CAS 294-93-9 1,4,7,10-Tetraoxacyclododecane (HCID 9269)

Overview

12-crown-4 is a crown ether that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 have been replaced by oxygen atoms. It is a saturated organic heteromonocyclic parent and a crown ether.

Names & identifiers

Preferred name: 1,4,7,10-Tetraoxacyclododecane
IUPAC: 1,4,7,10-tetraoxacyclododecane
English name: 12-Crown-4
Molecular formula: C8H16O4
Molecular weight: 176.21

Names & synonyms

12-Crown-4294-93-91,4,7,10-TETRAOXACYCLODODECANEEOCTEthylene oxide cyclic tetramerK6069P2C2ACHEBI:32399DTXSID6059780RefChem:73006DTXCID2037978206-036-512-Crown-4 ether

Show more names

Crown12-C-412C412 C 412-Crown-4,97%LITHIUM IONOPHORE V

12-crown-4-ether12-Crown 4-EtherMFCD00005103CCRIS 157SCHEMBL2367251,4,7,10tetraoxa-Cyclododecane1,4,7,10-tetraoxacyclo-dodecaneLS-13523

Database identifiers

CAS: 294-93-9
PubChem CID: 9269
DTXSID: DTXSID6059780
ChEMBL: CHEMBL4566196
ChEBI: CHEBI:32399
UNII: K6069P2C2A
EC Number: 206-036-5
Nikkaji: J66.351D

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 36.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 12
Formal charge: 0
Complexity: 65.1

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

LogP-0.04

Physicochemical properties

Melting point: 16 °C · 16 °C (lit.)
Boiling point: 61 · 61-70 °C/0.5 mmHg (lit.)
Density: 1.089 g/mL · 1.089 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.463(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: Liquid After Melting
Specific Gravity: 1.115 · 1.115 (20℃)
color: Clear colorless to slightly yellow
Water Solubility: MISCIBLE
Sensitive: Air Sensitive
BRN: 1363064 · 1363064
InChI: 1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2
InChIKey: XQQZRZQVBFHBHL-UHFFFAOYSA-N
SMILES: C1COCCOCCOCCO1
CAS DataBase Reference: 294 · 294-93-9(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 6069 P2C2A · K6069P2C2A
NIST Chemistry Reference: 12 · 12-Crown-4(294-93-9)
EPA Substance Registry System: 1 · 1,4,7,10-Tetraoxacyclododecane (294-93-9)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 330 · H330
Precautionary statements: 304 · P304+P340+P310
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: T+,Xn,Xi
Risk Statements: 26 · 26-36/37/38-20/21/22
Safety Statements: 28 · 28-36/37-45-36-26
RIDADR: 2810 · UN 2810
WGK Germany: 3 · 3
RTECS: 550000 · XF0550000
F: 3 · 3-9-23
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29329995 · 29329995
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 1 Inhalation · Acute Tox. 1 Inhalation
Toxicity: 50 oral · LD50 oral in rat: 2830mg/kg

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H319 (11.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P260, P264+P265, P271, P280, P284, P304+P340, P305+P351+P338, P316, P320, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 1,4,7,10-Tetraoxacyclododecane

1,4,7,10-Tetraoxacyclododecane: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesEye Irrit. 2 (11.1%)

Safety data

F: 3-9-23
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
rtecs: XF0550000
ridadr: UN 2810
hs_code: 29329995
Toxicity: LD50 oral in rat: 2830mg/kg
risk_code: 26-36/37/38-20/21/22
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+,Xn,Xi
safety_code: 28-36/37-45-36-26
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: III
Hazard statements: H330
Hazard Classifications: Acute Tox. 1 Inhalation
Precautionary statements: P304+P340+P310

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1,4,7,10-Tetraoxacyclododecane: ACTIVE

Applications · 3 items

UsesIt serves as an aprotic "solvent" for alkali metals, the sodium solution is a strong reducing agent.

Uses12-Crown-4 can be used as: A promoter in the synthesis of poly(diethylsiloxane) (PDES) from monomer hexaethylcyclotrisiloxane using NaOH as a catalyst via anionic ring-opening polymerization. As an additive in the preparation of triarylmethane derivatives by palladium-catalyzed cross coupling reaction of aryl bromides with diarylmethane derivatives. A phase transfer catalyst in organic synthesis.

General Description12-Crown-4 is a crown ether generally used as a ligand in coordination chemistry. It is also known as lithium ionophore because of its strong chelating property specific to lithium cation.