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516805

Sigma-Aldrich

4,4′-Oxydianiline

97%

Synonym(s):

4,4′-Diaminodiphenyl ether, 4-Aminophenyl ether

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About This Item

Linear Formula:
O(C6H4NH2)2
CAS Number:
101-80-4
Molecular Weight:
200.24
Beilstein:
475735
EC Number:
202-977-0
MDL number:
MFCD00007863
UNSPSC Code:
12352100
PubChem Substance ID:
24873898
NACRES:
NA.22

vapor pressure

10 mmHg ( 240 °C)

Assay

97%

form

solid

mp

188-192 °C (lit.)

SMILES string

Nc1ccc(Oc2ccc(N)cc2)cc1

InChI

1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2

InChI key

HLBLWEWZXPIGSM-UHFFFAOYSA-N

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Application

4,4′-Oxydianiline can be used as a reactant to synthesize:
  • Aromatic polyamides by polycondensation with aromatic dicarboxylic acids.
  • Azomethine bisphenols by reacting with aromatic aldehydes, which can be used to synthesize polyazomethines by the oxidative polycondensation in the presence of NaOCl as an oxidant.
  • Polyguanamines by the chemoselective polycondensation with 2-amino-4,6-dichloro-1,3,5-triazine in the presence of potassium carbonate as a base.
It can also be used for the functionalization of carbon nanotubes, which can react with terminal dianhydrides to synthesize polyimide aerogels.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 1 - Carc. 1B - Muta. 1B - Repr. 2 - Skin Sens. 1 - STOT RE 2 Oral

Target Organs

Thyroid

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

426.2 °F - closed cup

Flash Point(C)

219 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Gas permeability and permselectivity in polyimides based on 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride.
Tanaka K, et al.
Journal of Membrane Science, 47(1), 203-215 (1989)
Synthesis, characterization, optical and electrical properties of thermally stable polyazomethines derived from 4, 4'-oxydianiline.
Dineshkumar S, et al.
Journal of Adhesion Science and Technology, 29(23), 2605-2621 (2015)
Pervaporation of water/acetic acid through polyimide membranes from 3, 3', 4, 4'-benzophenone tetracarboxylic dianhydride and 4, 4'-oxydianiline.
Moon YD, et al.
Polym. Bull., 29(3-4), 431-438 (1992)
Copolyimides from 2, 3, 3', 4'-biphenyltetracarboxylic dianhydride and pyromellitic dianhydride with 4, 4'-oxydianiline.
Hergenrother PM, et al.
Polymer, 45(16), 5441-5449 (2004)
Anders Lennartson et al.
Chirality, 27(7), 425-429 (2015-06-03)
We studied the spontaneous formation of chiral crystals of four diaryl ethers, 3-phenoxybenzaldehyde, 1; 1,3-dimethyl-2-phenoxybenzene, 2; di(4-aminophenyl) ether, 3; and di(p-tolyl) ether, 4. Compounds 1, 3, and 4 form conformationally chiral molecules in the solid state, while the chirality of
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