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Merck
CN

529249

2-Chloro-1,3-dimethylimidazolinium chloride

for peptide synthesis

Synonym(s):

2-Chloro-4,5-dihydro-1,3-dimethyl-1H-imidazolium chloride, DMC

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About This Item

Empirical Formula (Hill Notation):
C5H10Cl2N2
CAS Number:
Molecular Weight:
169.05
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
MDL number:
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Product Name

2-Chloro-1,3-dimethylimidazolinium chloride,

form

crystalline

Quality Level

reaction suitability

reaction type: Coupling Reactions

mp

133-140 °C (lit.)

application(s)

peptide synthesis

functional group

chloro

SMILES string

[Cl-].CN1CC[N+](C)=C1Cl

InChI

1S/C5H10ClN2.ClH/c1-7-3-4-8(2)5(7)6;/h3-4H2,1-2H3;1H/q+1;/p-1

InChI key

AEBBXVHGVADBHA-UHFFFAOYSA-M

Application

Activating agent in total synthesis of macroviracin A, cycloviracin B1, and cyclic silanes.
Reagent for synthesis of:
Tagged glucose as an intermediate in the synthesis of branched oligosaccharides
Fluorescent chemosensors
1,2-Diamines as inhibitors of co-activator associated arginine methyltransferase 1
Allosteric glucokinase activators

Reactant for synthesis of:
Organic azides from primary amines

Reagent for aza-Henry reactions


pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Articles

N-Acylimidazoles and carbonylimidazoles are reactive intermediates used for amino compound acylation, surpassing DCC as coupling reagents.


Shunya Takahashi et al.
The Journal of organic chemistry, 69(13), 4509-4515 (2004-06-19)
The C(2)-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C(22)-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The
Alois Fürstner et al.
Journal of the American Chemical Society, 125(43), 13132-13142 (2003-10-23)
The first total synthesis of the antivirally active glycolipid cycloviracin B(1) (1) is described. The approach is based on a two-directional synthesis strategy which constructs the C(2)()-symmetrical macrodiolide core of the target by an efficient template-directed macrodilactonization reaction promoted by
Journal of Organometallic Chemistry, 686, 175-182 (2003)



Global Trade Item Number

SKUGTIN
529249-100G04061833548158
529249-5G04061832557977
529249-25G04061832557960