N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide

Name: N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide
Brand: ALDRICH
Price: 125 USD
Availability: InStock

97%

Synonym(s):

N,N-Bis[2-(tosyloxy)ethyl]-p-toluenesulfonamide, N,O,O′-Tritosyldiethanolamine

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About This Item

Linear Formula:

CH₃C₆H₄SO₂N(CH₂CH₂OSO₂C₆H₄CH₃)₂

CAS Number:

16695-22-0

Molecular Weight:

567.69

Beilstein/REAXYS Number:

2406580

EC Number:

412-920-3

MDL number:

MFCD00026000

UNSPSC Code:

12352100

PubChem Substance ID:

24863761

NACRES:

NA.22

Key Documents

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Quality Level

100

assay

97%

mp

92-98 °C (lit.)

functional group

sulfonamide
tosylate

SMILES string

Cc1ccc(cc1)S(=O)(=O)OCCN(CCOS(=O)(=O)c2ccc(C)cc2)S(=O)(=O)c3ccc(C)cc3

InChI

1S/C25H29NO8S3/c1-20-4-10-23(11-5-20)35(27,28)26(16-18-33-36(29,30)24-12-6-21(2)7-13-24)17-19-34-37(31,32)25-14-8-22(3)9-15-25/h4-15H,16-19H2,1-3H3

InChI key

VJDZYMIEDBLSDT-UHFFFAOYSA-N

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Show Differences

1 of 4

This Item	D28000	G111030	203895
Sigma-Aldrich 380687 N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide	Sigma-Aldrich D28000 Diazald^®	Sigma-Aldrich G111030 DMT-dG(ib) Phosphoramidite	Sigma-Aldrich 203895 BTS
assay 97%	assay 99%	assay ≥99% (³¹P-NMR), ≥99.0% (reversed phase HPLC)	assay ≥95% (HPLC)
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 100
mp 92-98 °C (lit.)	mp 61-62 °C (lit.)	mp -	mp -
functional group sulfonamide	functional group -	functional group -	functional group -

Application

N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide may be used in the preparation of :

2-(p-benzamidobenzyl)-1,4,7-tris(p-tolylsulfonyl)-1,4,7-triazacyclononane, via reaction with N,N′-bis(p-tolylsulfonyl)-1-(p-benzamidobenzyl)ethylenediamine[1]
selectively protected aza-macrocycles[2]
carbon-bridged metallacarboranes[3]
tetrakis(phosphonomethyl)-substituted cyclododecanes[4]

pictograms

GHS07

signalword

Warning

hcodes

H317,H413

pcodes

P261 - P272 - P273 - P280 - P302 + P352 - P333 + P313

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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The Journal of Organic Chemistry, 56, 4904-4904 (1991)

Synthesis of 2-(p-thiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid: application of the 4-methoxy-2,3,6-trimethylbenzenesulfonamide protecting group in the synthesis of macrocyclic polyamines.

T J McMurry et al.

Bioconjugate chemistry, 4(3), 236-245 (1993-05-01)

A synthesis of the bifunctional chelator 2-(p-thiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid [2-(p-NCS-Bz)-NOTA] is described which illustrates the especial utility of the (4-methoxy-2,3,6-trimethylphenyl)sulfonyl (Mtr) protecting group as an alternative to the p-tolylsulfonyl (Ts) moiety commonly used for Richman-Atkins type cyclizations. Reaction of N,N'-bis(p-tolylsulfonyl)-1-(p-benzamidobenzyl)ethylenediami ne

Rec. Trav. Chim., 110, 124-124 (1991)

Inorganic Chemistry, 31, 3558-3558 (1992)

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N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide