2443-46-1

Basic information

• Product Name: 1,6-Methano[10]annulen
• Synonyms: 1,6-Methano[10]annulen;1,6-Methano[10]annulene;Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaene;Bicyclo[4.4.1]undeca-2,4,6,8,10(1)-pentene
• CAS NO: 2443-46-1
• Molecular Formula: C₁₁H₁₀
• Molecular Weight: 142.2
• Mol File: 2443-46-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 324.9°Cat760mmHg
• Flash Point: 116.2°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 0.00045mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 1,6-Methano[10]annulen(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Methano[10]annulen(2443-46-1)
• EPA Substance Registry System: 1,6-Methano[10]annulen(2443-46-1)

Safety Data

• Hazardous Substances Data: 2443-46-1(Hazardous Substances Data)

Usage

General Description

1,6-Methano[10]annulen, also known as 1,6-methanocyclodecatriene, is a polycyclic hydrocarbon with a unique structural arrangement. It is composed of three fused benzene rings and a six-membered carbon ring, resulting in a non-planar and strained molecule. 1,6-Methano[10]annulen is of interest to organic chemists and material scientists due to its potential as a building block for the synthesis of novel materials and as a precursor to various functionalized derivatives. Its unique structure and reactivity make it a versatile intermediate for the development of new organic compounds with potential applications in pharmaceuticals, organic electronics, and materials science. Additionally, its strained structure and potential reactivity make it an intriguing target for synthetic organic chemists seeking to explore new chemical reactions and methodologies.

InChI:InChI=1/C11H10/c1-2-6-11-8-4-3-7-10(5-1)9-11/h1-8H,9H2

Upstream product

• 15825-93-1 2,7-dibromo-1,6-methano[10]annulene 
• 68-12-2 N,N-dimethyl-formamide 
• 87362-35-4 ((2Z,5Z)-Bicyclo[5.4.1]dodeca-1⁽¹¹⁾,2,5,7,9-pentaen-4-ylidene)-bromo-acetonitrile 
• 87362-34-3 ((2Z,5Z)-Bicyclo[5.4.1]dodeca-1⁽¹¹⁾,2,5,7,9-pentaen-4-ylidene)-acetonitrile 
• 30234-90-3 4,9-methano[11]annulenone 
• 298214-58-1 1,6-bis(1-hydroxyethyl)cyclohepta-1,3,5-triene 
• 73875-00-0 1,1'-(cyclohepta-3,5,7-triene-1,3-diyl)diethanone 
• 50785-96-1 1,6-divinylcyclohepta-1,3,5-triene 
• 115163-03-6 (1R,4S,4aS,8aR)-1,4-Diisothiocyanato-1,4-dihydro-4a,8a-methano-naphthalene 
• 75-77-4 chloro-trimethyl-silane 
• 15825-92-0 2-bromo-1,6-methano[10]annulene 
• 84175-55-3 potassium 1,6-methano<10>annulene anion radical 
• 87362-36-5 2,3-Bis-((2Z,5Z)-bicyclo[5.4.1]dodeca-1⁽¹¹⁾,2,5,7,9-pentaen-4-ylidene)-succinonitrile 
• 58081-06-4 2-trimethylsilyl-1,6-methano<10>annulene 

Downstream Products

• 58853-55-7 2-Methoxy-1,6-methano-<10>annulene 
• 58790-01-5 2-methyl-1,6-methano<10>annulene 
• 137594-08-2 3-<(triphenylphosphoranylidene)amino>-1,6-methano<10>annulene 
• 137594-21-9 6-(4-Chloro-phenyl)-4-phenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,5,8,10,12-heptaene 
• 137594-17-3 4,6-Diphenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,5,8,10,12-heptaene 
• 137594-15-1 4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,8,10,12-hexaene 
• 137594-16-2 6-(4-Chloro-phenyl)-4-phenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,8,10,12-hexaene 
• 137594-14-0 4,6-Diphenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,8,10,12-hexaene 
• 137594-27-5 2,4-diphenyl-5,10-methanocyclodecapyridine 
• 134858-17-6 2-<(triphenylphosphoranylidene)amino>-1,6-methano<10>annulene 
• 118684-46-1 2-nitro-3-(p-tolylsulfonylmethyl)bicyclo<4.4.1>undeca-1,3,5,7,9-pentaene 
• 118684-50-7 (+/-)-2-Nitro-5-(4-nitrobenzyl)bicyclo<4.4.1>undeca-1,3,5,7,9-pentaen 
• 15825-93-1 2,7-dibromo-1,6-methano[10]annulene 
• 6130-41-2 (7S,10R)-7,10-Dibromo-bicyclo[4.4.1]undeca-1,3,5,8-tetraene 

