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442666

Sigma-Aldrich

(+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid

97%

Sinonimo/i:

(2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid

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About This Item

Formula empirica (notazione di Hill):
C16H24O14
Numero CAS:
61696-54-6
Peso molecolare:
440.35
Beilstein:
4240375
Numero MDL:
MFCD00040514
Codice UNSPSC:
12352005
ID PubChem:
24867945
NACRES:
NA.22

Saggio

97%

Attività ottica

[α]20/D +62°, c = 1 in methanol

Punto di fusione

210-212 °C (lit.)

Gruppo funzionale

carboxylic acid
ether

Stringa SMILE

OC(=O)[C@@H]1OCCOCCO[C@H]([C@@H](OCCOCCO[C@H]1C(O)=O)C(O)=O)C(O)=O

InChI

1S/C16H24O14/c17-13(18)9-10(14(19)20)29-7-3-26-4-8-30-12(16(23)24)11(15(21)22)28-6-2-25-1-5-27-9/h9-12H,1-8H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24)/t9-,10-,11-,12-/m1/s1
FZERLKNAJSFDSQ-DDHJBXDOSA-N

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Applicazioni

Derived tetracarboxylic acid chloride of this crown ether reacts with meta- and para-xylylene diamines to form chiral captands in high yields.[1] Used as a chiral selector in capillary zone electrophoresis for the separation of a variety of optically active amines.[2] Synthesis of monoamides.[3]

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
07624JQ
07408DR
06812EN
05905BA
05623BS

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Crown ether/Dicyclohexyl-18-crown-6 (mixture of cis- and trans-isomers) for synthesis

Sigma-Aldrich

8.11866

Crown ether/Dicyclohexyl-18-crown-6

Crown ether/Dibenzo-18-crown-6 for synthesis

Sigma-Aldrich

8.11731

Crown ether/Dibenzo-18-crown-6

1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane ≥96%

Sigma-Aldrich

295809

1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane

12-Crown-4 98%

Sigma-Aldrich

194905

12-Crown-4

Dibenzo-18-crown-6 98%

Sigma-Aldrich

158399

Dibenzo-18-crown-6

18-Crown-6 ≥99.0%

Sigma-Aldrich

274984

18-Crown-6

Anna R M Hyyryläinen et al.
Journal of the American Society for Mass Spectrometry, 20(7), 1235-1241 (2009-03-20)
Chiral differentiation of four enantiomeric pairs of beta-amino acids, cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclopentanecarboxylic acids (cyclopentane beta-amino acids), and cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclohexanecarboxylic acids (cyclohexane beta-amino acids) was performed successfully by using host-guest complexes and ion/molecule reactions. The experiments
Myung Ho Hyun et al.
Chirality, 20(3-4), 325-329 (2007-07-07)
A doubly tethered chiral stationary phase (CSP) prepared by bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid to doubly tethered primary aminoalkyl silica gel was used for the resolution of various beta-amino acids. All the beta-amino acids tested were resolved quite well, the separation (alpha)
Hee Jung Choi et al.
Journal of chromatography. A, 1164(1-2), 235-239 (2007-08-04)
Two types of secondary amino alcohols were successfully resolved on a liquid chromatographic chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. The secondary amino alcohols containing a secondary amino group connected directly to the stereogenic center were resolved much better than
Areum Lee et al.
Chirality, 22(7), 693-698 (2009-12-17)
Flecainide, an antiarrythmic agent, and its analogs were resolved on a high performance liquid chromatographic chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid with the use of a mobile phase consisting of methanol-acetonitrile-trifluoroacetic acid-triethylamine (80/20/0.1/0.3, v/v/v/v). The chiral resolution was
Man-Jeong Paik et al.
Journal of chromatography. A, 1274, 1-5 (2013-01-08)
Chiral crown ethers have been widely used in the resolution of various chiral compounds containing a primary amino group. Covalently bonded chiral stationary phases derived from (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) were developed in our groups and utilized for the resolution for
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