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Chemical Structure| 121492-06-6 Chemical Structure| 121492-06-6
Chemical Structure| 121492-06-6

N-Boc-N-methylethylenediamine

CAS No.: 121492-06-6

N-Boc-N-methylethylenediamine is a protected diamine compound used in the synthesis of peptides, drugs, and complex organic molecules.

4.5 *For Research Use Only !

Cat. No.: A386673 Purity: 98%

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Product Details of N-Boc-N-methylethylenediamine

CAS No. :121492-06-6
Formula : C8H18N2O2
M.W : 174.24
SMILES Code : C(=O)(OC(C)(C)C)N(C)CCN
MDL No. :MFCD01317789
InChI Key :QYJVBVKFXDHFPQ-UHFFFAOYSA-N
Pubchem ID :2756424

Safety of N-Boc-N-methylethylenediamine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:2735
Packing Group:

Application In Synthesis of N-Boc-N-methylethylenediamine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 121492-06-6 ]

[ 121492-06-6 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 121492-06-6 ]
  • [ 1458-01-1 ]
  • [ 1201179-50-1 ]
  • 3
  • [ 1092400-82-2 ]
  • [ 121492-06-6 ]
  • tert-butyl methyl-(2-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamido)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; tert-Butyl methyl(2-(3-(5-(trifluoromethyl)-1 ,2,4-oxadiazol -3- yI)benzamido)ethyl)carbamate 3-(5-(Trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid (1 .24 g, 4.8 mmol), EDCI(922 mg, 4.8 mmol), HOBt (648 mg, 4.8 mmol), and DIPEA (774 mg, 6mmol) were added to a solution of crude tert-butyl (2-aminoethyl)(methyl)carbamate in DCM (5OmL). The reaction mixture was stirred at room temperature overnight. Water (20 mL) was added to the mixture and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (40 mL x3). The combined organic solvents was washed with brine (30 mL), driedover Na2SO4. After removal of solvents, the crude compound was purified by flash column (EtOAc: PE = 2:1) to provide tert-butyl methyl(2-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamido)ethyl)carbamate as a white solid (1.1 g, yield 66%). MS (ESI) m/z: Calculated for C18H21F3N404: 414.15; found: 437 (M-f-Na).
  • 4
  • [ 349-02-0 ]
  • [ 121492-06-6 ]
  • C15H22N4O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 90℃; for 5h; Di-tert-butyl dicarbonate (107 mg, 0.49 mmol) and triethylamine (0.07 ml, 0.49 mmol) were added to a solution of 2-bromoethanamine (100 mg, 0.49 mmol) in 1,4-dioxane at 0oC over 30 min. After stirring at rt for 48 h, precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was taken by CH2Cl2and the resulting solution was washed with water, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, Hexane:Acetone = 4:1) to givetert-butyl (2-bromoethyl)carbamate (100 mg, 0.45 mmol, 91% yield) as a colorless oil;1H NMR (400 MHz, (CD3)2CO) delta (ppm) 3.49 - 3.43 (m, 4H), 1.41(s, 9H).tert-Butyl (2-bromoethyl)carbamate obtained above (50 mg, 0.22mmol) was dissolved in DMF (1 ml). To this solution, NaN3(73 mg, 1.12 mmol) was added, and the mixture was stirred at 110oC for 12 h. Volatiles were removed under reduced pressure, and the residue was dissolved in water. The resulting aqueous solution was extracted with EtOAC. The organic layers were combined and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (SiO2, Hexane:Acetone = 4:1) to givetert-butyl (2-azidoethyl)carbamate (40 mg, 0.21 mmol, 98% yield) as a colorless oil;1H NMR (400 MHz, CDCl3) delta (ppm) 3.41 - 3.40 (m, 2H), 3.32 - 3.29 (m, 2H), 1.45 (s, 9H).tert-Butyl (2-azidoethyl)carbamate (50 mg, 0.27 mmol) was