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Key Documents

COO/COA

671304

(R)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol trimethylsilyl ether hydrochloride

Name: (<I>R</I>)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol trimethylsilyl ether hydrochloride
Brand: ALDRICH

97%

Synonym(s):

(R)-α,α-Bis(3,5-dimethylphenyl)prolinol-trimethylsilyl ether hydrobromide, (R)-2-[Bis(3,5-dimethylphenyl)(trimethylsilyloxy)methyl]pyrrolidine hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₄H₃₅NOSi · HCl

CAS Number:

1217450-13-9

Molecular Weight:

418.09

MDL number:

MFCD10566968

UNSPSC Code:

12352005

PubChem Substance ID:

329760416

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assay

≥96.5% (HPLC)
97%

optical purity

enantiomeric excess: ≥96.5% (HPLC)

mp

159-163 °C

storage temp.

2-8°C

SMILES string

Cl.Cc1cc(C)cc(c1)C(O[Si](C)(C)C)([C@H]2CCCN2)c3cc(C)cc(C)c3

InChI

1S/C24H35NOSi.ClH/c1-17-11-18(2)14-21(13-17)24(26-27(5,6)7,23-9-8-10-25-23)22-15-19(3)12-20(4)16-22;/h11-16,23,25H,8-10H2,1-7H3;1H/t23-;/m1./s1

InChI key

WTDMRDKYLPARGO-GNAFDRTKSA-N

Application

Catalyst for enantioselective ene reaction[1]; dienamine catalysis[2]; catalyst for alpha-sulfenylation of aldehydes[3]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

1332260V

1332260

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Enantioselective ene reaction of cyclopentadiene and alpha,beta-enals catalyzed by a diphenylprolinol silyl ether.

Hiroaki Gotoh et al.

Angewandte Chemie (International ed. in English), 45(41), 6853-6856 (2006-09-27)

Dienamine catalysis: organocatalytic asymmetric gamma-amination of alpha,beta-unsaturated aldehydes.

Søren Bertelsen et al.

Journal of the American Chemical Society, 128(39), 12973-12980 (2006-09-28)

A new concept in organocatalysis is presented, the direct asymmetric gamma-functionalization of alpha,beta-unsaturated aldehydes. We disclose that secondary amines can invert the usual reactivity of alpha,beta-unsaturated aldehydes, enabling a direct gamma-amination of the carbonyl compound using azodicarboxylates as the electrophilic

Enantioselective organocatalyzed alpha sulfenylation of aldehydes.

Mauro Marigo et al.

Angewandte Chemie (International ed. in English), 44(5), 794-797 (2005-01-20)

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