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Dibromo(phenyl)borane, also known as bromophenylborane or phenylbromineborane, is an organoborane compound with the chemical formula C6H5BBr2. It is a colorless, crystalline solid that is soluble in organic solvents. dibromo(phenyl)borane is a valuable reagent in organic synthesis, particularly in the formation of carbon-carbon bonds through the hydroboration-oxidation reaction sequence. Dibromo(phenyl)borane is synthesized by reacting phenylboronic acid with bromine in the presence of a Lewis acid catalyst. It is sensitive to moisture and air, and therefore, it should be handled under an inert atmosphere. Due to its reactivity, it is used in various applications, including the preparation of alkenes, cyclopropanes, and other complex organic molecules.

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  • 4151-77-3 Structure
  • Basic information

    1. Product Name: dibromo(phenyl)borane
    2. Synonyms: borane, dibromophenyl-; Dibromo(phenyl)borane
    3. CAS NO:4151-77-3
    4. Molecular Formula: C6H5BBr2
    5. Molecular Weight: 247.7229
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 4151-77-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 223°C at 760 mmHg
    3. Flash Point: 88.7°C
    4. Appearance: N/A
    5. Density: 1.78g/cm3
    6. Vapor Pressure: 0.147mmHg at 25°C
    7. Refractive Index: 1.571
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: dibromo(phenyl)borane(CAS DataBase Reference)
    11. NIST Chemistry Reference: dibromo(phenyl)borane(4151-77-3)
    12. EPA Substance Registry System: dibromo(phenyl)borane(4151-77-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4151-77-3(Hazardous Substances Data)

4151-77-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 4151-77-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,5 and 1 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4151-77:
(6*4)+(5*1)+(4*5)+(3*1)+(2*7)+(1*7)=73
73 % 10 = 3
So 4151-77-3 is a valid CAS Registry Number.

4151-77-3Relevant articles and documents

Structural identification of the factors that prevent an electronic spin-state crossover in Fe[(C6H5)B(3-Mepz)3]2 (pz = pyrazolyl ring)

Reger, Daniel L.,Elgin, J. Derek,Smith, Mark D.,Grandjean, Fernande,Rebbouh, Leila,Long, Gary J.

, p. 2616 - 2622 (2006)

The synthesis, structural, magnetic, and M?ssbauer spectral properties of Fe[(C6H5)B(3-Mepz)3]2 (2, pz = pyrazolyl ring) are reported. The single crystal X-ray structural results indicate that at both 294 and 90 K Fe[(C6H5)B(3-Mepz)3]2 (2) has a distorted octahedral iron(II) coordination environment with Fe-N bond distances that average ca. 2.18 ?, distances that clearly indicate the high-spin nature of the complex at these temperatures. Both the magnetic and M?ssbauer spectral results indicate that Fe[(C6H5)B(3-Mepz)3]2 (2) remains high-spin down to 4 K. This result is surprising because the closely related Fe[(p-R-C6H4)B(3-Mepz)3]2 [R = I, {single bond}C{triple bond, long}C{single bond}H, {single bond}C{triple bond, long}C{single bond}SiMe3, or {single bond}C{triple bond, long}C{single bond}C6H5] complexes do exhibit electronic spin-state changes on cooling. The absence of a spin-state crossover in Fe[(C6H5)B(3-Mepz)3]2 (2) is the result of its molecular structure in which the three pyrazolyl rings of each tridentate ligand are highly twisted away from an ideal C3v coordination symmetry, a twisting distortion that favors the high-spin form of the complex with longer Fe-N bond distances.

Functionalization of Bis-Diazaphospholene P–P Bonds with Diverse Electrophiles

Huchenski, Blake S. N.,Robertson, Katherine N.,Speed, Alexander W. H.

supporting information, p. 5140 - 5144 (2020/07/27)

Phosphorus-sp3 or -sp2 carbon bonds are readily formed by the reaction of bis-diazaphospholenes with several classes of electrophiles. These reactions result in cleavage of the phosphorus–phosphorus bond and formation of functionalized diazaphospholenes. The reactions proceed rapidly, without catalysis. Experimental evidence with aryl and alkyl halides suggests the intermediacy of radicals in some cases, however other evidence suggests either radical or polar mechanisms may be operative for certain substrates, with a dependence on reaction conditions. In three cases, the product aryl diazaphospholenes have been shown to transfer the aryl substituent to electrophiles. These results reveal that diazaphospholene dimers are potent participants in radical chemistry with organic substrates at room temperature without requiring chemical initiators.

