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Sigma-Aldrich

N-Boc-p-phenylenediamine

≥97.0% (NT)

Synonym(s):

4-(tert-Butoxycarbonylamino)aniline, tert-Butyl-4-aminophenylcarbamate

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About This Item

Linear Formula:
(CH3)3COCONHC6H4NH2
CAS Number:
71026-66-9
Molecular Weight:
208.26
Beilstein:
2969618
EC Number:
275-132-7
MDL number:
MFCD00043022
UNSPSC Code:
12352116
PubChem Substance ID:
57647460
NACRES:
NA.22

Quality Level

200

Assay

≥97.0% (NT)

form

powder

reaction suitability

reagent type: cross-linking reagent

functional group

Boc
amine

SMILES string

NC1=CC=C(NC(OC(C)(C)C)=O)C=C1

InChI

1S/C11H16N2O2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h4-7H,12H2,1-3H3,(H,13,14)

InChI key

WIVYTYZCVWHWSH-UHFFFAOYSA-N

Application

N-Boc-p-phenylenediamine can be used as:
  • A reactant to prepare perylene monoimide-based dyes for dye-sensitized solar cell applications.
  • A starting material to synthesize covalent organic frameworks, which are used as proton exchange membranes for hydrogen fuel cell applications.
  • A reactant in the synthesis of bestatin derived hydroxamic acids as potent pan-HDAC inhibitors.

Other Notes

Mono-N-acylated diamine, precursor of different Para-substituted anilines (e.g., 4-azido aniline); Synthesis of photoactivable derivative of ouabaine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD7833V
1341963
1420590
1418427
1329006

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M.P. Goeldner et al.
Trends in Biochemical Sciences, 7, 310-310 (1982)
Synthesis, photophysical and photovoltaic investigations of acceptor-functionalized perylene monoimide dyes for nickel oxide p-type dye-sensitized solar cells
Le Pleux L, et al.
Energy & Environmental Science, 4(6), 2075-2084 (2011)
Combined Intrinsic and Extrinsic Proton Conduction in Robust Covalent Organic Frameworks for Hydrogen Fuel Cell Applications
Yang Y, et al.
Angewandte Chemie (International ed. in English), 59(9), 3678-3684 (2020)
Development of a Bestatin-SAHA Hybrid with Dual Inhibitory Activity against APN and HDAC
Cao J, et al.
Molecules (Basel), 25(21), 4991-4991 (2020)
E. Escher et al.
Helvetica Chimica Acta, 62, 1217-1217 (1979)

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