4641-85-4

Basic information

• Product Name: 1,7-CYCLODODECADIYNE
• Synonyms: 1,7-CYCLODODECADIYNE
• CAS NO: 4641-85-4
• Molecular Formula: C12H16
• Molecular Weight: 160.25544
• Mol File: 4641-85-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 36.7-37.3 °C(Solv: methanol (67-56-1))
• Boiling Point: 257.5±20.0 °C(Predicted)
• Appearance: /
• Density: 0.91±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,7-CYCLODODECADIYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-CYCLODODECADIYNE(4641-85-4)
• EPA Substance Registry System: 1,7-CYCLODODECADIYNE(4641-85-4)

Safety Data

• Hazardous Substances Data: 4641-85-4(Hazardous Substances Data)

Usage

Structure

A 12-carbon ring with two carbon-carbon triple bonds

Reactivity

Highly reactive, unsaturated cyclic compound

Organic synthesis

undergoes numerous chemical transformations

Monomers

used in the production of polymers

Precursor

for the synthesis of various organic compounds

Materials science

potential use in the development of novel polymeric materials with unique properties

Reduction

can be reduced to form other compounds

Cross-coupling

can participate in cross-coupling reactions to form new compounds

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 74379-09-2 octa-1,7-diyne-1,8-diyl-bis-sodium 
• 136237-64-4 1,7-cyclododecanedione bissemicarbazone 
• 628-21-7 1,4-Diiodobutane 
• 871-84-1 1,7-Octadiyne 
• 39253-37-7 12-iodo-dodeca-1,7-diyne 
• 100313-92-6 cyclododec-7-yne-1,2-dione-dihydrazone 

Relevant articles and documents

179. Synthesis and structure of functionalized cyclododecadiynes and -dienes

The cyclododecadiynes 3b-d, 8b-d, and 10b-c with functionalities in two propargylic positions, as well as the monofunctionalized diyne 13b have been prepared from simple open-chain building blocks. In the DMPU (= N,N′-dimethylpropyleneurea)-assisted ring-closing alkylation of 1,7-diynes, the twelve-membered ring compounds have been prepared in yields of 16-55%. The preparation of the diene-diyne 15 and the cyclododeca-5,11-diyne-1,4-dione 18 are described.

Synthesis and properties of medium-sized (C9-C12) carbocyclic diacetylenes

The syntheses of 1,5-cyclononadiyne (3), 1,5-cyclodecadiyne (4), 1,5-cycloundecadiyne (5), 1,6-cycloundecadiyne (6), 1,6-cyclododecadiyne (7), and 1,7-cyclododecadiyne (8) have been carried out. Diacetylenes 3 and 4 are prepared from 5-cyclononynone and 5-cyclodecynone, respectively. Compounds 5-8 are synthesized from cyclic diones by thermolysis of the corresponding bisselenadiazoles. The obtained cyclic diacetylenes are further characterized by their bis(hexacarbonyldicobalt) complexes. The geometrical parameters of 3-8 were calculated with force field and semiempirical methods. From the structural data, a correlation between the 13C resonance of the sp-hybridized carbon atoms adjacent to the ethano bridge in 3-5 and the corresponding resonance of the symmetric dialkynes 1,5-cyclooctadiyne (1), 1,6-cyclodecadiyne (2), and 1,7-cyclododecadiyne (8) with the bending angle at this center can be verified. The PE spectra of 3-8 have been recorded, and an interpretation of the bands in the low-energy region is presented. It is found that the splitting of the PE bands that are assigned to the in-plane π-MO's (π1) strongly depends on the size of the methylene bridge. In the case of a propano bridge (e.g., in 3, 6, and 7), the splitting between πi- and πi+ is relatively large. The splitting of the bands that are assigned to the out-of-plane π-MO's (πo) decreases with increasing transannular distance.