tert-Butyl 2-(methylamino)ethylcarbamate Chemical Properties

Melting point:

35 °C

Boiling point:

260.1±23.0 °C(Predicted)

Density 

0.958±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump

pka

12?+-.0.46(Predicted)

color 

White to Almost white

InChI

InChI=1S/C8H18N2O2/c1-8(2,3)12-7(11)10-6-5-9-4/h9H,5-6H2,1-4H3,(H,10,11)

InChIKey

GKWGBMHXVRSFRT-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCNC

CAS DataBase Reference

122734-32-1

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

HS Code 

2921490090

tert-Butyl 2-(methylamino)ethylcarbamate Usage And Synthesis

Uses

2-(methylamino)ethylcarbamate tert-butyl ester was used in the study of hydrophilic derivatives of the antibody-drug conjugate gentamicin.

Chemical Properties

White to very pale yellow solid

Synthesis

General procedure for the synthesis of tert-butyl 2-(methylamino)ethyl carbamate from (2-(benzyl(methyl)amino)ethyl)carbamate: 1. To a reaction flask were added 20% Pd(OH)2/carbon catalyst (3.1 g), tert-butyl (2-(benzyl(methyl)amino)ethyl)carbamate (3.3 g, 12.5 mmol), methanol (200 mL) and water (2 mL). 2. The reaction system was placed under a hydrogen atmosphere (40 psi) for 2.5 hours. 3. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth and concentrated under vacuum to remove the solvent. 4. Water (50 mL) was added to the concentrate and the pH was adjusted to 12 with alkali. 5. The aqueous phase was extracted with dichloromethane (3 x 50 mL) and the organic layers were combined. 6. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated in vacuum to give tert-butyl 2-(methylamino)ethylcarbamate (2.0 g, 11.7 mmol, 94% yield) as a colorless oil. LC-MS [M + H] 686.5 (C35H51N5O7S + H, calculated value: 685.9).

References

[1] Patent: US2011/262355, 2011, A1. Location in patent: Page/Page column 136
[2] Patent: WO2011/133149, 2011, A1. Location in patent: Page/Page column 298
[3] Patent: WO2011/133150, 2011, A1. Location in patent: Page/Page column 300
[4] Patent: JP2016/41698, 2016, A. Location in patent: Paragraph 0364; 0377
[5] Patent: US2010/41748, 2010, A1. Location in patent: Page/Page column 120

tert-Butyl 2-(methylamino)ethylcarbamate(122734-32-1)Related Product Information

• 4-Aminobenzoic acid
• 2-Butoxyethanol
• tert-Butyl 4-aminobenzoate
• tert-Butyl glycinate
• Diisobutyl phthalate
• BUTYL OLEATE
• tert-Butyl peroxybenzoate
• tert-Butyl peroxyacetate
• tert-Butanol
• POLYURETHANE
• Butyl formate
• tert-Butyl carbazate
• Urethane
• Buprofezin
• Butyl acetate
• tert-Butyl carbamate
• Cyhalofop-butyl
• Methyl anthranilate