2H-1,3,2-benzodioxaborole

• ChemBase ID: 88485
• Molecular Formular: C6H5BO2
• Molecular Mass: 119.9137
• Monoisotopic Mass: 120.0382598
• SMILES: O1c2ccccc2OB1
• Canonical SMILES: B1Oc2c(O1)cccc2
• InChI: InChI=1S/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H
• InChIKey: CENMEJUYOOMFFZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2H-1,3,2-benzodioxaborole
• IUPAC Traditional name: catecholborane
• Synonyms: Catecholborane solution; Catecholborane; 1,3,2-Benzodioxaborole; Catecholborane; Benzo[d][1,3,2]dioxaborole; 1,3,2-Benzodioxaborole; 1,3,2-benzodioxaborole; 7,9-dioxa-8λ2-borabicyclo[4.3.0]nona-1,3,5-triene; Catecholborane; 儿茶酚硼烷 溶液; 儿茶酚硼烷; 儿茶酚硼烷

Database IDs

• CAS Number: 274-07-7
• EC Number: 205-991-5
• MDL Number: MFCD00005846
• Beilstein Number: 972072
• PubChem SID: 24851357; 24853519; 162075431
• PubChem CID: 6327445
• Chemspider ID: 10617125
• Wikipedia Title: Catecholborane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.2384
• LogD (pH = 7.4): 2.2384
• Log P: 1.4184
• Molar Refractivity: 51.7702 cm^3
• Polarizability: 13.616939 Å^3
• Polar Surface Area: 26.28 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Melting Point: 12 °C; 12 °C(lit.); 12°C; 12°C
• Boiling Point: 50 °C/50 mmHg; 50 °C/50 mmHg(lit.); 50°C; 50°C/50mm
• Flash Point: 1.4 °F; -17 °C; 2 °C; 2°C; 2°C(35°F); 35.6 °F
• Density: 0.958 g/mL at 25 °C; 1.125; 1.125 g/cm3, liquid; 1.125 g/mL at 25 °C(lit.)
• Refractive Index: 1.5025; n20/D 1.507(lit.)

Safety Information

• Storage Warning: Highly Flammable/Corrosive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 2924; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-14-19-34-37; 11-14-34; 11-14-34-48/20-63-67; R11, R14, R34
• Safety Statements: 16-26-36/37/39-45; 26-36/37/39-43-45; 8-26-36/37/39-45; S16, S26, S36/37/39, S43, S45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  4

  1

  2

  W
• GHS Hazard statements: H224-H314-H318-H361-H373-H336; H225-H314; H225-H314-H318; H225-H314-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338-P310; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides., Reacts violently with water.; Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 50% w/w in toluene (98% dry wt.); 97%; 98%
• Concentration: 1.0 M in THF
• Grade: technical
• Empirical Formula (Hill Notation): C6H5BO2

DETAILS

Apollo Scientific Ltd - OR40616

Packaged in Safebreak bottles

Sigma Aldrich - 188913

Application
A monofunctional hydroborating agent which reduces β-hydroxyketones to 1,3-diols.1 Effects conjugate reduction of α,β-enones.2
Used to prepare B-alkylcatecholboranes which were used, in turn, to generate alkyl radicals forming aryl ethers from quinones. Employed in a preparation of C2-symmetric boron complexes from methylenebis(oxazolines) used for enantioselective reduction of ketones.
Packaging
25, 100 g in Sure/Seal™

Sigma Aldrich - 225762

Packaging
100, 800 mL in Sure/Seal™
Application
Used in the transition metal catalyzed hydroboration of alkenes.1,2,3

Sigma Aldrich - 12345

Caution
may become turbid on storage

REFERENCES

• Mild, selective hydroborating agent: J. Am. Chem. Soc., 97, 5249 (1975); Tetrahedron, 32, 981 (1976). Use of Rh(I) and Ir(I) catalysis increases stereo- and regioselectivity: J. Am. Chem. Soc., 114, 6671, 6674 (1992). For Rh catalyzed enantioselective hydroboration of alkenylboronic acids, see: Tetrahedron: Asymmetry, 7, 5 (1996). Hydroboration of olefins can be accomplished at room temperature in the presence of N,N-dimethylacetamide: J. Org. Chem., 61, 3224 (1996).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 666 (2007).