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

Base Information

• Chemical Name: N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide
• CAS No.: 16695-22-0
• Molecular Formula: C25H29 N O8 S3
• Molecular Weight: 567.705
• Hs Code.: 2935009090
• European Community (EC) Number: 412-920-3,627-486-2
• NSC Number: 106624
• DSSTox Substance ID: DTXSID20295976
• Nikkaji Number: J986.050I
• Wikidata: Q82036243
• Mol file: 16695-22-0.mol

Synonyms:16695-22-0;N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide;(Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate);N,N-Bis[2-(tosyloxy)ethyl]-p-toluenesulfonamide;2-[(4-methylphenyl)sulfonyl-[2-(4-methylphenyl)sulfonyloxyethyl]amino]ethyl 4-methylbenzenesulfonate;EC 412-920-3;N-tosyl-bis(2-tosyloxyethyl)amine;MFCD00026000;NSC 106624;N,N-bis(2-(p-toluenesulfonyloxy)ethyl)-p-toluenesulfonamide;NSC106624;N,O,O'-Tritosyldiethanolamine;N,O,O?-Tritosyldiethanolamine;SCHEMBL2335489;DTXSID20295976;N-Tosylbis[2-(tosyloxy)ethyl]amine;AKOS002312791;NSC-106624;s10574;SY052009;B4136;CS-0153041;FT-0637402;(N,O,O'-tri(p-toluen-sulfonyl)-diethanolamine);A882291;J-010324;n,n-bis(2-(p-tolylsulfonyloxy)ethyl)p-toluenesulfonamide;N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide, 97%;N-(tolyl-p-sulfonyl)-3-aza-1,5-bis(tolyl-p-sulfonyloxy)pentane;2,2'-(tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate);4-methyl-N,N-bis[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]benzenesulfonamide;N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide, technical, >=95% (HPLC);[(4-Methylbenzene-1-sulfonyl)azanediyl]di(ethane-2,1-diyl) bis(4-methylbenzene-1-sulfonate);2-(N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}-4-methylbenzenesulfonamido)ethyl 4-methylbenzene-1-sulfonate;2-[[(4-methylphenyl)sulfonyl](2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)amino]ethyl 4-methyl-1-benzenesulfonate

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

Chemical Property:

• Vapor Pressure: 2.6E-21mmHg at 25°C
• Melting Point: 92-98 °C(lit.)
• Boiling Point: 732.4°Cat760mmHg
• Flash Point: 396.8°C
• PSA: 149.26000
• Density: 1.345g/cm³
• LogP: 6.65590
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 567.10553040
• Heavy Atom Count: 37
• Complexity: 945

Purity/Quality:

99.9% ^*data from raw suppliers

N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 43-53
• Safety Statements: 24-37-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N(CCOS(=O)(=O)C2=CC=C(C=C2)C)CCOS(=O)(=O)C3=CC=C(C=C3)C
• Uses: N,N-BIS[2-(P-TOLYLSULFONYLOXY)ETHYL]-P-TOLUENESULFONAMIDE used to prepare selectively protected aza-macrocycles,1 carbon-bridged metallacarboranes,2 and tetrakis(phosphonomethyl)-substituted cyclododecanes.3 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)ethylenediamineselectively protected aza-macrocyclescarbon-bridged metallacarboranestetrakis(phosphonomethyl)-substituted cyclododecanes

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

There total 8 articles about N,N-Bis[2-(p-tolylsulfonyloxy)ethyl]-p-toluenesulfonamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,2'-iminobis[ethanol] (111-42-2) + p-toluenesulfonyl chloride (98-59-9) → N,N-bis(tosyloxyethyl)-p-toluenesulfonamide (16695-22-0)

Guidance literature:

2,2'-iminobis[ethanol]; With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.2174/1570178612666150108001219

Reference yield: 80.0%

toluene sulfonyl chloride + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(tosyloxyethyl)-p-toluenesulfonamide (16695-22-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo3012896

Reference yield: 79.7%

→ N,N-bis(tosyloxyethyl)-p-toluenesulfonamide (16695-22-0)

Guidance literature:

upstream raw materials:

2,2'-iminobis[ethanol]

p-toluenesulfonyl chloride

N-tosyldiethanolamine

Downstream raw materials:

N,N-bis-(2-fluoro-ethyl)-toluene-4-sulfonamide

cyclen tetratosylate

1,4,7,11-tetratosyl-1,4,7,11-tetraazacyclotetradecane

1,4,7,11,14-pentatosyl-1,4,7,11,14-pentaazacycloheptadecane

Refernces

• 1、 Davis, Carol A.,Duckworth, Paul A.,Lindoy, Leonard F.,Moody, Wayne E.. "New Macrocyclic Ligands. VI. 20- to 22-Membered Dibenzo-Substituted Rings Incorporating Mixed Nitrogen, Oxygen and/or Sulfur Donor Atoms". . p. 1819 - 1826. Retrieved 1995.
• 2、 Sabatini,Fabbrizzi. "". . p. 438,439. Retrieved 1979.
• 3、 -. "Preparation method of (by machine translation)". Paragraph 0099-0103. . Retrieved 2019/11/28.