N-BOC-M-PHENYLENEDIAMINE Chemical Properties

Melting point:

109-110℃ (dichloromethane )

Boiling point:

295.1±23.0 °C(Predicted)

Density 

1.152±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

F 

10-23

HS Code 

2924297099

N-BOC-M-PHENYLENEDIAMINE Usage And Synthesis

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

N-BOC-M-PHENYLENEDIAMINE(68621-88-5)Related Product Information

• (5-AMINO-2-CHLORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (3-AMINO-2-METHYL-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (5-AMINO-2-FLUORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (5-AMINO-2-METHYL-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (3-BOC-AMINO-5-NITROPHENYL)BORONIC ACID
• (3-AMINO-4-METHYL-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (5-AMINO-2-BROMO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• BOC-3-AMINO-5-(FMOC-AMINO)-BENZOIC ACID
• (3-AMINO-4-FLUORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (3-AMINO-4-CHLORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• 3,5-BIS-BOC-AMINOBENZOIC ACID
• (3-AMINO-4-BROMO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• N,N-DI-TERT-BUTOXYCARBONYL-BENZENE-1,3-DIAMINE
• N-BOC-M-PHENYLENEDIAMINE
• (5-AMINO-2-METHOXY-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• 3-T-BUT-(OXYCARBOXYLAMINO-5-NITROPHENYL) CARBAMIC ACID T-BUTYL ESTER
• 2-TERT-BUTOXYCARBONYLAMINO-4-NITROBENZOIC ACID
• AURORA KA-8078