CAS 274-07-7|1,3,2-benzodioxaborole|2H-1,3,2-benzodioxaborole|Catecholborane|7,9-dioxa-8λ2-borabicyclo[4.3.0]nona-1,3,5-triene|catecholborane|Catecholborane|Benzo[d][1,3,2]dioxaborole|1,3,2-Benzodi...

InChI=1S/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H

CENMEJUYOOMFFZ-UHFFFAOYSA-N

H Acceptors

H Donor

LogD (pH = 5.5)

2.2384

LogD (pH = 7.4)

2.2384

Log P

1.4184

Molar Refractivity

51.7702

Polarizability

13.616939

Polar Surface Area

26.28

Rotatable Bonds

Lipinski's Rule of Five

true

1,3,2-benzodioxaboroleCatecholborane7,9-dioxa-8λ2-borabicyclo[4.3.0]nona-1,3,5-triene1,3,2-BenzodioxaboroleBenzo[d][1,3,2]dioxaboroleCatecholborane儿茶酚硼烷CatecholboraneCatecholborane solution1,3,2-Benzodioxaborole儿茶酚硼烷溶液儿茶酚硼烷

2H-1,3,2-benzodioxaborole

IUPAC Traditional name

Highly Flammable/Corrosive/Moisture Sensitive/Keep Cold/Store under Argon

Moisture Sensitive

S16,S26,S36/37/39,S43,S45

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OR40616

Packaged in Safebreak bottles

225762

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

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™

12345

Caution
may become turbid on storage

• 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).

Names and Identifiers

Synonyms

IUPAC name

2H-1,3,2-benzodioxaborole

IUPAC Traditional name

catecholborane

Registration numbers

CAS Number

274-07-7

Chemspider ID

10617125

Wikipedia Title

Catecholborane

PubChem SID

1620754312485351924851357

PubChem CID

EC Number

Beilstein Number

MDL Number

Molecule Details

OR40616

Packaged in Safebreak bottles

Wikipedia

Catecholborane

Sigma Aldrich

225762

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

188913

12345

Caution
may become turbid on storage

References

PubChem Literature

From Data Sources

• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 666 (2007).

Bioactivity

PubChem BioAssay

16-26-36/37/39-45

26-36/37/39-43-45

8-26-36/37/39-45

Risk Statements

R11,R14,R34

11-14-19-34-37

11-14-34

11-14-34-48/20-63-67

NFPA704

GHS Pictograms

Corrosive to metals, category 1

Skin corrosion, categories 1A,1B,1C

Serious eye damage, category 1

Flammable gases, category 1

Flammable aerosols, categories 1,2

Flammable liquids, categories 1,2,3

Self-reactive substances and mixtures, Types B,C,D,E,F

Pyrophoric liquids, category 1

Pyrophoric solids, category 1

Self-heating substances and mixtures

Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3

Organic peroxides, Types B,C,D,E,F

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

GHS Hazard statements

H225-H314-H335

H225-H314

H224-H314-H318-H361-H373-H336

H225-H314-H318

MSDS Link

Download link

Packing Group

UN Number

2924

UN2924

European Hazard Symbols

Flammable (F)

Corrosive (C)

Harmful (X)

German water hazard class

GHS Signal Word

Danger

Supplemental Hazard Statements

May form explosive peroxides., Reacts violently with water.

Reacts violently with water.

RID/ADR

UN 2924 3/PG 2

Storage Temperature

2-8°C

GHS Precautionary statements

P210-P261-P280-P305+P351+P338-P310

P210-P280-P305+P351+P338-P310

P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A

Hazard Class

Personal Protective Equipment

Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

TSCA Listed

是

Empirical Formula (Hill Notation)

Molecule

ID:88485