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442666

Sigma-Aldrich

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

97%

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C16H24O14
Número CAS:
61696-54-6
Peso molecular:
440.35
Beilstein:
4240375
Número MDL:
MFCD00040514
Código UNSPSC:
12352005
ID de substância PubChem:
24867945
NACRES:
NA.22

Ensaio

97%

atividade óptica

[α]20/D +62°, c = 1 in methanol

pf

210-212 °C (lit.)

grupo funcional

carboxylic acid
ether

cadeia de caracteres SMILES

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

chave InChI

FZERLKNAJSFDSQ-DDHJBXDOSA-N

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Aplicação

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

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Escolha uma das versões mais recentes:

Certificados de análise (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)
Myung Ho Hyun
Methods in molecular biology (Clifton, N.J.), 970, 165-176 (2013-01-04)
Liquid chromatographic resolution of racemic compounds containing a primary amino group has been known to be most successful when chiral crown ether-based chiral stationary phases (CSPs) are used. Among various crown ether-based CSPs, the stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid
Areum Lee et al.
Journal of chromatography. A, 1218(26), 4071-4076 (2011-05-25)
A liquid chromatographic chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied for the first time to the resolution of biologically important 1-aryl-1,2,3,4-tetrahydroisoquinolines. The unusual resolution of cyclic secondary amino compounds on a chiral crown ether-based CSP was quite
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
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