benzene-1,2-diol

• ChemBase ID: 1983
• Molecular Formular: C6H6O2
• Molecular Mass: 110.11064
• Monoisotopic Mass: 110.03677943
• SMILES: Oc1ccccc1O
• Canonical SMILES: Oc1ccccc1O
• InChI: InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
• InChIKey: YCIMNLLNPGFGHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzene-1,2-diol
• IUPAC Traditional name: catechol; 1,2-dihydroxybenzene
• Synonyms: Catechol; Oxyphenic Acid; Phthalhydroquinone; Phthalic Alcohol; Pyrocatechin; o-Benzenediol; o-Dihydroxybenzene; o-Dioxybenzene; o-Hydroquinone; o-Hydroxyphenol; o-Phenylenediol; NSC 1573; pyrocatechol; Catechol; Pyrocatechol; 1,2-Benzenediol, 1,2-Dihydroxybenzene; CATECHOL; 1,2-Dihydroxybenzene; Pyrocatechol; 1,2-benzenediol; 2-hydroxyphenol; 1,2-dihydroxybenzene; 1,2-Dihydroxybenzene; 1,2-Benzenediol; 1,2-二羟基苯; 1,2-苯二酚; 儿茶酚; 邻苯二酚; 邻苯二酚

Database IDs

• CAS Number: 120-80-9
• EC Number: 204-427-5
• MDL Number: MFCD00002188
• Beilstein Number: 471401
• Merck Index: 147999
• PubChem SID: 24866940; 24278346; 46507748; 24892626; 160965438; 24848193
• PubChem CID: 289
• CHEMBL: 280998
• Chemspider ID: 283
• KEGG ID: C00090
• Wikipedia Title: Catechol

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.342309
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.3660531
• LogD (pH = 7.4): 1.3612154
• Log P: 1.3661152
• Molar Refractivity: 30.0198 cm^3
• Polarizability: 11.539352 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.74
• LOG S: -0.17
• Solubility (Water): 7.50e+01 g/l

PROPERTIES

Physical Property

• Solubility: 43 g/100 mL in water; 461 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; Methanol
• Apperance: Powder; white solid; White Solid; white to faintly beige powder
• Melting Point: 100-103 °C(lit.); 101-106 °C; 103-106 °C; 104-106°C; 104-106°C; 104-107°C; 105°C
• Boiling Point: 245 °C(lit.); 245.5°C; 245-246°C; 246°C
• Flash Point: 127 °C (closed cup); 127 °C; 127°C(260°F); 260.6 °F; 261 °F
• Auto Ignition Point: 510 °C
• Density: 1.344 g/cm^3 at 15 °C; 1.344 g/cm3, solid; 1.370
• Vapor Pressure: .1 hPa at 35 °C; 1 mmHg ( 75 °C); 10 mmHg ( 118.3 °C)
• Vapor Density: 3.8 (vs air)
• Hydrophobicity(logP): 0.88 [HANSCH,C ET AL. (1995)]
• pKa: 9.5

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: UX1050000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 1759; 2811; UN2811
• German water hazard class: 2
• Hazard Class: 6.1; 8
• Packing Group: 3; II; III
• Australian Hazchem: 2X
• Risk Statements: 21/22-36/38; R:21/22-36/38; R21/22, R36/38
• Safety Statements: 22-26-37; S:22-26-37; s2, S22, S26, S37
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  2
• GHS Hazard statements: H301-H311-H315-H319; H302-H312-H315-H319
• GHS Precautionary statements: P280-P301+P310-P305+P351+P338-P361-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥98.0% (HPLC); ≥99%; ≥99% (HPLC); ≥99.5%; 99%
• Grade: puriss.; purum; ReagentPlus®
• Suitability: plant cell culture tested
• Ignition Residue: ≤0.01% (as SO4)
• Purified By: sublimation
• Linear Formula: C6H4-1,2-(OH)2
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02101296

Crystalline
Purity: 99%

DrugBank - DB02232

Drug information: experimental

Sigma Aldrich - 430749

Packaging
5 g in glass bottle

Sigma Aldrich - 135011

Packaging
100, 500 g in poly bottle
3, 5 kg in fiber drum
5 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - C9510

Caution
暴露于空气和光线中时可能变色。

Sigma Aldrich - C3561

Caution
暴露于空气和光线中时可能变色。

REFERENCES

• Ring-opening with O₂ in the presence of CuCl, pyridine and methanol gives the monoester of cis,cis-muconic acid: Org. Synth. Coll., 8, 490 (1993).
• In the presence of catechol, carboxylic acids are reduced to alcohols by NaBH₄: Tetrahedron, 48, 371 (1992).
• For an example of the use of catechol in the synthesis of crown ethers, see: Org. Synth. Coll., 6, 395 (1988).