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279633

Sigma-Aldrich

p-Xylylenediamine

99%

Synonym(s):

1,4-Bis(aminomethyl)benzene, α,α′-Diamino-p-xylene

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About This Item

Linear Formula:
C6H4(CH2NH2)2
CAS Number:
539-48-0
Molecular Weight:
136.19
Beilstein/REAXYS Number:
2206190
EC Number:
208-719-3
MDL number:
MFCD00009821
UNSPSC Code:
12162002
PubChem Substance ID:
24856898
NACRES:
NA.23

Quality Level

200

assay

99%

form

solid

bp

230 °C/10 mmHg (lit.)

mp

60-63 °C (lit.)

SMILES string

NCc1ccc(CN)cc1

InChI

1S/C8H12N2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6,9-10H2

InChI key

ISKQADXMHQSTHK-UHFFFAOYSA-N

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General description

p-Xylylenediamine (p-XDA) is an aromatic diamine monomer characterized by its two primary amino groups and rigid aromatic structure, which contribute to its exceptional thermal stability and mechanical strength. Its reactivity allows for versatile functionalization and effective cross-linking, making it a suitable building block in polymer synthesis. p-XDA′s solubility in organic solvents facilitates its incorporation into various formulations, including hydrogels for drug delivery systems.

Application

p-Xylylenediamine can be used:
  • As a monomer to synthesize ultra heat-resistant thermoplastic polyamide elastomers suitable for high-temperature applications. It contributes to increased tensile strength, toughness, and Young′s modulus of the elastomer, thereby enhancing its overall mechanical strength.
  • As a cross-linking agent to prepare solvent resistant high performance nanofiltration membranes. p-Xylylenediamine facilitates superior separation performance and stability for N,N-dimethylformamide (DMF) solution.
  • As a dendrimer core to synthesize stimuli responsive nanocarriers for cancer drug delivery.
  • As a capping agent to prepare fluorescent organic–inorganic hybrid CH3NH3PbBr3 nanocrystals to fabricate 3D-printed paper-based microfluidic optical sensor for naked-eye detection of picric acid.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000316437
MKCW7186
0000316437
MKCT0875
MKCT0874

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Ammara Ejaz et al.
Journal of colloid and interface science, 570, 322-331 (2020-03-15)
Solvent properties such as surface tension, dielectric constant, and viscosity have been extensively studied over more than 150 years to understand their influence on the growth kinetics of nanostructures. Interestingly, these nanoparticles-based studies have missed the influence of solvent molecular geometry.
Weiqiang Zhan et al.
Journal of medicinal chemistry, 50(23), 5655-5664 (2007-10-26)
In light of a proposed molecular mechanism for the C-X-C chemokine receptor type 4 (CXCR4) antagonist 1 (AMD3100), a template with the general structure 2 was designed, and 15 was identified as a lead by means of an affinity binding
Choon Young Lee et al.
Bioorganic & medicinal chemistry letters, 19(22), 6326-6330 (2009-10-14)
Three dendritic polyphenols (generation 1) were synthesized: a syringaldehyde-based dendrimer (1), a vanillin-based dendrimer (2), and an iodinated vanillin-based dendrimer (3). They all showed strong antioxidant activity according to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical assay. The syringaldehyde dendrimer was twice and
Francesc Yraola et al.
Journal of medicinal chemistry, 49(21), 6197-6208 (2006-10-13)
Structure activity relationships for semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 (SSAO/VAP-1) were studied using a library of arylalkylamine substrates, with the aim of contributing to the discovery of more efficient SSAO substrates. Experimental data were contrasted with computational docking studies, thereby

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