benzene-1,2-diamine

• ChemBase ID: 103448
• Molecular Formular: C6H8N2
• Molecular Mass: 108.14112
• Monoisotopic Mass: 108.06874827
• SMILES: Nc1c(N)cccc1
• Canonical SMILES: Nc1ccccc1N
• InChI: InChI=1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2
• InChIKey: GEYOCULIXLDCMW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzene-1,2-diamine
• IUPAC Traditional name: o-phenylenediamine
• Synonyms: o-Phenylenediamine; C.I. 76010; C.I. Oxidation Base 16; IK 3; NSC 5354; Orthamine; o-Aminoaniline; o-Aminophenylamine; o-Benzenediamine; o-Diaminobenzene; 1,2-Phenylenediamine; o-Phenylenediamine; 1,2-Phenylenediamine; 2-Aminoaniline; 1,2-Benzenediamine; 1,2-Diaminobenzene; 1,2-Phenylenediamine; OPD; o-PHENYLENEDIAMINE; o-Phenylene diamine; Benzene-1,2-diamine; 1,2-二氨基苯; 1,2-苯二胺; 邻苯二胺; 邻苯二胺; 1,2-苯二胺

Database IDs

• CAS Number: 95-54-5
• EC Number: 202-430-6
• MDL Number: MFCD00007721
• Beilstein Number: 606074
• Merck Index: 147284
• PubChem SID: 24898638; 24899004; 24887299; 24898319; 24856671; 24887298; 162102922; 24887300
• PubChem CID: 7243
• CHEBI ID: 34043
• CHEMBL: 70582
• Chemspider ID: 13837582
• Unique Ingredient Identifier: 8B713N8Q0F
• Wikipedia Title: O-Phenylenediamine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.24660818
• LogD (pH = 7.4): 0.31445572
• Log P: 0.3153939
• Molar Refractivity: 35.4588 cm^3
• Polarizability: 12.615475 Å^3
• Polar Surface Area: 52.04 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble1 tablet/10 mL, clear, colorless; Methanol; Soluble in alcohol, chloroform, ether, slightly soluble in water; soluble in hot water
• Apperance: sublimed; tablet; White Solid; white to off-white powder
• Melting Point: 100-102 °C; 100-102 °C(lit.); 100-103°C; 101.1 - 101.3 °C; 102 - 104°C; 116-118°C; 98-102 °C; 99-102 °C
• Boiling Point: 252°C (Other sources: 256 — 258 °C.); 256 - 258 °C at 1013 hPa; 256-258 °C; 256-258 °C(lit.); 256-258°C
• Flash Point: 110 °C (method not stated); 136 °C; 136°C(277°F); 276.8 °F; 277 °F
• Auto Ignition Point: 540 °C
• Density: 1.031 g/cm^3; 1.14 g/cm^3 at 20 °C; 1.270
• Vapor Pressure: .013 hPa at 20 °C; 0.01 mmHg ( 25 °C)
• Vapor Density: 3.7 (vs air); 3.73 (air = 1)
• Fluorescence: λex 337 nm; λem 417 nm (after derivatization); λex 337 nm; λem 417 nm (Pyruvic acid derivative)

Safety Information

• Storage Condition: Amber Vial, Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Store Under Nitrogen, Protect from light
• Storage Warning: Air & Light Sensitive
• RTECS: SS7875000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 1673; UN1673
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 20/21-25-36-40-43-50/53-68; 20/21-25-36-40-43-68-50/53; R:20/21-25-36-40-43-50/53
• Safety Statements: 28-36/37-45-60-61; R; S:28-45-60-61-36/37
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H301-H312 + H332-H317-H319-H341-H351-H371-H410; H301-H312-H317-H319-H332-H341-H351-H410; H301-H330-H319-H317-H341-H351-H400-H410
• GHS Precautionary statements: P260-P273-P280-P301 + P310-P305 + P351 + P338-P501; P260-P301+P310-P305+P351+P338-P320-P405-P501A; P273-P280-P301 + P310-P305 + P351 + P338-P501
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1673 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0%; ≥98.0% (GC); ≥99%; ≥99.0% (NT); 98%; 99.5%
• Concentration: 20 mg/tablet (~45 mg)
• Grade: for fluorescence; technical; zone-refined
• Suitability: suitable for fluorescence
• Purified By: sublimation
• Linear Formula: C6H4(NH2)2
• Empirical Formula (Hill Notation): C6H8N2

DETAILS

MP Biomedicals - 02151828

Free Base
Tan to brown crystals
A less expensive alternative to our Grade I material.

MP Biomedicals - 02151827

Grade I
Free Base
This product is a white to off-white solid which may darken during storage.

Sigma Aldrich - P9029

Application
o-Phenylenediamine Free Base is a peroxidase substrate suitable for use in ELISA procedures. The substrate produces a soluble end product that is orange-brown in color and can be read spectrophotometrically at 450 nm. The OPD reaction may be stopped with 3 N HCl or 3 M H2SO4 and read at 492 nm.
Caution
May darken in storage.

Sigma Aldrich - P5412

Application
o-Phenylenediamine Free Base is a peroxidase substrate suitable for use in ELISA procedures. The substrate produces a soluble end product that is orange-brown in color and can be read spectrophotometrically at 450 nm. The OPD reaction may be stopped with 3 N HCl or 3 M H2SO4 and read at 492 nm.
Reconstitution
Dissolve one tablet in 0.05 M phosphate-citrate buffer, pH 5.0, to the desired concentration (typically an OPD concentration of 0.4 mg/ml is used). Add 40 μl of fresh 30% hydrogen peroxide per 100 ml of substrate buffer solution, immediately prior to use. Tablets are individually packaged in foil packets.

Sigma Aldrich - 78412

Packaging
50 g in glass bottle

Sigma Aldrich - P23938

Packaging
5, 100, 500 g in glass bottle
Legal Information
DuPont product

Sigma Aldrich - 694975

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 275786

Packaging
1 g in glass bottle

Sigma Aldrich - 78411

Other Notes
Oxidation to 2,3-diaminophenazine1; Determination of urinary oxalate by HPLC2; Fluorescent detection of pyruvate3

Toronto Research Chemicals - P319840

An amino substituted benzene used in the manufacture of dyes. Potential use in sensitive immunosensor for cancer biomarker.

REFERENCES

• Wu, Y. et al.: Anal. Bioanal. Chem., 400, 2141 (2011)
• Du, D. et al.: Anal. Chem., 82, 2989 (2011)