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PHENYLBORON DICHLORIDE is an organoboron compound that serves as a versatile reagent and catalyst in various chemical reactions. It is known for its ability to facilitate enantioselective and stereoselective processes, making it a valuable tool in the synthesis of complex organic molecules.

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  • 873-51-8 Structure
  • Basic information

    1. Product Name: PHENYLBORON DICHLORIDE
    2. Synonyms: Borane,dichlorophenyl-;C6H5BCl2;PHENYLDICHLOROBORANE;PHENYLBORON DICHLORIDE;DICHLOROPHENYLBORANE;DICHLOROPHENYL BORON;Phenylborondichloride,95%;Phenylborondichloride,min.97%
    3. CAS NO:873-51-8
    4. Molecular Formula: C6H5BCl2
    5. Molecular Weight: 158.82
    6. EINECS: N/A
    7. Product Categories: organoboron and borato-metal complexes
    8. Mol File: 873-51-8.mol
  • Chemical Properties

    1. Melting Point: 7 °C
    2. Boiling Point: 66 °C11 mm Hg(lit.)
    3. Flash Point: −5 °F
    4. Appearance: Colorless/Liquid
    5. Density: 1.224 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.92mmHg at 25°C
    7. Refractive Index: n20/D 1.545(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. Water Solubility: Soluble in water (Reacts violently).
    11. Sensitive: Moisture Sensitive
    12. BRN: 2243576
    13. CAS DataBase Reference: PHENYLBORON DICHLORIDE(CAS DataBase Reference)
    14. NIST Chemistry Reference: PHENYLBORON DICHLORIDE(873-51-8)
    15. EPA Substance Registry System: PHENYLBORON DICHLORIDE(873-51-8)
  • Safety Data

    1. Hazard Codes: F,C
    2. Statements: 11-34-37
    3. Safety Statements: 16-26-36/37/39-45
    4. RIDADR: UN 2924 3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. F: 10-23
    8. HazardClass: 3
    9. PackingGroup: II
    10. Hazardous Substances Data: 873-51-8(Hazardous Substances Data)

873-51-8 Usage

Uses

Used in Pharmaceutical Industry:
PHENYLBORON DICHLORIDE is used as a catalyst for the enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions. This application is crucial for the production of biologically active compounds and drug candidates.
Used in Organic Synthesis:
PHENYLBORON DICHLORIDE is used as a catalyst for enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives. This reaction is essential for the synthesis of complex organic molecules with high stereoselectivity.
Used in Polymer Science:
PHENYLBORON DICHLORIDE is used as a catalyst for the stereoselective alkylative ring opening of cyclic anhydrides. This process is vital for the development of new polymer materials with specific properties.
Used in Chemical Research:
PHENYLBORON DICHLORIDE is used as a catalyst in cross-metathesis reactions of amino derivatives with olefins. This reaction is important for the synthesis of various organic compounds and the study of reaction mechanisms.
Used in Asymmetric Synthesis:
PHENYLBORON DICHLORIDE is used as a catalyst for asymmetric acetate aldol reactions. This application is crucial for the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical and agrochemical industries.
Used in the Synthesis of Lactimidomycin:
PHENYLBORON DICHLORIDE is used as a catalyst in the synthesis of lactimidomycin, an antiproliferative macrolide and cell migration inhibitor. This application highlights the compound's role in the development of potential therapeutic agents.
Used in the Reaction of Aryl Aldehydes:
PHENYLBORON DICHLORIDE is used in the reaction of aryl aldehydes with styrene and (E)-β-methylstyrene. This reaction is important for the synthesis of various organic compounds and the study of reaction mechanisms.

