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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
E. Escher et al.
Helvetica Chimica Acta, 62, 1217-1217 (1979)

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