PHENYLBORON DICHLORIDE

Base Information

• Chemical Name: PHENYLBORON DICHLORIDE
• CAS No.: 873-51-8
• Molecular Formula: C6H5 B Cl2
• Molecular Weight: 158.823
• Hs Code.: 29310099
• Mol file: 873-51-8.mol

Synonyms:Borine,dichlorophenyl- (6CI); Dichlorophenylborane; NSC 93889; Phenylboron dichloride;Phenyldichloroborane; Phenyldichloroboron

Chemical Property of PHENYLBORON DICHLORIDE

Chemical Property:

• Appearance/Colour: Colourless or yellow transparent liquid.
• Vapor Pressure: 0.92mmHg at 25°C
• Melting Point: 7 °C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 66 °C11 mm Hg(lit.),186.2 °C at 760 mmHg
• Flash Point: ?5 °F
• PSA: 0.00000
• Density: 1.224 g/mL at 25 °C(lit.)
• LogP: 1.85940
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in water (Reacts violently).

Purity/Quality:

98% ^*data from raw suppliers

Dichlorophenylborane ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Uses: Dichlorophenylborane is widely used as a catalyst in Antiproliferative macrolide and cell migration inhibitor lactimidomycin and in enantioselective synthesis of polypeptide segments using vinylogous Mukaiyama aldol reactions and in enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives. It is a stereo selective alkylative ring opening of cyclic anhydrides and in cross-metathesis reaction of amino derivatives with olefines. Catalyst for: Antiproliferative macrolide and cell migration inhibitor lactimidomycinEnantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactionsEnantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivativesStereoselective alkylative ring opening of cyclic anhydridesCross-metathesis reaction of amino derivatives with olefinsAsymmetric acetate aldol reactionsThe reaction of aryl aldehydes with styrene and (E)-β-methylstyrene

Technology Process of PHENYLBORON DICHLORIDE

There total 64 articles about PHENYLBORON DICHLORIDE 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: 98.0%

trimethylphenylsilane (768-32-1) + boron trichloride (10294-34-5) → phenylborondichloride (873-51-8)

Guidance literature:

In neat (no solvent); byproducts: ClSi(CH3)3; 60°C, 12h, ampul;

DOI:10.1016/0022-328X(86)80405-3

Reference yield: 67.0%

diethyl phenylboronate (31044-59-4) + boron trichloride (10294-34-5) → phenylborondichloride (873-51-8)

Guidance literature:

iron(III) chloride; In dichloromethane; byproducts: BCl2(OC2H5); slow addn. of boronate to BCl3 soln. contg. FeCl3 under N2, 0°C, within 10 min; stirring at 0°C, 1 h and at 25°C, 1 h; evapn.; extn. (CH2Cl2); evapn.; distn.;

DOI:10.1021/om00045a025

Reference yield: 56.0%

tetraphenyltin(IV) (595-90-4) + boron trichloride (10294-34-5) → phenylborondichloride (873-51-8)

Guidance literature:

In benzene; BCl3 cooled at -78°C and quickly added to Sn(C6H5)4, cooled at 5°C while stirring; warming at ambient temp., boiled for 3.5 h using back-flow; best lab. method; solvent must be distd. below 140°C (immersion thermometer!); crude product distd. between 150-200°C; fractional vac. distn.;

upstream raw materials:

triphenylboroxine

bis(s-butyloxy)phenyl borane

diphenylboronchloride

diethyl phenylboronate

Downstream raw materials:

10-phenyl-9,10-azaboraphenanthrene

2-phenyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

2-phenyl-2,3-dihydro-benzo[1,3,2]oxazaborole

diphenylboronchloride

Refernces

• 1、 Fox,Wartik. "". . p. 498,499. Retrieved 1961.
• 2、 -. "PROCESS FOR REDUCING THE CONTENT OF BORON COMPOUNDS IN HALOSILANE-CONTAINING COMPOSITIONS". Paragraph 0030; 0059. . Retrieved 2022/01/24.
• 3、 Yasuike, Shuji,Nakata, Kazuhide,Qin, Weiwei,Matsumura, Mio,Kakusawa, Naoki,Kurita, Jyoji. "Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions". . p. 9 - 16. Retrieved 2015/05/13.