Basic information
- Standard SMILES
C1COCCOCCOCCOCCO1- InChIKey
VFTFKUDGYRBSAL-UHFFFAOYSA-N- Molecular formula
- C10H20O5
- Average molar mass
- 220.26 g/mol
- Monoisotopic mass
- 220.13107374
Overview
15-crown-5 is a saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether. It is a saturated organic heteromonocyclic parent and a crown ether.
Names & identifiers
- Preferred name
- 15-Crown-5
- IUPAC
- 1,4,7,10,13-pentaoxacyclopentadecane
- English name
- 15-Crown-5
- Molecular formula
- C10H20O5
- Molecular weight
- 220.26
Names & synonyms
15-Crown-533100-27-51,4,7,10,13-PENTAOXACYCLOPENTADECANEDTXSID70677467G6K9SB27YCHEBI:32401RefChem:78755DTXCID9038634251-379-615-Crown-5 ether15-Crown 5-EtherMFCD00005110
Show more names
crown ether15-Crown-615-Crown-5 98%15-ether-5Crownethers15-CROWN-5,99%JACS-33100-27-5
AKOS005622525CS-W00745115C51, 4, 7, 10, 13-pentaoxacyclopentadecane15-Crown-5, Vetec(TM) reagent grade, 98%EN300-67436101,4,10,13-PentaoxacyclopentadecaneEYO
Database identifiers
- CAS
33100-27-5- PubChem CID
- 36336
- DTXSID
DTXSID7067746- ChEMBL
CHEMBL156289- ChEBI
CHEBI:32401- UNII
- 7G6K9SB27Y
- EC Number
- 251-379-6
- Nikkaji
- J53.730F
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 46.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 86.2
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesChemical shift
LogP-0.48
Vapor Pressure0.00144 [mmHg]
Physical DescriptionClear colorless liquid; [Aldrich MSDS]
Physicochemical properties
- Melting point
- -20 °C · -20°C(lit.)
- Boiling point
- 93 · 93-96 °C/0.05 mmHg (lit.)
- Density
- 1.113 g/mL · 1.113 g/mL at 20 °C (lit.)
- vapor pressure
- 0.5 · 0.5-0.82Pa at 20-25℃
- refractive index
- 20 · n20/D 1.465(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- room temp
- solubility
- Miscible with organic solvents.
- form
- Liquid
- color
- Clear colorless to light yellow
- Specific Gravity
- 1.109 · 1.109
- Water Solubility
- MISCIBLE
- Sensitive
- Hygroscopic
- BRN
- 1618144 · 1618144
- Stability
- Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air.
- InChI
- 1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
- InChIKey
- VFTFKUDGYRBSAL-UHFFFAOYSA-N
- SMILES
- O1CCOCCOCCOCCOCC1
- LogP
- -0.9 at · -0.9 at 20℃ and pH7.7
- Surface tension
- 68.5 mN/m · 68.5mN/m at 1g/L and 20℃
- CAS DataBase Reference
- 33100 · 33100-27-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NIST Chemistry Reference
- 15 · 15-Crown-5(33100-27-5)
- EPA Substance Registry System
- 1 · 1,4,7,10,13-Pentaoxacyclopentadecane (33100-27-5)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/38-36-20/22-36/37/38-20/21/22
- Safety Statements
- 26 · 26-39-36
- RIDADR
- 2810 · 2810
- WGK Germany
- 3 · 3
- RTECS
- 200000 · SB0200000
- F
- 10 · 10-21
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29329995 · 29329995
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 1410 mg/kg DCTODJ 1,339,78
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 176 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 14-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33251
Crown ether 15-crown-5: 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 tremor, convulsions, and weight loss in dermal lethal-dose studies of rabbits; Causes tremor, convulsions, weight loss, tetany, other changes in lungs, and other liver changes in intraperitoneal lethal-dose studies of rats; [RTECS] An irritant; Harmful by ingestion; [Aldrich MSDS] See 18-Crown-6.
Peroxide Forming Chemical
15-Crown-5 ether
D*: Other compounds that may form peroxides
1 samples, >8 yrs, 1 ppm
Management of time-sensitive chemicals (JCHAS)
Hazard Classes and CategoriesAcute Tox. 4 (98.9%)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- F
- 10-21
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SB0200000
- ridadr
- 2810
- hs_code
- 29329995
- Toxicity
- LD50 orl-rat: 1410 mg/kg DCTODJ 1,339,78
- risk_code
- 22-36/38-36-20/22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-39-36
- hazard_class
- 6.1(b)
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Uses & manufacturing
General Manufacturing Information1,4,7,10,13-Pentaoxacyclopentadecane: ACTIVE
Applications
Uses15-Crown-5 is used as an efficient phase transfer catalyst and as a complexing agent. It is used to isolate oxonium ion (H7O3)+ salts especially from a solution of tetrchloroauric acid. It catalyzes the O-alkylation of the sodium salts of carboxylic acids in the penicillin and cephalosporin series, thereby facilitating esterification reaction without usage of acid. It is also used to facilitate the Williamson synthesis of ethers with hindered alcohols and sodium hydride. It is used with lithium aluminum hydride, for performing reduction reactions in hydrocarbon solvents. Further, it is involved in the Horner-Wadsworth-Emmons reaction to prepare stilbenes from aldehydes.
General Description15-Crown-5 is a crown ether generally used as a ligand in coordination chemistry because of its strong chelating property with certain alkali cations to form complexes. Some derivatives of 15-crown-5 are used as sensors and probes in different physical-chemical processes, phase-transfer reactions, and selective capture of ions for separation and transport.
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Additional notes
DefinitionChEBI: A saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.
Related reactions
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