methyl N-[(chloroimino)[(methoxycarbonyl)amino]methyl]carbamate

EN300-3543882

Product class

Building Blocks

CAS number

1596379-00-8

MW

209.59

Purity

95%

Stock Availability

UA, US, EU

Lead time

1-5 days delivery time

Chlorinating reagent for hetero arens

Palau'chlor is a powerful chlorinating reagent that is at the same time reactive and safe. It is a white powder, soluble in CH2Cl2, and CHCl3, partially soluble in acetonitrile, DMSO, but insoluble in alcohols[1]. The reagent can be stored under air and without any precautions. This reagent finds application in the direct chlorination of various electron-rich (hetero)arenes, methyl ketones, enones, and conjugated systems. It is particularly effective in chlorinating heteroarenes like imidazoles, pyrroles, indoles, pyrazoles, and indazoles[2]. Palau'chlor's high regiochemical selectivity and excellent tolerance for different functional groups make it a valuable tool for chlorinating a wide range of natural compounds containing arene.

Synonyms: 2-chloro-1,3-bis(methoxycarbonyl) guanidine; CBMG

1. Palau’chlor. Pan C.-M.; Ishihara Y.; Baran P. S. Encyclopedia of Reagents for Organic Synthesis 2016, 1–2. DOI: 10.1002/047084289X.rn01901 2. Palau’chlor: A Practical and Reactive Chlorinating Reagent. Rodriguez R. A.; Pan C.-M.; Yabe Y.; Kawamata Y.; Eastgate M. D.; Baran P. S. J Am Chem Soc 2014, 136 (19), 6908–6911. DOI: 10.1021/ja5031744

Name:

methyl N-[(chloroimino)[(methoxycarbonyl)amino]methyl]carbamate

SMILES:

COC(=O)NC(=NCl)NC(=O)OC

CAS number:

1596379-00-8

Product class:

Building Blocks

ACD number:

MFCD28016343

CLogP:

1.132

Class:

Other

Formula:

C₅H₈ClN₃O₄

Subclass:

Other

MW:

209.59