Triazole derivative containing boron-nitrogen group, polymer and preparation methods and applications of triazole derivative and polymer

-

Paragraph 0052; 0061-0062, (2020/07/07)

The invention belongs to the technical field of organic photoelectricity, and discloses a triazole derivative containing a boron-nitrogen group, a polymer and preparation methods and applications of the triazole derivative and the polymer. The chemical st

Structural and spectroscopic analysis of a new family of monomeric diphosphinoboranes

Ordyszewska, Anna,Szynkiewicz, Natalia,Perzanowski, Emil,Chojnacki, Jaros?aw,Wi?niewska, Aleksandra,Grubba, Rafa?

, p. 12482 - 12495 (2019/08/26)

We present a series of amino- and aryl(diphosphino)boranes R2PB(R′′)PR′2, where R2P, R′2P = tBu2P, tBuPhP, Ph2P, Cy2P, and R′′ = iPr2N, Ph, which were obtained via the

The preparation of pentafluorophenyldihaloboranes from pentafluorophenylmercurials C6F5HgR and BX3: the dramatic dependence of the reaction direction on the ligand R

Bardin, Vadim V.,Adonin, Nicolay Yu.

, p. 1523 - 1531 (2019/07/22)

Abstract: In search of convenient preparations of C6F5BX2 (X = Cl, Br), reactions of C6F5HgR (R = C6F5, C6H5, C2H5, Br and Cl) with BX3 were studied. Under the action of BCl3 the order of the C–Hg bond cleavage is C6F5Hg–C6H5 > C6F5–HgC2H5 > C6F5–HgC6F5 >> C6F5–HgCl. With more reactive BBr3 the sequence is C6F5Hg–C6H5 > C6F5–HgC2H5 ~ C6F5Hg–C2H5 > C6F5–HgC6F5 ≥ C6F5–HgBr. During the study we found the simple way to alkyldibromoboranes which is presented by the preparation of C2H5BBr2 from C2H5HgBr and BBr3. It is the second example of synthesis of alkylmercury derivative in an addition to the earlier reported formation of cyclopropylmercurials from di(cyclopropyl)mercury and BX3. Graphic abstract: [Figure not available: see fulltext.].

Compounds for organic electroluminescent devices

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Page/Page column 39, (2018/08/12)

The present invention relates to boron compounds for use in electronic devices, especially organic electroluminescent devices, and to a process for preparing these compounds and to electronic devices, especially organic electroluminescent devices, comprising these compounds.

Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers

Lik, Artur,Fritze, Lars,Müller, Lars,Helten, Holger

supporting information, p. 5692 - 5695 (2017/05/04)

Conjugated organoboranes have emerged as attractive hybrid materials for optoelectronic applications. Herein, a highly efficient, environmentally benign catalytic B-C bond formation method is presented that uses organosilicon compounds, dibromoboranes, and the metal-free organocatalyst Me3SiNTf2. This Si/B exchange approach has been successfully applied to the synthesis of arylborane molecules 4a-c, oligomers 8a,b, and polymers 8a′,b′. Photophysical investigations, supported by TD-DFT calculations, reveal highly effective π-conjugation in thienyl- and furylborane species; the latter are also highly emissive.

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

Yasuike, Shuji,Nakata, Kazuhide,Qin, Weiwei,Matsumura, Mio,Kakusawa, Naoki,Kurita, Jyoji

, p. 9 - 16 (2015/05/13)

The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl chloride in the presence of H2O afforded the corresponding cross-coupling products, unsymmetrical biaryls (4) and ketones (5), in moderate to good yields. The potential energy surfaces for the transmetallations of triarylstibanes (1) with BCl3 affording 2 were determined by molecular orbital calculations. The analyses of substituent effects on theoretically calculated reactivities showed the importance of the resonance effects of the ring substituents on these transmetallations.

Access to ultra-high-molecular weight poly(ethylene) and activity boost in the presence of cyclopentene with group 4 bis-amido complexes

Narayana, Gurram Venkata,Xu, Guangjuan,Wang, Dongren,Frey, Wolfgang,Buchmeiser, Michael R.

, p. 151 - 162 (2014/03/21)

ZrIV complexes of the type [Me2Si{(NR)(6-{2-(diethylboryl) phenyl} pyridyl-2-yl-N)}ZrCl2 thf] (R=tBu (4), adamantyl (7a); thf= tetrahydrofuran), [Me2Si{(NAd)(6-{2-(diphenylboryl)phenyl}pyridyl- 2-yl-N)}ZrCl2] (Ad=adamantyl (7b)), the

Structural characteristics of dibromo-borylated benzene derivatives

Popp, Sebastian,Ruth, Kai,Lerner, Hans-Wolfram,Bolte, Michael

experimental part, p. o226-o230 (2012/07/14)

The crystal structures of five dibromobenzene derivatives, namely dibromoborylbenzene, C6H5BBr2, (I), 1-dibromoboryl-4-(trimethylsilyl)benzene, C9H13BBr 2Si, (II), 4-bromo-1-(dibromoboryl)

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