105104-40-3

Basic information

• Product Name: 2-(CHLOROMETHYL)-3,5-DIOXAHEX-1-ENE
• Synonyms: 3-CHLORO-2-(METHOXYMETHOXY)-1-PROPENE;2-(CHLOROMETHYL)-3,5-DIOXAHEX-1-ENE;Chloromethyldioxahexene;2-(CHLOROMETHYL)-3,5-DIOXAHEX-1-ENE 96+%;2-(Chloromethyl)-3,5-dioxa-1-hexene;2-(Methoxymethoxy)-3-chloro-1-propene;2-(Methoxymethoxy)allyl chloride
• CAS NO: 105104-40-3
• Molecular Formula: C₅H₉ClO₂
• Molecular Weight: 136.58
• Mol File: 105104-40-3.mol

Chemical Properties

• Boiling Point: 63°C 3,5mm
• Appearance: /
• Density: 1,1 g/cm3
• Refractive Index: 1.4430-1.4450
• CAS DataBase Reference: 2-(CHLOROMETHYL)-3,5-DIOXAHEX-1-ENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-3,5-DIOXAHEX-1-ENE(105104-40-3)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-3,5-DIOXAHEX-1-ENE(105104-40-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 105104-40-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 3192, 1987 DOI: 10.1021/jo00391a003

Upstream product

• 70905-45-2 1,3-dichloro-2-(methoxymethoxy)propane 

Downstream Products

• 108270-23-1 trans-1-(phenylthio)-6-oxo-4-oxahept-1-ene 
• 163128-46-9 4,4-dimethyl-2-(2-oxopropyl)cyclohexanone 
• 61879-68-3 2,2-dimethyl-6-(2-oxopropyl)cyclohexanone 
• 2316-84-9 4-cyclohexyl-4-hydroxybutan-2-one 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 1200478-33-6 3-(methoxymethoxy)-1-phenylbut-3-en-1-ol 
• 117184-95-9 4-(4-chlorophenyl)-4-hydroxybutan-2-one 
• 1200478-37-0 1-(4-chlorophenyl)-3-(methoxymethoxy)but-3-en-1-ol 
• 38836-24-7 4-hydroxy-decan-2-one 
• 705933-36-4 (E)-4-hydroxyhept-5-en-2-one 
• 1038864-69-5 C₂₈H₃₂O₈ 
• 151344-42-2 Pd(η(2)-CH2C(O)CH2)(PPh3)2 

Relevant articles and documents

On the Hodge Mechanism of the Bread Flavor Component 6-Acetyl-1,2,3,4-tetrahydropyridine from Proline and Sugars

The so-called Hodge mechanism for the generation of 6-acetyl-1,2,3,4-tetrahydropyridine, a major Maillard flavor compound in processed foods, from proline and 1,2-propanedione most probably does not involve the intermediacy of N-acetonyl-4-aminobutanal.This finding is based on model experiments in which suitably and doubly protected N-acetonyl-4-aminobutanal was hydrolyzed into the parent compound and in which no trace of the flavor compound could be detected.Keywords: Bread flavor; Maillard reaction; Hodge mechanism; 6-acetyl-1,2,3,4-tetrahydropyridine; flavor formation

Expedient route to the functionalized calyciphylline a- Type skeleton via a michael addition- RCM strategy

An efficient, robust, and scalable strategy to access the functionalized core of calyciphylline A-type alkaloids has been developed starting from commercially available 3-methylanisole. Key features of this approach are an intramolecular Michael addition/allylation sequence and a ringclosing metathesis step.

HYDROXY-PROTECTING REAGENT AND METHOD OF PROTECTING HYDROXY WITH THE SAME

The present invention relates to a method of protecting a hydroxyl group, which includes reacting a hydroxyl group-containing compound with a compound represented by the formula (I) : wherein R is a phenyl group optionally having substituent(s), an alkyl

A unified approach to the enantioselective synthesis of 2,6-cis and trans disubstituted tetrahydropyranones

A stereoselective construction of cis- and trans-2,6-disubstituted tetrahydropyranones, based on strategy which combines an asymmetric alkylation and ring closing metathesis for the formation of a cyclic enol ether, is reported.

A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a 50 mmol scale.

2-(Chloromethyl)-3,5-dioxahex-1-ene. An Effective Acetonylating Reagent

By β-elimination of 2-chloro-1-(chloromethyl)ethyl methoxymethyl ether (1) under solid-liquid phase-transfer catalytic conditions, 2-(chloromethyl)-3,5-dioxahex-1-ene (2) of high purity was readily obtained in 85percent.Allyl chloride (2) is found to be stable at ambient conditions and to be a superior reagent as CH3COCH2+ synthon for converting active proton-containing compounds such as carboxylic acids, amines, phenols, alcohols, thiols, malonate, β-diketones, β-keto esters, phenylacetonitrile, fluorene, and indene to the corresponding acetonyl derivatives in good to excellent yields (61-93percent), usually under phase-transfer catalytic conditions or in a t-BuONa-t-BuOH system.