1,3,2-Benzodioxaborole

Base Information

• Chemical Name: 1,3,2-Benzodioxaborole
• CAS No.: 274-07-7
• Molecular Formula: C6H5BO2
• Molecular Weight: 119.915
• Hs Code.: 29209090
• European Community (EC) Number: 205-991-5
• UNII: UB69382H5J
• DSSTox Substance ID: DTXSID3059769
• Nikkaji Number: J193.697B,J2.186.662H
• Wikipedia: Catecholborane
• Wikidata: Q730606
• Mol file: 274-07-7.mol

Synonyms:Catecholborane;1,3,2-Benzodioxaborole;274-07-7;Benzo[d][1,3,2]dioxaborole;Benzcatechinborane;Catecholatoborane;Pyrocatecholborane;Benzo[1,3,2]dioxaborole;CB;1,3,2-benzodioxaborolane;CID 67506;catechol borane;1,3,2$l^{2}-benzodioxaborole;c6h5bo2;Catecholborane, 98%;1,3,22-benzodioxaborole;CATECHOLBORANE [MI];SCHEMBL7747;2H-1,3,2-benzodioxaborole;DTXSID3059769;Catechol borane 50% in Toluene;ZDQWVKDDJDIVAL-UHFFFAOYSA-N;C6-H5-B-O2;AMY14855;BCP15959;1,3-Dioxa-2-bora(IV)-2H-indene;Catecholborane, 50% w/w in toluene;MFCD00005846;AKOS015909822;AS-55580;FT-0606485;A819050;Q730606;J-519721

Chemical Property of 1,3,2-Benzodioxaborole

Chemical Property:

• Appearance/Colour: clear colorless solution
• Vapor Pressure: 17.554mmHg at 25°C
• Melting Point: 12 °C(lit.)
• Refractive Index: n20/D 1.507(lit.)
• Boiling Point: 121.385 °C at 760 mmHg
• Flash Point: 27.213 °C
• PSA: 18.46000
• Density: 1.125g/mLat 25°C(lit.)
• LogP: 0.72430
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with diethyl ether, tetrahydrofuran, dichloromethane, c
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 119.0304345
• Heavy Atom Count: 9
• Complexity: 95.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

Catecholborane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, C
• Hazard Codes: F,C
• Statements: 11-19-34-67-65-63-48/20-14-40-37
• Safety Statements: 26-36/37/39-45-62-16-43

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [B]1OC2=CC=CC=C2O1
• Uses: CATECHOLBORANE is used in the transition metal catalyzed hydroboration of alkenes.1,2,3 Catecholborane is used to prepare B-alkylcatecholboranes. It finds application for the preparation of amides and macrocyclic lactams from carboxylic acids. It is used as a stereoselective reducing agent to convert beta-hydroxy ketones to syn 1,3-diols. Further, it reacts with alkyne through hydroboration to form trans vinyl borane, which is a precursor to Suzuki reaction.

Technology Process of 1,3,2-Benzodioxaborole

There total 32 articles about 1,3,2-Benzodioxaborole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

sodium tetrahydroborate (16940-66-2) + tris(catecholato)diboron (37737-62-5) → sodium bis(catecholato)borate (22364-91-6) + diborane (19287-45-7) + benzo[1,3,2]dioxaborole (274-07-7)

Guidance literature:

In diethylene glycol dimethyl ether; (N2); soln. of Na(BH4) (34.1 mmol) in diglyme was added to the phenylene compd. (68.3 mmol) in diglyme; B2H6 carried away by an N2 stream, was absorbed in acetone; stirring overnight; (N2); distn. (80-100 °C, 100 mmHg) gave a soln. of the catecholatoborane (yield 97%); the non-volatile residue dried (100 °C, 0.01 mmHg) and identfied as Na(B(O2C6H4)2) (11B NMR spectrum);

DOI:10.1039/DT9850001689

Reference yield: 88.0%

(C5H5)2Ti(C6H4O2BH)2 + carbon monoxide (201230-82-2) → dicarbonylbis(η-cyclopentadienyl)titanium(II) + benzo[1,3,2]dioxaborole (274-07-7)

Guidance literature:

2 atm. of CO, 1 d at -10°C;

DOI:10.1021/ja962086v

Reference yield: 86.0%

tris(catecholato)diboron (37737-62-5) → benzo[1,3,2]dioxaborole (274-07-7)

Guidance literature:

With diborane; In toluene; at 90 ℃; for 4h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Green chemistry;

DOI:10.1021/op000291w

upstream raw materials:

benzene-1,2-diol

tris(catecholato)diboron

phenylsilane

BH₃*THF-d8

Downstream raw materials:

2-cyclopentyl-benzo[1,3,2]dioxaborole

2-cyclohexylbenzo-[d][1,3,2]dioxaborole

(E)-1-vinyl-2-cyclohexyl-catecholborane

(2E,4Z)-5-(Benzo[1,3,2]dioxaborol-2-yloxy)-1,3,5-triphenyl-penta-2,4-dien-1-one

Refernces

• 1、 Kanth, Josyula V.B.,Periasamy, Mariappan,Brown, Herbert C.. "New economical, convenient procedures for the synthesis of catecholborane". . p. 550 - 553. Retrieved 2000.
• 2、 Hartwig, John F.,He, Xiaoming. "Reactivity". . p. 315 - 317. Retrieved 1996.
• 3、 Cid, Jessica,Hermann, Alexander,Radcliffe, James E.,Curless, Liam D.,Braunschweig, Holger,Ingleson, Michael J.. "Synthesis of Unsymmetrical Diboron(5) Compounds and Their Conversion to Diboron(5) Cations". . p. 1992 - 1998. Retrieved 2018.
• 4、 Braunschweig, Holger,Guethlein, Frank,Mailaender, Lisa,Marder, Todd B.. "Synthesis of catechol-, pinacol-, and neopentylglycolborane through the heterogeneous catalytic B-B hydrogenolysis of diboranes(4)". . p. 14831 - 14835. Retrieved 2013/11/06.