Check Digit Verification of cas no

The CAS Registry Mumber 873-51-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 873-51:
(5*8)+(4*7)+(3*3)+(2*5)+(1*1)=88
88 % 10 = 8
So 873-51-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H5BCl2/c8-7(9)6-4-2-1-3-5-6/h1-5H

873-51-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (32583)  Dichlorophenylborane, 96%   

  • 873-51-8

  • 1g

  • 290.0CNY

  • Detail
  • Alfa Aesar

  • (32583)  Dichlorophenylborane, 96%   

  • 873-51-8

  • 5g

  • 1141.0CNY

  • Detail
  • Alfa Aesar

  • (32583)  Dichlorophenylborane, 96%   

  • 873-51-8

  • 25g

  • 5061.0CNY

  • Detail
  • Aldrich

  • (101346)  Dichlorophenylborane  97%

  • 873-51-8

  • 101346-1G

  • 334.62CNY

  • Detail
  • Aldrich

  • (101346)  Dichlorophenylborane  97%

  • 873-51-8

  • 101346-5G

  • 770.80CNY

  • Detail
  • Aldrich

  • (101346)  Dichlorophenylborane  97%

  • 873-51-8

  • 101346-25G

  • 2,770.56CNY

  • Detail

873-51-8Synthetic route

trimethylphenylsilane
768-32-1

trimethylphenylsilane

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
In neat (no solvent) byproducts: ClSi(CH3)3; 60°C, 12h, ampul;98%
In dichloromethane byproducts: ClSi(CH3)3; in inert atmosphere, dropwise addn. of trimethylphenylsilane to a stirred soln. of BCl3 at -78°C, stirring (-78°C, 1 h), slow warming to room temp.; evapn. in vac. at 30°C.;92%
boron trichloride
10294-34-5

boron trichloride

diborane
19287-45-7

diborane

benzene
71-43-2

benzene

A

phenylborondichloride
873-51-8

phenylborondichloride

B

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
byproducts: boron hydride; High Pressure; under N2; diborane and trihalogen-borane was added to benzene at -130°C, then in a closed autoclave the mixture was heated to 130°C for 90 min; at -195.8°C H2 was removed, at room temp. the residue of trihalogen-borane and diborane were removed;A 46%
B 77%
triphenylboroxine
3262-89-3

triphenylboroxine

aluminium trichloride
7446-70-0

aluminium trichloride

A

2,2,8,8,13-pentachloro-4,6,10,12-tetraphenyl-1,3,5,7,9,11-hexaoxa-4,6,10,12-tetrabora-2,8,13-trialuminatetracyclo{7.3.1.0(3,13)0(7,13)}tridecane

2,2,8,8,13-pentachloro-4,6,10,12-tetraphenyl-1,3,5,7,9,11-hexaoxa-4,6,10,12-tetrabora-2,8,13-trialuminatetracyclo{7.3.1.0(3,13)0(7,13)}tridecane

B

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
In octane boroxine was added under Ar to a soln. of AlCl3, the mixt was heated at about 100 °C for 10 h (stirring);; filtration, residue washed with hexane, dried in vac. at 20°C, recrystd. from benzene; elem. anal.;;A 68%
B n/a
ethylbenzene
100-41-4

ethylbenzene

boron trichloride
10294-34-5

boron trichloride

diborane
19287-45-7

diborane

A

ethyl-dichloro-borane
1739-53-3

ethyl-dichloro-borane

B

phenylborondichloride
873-51-8

phenylborondichloride

C

(3-ethylphenyl)dichloroborane
76782-86-0

(3-ethylphenyl)dichloroborane

D

(4-ethylphenyl)dichloroborane
4250-50-4

(4-ethylphenyl)dichloroborane

E

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
With sodium hydroxide byproducts: benzene, boron hydride, CH3CH2C6H5; High Pressure; under N2; diborane and trihalogen-borane was added to ethylbenzene at -130°C, then in a closed autoclave the mixture was heated to 125°C for 85 min; at -195.8°C H2 was removed, at room temp. the residue of trihalogen-borane and diborane were removed;A 16%
B 4.5%
C n/a
D n/a
E 68%
diethyl phenylboronate
31044-59-4

diethyl phenylboronate

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
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.;67%
Isopropylbenzene
98-82-8