dissolved in DMF (2 ml). To this solution, NaH (20 mg, 0.4 mmol) and MeI (0.03 ml, 0.4 mmol) were added at 0oC. After stirring for 5 h, the reaction mixture was treated with water followed by sodium thiosulfate and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, Hexane:Acetone = 4:1) to givetert-butyl (2-azidoethyl)(methyl)carbamate (40 mg, 0.20 mmol, 74% yield);1H NMR (400 MHz, CDCl3) delta (ppm) 3.38 (s, 4H), 2.90 (s, 3H), 1.45 (s, 9H).tert-Butyl (2-azidoethyl)(methyl)carbamate (180 mg, 0.9 mmol) obtained above was dissolved in THF. Water (0.1 ml) and triphenylphosphine (260 mg, 0.99 mmol) were added, and the mixture was stirred at rt for 10 h. After concentration under reduced pressure, the residue was purified by column chromatography (SiO2, Hexane:Acetone = 4:1 to CH2Cl2:MeOH:NH4OH:H2O=80:20:1:1) to givetert-butyl (2-aminoethyl)(methyl)carbamate (130 mg, 0.75 mmol, 83% yield);1H NMR (400 MHz, CDCl3) delta (ppm) 3.29 (br s, 2H) 2.92 - 2.89 (m, 5H), 1.46 (s, 9H).A solution of <strong>[349-02-0]4-fluoro-3-nitrobenzamide</strong> (238 mg, 1.3 mmol) ini-PrOH (5 ml) was treated with DIPEA (0.22 ml, 3.8 mmol) andtert-butyl (2-aminoethyl)(methyl)carbamate (450 mg, 3.8 mmol). After stirring for 5 h at 90oC, solvent was removed under reduced pressure to give a crude product which was purified by column chromatography (SiO2, CH2Cl2:MeOH:NH4OH:H2O = 80:20:1:1) to give5das a yellow powder (260 mg, 1.09 mmol, 85% yield);1H NMR (400 MHz, CD3OD) delta (ppm) 8.75 (s, 1H), 8.49 (br s, 1H), 7.98 (d,J= 7.2 Hz, 1H), 7.14 (d,J= 9.0 Hz, 1H), 3.52-3.48 (m, 2H), 3.37-3.34 (m, 2H), 3.31 (s, 3H), 1.42 (s, 9H).
  • 5
  • [ 97-08-5 ]
  • [ 121492-06-6 ]
  • tert-butyl (2-((4-chloro-3-nitrophenyl)sulfonamido)ethyl)(methyl)carbamate [ No CAS ]
  • 6
  • [ 62254-74-4 ]
  • [ 121492-06-6 ]
  • tert-butyl N-methyl-N-[2-[(5-methylisoxazol-3-yl)methylamino]ethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.18% With sodium tris(acetoxy)borohydride; glacial acetic acid; at 25℃; for 16h; To a solution of 5-methylisoxazole-3-carbaldehyde (6.50 g, 58.0 mmol, 1 eq.), tert-butyl N-(2-aminoethyl)-N-methyl-carbamate (11.2 g, 64.4 mmol, 11.5 mL, 1.1 eq.) in DCE (50 mL) was added AcOH (3.50 g, 58.0 mmol, 1 eq) and NaBH(OAc)3 (24.8 g, 117 mmol, 2 eq). The mixture was stirred at 25 C for 16 h. On completion, 50 mL water was added, and the reaction was extracted with EtOAc (3*50ml). The combined extracts were concentrated in vacuum. The residue was purified by column chromatography (SiO2, DCM/MeOH, from 100:0 to 100:10) to give tert-butyl N-methyl-N-[2-[(5-methylisoxazol-3-yl) methylamino] ethyl] carbamate (1.30 g, 4.20 mmol, 7.18% yield) as colorless oil. LC-MS: m/z 270.2 (M+1)+.
7.18% With sodium tris(acetoxy)borohydride; glacial acetic acid; at 25℃; for 16h; To a solution of 5-methylisoxazole-3-carbaldehyde (6.50 g, 58.0 mmol, 1 eq.), tert-butyl N-(2-aminoethyl)-N-methyl-carbamate (11.2 g, 64.4 mmol, 11.5 mL, 1.1 eq.) in DCE (50 mL) was added AcOH (3.50 g, 58.0 mmol, 1 eq) and NaBH(OAc)3 (24.8 g, 117 mmol, 2 eq). The mixture was stirred at 25 C for 16 h. On completion, 50 mL water was added, and the reaction was extracted with EtOAc (3*50ml). The combined extracts were concentrated in vacuum. The residue was purified by column chromatography (SiO2, DCM/MeOH, from 100:0 to 100:10) to give tert-butyl N-methyl-N-[2-[(5-methylisoxazol-3-yl) methylamino] ethyl] carbamate (1.30 g, 4.20 mmol, 7.18% yield) as colorless oil. LC-MS: m/z 270.2 (M+1)+.
 

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