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Sigma-Aldrich

2,3-Diaminophenol

97%

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Linear Formula:
(H2N)2C6H3OH
CAS Number:
59649-56-8
Molecular Weight:
124.14
MDL number:
MFCD00075199
PubChem Substance ID:
24860835
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

161-165 °C (lit.)

SMILES string

Nc1cccc(O)c1N

InChI

1S/C6H8N2O/c7-4-2-1-3-5(9)6(4)8/h1-3,9H,7-8H2

InChI key

PCAXITAPTVOLGL-UHFFFAOYSA-N

Related Categories

General description

2,3-Diaminophenol is an aromatic diamine and forms Pd(II) and Pt(II) complexes. 2,3-Diaminophenol reacts with 2,4-pentanedione to yield the corresponding benzo[b][1,4]diazepinium salts. 2,3-Diaminophenol reacts with salicylaldehyde or 5-bromosalicylaldehyde in absolute ethanol to yield new unsymmetrical Schiff base.

Application

2,3-Diaminophenol was used:
  • in one-pot microwave assisted synthesis of amino-1,5-benzoxazepines and hydroxyl-1,5-benzodiazepines
  • in the electrosynthesis of poly(2,3-diaminophenol) via electro-oxidation
  • in a synthesis of tetradentate Schiff base complexes via reaction with salicylaldehyde or 5-bromosalicylaldehyde and metals such as Mn(III), Ni(II) and Cu(II)

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Unsymmetrical tetradentate Schiff base complexes derived from 2, 3-diaminophenol and salicylaldehyde or 5-bromosalicylaldehyde.
Ourari A, et al.
Transition Metal Chemistry, 31(2), 169-175 (2006)
Transition Met. Chem. (London), 31, 169-169 (2006)
Constantinos G Neochoritis et al.
Journal of medicinal chemistry, 53(23), 8409-8420 (2010-11-06)
Amino-1,5-benzoxazepines 2 and 5 and hydroxyl-1,5-benzodiazepines 3 and 6 have been synthesized in one-pot solvent-free conditions from 2,3-diaminophenol and ketones through microwave assisted acid catalysis, the benzoxazepine/benzodiazepine ratio depending on the R(1) and R(3) aryl substituents. The otherwise inaccessible and
Electropolymerization of 2, 3-diaminophenol.
Del Valle MA, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 38(9), 1698-1703 (2000)
Andreas Schmidt et al.
Organic & biomolecular chemistry, 1(23), 4342-4350 (2003-12-20)
2,3-Diaminophenol 4, 3,4-diaminophenol 5, 4-methoxy-1,2-diaminobenzene 6, 3,4-diaminobenzenethiol 7, 2,3-diaminobenzoic acid 8, and 3,4-diaminobenzoic acid 9 were reacted with 2,4-pentanedione to yield the corresponding benzo[b][1,4]diazepinium salts, respectively. The hydroxy-benzo[b][1,4]diazepinium salts 17 and 18 do not form mesomeric betaines (MB) on deprotonation.
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