Basic information
- Standard SMILES
c1ccc2c(c1)OCCOCCOc1ccccc1OCCOCCO2- InChIKey
YSSSPARMOAYJTE-UHFFFAOYSA-N- Molecular formula
- C20H24O6
- Average molar mass
- 360.4 g/mol
- Monoisotopic mass
- 360.15728849
Overview
Dibenzo-18-crown-6 is a crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18. It has a role as a phase-transfer catalyst. It is a member of benzenes and a crown ether.
Names & identifiers
- Preferred name
- Dibenzo-18-crown-6
- IUPAC
- 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaene
- English name
- Dibenzo-18-crown-6
- Molecular formula
- C20H24O6
- Molecular weight
- 360.4
Names & synonyms
DIBENZO-18-CROWN-614187-32-7Dibenzo-18-crown-6-etherCrown 18Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-2,3:11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadecane0A7W45JCS9Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecane2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaeneNSC-147771Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecaneDTXSID6022428
Show more names
DB18C6ibenzo-18-crown-66,7,9,10,12,13,15,16-Octahydrodibenzo[b,e][1,4,7,10,13,16]hexaoxacyclooctadecinecrown18crown-18DibenzocrownDibenzo-18-crown-8
CHEBI:358732Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-2,5,8,15,18,21-hexaoxatricyclo(20.4.0.09,14)hexacosa-1(26),9,11,13,22,24-hexaeneRefChem:132840DTXCID802428238-041-36,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecineMFCD00005098
Database identifiers
- CAS
14187-32-7- PubChem CID
- 26541
- DTXSID
DTXSID6022428- ChEMBL
CHEMBL345536- ChEBI
CHEBI:358732- UNII
- 0A7W45JCS9
- EC Number
- 238-041-3
- Nikkaji
- J14.747H
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 55.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 300
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesFusion temperature
LogP2.2
Physical DescriptionLight beige fibers or powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 162 · 162-164 °C (lit.)
- Boiling point
- 380 · 380-384 °C (679 mmHg)
- Density
- 1.1801 · 1.1801 (rough estimate)
- refractive index
- 1.52 · 1.5200 (estimate)
- Flash point
- 380 · 380-384°C/679mm
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.007 g/l · 0.007g/l
- form
- Fluffy Powder
- color
- White to slightly beige
- Water Solubility
- sparingly soluble
- Sensitive
- air sensitive
- λmax
- 277 nm · 277nm(CH2Cl2)(lit.)
- Merck
- 14 · 14,2602
- BRN
- 1162153 · 1162153
- InChI
- 1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2
- InChIKey
- YSSSPARMOAYJTE-UHFFFAOYSA-N
- SMILES
- C1COc2ccccc2OCCOCCOc3ccccc3OCCO1
- CAS DataBase Reference
- 14187 · 14187-32-7(CAS DataBase Reference)
- FDA UNII
- 0 A7W45JCS9 · 0A7W45JCS9
- NIST Chemistry Reference
- -18 · Dibenzo-18-crown-6(14187-32-7)
- EPA Substance Registry System
- 1 · Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro- (14187-32-7)
- UNSPSC Code
- 12352005 · 12352005
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319-H315-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P305+P351+P338+P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36-36/37/38-20/21/22
- Safety Statements
- 26 · 26-37/39-36
- WGK Germany
- 2 · 2
- RTECS
- 5386000 · HP5386000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29329995 · 29329995
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2600 mg/kg
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (35.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 64 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-
Dibenzob,k1,4,7,10,13,16hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A mild skin and moderate eye irritant; Causes convulsions, lung changes and other liver changes in oral lethal-dose studies of rats; [RTECS] Crown ethers have caused convulsions, liver injury, and dermatitis in experimental animals; A skin and strong eye irritant; [Alfa Aesar MSDS] See 18-Crown-6.
Hazard Classes and CategoriesSkin Irrit. 2 (35.9%)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- HP5386000
- hs_code
- 29329995
- Toxicity
- LD50 orally in Rabbit: 2600 mg/kg
- risk_code
- 36-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319-H315-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P305+P351+P338+P337+P313
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationDibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: ACTIVE
Applications
DescriptionDibenzo-18-crown-6 (DB18C6) is the first crown ether synthesized by Pedersen in 1967 and has the strongest binding affinity to a potassium cation (K+) among alkali metal cations. With the similarity of the sizes between K+ and the cavity of crown ether, it had long been believed that the binding selectivity comes from the size relationship between the metal cation and the cavity. However, it was reported that under identical experimental conditions, K+ bound strongly to all crown ethers (12-crown-4 to 24-crown-8) irrespective of the ring size among other cations such as Na+, Ca2+, and NH4+. Moreover, in the gas phase, 18-crown-6 (18C6) and dibenzo18-crown-6 (DB18C6) form preferential complexation in the order Li+ > Na+ > K+ > Rb+ > Cs+, while in the aqueous solution both of them show highest complexion capacity for K+ rather than Li+[1-2].
UsesDibenzo-18-crown-6, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is an important organic intermediate.
UsesCrown ether/Dibenzo-18-crown-6 for synthesis. CAS 14187-32-7, molar mass 360.41 g/mol.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Dibenzo-18-crown-6 is a crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18. It has a role as a phase-transfer catalyst. It is a member of benzenes and a crown ether.
Related reactions
94 records
Linked notes
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