSIUM CARBONATE;1-CHLORO-3-METHYL-2-BUTENE 96+%;1-Chloro-3-methyl-2-butene (stabilized with K2CO3);Isopentenyl chloride;1-Chloro-3-methyl-2-butene,95% (99% min. total isomers);1-Chloro-3-methyl-2-;3,3-Dimethylallyl chloride, Prenyl chloride
• CAS NO: 503-60-6
• Molecular Formula: C₅H₉Cl
• Molecular Weight: 104.58
• EINECS: 207-972-7
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks;API Intermediate
• Mol File: 503-60-6.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 58-59 °C120 mm Hg(lit.)
• Flash Point: 56 °F
• Appearance: light yellow transparent liquid
• Density: 0.928 g/mL at 25 °C(lit.)
• Vapor Pressure: 29.6mmHg at 25°C
• Refractive Index: n20/D 1.4488(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Miscible with chloroform, acetone, diethyl ether and alcohol. Immiscible with water.
• CAS DataBase Reference: 1-Chloro-3-methyl-2-butene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-3-methyl-2-butene(503-60-6)
• EPA Substance Registry System: 1-Chloro-3-methyl-2-butene(503-60-6)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-27-36/37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• RTECS: EM4298500
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 503-60-6(Hazardous Substances Data)

Usage

Description

1-Chloro-3-methyl-2-butene is a colorless liquid that has been studied for its kinetics in gas-phase reactions with ozone. It is known for its reactivity with potassium iodide in acetone and sodium ethoxide in ethanol.

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

• 556-82-1 3-methyl-2-buten-1-ol 
• 98-88-4 benzoyl chloride 
• 763-32-6 2-methyl-1-buten-4-ol 
• 68-12-2 N,N-dimethyl-formamide 
• 115-18-4 2-methyl-3-buten-2-ol 
• 75-36-5 acetyl chloride 
• 69065-31-2 4-Octen-3-one 
• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 
• 870-63-3 prenyl bromide 
• 14309-15-0 phenyl prenyl ether 
• 7719-12-2 phosphorus trichloride 
• 7647-01-0 hydrogenchloride 
• 2568-33-4 3-methyl-butane-1,3-diol 
• 78-79-5 isoprene 

Downstream Products

• 101738-79-8 2,5-dimethyl-1-(3-methyl-but-2-enyl)-piperidin-4-one 
• 4490-10-2 geranyl chloride 
• 53477-48-8 3-Chlormethyl-2,6-dimethyl-hepta-1,5-dien 
• 17465-54-2 1,2,3,5,6,7-hexahydro-1,1,5,5-tetramethyl-s-indacene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 111712-51-7 2,3-dibromo-1-chloro-3-methyl-butane 
• 103483-02-9 1-(4',5'-dihydrothiazol-2'-yl)thio-3-methylbut-2-ene 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 2520-63-0 3-isopropylidene-6-methyl-hept-5-en-2-one 
• 26533-38-0 6-Methyl-3-isopropenyl-5-hepten-2-one 
• 34593-50-5 methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate 
• 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 articles and documents

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.

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.