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Key Documents

P6001

Sigma-Aldrich

p-Phenylenediamine

98% (GC)

Synonym(s):

1,4-Benzenediamine, 1,4-Diaminobenzene, 1,4-Phenylenediamine

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About This Item

Linear Formula:
C6H4(NH2)2
CAS Number:
Molecular Weight:
108.14
Beilstein/REAXYS Number:
742029
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83

vapor density

3.7 (vs air)

vapor pressure

1.08 mmHg ( 100 °C)

description

anti-fade reagent

assay

98% (GC)

bp

267 °C (lit.)

mp

138-143 °C (lit.)

SMILES string

Nc1ccc(N)cc1

InChI

1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2

InChI key

CBCKQZAAMUWICA-UHFFFAOYSA-N

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Application

p-Phenylenediamine has been used:
  • to evaluate its sensitization potential in vitro in langerhans-like dendritic cells and autologous T cells
  • to treat the dorsal sides of the ears of mice, to study its systemic immunological effects
  • in glycerol to coverslip coronal sections in the attempt to count Aβ plaques

Anti-fade reagent is added to the mounting medium in fluorescence microscopy to retard photobleaching of fluorescein and other fluorescent dyes.

Biochem/physiol Actions

p-Phenylenediamine causes allergic reactions with skin. It is widely used in hair dyes. It eventually forms Bandrowski′s base, which is found to be the primary cause for allergy. p-Phenylenediamine exposure results in dermatitis, urticaria and anaphylaxis. It acts as an electron donor and is known to reduce cytochrome c.

Caution

Darkens in storage.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Sens. 1 - STOT SE 1 Oral

target_organs

Kidney,Heart,Musculo-skeletal system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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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Ying-Zhi Xu et al.
NAR cancer, 2(4), zcaa029-zcaa029 (2020-10-24)
Diffuse large B-cell lymphoma (DLBCL) is a molecularly heterogeneous group of malignancies with frequent genetic abnormalities. G-quadruplex (G4) DNA structures may facilitate this genomic instability through association with activation-induced cytidine deaminase (AID), an antibody diversification enzyme implicated in mutation of
p-Phenylenediamine allergy: the role of Bandrowski's base
White JML, et al.
Clinical and Experimental Allergy, 36(10), 1289-1293 (2006)
A TgCRND8 mouse model of Alzheimer?s disease exhibits sexual dimorphisms in behavioral indices of cognitive reserve
Granger MW, et al.
Journal of Alzheimer'S Disease, 51(3), 757-773 (2016)
Jesper Dyrendom Svalgaard et al.
Immunologic research, 58(1), 40-50 (2014-01-05)
p-Phenylenediamine (PPD) and Diphenylcyclopropenone (DPCP) are two potent haptens. Both haptens are known to cause delayed-type hypersensitivity, involving a cytokine response and local infiltration of T-cell subpopulations, resulting in contact dermatitis. We investigated the systemic immune effects of PPD and
p-Phenylenediamine
DeLeo VA
Dermatitis : Contact, Atopic, Occupational, Drug : Official Journal of the American Contact Dermatitis Society, North American Contact Dermatitis Group, 17(2), 53-55 (2006)

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