| Identification | More | [Name]
Ethyl acetimidate hydrochloride | [CAS]
2208-07-3 | [Synonyms]
EAH
ETHYL ACETAMIDATE HCL
ETHYL ACETIMIDATE HYDROCHLORIDE
1-ethoxyethylideneammonium chloride
ACETIMIDIC ACID ETHYL ESTER
ETHYL ACETIMIDATE HCL
Ethyl acetimidate hydrochloride, 98.5%
EthyliminoacetateHCl
ethylacetimidate,HCl98.5%
ethyl iminoacetate hydrochloride
Ethanimidic acid, ethyl ester, hydrochloride
(1-Ethoxyethane)imine hydrochloride
1-Ethoxy-1-iminoethane·hydrochloride | [EINECS(EC#)]
218-631-7 | [Molecular Formula]
C4H10ClNO | [MDL Number]
MFCD00012572 | [Molecular Weight]
123.58 | [MOL File]
2208-07-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
112-114 °C(lit.) | [storage temp. ]
2-8°C | [solubility ]
water: soluble50mg/mL, clear, colorless | [form ]
Crystalline Powder | [color ]
White | [Water Solubility ]
Soluble in water (50mg/L). | [Sensitive ]
Moisture Sensitive | [BRN ]
3552401 | [Stability:]
Hygroscopic, Moisture Sensitive | [InChI]
InChI=1S/C4H9NO.ClH/c1-3-6-4(2)5;/h5H,3H2,1-2H3;1H | [InChIKey]
WGMHMVLZFAJNOT-UHFFFAOYSA-N | [SMILES]
O(CC)C(=N)C.Cl | [CAS DataBase Reference]
2208-07-3(CAS DataBase Reference) | [EPA Substance Registry System]
2208-07-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280a-P304+P340-P305+P351+P338-P405-P501a | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
3-10-21 | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29252900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
Ethyl acetimidate hydrochloride was used in preparation of amidinated carbonic anhydrase via chemical modification of human erythrocyte carbonic anhydrase. It was also used in synthesis of methyl 2-methyl-2-thiazoline-4-carboxylate hydrochloride. | [Uses]
Ethyl acetimidate hydrochloride was used in preparation of amidinated carbonic anhydrase via chemical modification of human erythrocyte carbonic anhydrase. It was also used in synthesis of methyl 2-methyl-2-thiazoline-4-carboxylate hydrochloride. | [Synthesis]
2) Example 1-2: Preparation of ethyl acetimidate hydrochloride
1.6 kg of acetonitrile and 4.3 kg of ethanol were added to the reactor and the reactor was cooled to -10°C. 3.67 kg of acetyl chloride was slowly added under stirring and the reaction mixture was kept stirred at 0°C for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure at 45°C. To the residue was added 11.8 kg of tert-butyl methyl ether and stirred at room temperature for 3 hours. The precipitated solid was collected by filtration and dried under vacuum at 40 °C to give 4.58 kg ethyl acetimidate hydrochloride (yield: 95%).
Product characterization data: 1H-NMR (400 MHz, DMSO-d6) δ: 11.7 (s, 2H), 4.26 (q, 2H), 2.38 (s, 3H), 1.36 (t, 3H). | [Purification Methods]
Recrystallise the hydrochloride by dissolving it in the minimum volume of super dry EtOH and adding dry Et2O or from dry Et2O. Dry it in a vacuum and store it in a vacuum desiccator with P2O5. Alternatively it could be crystallised from EtOH (containing a couple of drops of ethanolic HCl) and adding dry Et2O. Filter and dry it in a vacuum desiccator over H2SO4 and NaOH. [Pinner Chem Ber 16 1654 1883, Glickman & Cope J Am Chem Soc 67 1020 1945, Chaplin & Hunter J Chem Soc 1118 1937, McElvain & Schroeder J Am Chem Soc 71 40 1949, McElvain & Tate J Am Chem Soc 73 2233 1951, Methods Enzymol 25 585 1972, Beilstein 2 III 418.] | [References]
[1] Combinatorial Chemistry and High Throughput Screening, 2011, vol. 14, # 2, p. 132 - 137
[2] Patent: WO2015/5615, 2015, A1. Location in patent: Paragraph 142; 143; 144
[3] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13367 - 13374
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 915 - 927
[5] Chemische Berichte, 1985, vol. 118, # 8, p. 3089 - 3104 |
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