Identification | More | [Name]
Ethyl cyanoglyoxylate-2-oxime | [CAS]
3849-21-6 | [Synonyms]
ETHYL 2-(HYDROXYIMINO)-3-NITRILOPROPANOATE ETHYL 2-(HYDROXYIMINO) CYANOACETATE ETHYL CYANOGLYOXALATE-2-OXIME ETHYL CYANOGLYOXYLATE-2-OXIME ETHYL CYANOGLYOXYLATE OXIME ETHYL CYANO(HYDROXYIMINO)-ACETATE ETHYL (HYDROXYIMINO)CYANOACETATE ETHYL ISONITROSOCYANOACETATE ETHYL OXIMINOCYANOACETATE TIMTEC-BB SBB007937 Ethyl[Hydroximino]Cyanoacetate Ethyl cyanoglyoxalate-2-oxime, Ethyl isonitrosocyanoacetate Oximinocyanoaceticacidethylester Ethylcyanoglyoxylate-2-oxime=Ethyloximinocyanoacetate isonitrosocyanoacetic acid ethyl ester Ethyl2-cyano-2-oximinoacetate Ethyl cyanoximidoacetate 2-Ethyloximinocyanocaetate Ethyl cyano(hydroxyimino)acetate, Ethyl cyanoglyoxalate-2-oxime, Ethyl isonitrosocyanoacetate Ethyl 2-cyano-2-hydroxyiminoacetate | [EINECS(EC#)]
223-351-3 | [Molecular Formula]
C5H6N2O3 | [MDL Number]
MFCD00002112 | [Molecular Weight]
142.11 | [MOL File]
3849-21-6.mol |
Chemical Properties | Back Directory | [Appearance]
light yellow crystals or chunks | [Melting point ]
130-132 °C (lit.) | [Boiling point ]
259.65°C (rough estimate) | [density ]
1.4801 (rough estimate) | [refractive index ]
1.5090 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
6.18±0.10(Predicted) | [color ]
Off-White | [BRN ]
774783 | [InChI]
InChI=1S/C5H6N2O3/c1-2-10-5(8)4(3-6)7-9/h9H,2H2,1H3 | [InChIKey]
LCFXLZAXGXOXAP-QPJJXVBHSA-N | [SMILES]
C(OCC)(=O)C(C#N)=NO | [CAS DataBase Reference]
3849-21-6(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3276 | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29280000 |
Hazard Information | Back Directory | [Chemical Properties]
light yellow crystals or chunks | [Uses]
A non-explosive alternative to HOBt. | [reaction suitability]
reaction type: Coupling Reactions | [Synthesis]
Example 1: Preparation of ethyl 2-oxime cyanoacetate
To a suspension of ethyl cyanoacetate (1.0 kg, 8.84 mol) and sodium nitrite (0.735 kg, 10.65 mol) in water (0.80 L) was slowly added acetic acid (0.70 kg, 11.66 mol), and the reaction temperature was controlled to be in the range of 0-50°C. The reaction temperature was slowly raised to 23-27 °C over a period of 1 h and the reaction mixture was continuously stirred at this temperature for 1 h. The reaction temperature was then adjusted to the temperature of the reaction mixture. After confirming complete consumption of ethyl cyanoacetate by TLC or GC monitoring, the reaction mixture was extracted with ethyl acetate (5 x 1.5 L). The organic layers were combined and washed sequentially with 10% sodium bicarbonate solution (2 x 1.25 L) and saturated brine (1.25 L). The organic layer was dried over anhydrous sodium sulfate and filtered through a hyflow bed. The solvent was removed by distillation under reduced pressure at 40-45 °C. The resulting solid was stirred with cyclohexane (3.0 L) at 25-30 °C for 30 min, filtered and dried in vacuum at 40-45 °C to give ethyl 2-oxime cyanoacetate 1.14 kg (91.2% yield) with 99.82% HPLC purity. | [References]
[1] Chemistry - A European Journal, 2015, vol. 21, # 16, p. 6090 - 6099 [2] Synthesis, 1999, # 1, p. 46 - 48 [3] Patent: WO2010/140168, 2010, A1. Location in patent: Page/Page column 14 [4] PLoS ONE, 2014, vol. 9, # 10, [5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 553 - 557 |
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