38401-84-2

Basic information

• Product Name: 2-ETHYL-1,6-DIOXASPIRO[4.4]-NONANE
• Synonyms: 2-ETHYL-1,6-DIOXASPIRO[4.4]-NONANE;Chalcogran;Ethyl-1,6-dioxaspiro[4.4]-nonane, GC 95%;7-Ethyl-1,6-dioxaspiro[4.4]nonane;(2S,5R)-2-ethyl-1,6-dioxaspiro[4.4]nonane
• CAS NO: 38401-84-2
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22
• Mol File: 38401-84-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 206.1°Cat760mmHg
• Flash Point: 74.3°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 0.347mmHg at 25°C
• Refractive Index: n20/D 1.446
• CAS DataBase Reference: 2-ETHYL-1,6-DIOXASPIRO[4.4]-NONANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHYL-1,6-DIOXASPIRO[4.4]-NONANE(38401-84-2)
• EPA Substance Registry System: 2-ETHYL-1,6-DIOXASPIRO[4.4]-NONANE(38401-84-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 38401-84-2(Hazardous Substances Data)

Usage

Description

2-Ethyl-1,6-dioxaspiro[4.4]nonane is a cyclic ether compound with the molecular formula C?H??O?. It is characterized by a spiro structure, which consists of two rings connected by a single atom. This unique structure endows it with specific chemical and physical properties, making it suitable for various applications.

Uses

Used in Insect Control:
2-Ethyl-1,6-dioxaspiro[4.4]nonane is used as an insect pheromone in the insecticide industry. It is a natural product secreted by Bark Beetle species to attract females. By mimicking the pheromone, it can be utilized in pest control strategies to trap and control the population of these insects, reducing the need for chemical insecticides and promoting environmentally friendly pest management practices.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 3140, 1982 DOI: 10.1021/jo00137a020Synthetic Communications, 13, p. 1235, 1983 DOI: 10.1080/00397918308063739

InChI:InChI=1/C9H16O2/c1-2-8-4-6-9(11-8)5-3-7-10-9/h8H,2-7H2,1H3

Upstream product

• 695-06-7 hexan-4-olide 
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• 13888-01-2 3-ethyltetrahydrofuran-2-one 
• 129102-66-5 C₃H₆CeCl₂O^(1-)*Ce⁽³⁺⁾*2Cl^(1-) 
• 69978-25-2 1-(α-furyl)pentan-3-ol 
• 134786-63-3 5-(1-hydroxypropyl)-3-methoxy-2-thiophenethanol 
• 117973-53-2 2-Ethenyl-1,6-dioxaspiro<4.4>nonan 
• 69681-94-3 5-Ethyl-2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-tetrahydro-furan-2-ol 
• 116467-52-8 4,4-(Ethylenedioxy)-7-oxononanoate 
• 81540-28-5 1-tetrahydrofuranyl-pentan-3-yl acetate 
• 4469-84-5 1,7-nonanediol 
• 546-67-8 lead(IV) tetraacetate 
• 1192-30-9 tetrahydrofurfuryl bromide 
• 4469-83-4 1-(α-tetrahydrofuryl)pentan-3-ol 

Downstream Products

• 69744-43-0 (2R,5S)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 70427-58-6 (2S,5S)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 70427-57-5 (2S,5R)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 69744-44-1 (2R,5R)-2-ethyl-1,6-dioxaspiro<4.4>nonane 

Relevant articles and documents

A Method for the Synthesis of Ketones and Spiroketals via Desulfurization of Thienylethers

Starting from substituted methoxythiophenes 1 ketones and spiroketals can be synthesized in one step by desulfurization with partial hydrogenation.The bark beetle pheromone chalcogran 2a and the wasp anti aggression pheromone 2b were prepared by this method.

SYNTHESIS OF 2-ETHYL-1,6-DIOXASPIRONONANE, THE MAJOR COMPONENT OF THE PHEROMONE OF THE CHALCOGRAPH BEETLE PITYOGENES CHALCOGRAPHUS (L.)

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Consecutive reactions with sulfoximines: Straightforward synthesis of substituted 5,5-spiroketals

An efficient synthesis of 5,5-spiroketals (i.e., 1,6-dioxa-spiro[4.4]nonane derivatives) is described from 2-(sulfonimidoyl-methylene)tetrahydrofurans involving a consecutive epoxide opening/oxa-Michael spiroketalization sequence. This methodology was applied to the very direct synthesis of chalcogran, a beetle pheromone. Georg Thieme Verlag Stuttgart ? New York.

Exo and endohormones. XX. Synthesis of racemic 2-ethyl-1,6-dioxaspiro[4,4]nonane, the aggregation pheromone of pityogenes chalcographus (Coleoptera, Scolytidae)

The synthesis of a diastereoisomeric mixture of 2-etyl-1,6-dioxaspiro[4,4]nonane (chalcograne) a main component of the aggregation pheromone of the spruce bark beetle Pityogenes chalcographus (Coleoptera, Scolytidae), a serious pest in European forests, by 1,7-nonanediol cyclization using Pb(OAc)4 is given below. The side products of spirocyclization were identified by GC/MS.