| Identification | Back Directory | [Name]
Carbamic acid, (2-chloroethyl)-, 1,1-dimethylethyl ester (9CI) | [CAS]
71999-74-1 | [Synonyms]
N-Boc-2-Chloroethylamine
1-Boc-2-chloroethylamine
2-(Boc-amino)ethyl Chloride
tert-butyl 2-chloroethylcarbamate
2-Chloroethylamine, N-BOC protected
N-t-Butoxycarbonyl-2-chloroethylaMine
tert-Butyl N-(2-chloroethyl)carbamate
1-Amino-2-chloroethane, N-BOC protected
N-(tert-Butoxycarbonyl)-2-chloroethylaMine
(tert-butoxy)-N-(2-chloroethyl)-carboxaMide
2-[(tert-Butoxycarbonyl)aMino]-1-chloroethane
(2-Chloroethyl)carbamic acid 1,1-dimethylethyl ester
N-(2-Chloroethyl)carbaMic Acid 1,1-DiMethylethyl Ester
CarbaMic acid, (2-chloroethyl)-, 1,1-diMethylethyl ester
Carbamic acid, N-(2-chloroethyl)-, 1,1-dimethylethyl ester
Carbamic acid, (2-chloroethyl)-, 1,1-dimethylethyl ester (9CI)
tert-Butyl (2-chloroethyl)carbamate, 1-[(tert-Butoxycarbonyl)amino]-2-chloroethane | [Molecular Formula]
C7H14ClNO2 | [MDL Number]
MFCD04004074 | [MOL File]
71999-74-1.mol | [Molecular Weight]
179.64 |
| Chemical Properties | Back Directory | [Melting point ]
Oil° | [Boiling point ]
75℃ (8 Torr) | [density ]
1.070±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Colourless to Yellow Oil to Off-White to Yellow Semi-Solid | [pka]
11.93±0.46(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Chemical Properties]
Clear Yellow Oil | [Uses]
tert-Butyl (2-chloroethyl)carbamate is used in the preparation of neurotransmitter receptor agonists with antagonist potential as well as anti-cancer agents.
| [Synthesis]
In a round-bottom flask, 2-chloroethylamine hydrochloride (2 g, 17.0 mmol) and triethylamine (Et3N, 2.37 mL, 11.0 mmol) were dissolved in anhydrous dichloromethane (CH2Cl2, 24 mL). Di-tert-butyl dicarbonate (Boc2O, 3.6 mL, 15.3 mmol) was slowly added at 0 °C under the protection of nitrogen (N2). The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the mixture was washed sequentially with water (H2O) and brine, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to afford N-Boc-2-chloroethylamine as a dark liquid in a yield of 2.91 g (16.21 mmol, 99% yield), which was used directly in the next step of the reaction. The product was confirmed by infrared spectroscopy (IR, pure): 3347, 2924, 2854, 2361, 2342, 1725, 1709, 1503, 1462 cm-1. nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, CDCl3): δ = 1.18 [s, 9H, C(CH3)3], 3.36-3.48 (m, 2H. CH2NH), 3.49-3.63 (m, 2H, ClCH2), 4.93 (br s, 1H, NHCO). Nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3): δ = 28.2 [C(CH3)3], 32.8 (CH2NH), 45.7 (CH2Cl), 79.8 [C(CH3)3], 155.8 (C=O). Elemental analysis (C7H14ClNO2) calculated values: C, 46.80; H, 7.86; N, 7.80. measured values: C, 46.91; H, 7.89; N, 7.74. | [References]
[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7731 - 7757
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1845 - 1857
[3] Synthesis (Germany), 2015, vol. 47, # 23, p. 3767 - 3775
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2018, vol. 56, # 19, p. 2154 - 2160
[5] Patent: WO2009/61131, 2009, A2. Location in patent: Page/Page column 81-82 |
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