1123-11-1

Basic information

• Product Name: 1,2-Cyclononadiene
• Synonyms: 1,2-Cyclononadiene
• CAS NO: 1123-11-1
• Molecular Formula: C₉H₁₄
• Molecular Weight: 122.20746
• Mol File: 1123-11-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 182.9°Cat760mmHg
• Flash Point: 45.2°C
• Appearance: /
• Density: 0.8g/cm³
• Vapor Pressure: 1.08mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: 1,2-Cyclononadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclononadiene(1123-11-1)
• EPA Substance Registry System: 1,2-Cyclononadiene(1123-11-1)

Safety Data

• Hazardous Substances Data: 1123-11-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 3518, 1961 DOI: 10.1021/jo01067a609Tetrahedron Letters, 22, p. 1203, 1981 DOI: 10.1016/S0040-4039(01)90274-6

InChI:InChI=1/C9H14/c1-2-4-6-8-9-7-5-3-1/h1,5H,2,4,6-9H2

Upstream product

• 931-88-4 cis-Cyclooctene 
• 931-88-4 1,2-cyclooctene 
• 32644-18-1 9,9-dibromo-bicyclo[6.1.0]nonane 
• 3667-55-8 Bicyclo<6.1.0>nonan-9,9-dicarbonsaeure 
• 96308-48-4 cyclooctene-1-carbaldehyde 
• 1196-95-8 9,9-dibromobicyclo[6.1.0]nonane 
• 96308-45-1 cyclooctene-1-carboxaldehyde tosylhydrazone 
• 54031-22-0 bicylo<6.1.0>non-1(9)-ene 
• 83508-78-5 N-(Bicyclo<6.1.0>non-exo-9-yl)-N-nitrosoharnstoff 
• 78616-86-1 C₁₁H₁₄O₄ 
• 67-56-1 methanol 
• 6573-52-0 cyclononyne 

Downstream Products

• 38202-52-7 4-Nitro-benzoic acid 3-hydroxy-2-oxo-cyclononyl ester 
• 134733-21-4 (R)-(-)-10-Phenyl-10,11,12-triaza-Δ¹¹-bicyclo<7.3.0>dodec-1-ene 
• 134733-20-3 (S)-(+)-10-Phenyl-10,11,12-triaza-Δ¹¹-bicyclo<7.3.0>dodec-1-ene 
• 91076-13-0 1-[(E)-2-(Dimethyl-phenyl-silanyl)-cyclonon-2-enyl]-ethanol 
• 135219-40-8 ((E)-Cyclonon-1-enyl)-diphenyl-phosphane 
• 120978-61-2 1-(triphenylstannyl)cyclononene 
• 123668-94-0 chloro(1,2-cyclononadiene)bis(triphenylphosphine)rhodium(I) 
• 1607843-88-8 (Z)-2,2,6,6-tetramethyl-1-((2-phenylcyclonon-2-en-1-yl)oxy)piperidine 
• 1607843-87-7 (E)-2,2,6,6-tetramethyl-1-((2-phenylcyclonon-2-en-1-yl)oxy)piperidine 
• 16312-79-1 4-methylurazole 
• 91108-22-4 1-[(E)-2-(Dimethyl-phenyl-silanyl)-cyclonon-2-enyl]-prop-2-en-1-ol 
• 91076-12-9 [(E)-2-(Dimethyl-phenyl-silanyl)-cyclonon-2-enyl]-phenyl-methanol 

Relevant articles and documents

A three-carbon (n+1+2) ring expansion method for the synthesis of macrocyclic enones. Application to muscone synthesis

The three-carbon ring expansion methodology commences with the preparation of a cyclic allene (C9, C11, C13), readily available from the corresponding cycloalkene via dibromocarbene addition and subsequent treatment with methyllithium. Dichloroketene addition to the cyclic allene regioselectively provides the [2+2] cycloadduct, which is reductively dechlorinated with zinc in methanol. The resulting cyclobutanone is then catalytically hydrogenated; cyclobutanone ring opening is affected with trimethylsilyl iodide; immediate dehydroiodination of the resulting β-iodocycloalkanone with diazabicycloundecane (DBU) provides the corresponding macrocyclic enone. The 15-membered enone was converted to d,l-muscone with (CH3)2CuLi.

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Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles

A complementing Pd- and Rh-catalyzed dynamic kinetic resolution (DKR) of racemic allenes leading to N-allylated pyrazoles is described. Such compounds are of enormous interest in medicinal chemistry as certified drugs and potential drug candidates. The new methods feature high chemo-, regio- and enantioselectivities aside from displaying a broad substrate scope and functional group compatibility. A mechanistic rational accounting for allene racemization and trans-alkene selectivity is discussed.

Regioselective radical bromoallylation of allenes leading to 2-bromo-substituted 1,5-dienes

The regioselective radical bromoallylation of allenes proceeded efficiently in the presence of AIBN as a radical initiator to give 2-bromo-substituted 1,5-dienes in excellent yields. The addition of a bromine radical took place regioselectively onto the central carbon of allenes generating a stable allyl radical, which underwent addition/β-fragmentation reactions with allylbromides. The products could be further functionalized by Pd-catalyzed coupling reactions.