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100242

Sigma-Aldrich

3-Aminophenol

98%

Synonym(s):

m-Aminophenol

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About This Item

Linear Formula:
H2NC6H4OH
CAS Number:
591-27-5
Molecular Weight:
109.13
Beilstein:
636059
EC Number:
209-711-2
MDL number:
MFCD00007786
UNSPSC Code:
12352100
PubChem Substance ID:
24846518
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

bp

164 °C/11 mmHg (lit.)

mp

120-124 °C (lit.)

SMILES string

Nc1cccc(O)c1

InChI

1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2

InChI key

CWLKGDAVCFYWJK-UHFFFAOYSA-N

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Application

3-Aminophenol has been used in the synthesis of disulfonated bis[4-(3-aminophenoxy)phenyl]sulfone (S-BAPS).
It can be used to synthesize:
  • Methyl 2-oxo-7-[(triphenylphosphoranylidene)amino]-2H-chromene-4-carboxylate by reacting with dimethyl acetylenedicarboxylate (DMAD) in the presence of triphenylphosphine.
  • 3-Amino-2-cyclohexen-1-one via palladium-catalyzed hydrogenation.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302 + H332 - H319 - H411

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2

Storage Class Code

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

WGK

WGK 2

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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SAFC

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A Practical and One-Pot Procedure for the Synthesis of 3-Amino-2-cyclohexen-1-one from 3-Aminophenol.
Sajiki H
Organic Process Research & Development, 9(2), 219-220 (2005)
Sijing Chen et al.
Polymers, 11(6) (2019-06-20)
Benzoxazine containing fluorinated aromatic ether nitrile linkage (FAEN-Bz) had been synthesized from 2,6-dichlorobenzonitrile, 4,4'-(hexafluoroisopropylidene)diphenol (bisphenol AF), 3-Aminophenol, formaldehyde, phenol by condensation polymerization and Mannich ring-forming reaction. Structures of the monomer were verified by Proton NMR spectrum (1H-NMR) and Fourier transform
Vinyltriphenylphosphonium salt mediated synthesis of 1, 4-benzoxazine and coumarin derivatives.
Yavari I, et al.
Tetrahedron, 58(34), 6895-6899 (2002)
Ping-Chih Hsu et al.
Oncology reports, 42(2), 697-707 (2019-06-25)
Human non‑small cell lung cancer (NSCLC) is associated with an extremely poor prognosis especially for the 40% of patients who develop brain metastasis, and few treatment strategies exist. Cucurbitacin E (CuE), an oxygenated tetracyclic triterpenoid isolated from plants particularly of
Jennifer A Reese et al.
Journal of the American Chemical Society, 126(36), 11387-11392 (2004-09-10)
Rotationally resolved electronic spectroscopy in the gas phase, in the absence and presence of an applied electric field, has been used to distinguish the two conformers of 3-aminophenol (3AP) on the basis of differences in their electric dipole moments. cis-3AP
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