| Identification | More | [Name]
tert-Butyl N-(3-aminopropyl)-N-methylcarbamate | [CAS]
150349-36-3 | [Synonyms]
1-N-BOC-1-N-METHYL-1,3-DIAMINOPROPANE
(3-AMINO-PROPYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER
BOC-N-ME-1,3-DIAMINOPROPANE
BUTTPARK 90\06-20
N-(3-AMINO-PROPYL)-N-METHYLCARBAMIC ACID T-BUTYL ESTER
N-(3-AMINOPROPYL)-N-METHYLCARBAMIC ACID TERT-BUTYL ESTER
N-(4-AMINOPROPYL)-N-METHYL CARBAMIC ACID TERT-BUTYL ESTER
N-(3-Aminopropyl)-N-methylcarbamic acid tert-butyl
Boc-N-Me-1,3-diaminopropane·HCl
N-(3-Aminopropyl)-N-methylcarbamic acid ert-butyl ester | [Molecular Formula]
C9H20N2O2 | [MDL Number]
MFCD01631189 | [Molecular Weight]
188.27 | [MOL File]
150349-36-3.mol |
| Chemical Properties | Back Directory | [Boiling point ]
254.6±19.0 °C(Predicted) | [density ]
0.982±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [pka]
10.06±0.10(Predicted) | [color ]
Pale yellow | [Water Solubility ]
Slightly soluble in water. | [CAS DataBase Reference]
150349-36-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HS Code ]
2924190090 |
| Hazard Information | Back Directory | [Uses]
It is an important raw material and intermediate used in organic synthesis, agrochemicals and dyestuff. | [Synthesis]
GENERAL STEPS: Preparation Example 1 Synthesis of tert-butyl-N-(3-aminopropyl)-N-methylcarbamate (2). N-methyl-1,3-propanediamine (1) (3.26 g, 37.03 mmol) was dissolved in methanol (100 ml), and a 35% hydrochloric acid solution was slowly added at 0 °C, followed by stirring. The reaction solution was stirred at room temperature for 30 min, then cooled to -10 °C and di-tert-butyl dicarbonate (10.51 g, 48.14 mmol) was slowly added. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and alkalized with 10% aqueous sodium hydroxide solution. The alkalized solution was extracted with dichloromethane and the organic phase was dried with anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent ratio: dichloromethane: methanol: ammonia = 100:9:1, v/v/v) to give tert-butyl N-(3-aminopropyl)-N-methylcarbamate (2). Yield: 3.03 g (43%).1H NMR (400 MHz, CDCl3) δ 3.29 (2H, br, -CH2-NH2), 2.83 (3H, s, -N-CH3), 2.69 (2H, t, J = 6Hz, -N-CH2-CH2-), 1.64 (2H, m, -CH2-CH2-CH2-). 1.46 (9H, s, (CH3)3C-O-CO-), 1.38 (2H, s, -CH2-CH2-NH2). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 1073 - 1079
[2] Patent: US2017/81291, 2017, A1. Location in patent: Paragraph 0023; 0046; 0047; 0048
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1565 - 1570 |
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