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D12600

Sigma-Aldrich

3,4-Diaminobenzoic acid

97%

Synonym(s):

4-Carboxy-o-phenylenediamine

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About This Item

Linear Formula:
(H2N)2C6H3CO2H
CAS Number:
619-05-6
Molecular Weight:
152.15
Beilstein:
775892
EC Number:
210-577-2
MDL number:
MFCD00007726
UNSPSC Code:
12352200
PubChem Substance ID:
24893391
NACRES:
NA.22

Assay

97%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

mp

208-210 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Nc1ccc(cc1N)C(O)=O

InChI

1S/C7H8N2O2/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3H,8-9H2,(H,10,11)

InChI key

HEMGYNNCNNODNX-UHFFFAOYSA-N

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Application

3,4-Diaminobenzoic acid can be used to prepare:
  • Schiff base derivatives by reacting with substituted aldehydes and their corresponding metal complexes.
  • Poly(2,5-benzimidazole) (ABPBI) polymer by reacting with methanesulfonic acid and P2O5.
  • Pt-based Schiff base complexes applicable in H2O splitting reactions.

3,4-Diaminobenzoic acid undergoes cyclocondensations to form, for example, quinoxalines and benzimidazoles.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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S Ram et al.
Journal of medicinal chemistry, 35(3), 539-547 (1992-02-07)
A series of methyl and ethyl 5-(alkoxycarbonyl)-1H-benzimidazole-2-carbamates (7-19) and methyl 5-carbamoyl-1H-benzimidazole-2-carbamates (24-34) have been synthesized via the reaction of an appropriate alcohol or amine with the acid chloride derivatives 6a or 6b at room temperature. Reaction of an alcohol with
L A Cooper et al.
Antonie van Leeuwenhoek, 50(1), 53-62 (1984-01-01)
The effect of various compounds on growth, melanin biosynthesis and cell differentiation was studied in a hyaline (SH25) and a pigmented (SH25B) strain of Microdochium bolleyi. Dark pigment production by the hyaline strain was induced by the presence of DOPA
New 3, 4-diaminobenzoic acid Schiff base compounds and their complexes: Synthesis, characterization and thermodynamics
Mohammadi K, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 122, 179-185 (2014)
Tetrahedron, 49, 9823-9823 (1993)
N Sundaraganesan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 70(2), 376-383 (2007-12-28)
The Fourier Transform Raman and Fourier Transform infrared spectra of 3,4-diaminobenzoic acid (3,4-DABA) were recorded in the solid phase. Geometry optimizations were done without any constraint and harmonic-vibrational wave numbers and several thermodynamic parameters were calculated for the minimum energy
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