(Methoxycarbonylsulfamoyl)triethylammonium hydroxide

Base Information

• Chemical Name: (Methoxycarbonylsulfamoyl)triethylammonium hydroxide
• CAS No.: 29684-56-8
• Molecular Formula: C8H18N2O4S
• Molecular Weight: 238.308
• Hs Code.: 29299090
• European Community (EC) Number: 629-648-8
• Wikipedia: Burgess_reagent
• Mol file: 29684-56-8.mol

Synonyms:(Methoxycarbonylsulfamoyl)triethylammonium hydroxide;29684-56-8;[methoxycarbonylsulfamoyl]triethylammonium hydroxide;4-Piperidone(Hclform);SCHEMBL117889;VHKIEYIESYMHPT-UHFFFAOYSA-N;AKOS030228484;carbomethoxysulfamoyltriethylammonium hydroxide;methoxycarbonylsulfamoyltriethylammonium hydroxide;methoxycarbonylsulphamoyltriethylammonium hydroxide;methoxy-carbonylsulfamoyltriethylammonium hydroxide;methoxycarbonylsulfa-moyl-triethylammonium hydroxide;methoxycarbonylsulfamoyl triethylammonium hydroxide;methoxycarbonylsulphamoyl-triethylammonium hydroxide;(methoxycarbonyl-sulfamoyl)triethylammonium hydroxide;(methoxycarbonylsulfamoyl) triethylammonium hydroxide;(methoxycarbonylsulfamoyl)-triethylammonium hydroxide;(methoxycarbonylsulfamoyl)triethyl ammonium hydroxide;(methoxycarbonylsulfamoyl)triethyl-ammonium hydroxide;(methoxy-carbonylsulfamoyl) triethylammonium hydroxide;(methoxycarbonylsulfamoyl)-triethyl ammonium hydroxide;(methoxycarbonylsulfamoyl)-triethyl-ammonium hydroxide;methyl N-[(triethylazaniumyl)sulfonyl]carbamate oxidanide

Chemical Property of (Methoxycarbonylsulfamoyl)triethylammonium hydroxide

Chemical Property:

• Appearance/Colour: off-white crystals
• Melting Point: 76-79 ºC
• Refractive Index: 1.6300 (estimate)
• PSA: 68.82000
• Density: 1.3023 (rough estimate)
• LogP: 2.32860
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in organic solvents.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 256.10929292
• Heavy Atom Count: 16
• Complexity: 295

Purity/Quality:

98% ^*data from raw suppliers

BurgessReagent ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[N+](CC)(CC)S(=O)(=O)NC(=O)OC.[OH-]
• General Description: The Burgess reagent is a versatile chemical agent that functions both as a carbamate source and a desulfurizing agent, enabling the mild and efficient synthesis of carbamate-protected guanidines from primary amines. It facilitates the conversion of thioureas into differentially N,N'-diprotected guanidines through stepwise or one-pot procedures, with the ability to adjust carbamoyl units for selective deprotection to yield N-monoprotected guanidines. Its reactivity and mechanistic role in forming and rearranging intermediates make it valuable for constructing guanidine derivatives under controlled conditions.

Technology Process of (Methoxycarbonylsulfamoyl)triethylammonium hydroxide

There total 2 articles about (Methoxycarbonylsulfamoyl)triethylammonium hydroxide 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: 85.0%

methyl chlorosulfonylcarbamate (36914-92-8) + triethylamine (121-44-8) → Burgess Reagent (29684-56-8)

Guidance literature:

In benzene; Ambient temperature;

Reference yield:

→ Burgess Reagent (29684-56-8)

Guidance literature:

/BRN= 777288/, Triaethylamin, Bzl.;

Reference yield: 97.0%

tert-Butyl (3R)-6-cyclohexyl-3-({[(1S)-2-ethoxy-1-(hydroxymethyl)-2-oxoethyl]amino}carbonyl)hexanoate (348623-62-1) + Burgess Reagent (29684-56-8) → ethyl (4S)-2-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-4,5-dihydro-1,3-oxazole-4-carboxylate (348623-63-2)

Guidance literature:

In tetrahydrofuran; ethyl acetate;

upstream raw materials:

methyl chlorosulfonylcarbamate

triethylamine

Downstream raw materials:

methyl N-benzylcarbamate

(R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline)

Refernces

A mild method for the synthesis of carbamate-protected guanidines using the burgess reagent

10.1021/ol5002208

The study presents a mild method for synthesizing carbamate-protected guanidines from primary amines using the Burgess reagent. The researchers found that various thioureas derived from primary amines and isothiocyanates react with the Burgess reagent to produce the corresponding guanidines through either a stepwise or one-pot procedure. The Burgess reagent serves dual roles as a carbamate source and a desulfurizing agent, allowing for the preparation of differentially N,N'-diprotected guanidines. By adjusting the carbamoyl units of the isothiocyanates and the Burgess reagent, these guanidines can be obtained, and selective deprotection of the products yields N-monoprotected guanidines. The study explores the reactivity of different thioureas and Burgess-type reagents, examines the generality and scope of the reaction with various substrates, and proposes a reaction mechanism involving the formation and rearrangement of an intermediate.

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