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529249

Sigma-Aldrich

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:
37091-73-9
Molecular Weight:
169.05
MDL number:
MFCD09039290
UNSPSC Code:
12352005
PubChem Substance ID:
24877665
NACRES:
NA.22

product name

2-Chloro-1,3-dimethylimidazolinium chloride,

form

crystalline

reaction suitability

reaction type: Coupling Reactions

mp

133-140 °C (lit.)

application(s)

peptide synthesis

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

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
Activating agent in total synthesis of macroviracin A, cycloviracin B1, and cyclic silanes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Yanzi Gou et al.
Journal of polymer science. Part A, Polymer chemistry, 51(12), 2588-2597 (2013-06-14)
Synthetic glycopolymers are important natural oligosaccharides mimics for many biological applications. To develop glycopolymeric drugs and therapeutic agents, factors that control the receptor-ligand interaction need to be investigated. A library of well-defined glycopolymers has been prepared by the combination of
Shonoi A Ming et al.
Glycobiology, 28(2), 100-107 (2017-12-12)
Neisseria meningitidis Group X is an emerging cause of bacterial meningitis in Sub-Saharan Africa. The capsular polysaccharide of Group X is a homopolymer of N-acetylglucosamine α(1-4) phosphate and is a vaccine target for prevention of disease associated with this meningococcal

Articles

Imidazolium-Derived Reagents

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

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