| Identification | Back Directory | [Name]
N-BOC-M-PHENYLENEDIAMINE | [CAS]
68621-88-5 | [Synonyms]
3-(Boc-amino)aniline
Boc-m-phenylenediamine
N-BOC-m-Phenylenediaimne
N-Boc-1,3-phenylenediaMine
tert-butyl (3-aminophenyl)carbam
tert-butyl N-(3-aMinophenyl)carbaMate
N-Boc-m-phenylenediamine >=98.0% (HPLC)
1,1-Dimethylethyl (3-aminophenyl)carbamate
N-(tert-Butoxycarbonyl)-benzene-1,3-diamine
N-(tert-Butoxycarbonyl)-1,3-phenylenediaMine
N-(tert-Butoxycarbonyl)-1,3-phenylenediamine >
(3-aMinophenyl)carbaMic acid, 1,1-diMethylethyl ester
CarbaMic acid, (3-aMinophenyl)-, 1,1-diMethylethyl ester
CarbaMic acid, N-(3-aMinophenyl)-, 1,1-diMethylethyl ester
Carbamic acid, (3-aminophenyl)-, 1,1-dimethylethyl ester (9CI)
3-(tert-Butoxycarbonylamino)aniline, tert-Butyl-3-aminophenylcarbamate | [EINECS(EC#)]
626-915-0 | [Molecular Formula]
C11H16N2O2 | [MDL Number]
MFCD06657915 | [MOL File]
68621-88-5.mol | [Molecular Weight]
208.257 |
| Chemical Properties | Back Directory | [Melting point ]
109-110℃ (dichloromethane ) | [Boiling point ]
295.1±23.0 °C(Predicted) | [density ]
1.152±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
slightly sol. in Methanol | [form ]
powder to crystal | [pka]
13.57±0.70(Predicted) | [color ]
White to Gray to Brown | [InChI]
InChI=1S/C11H16N2O2/c1-11(2,3)15-10(14)13-9-6-4-5-8(12)7-9/h4-7H,12H2,1-3H3,(H,13,14) | [InChIKey]
IEUIEMIRUXSXCL-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)NC1=CC=CC(N)=C1 | [CAS DataBase Reference]
68621-88-5 |
| Hazard Information | Back Directory | [Uses]
N-Boc-m-phenylenediamine (tert-Butyl-3-aminophenylcarbamate) may be used in the preparation of:
- 5,5′-(propane-2,2-diyl)bis(N-(3-aminophenyl)-4-methyl-3-phenyl-1H-pyrrole-2-carboxamide)
- ethyl 4-[{3-[(tert-butoxycarbonyl)amino]phenyl}amino]-2-chloropyrimidine-5-carboxylate
- ethyl 4-(3-(tert-butoxycarbonyl)phenylamino)-2-(methylthio)pyrimidine-5-carboxylate
| [reaction suitability]
reagent type: cross-linking reagent | [Synthesis]
General procedure: tert-butyl (3-nitrophenyl)carbamate (10.75 g, 45.12 mmol) was used as raw material and dissolved in methanol (150 mL). To this solution, 10% Pd/C catalyst (0.48 g) was added. The reaction mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (4:1, v/v) to give N-BOC-mesophenylenediamine as a light yellow solid (7.59 g, 8% yield). | [References]
[1] Tetrahedron Letters, 1993, vol. 34, # 49, p. 7823 - 7826
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 623 - 639
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2253 - 2261
[4] Journal of the American Chemical Society, 2008, vol. 130, # 45, p. 15193 - 15202
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 212 - 221 |
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