Acetamidine hydrochloride Chemical Properties

Melting point:

165-170 °C(lit.)

Boiling point:

129.78°C (rough estimate)

Density 

1.0596 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

pka

pK1: 1.60(+1) (25°C)

form 

Crystalline Powder, Crystals and/or Chunks

color 

White to cream

Water Solubility 

1 g/mL

Sensitive 

Hygroscopic

Merck 

14,44

BRN 

3591762

InChIKey

WCQOBLXWLRDEQA-UHFFFAOYSA-N

CAS DataBase Reference

124-42-5(CAS DataBase Reference)

EPA Substance Registry System

Ethanimidamide, monohydrochloride (124-42-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38

Safety Statements 

26-37/39

WGK Germany 

3

F 

3

TSCA 

Yes

HS Code 

29252000

MSDS

• Language:English Provider:Acetamidine hydrochloride
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Acetamidine hydrochloride Usage And Synthesis

Uses

Acetamidine Hydrochloride is a compound useful in organic synthesis.

Chemical Properties

WHITE FINE CRYSTALLINE POWDER

Uses

Acetamidine hydrochloride was used in the preparation of decarboxyectoine. It was also used in the synthesis of ethyl 4-(4-hydroxyphenyl)methylidene-2-methyl-5-oxo-1-imidazolacetate.

Application

Acetamidine hydrochloride can be used as an organic synthesis reactant for the preparation of other compounds such as 2-aminopyridine derivatives. Nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride can be used to synthesise 2-aminopyridine derivatives under catalyst-free conditions^[1]. This amination reaction has the advantages of high yield, high chemoselectivity and wide substrate adaptability using acetamidine hydrochloride as the ammonia source. In addition, an efficient heterogeneous copper-catalysed cascade reaction of aryl iodides with acetamidine hydrochloride produces primary amines^[2].

General Description

Acetamidine hydrochloride is an amidine salt and its conversion to 2,4,6-trimethyl-sym-triazine has been studied.

Purification Methods

The hydrochlorde can be recrystallised from small volumes of EtOH. Alternatively it is dissolved in EtOH, filtered, Et2O is added; filter the crystalline salt off under N2 and dry it in a vacuum desiccator over H2SO4. The salt is deliquescent and should be stored in a tightly stoppered container. Its solubility in H2O is 10% at room temperature and it is soluble in Me2CO. The free base reacts strongly alkaline in H2O. It has max 224nm ( 4000) in H2O. The picrate has m 252o (sintering at ~245o). [Dox Org Synth Coll Vol I 5 1941, Davies & Parsons Chem Ind (London) 628 1958, Barnes et al. J Am Chem Soc 62 1286 1940 give m 177-178o, Beilstein 2 H 185, 2 I 85, 2 II 183, 2 III 416, 2 IV 428.]

References

[1] YIBIAO LI . Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride1[J]. Organic & Biomolecular Chemistry, 2018, 16 41: Pages 7564-7567. DOI:10.1039/c8ob02129e.
[2] XUE HUANG. A highly efficient heterogeneous copper-catalysed cascade reaction of aryl iodides with acetamidine hydrochloride leading to primary arylamines[J]. Journal of Chemical Research-s, 2017, 46 1: 315-320. DOI:10.3184/174751917X14931195075580.

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