| Identification | More | [Name]
Acetamidine hydrochloride | [CAS]
124-42-5 | [Synonyms]
A-AMINO-A-IMINOETHANE HYDROCHLORIDE
ACEDIAMINE HYDROCHLORIDE
ACETAMIDINE HCL
ACETAMIDINE HYDROCHLORIDE
ACETAMIDINIUM CHLORIDE
ETHANAMIDINE HYDROCHLORIDE
ETHANIMIDAMIDE HYDROCHLORIDE
ETHENYLAMIDINE HYDROCHLORIDE
Ethaneamidinehydrochloride
ethanimidamide,monohydrochloride
Ethylamidinehydrochloride
Acetalmidine hydrochioride
Acetamidine
ACECAMIDINE HYDROCHLORIDE
Acetamidine hydrochloride, 98+%
ethanamidine
Acetoamidine hydrochloride
Methylamidine hydrochloride | [EINECS(EC#)]
204-700-9 | [Molecular Formula]
C2H7ClN2 | [MDL Number]
MFCD00013016 | [Molecular Weight]
94.54 | [MOL File]
124-42-5.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE FINE CRYSTALLINE POWDER | [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 | [form ]
Crystalline Powder, Crystals and/or Chunks | [pka]
pK1: 1.60(+1) (25°C) | [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]
124-42-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
3 | [TSCA ]
Yes | [HS Code ]
29252000 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE FINE CRYSTALLINE POWDER | [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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