Relevant articles and documents

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Relative Thermodynamic Stabilities of 1,6-Methanoannulene, Dinorcaradiene, and the1,6-Methanoannulene Anion Radical

The enthalpies of reaction of both the solvated and solid salts of potasssium 1,6-metanoannulene (M10) anion radical were measured with calorimetric techniques.These measurements show that anion radical of M10 has suprising degree of thermodynamic stability.The heat of formation of K+M10-*(s) from gas-phase potassium and gas-phase hydrocarbon (-61.9 kcal/mol) is about 16 kcal/mol more negative than that for the solid potassium salt of the naphthalene anion radical.Combustion experiments were used to show that the open form of M10 is about 5.7 kcal/mol lower in energy than dinorcaradiene.

A convenient synthetic method for preparing 2,5-disubstituted 1,6- methano[10]annulenes from 1,6-diacetylcyclohepta-1,3,5-triene

The reaction of 1,6-diacetylcyclohepta-1,3,5-triene with various Grignard reagents gave high yields of addition products 5, which were treated with a catalytic amount of p-toluenesulfonic acid or pyridinium p- toluenesulfonate to afford 2,5-disubstituted 2,3-dihydro-1,6- methano[10]annulenes 6 via 1,6-bis(1-substituted vinyl)cyclohepta-1,3,5- trienes 8 and 2,5-disubstituted 3,4-dihydro-1,6-methano[10]annulenes 9. On the other hand, reactions under more forcing conditions gave the rearrangement products: 4,7-disubstituted 1,2-benzocyclohepta-1,3-dienes 7. The oxidation of 6 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone gave the 2,5-disubstituted 1,6-methano[10]annulens 4 in moderate-to-good yields. Conversion from 5 into 4 can be achieved by a one-flask procedure, providing a convenient synthetic method for preparing the title annulenes, particularly 2,5-diaryl ones. The reaction mechanism from 8 to 6, 7, and 9 is discussed on the basis of semiempirical molecular orbital calculations.

Studies in the Cycloproparene Series: Approaches to Bicycloocta-1,3,6-triene, a Cyclopropa-Fused Cycloheptatriene

The dichloromethylene-bridged annulene (5) is available in four steps (47percent) from 1,4,5,8-tetrahydronaphthalene (11) via the dibromide (15); the minor (5percent) product of dehydrobromination of (15) is 2-bromo-9,9-dichloro-1,4-dihydro-4a,8a-methanonaphthalene (16).Dichlorocarbene adds to the norcaradiene form of (5) to give adduct (6) with 80percent efficiency.Diene (6) resists both ?4 + ?2> cycloadditions and reductive dechlorination.Neither (5) nor parent 1,6-methanoannulene (18) adds methylene from Simmons-Smith cyclopropanation procedures.

Electrophilic Substitution in Annulenes. Part 4. Transmission of Substituent Effects in 1,6-Methanoannulene, determined via Protiodesilylation: Evidence for Substantial C(1)-C(6) Transannular Orbital Interaction

The rates of acid-catalysed desilylation of a series of 7-substituted 2-trimethylsilyl-1,6-methanoannulenes have been measured spectrophotometrically at 50 degC using a mixture of aqueous perchloric acid and methanol (2:5 v/v).The substituent effects