| Identification | Back Directory | [Name]
O-ALLYL-2,2,2-TRICHLOROACETIMIDATE | [CAS]
51479-73-3 | [Synonyms]
Allyl Trichloroacetimidate
ALLYL 2,2,2-TRICHLOROACETIMIDATE
O-ALLYL-2,2,2-TRICHLOROACETIMIDATE
Allyl 2,2,2-Trichloroacetimidate >
O-Allyl 2,2,2-trichloroacetimidate 96%
2,2,2-TRICHLORACETIMIDIC ACID ALLYLESTER
2,2,2-TRICHLOROACETIMIDIC ACID ALLYL ESTER
Ethanimidic acid, 2,2,2-trichloro-, 2-propen-1-yl ester | [Molecular Formula]
C5H6Cl3NO | [MDL Number]
MFCD00190710 | [MOL File]
51479-73-3.mol | [Molecular Weight]
202.47 |
| Chemical Properties | Back Directory | [Boiling point ]
54-70 °C/7.5-11.25 mmHg | [density ]
1.333 g/mL at 25 °C | [refractive index ]
n20/D 1.489 | [Fp ]
74 °C | [storage temp. ]
2-8°C | [solubility ]
sol hexane, ether, dichloromethane. | [form ]
clear liquid | [pka]
2?+-.0.70(Predicted) | [color ]
Colorless to Almost colorless | [BRN ]
1907084 |
| Hazard Information | Back Directory | [Uses]
Reagent used for the protection of an alcohol as its allyl ether in the presence of base sensitive functionality. | [Application]
O-allyl-2,2,2-trichloroacetimidate can be used to release allyl groups under mild conditions; used to prepare nitrogen-containing intermediates. | [Preparation]
Sodium Hydride (0.5 g, 21 mmol) is slurried in anhydrous ether
(20 mL) under a nitrogen blanket. Allyl alcohol (210 mmol) is introduced in ether (30 mL) dropwise with
stirring to the slurry. After 20 min, the homogeneous solution is cooled to 0 °C and Trichloroacetonitrile
(20 mL, 200 mmol) is added over 15 min. The mixture is allowed to warm to 20 °C over 60 min and then
concentrated to a syrup. Pentane (20 mL) containing methanol (0.8 mL, 21 mmol) is added followed by
vigorous shaking, filtration, and concentration of the filtrate and pentane washings (2 × 20 mL). The
product imidate is obtained as a clear liquid (90-97%). No further purification is required. Alternatively, the
imidate can be prepared by using sodium methoxide as a catalyst instead of sodium hydride. Other
procedures for the preparation of allyl trichloroacetimidate have been reported. |
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