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194905

12-Crown-4

98%

Synonym(s):

1,4,7,10-Tetraoxacyclododecane

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1 g

Available to ship TODAYfromMILWAUKEE

$70.00
5 g

Available to ship TODAYfromMILWAUKEE

$163.00

About This Item

Empirical Formula (Hill Notation):
C8H16O4
CAS Number:
Molecular Weight:
176.21
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-036-5
Beilstein/REAXYS Number:
1363064
MDL number:
Assay:
98%
Form:
liquid

$70.00


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Quality Segment

assay

98%

form

liquid

reaction suitability

core: crown ether

refractive index

n20/D 1.463 (lit.)

bp

61-70 °C/0.5 mmHg (lit.)

mp

16 °C (lit.)

density

1.089 g/mL at 25 °C (lit.)

functional group

ether

SMILES string

C1COCCOCCOCCO1

InChI

1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2

InChI key

XQQZRZQVBFHBHL-UHFFFAOYSA-N

General description

12-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.

Application

12-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.



pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 1 Inhalation

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter



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Articles

Crown ethers and cryptands, complexing agents able to selectively bind metal cations, are vital for diverse synthesis and analytical applications.


Multilayered ion-imprinted membranes with high selectivity towards Li+ based on the synergistic effect of 12-crown-4 and polyether sulfone
Lu J, et al.
Applied Surface Science, 427, 931-941 (2018)
Márkó Grabarics et al.
The Analyst, 145(19), 6313-6333 (2020-07-28)
In the past decade, ion mobility spectrometry (IMS) in combination with mass spectrometry (IM-MS) became a widely employed technique for the separation and structural characterization of ionic species in the gas phase. Similarly to chromatography, where studies on the mechanism
Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp 3 C-H bonds in diarylmethanes
Bellomo A, et al.
Chemical Science, 4(2), 849-857 (2013)



Global Trade Item Number

SKUGTIN
194905-5G04061838761378
194905-1G04061838096395

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. Regarding product 194905- 12-Crown-4. I received the product in liquid form, as mentioned. I want to know in which liquid the 12-Crown-4 is dissolved.Is it in any solvent or water?

    1 answer
    1. This compound is a neat or pure liquid with a melting point of 16 °C. The product has not been diluted in any solvent or buffer.

      Helpful?

  3. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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