2-Chloro-1,3,2-benzodioxaborole

Base Information

• Chemical Name: 2-Chloro-1,3,2-benzodioxaborole
• CAS No.: 55718-76-8
• Molecular Formula: C6H4BClO2
• Molecular Weight: 154.361
• Hs Code.: 2934999090
• European Community (EC) Number: 628-352-6
• DSSTox Substance ID: DTXSID10399755
• Nikkaji Number: J510.753I
• Wikidata: Q82202468
• Mol file: 55718-76-8.mol

Synonyms:55718-76-8;2-Chloro-1,3,2-benzodioxaborole;B-Chlorocatecholborane;2-Chlorobenzo[d][1,3,2]dioxaborole;Beta-chlorocatecholborane;1,3,2-Benzodioxaborole, 2-chloro-;chlorocatecholborane;SCHEMBL28709;B-Chlorocatecholborane, 97%;DTXSID10399755;AZYGEWXDKHFOKB-UHFFFAOYSA-N;2-Chloro-1,3-dioxa-2-boraindan;3,3-DIETHOXY-PROPIONICACID;MFCD00043395;2-chloro-2H-1,3,2-benzodioxaborole;AKOS025213343;AS-55608;C1669;CS-0142780;FT-0691596;D89444;A902520

Chemical Property of 2-Chloro-1,3,2-benzodioxaborole

Chemical Property:

• Vapor Pressure: 0.906mmHg at 25°C
• Melting Point: 56-58 °C(lit.)
• Refractive Index: 1.536
• Boiling Point: 186.554 °C at 760 mmHg
• Flash Point: 66.626 °C
• PSA: 18.46000
• Density: 1.32 g/cm³
• LogP: 1.68150
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 153.9992872
• Heavy Atom Count: 10
• Complexity: 119

Purity/Quality:

97% ^*data from raw suppliers

2-?Chloro-?1,?3,?2-?benzodioxaborole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F
• Hazard Codes: F,C
• Statements: 11-14-34-37
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC2=CC=CC=C2O1)Cl
• Uses: B-Chlorocatecholborane can be used:To prepare 2-arachidonoylglycerol by acetal cleavage of cis-arachidonoylbenzylidene glycerol.To prepare metal boryl complexes (Rh and Ir complexes) through oxidative addition.To remove the trityl group in one of the key steps for the synthesis of (?)-dictyostatin.

Technology Process of 2-Chloro-1,3,2-benzodioxaborole

There total 2 articles about 2-Chloro-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: 70.0%

[OsCl(η6-p-cymene)(1,3-bis(2,6-diisopropylphenyl)imidazolylidene)][trifluoromethanesulfonate] + benzo[1,3,2]dioxaborole (274-07-7) → 2-chloro-1,3,2-benzodioxaborole (55718-76-8) + [OsH2(η6-p-cymene)(1,3-bis(2,6-diisopropylphenyl)imidazolylidene)(catecholborane(-1H))][trifluoromethanesulfonate]

Guidance literature:

In diethyl ether; dichloromethane; at 20 ℃;

DOI:10.1021/om400188z

Reference yield:

(o-C6H4O2)BSH (57100-59-1) → sulfur (10544-50-0) + 2-chloro-1,3,2-benzodioxaborole (55718-76-8) + hydrogen sulfide (7783-06-4)

Guidance literature:

With chlorine;

Reference yield: 100.0%

2-chloro-1,3,2-benzodioxaborole (55718-76-8) + 2-phenylethynylphenol (92151-73-0) → C20H13BO3 (1581275-98-0)

Guidance literature:

In diethyl ether; at -78 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.organomet.5b00939

upstream raw materials:

(o-C₆H₄O₂)BSH

benzo[1,3,2]dioxaborole

Downstream raw materials:

catechol butyl borate

2-(benzylthio)benzo[d][1,3,2]dioxaborole

(4-methylphenylthio)catecholborane

2-(phenylethynyl)benzo[d][1,3,2]dioxaborole

Refernces

Cross-metathesis between α-methylene-γ-butyrolactone and olefins: A dramatic additive effect

10.1021/ol0703940

The research focuses on the cross-metathesis reaction between r-methylene-γ-butyrolactone and terminal olefins, aiming to develop an efficient and highly stereoselective method for synthesizing r-alkylidene-γ-butyrolactones, which are valuable building blocks in organic synthesis. The experiments involved using various ruthenium-based catalysts, with [Ru]-II being the most effective, and a range of additives to enhance the reaction efficiency and minimize the formation of undesired isomerized byproducts. The reactions were conducted in refluxing CH2Cl2, with the products and reaction progress analyzed using 1H NMR spectroscopy. Key additives identified were chlorocatecholborane and 2,6-dichloro-1,4-benzoquinone, which significantly improved the reaction's yield and selectivity. The study also explored the reaction with a variety of olefinic partners, achieving moderate to excellent yields with high E-stereoselectivity.

Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration

10.1021/acs.orglett.8b02727

The study presents a transition-metal-free method for synthesizing 3-borylated thiophenes through formal thioboration. (Z)-Organylthioenyne substrates are activated by the commercially available B-chlorocatecholborane reagent (ClBcat), which acts as a carbophilic Lewis acid. This activation initiates the formal thioboration and subsequent sulfur dealkylation, yielding 3-borylated thiophenes. The resulting borylated thiophenes can be isolated as boronic esters (Bpin) or boronamides (Bdan), and are amenable to diverse downstream functionalization reactions such as cross-coupling, azidation, bromination, and C?H activation. The study explores the effects of different sulfur substituents (R2) on the reaction outcomes, finding that a methyl group attached to the sulfur atom leads to improved yields of the desired borylated thiophenes. The methodology is demonstrated to be robust with various substitutions and functional groups, and its potential applications in synthesizing important building blocks for late-stage modifications are showcased through a range of functionalization reactions.