Isopropylbenzene

boron trichloride
10294-34-5

boron trichloride

diborane
19287-45-7

diborane

A

dichloro-isopropyl-borane
7680-99-1

dichloro-isopropyl-borane

B

m-Dichlor(isopropylphenyl)boran
76782-87-1

m-Dichlor(isopropylphenyl)boran

C

p-Dichlor(isopropylphenyl)boran
76782-88-2

p-Dichlor(isopropylphenyl)boran

D

phenylborondichloride
873-51-8

phenylborondichloride

E

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
byproducts: boron hydride, benzene, C3H8; High Pressure; under N2; diborane and trihalogen-borane was added to cumene at -130°C, then in a closed autoclave the mixture was heated to 130°C for 90 min; at -195.8°C H2 was removed, at room temp. the residue of trihalogen-borane and diborane were removed, unseparable isomers; elem. anal.;A 4%
B n/a
C n/a
D 20%
E 61%
tetraphenyltin(IV)
595-90-4

tetraphenyltin(IV)

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
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.;56%
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.;56%
bis(chlorophenylboryl)phenylamine

bis(chlorophenylboryl)phenylamine

A

phenylborondichloride
873-51-8

phenylborondichloride

B

hexaphenylborazine
16672-48-3

hexaphenylborazine

Conditions
ConditionsYield
In neat (no solvent, solid phase) N2 atmosphere, (room temp., 1E-3 Torr); pptn. (petroleum ether, room temp., 2 d), recrystn. (decane); elem. anal.;A n/a
B 26%
(μ-H)3Os3(CO)9{μ3-η2-C(OB(Ph)Cl)B(Cl)}

(μ-H)3Os3(CO)9{μ3-η2-C(OB(Ph)Cl)B(Cl)}

A

(μ-H)3(CO)9Os3(μ3-CH)

(μ-H)3(CO)9Os3(μ3-CH)

B

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane-d2 byproducts: B3Cl3O3; under N2, stirred at room temp. for 2 h; decanted in an NMR tube, cooled to -196°C and sealed; NMR, IR, mass spectra;A 25%
B n/a
triphenylboroxine
3262-89-3

triphenylboroxine

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride
With phosphorus pentachloride
bis(s-butyloxy)phenyl borane
98109-89-8

bis(s-butyloxy)phenyl borane

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride
diphenylboronchloride
3677-81-4

diphenylboronchloride

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride at 200℃;
diethyl phenylboronate
31044-59-4

diethyl phenylboronate

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride
dibutoxyphenylborane
7330-48-5

dibutoxyphenylborane

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride
With phosphorus pentachloride
diisobutyl phenylborate
59024-15-6

diisobutyl phenylborate

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With phosphorus pentachloride
chloro-phenoxy-phenyl-borane
100123-15-7

chloro-phenoxy-phenyl-borane

A

phenylborondichloride
873-51-8

phenylborondichloride

B

diphenyl phenylboronate
2938-75-2

diphenyl phenylboronate

Conditions
ConditionsYield
at 155 - 160℃; under 0.05 Torr;
diphenylmercury(II)
587-85-9

diphenylmercury(II)

A

triphenylboroxine
3262-89-3

triphenylboroxine

B

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride; benzene at 180 - 200℃; ueber mehrere Stufen;
diphenylmercury(II)
587-85-9

diphenylmercury(II)

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride at 180 - 200℃;
benzene
71-43-2

benzene

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With boron trichloride; aluminium
With aluminium trichloride; boron trichloride
With iodine; boron trichloride
boron trichloride
10294-34-5

boron trichloride

benzene
71-43-2

benzene

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With Al(I2,AlCl3)
With aluminium trichloride; iodine for tech. application;
With palladium thermally;
aluminium trichloride
7446-70-0

aluminium trichloride

boron trichloride
10294-34-5

boron trichloride

benzene
71-43-2

benzene

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
In octane
In octane
diboron tetrachloride
13701-67-2

diboron tetrachloride

benzene
71-43-2

benzene

phenylborondichloride
873-51-8

phenylborondichloride

triphenylboroxine
3262-89-3

triphenylboroxine

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

triphenylboroxine
3262-89-3

triphenylboroxine

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

phenylborondichloride
873-51-8

phenylborondichloride

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
With (dialkoxy)phenylborane
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

boron trichloride
10294-34-5

boron trichloride

diphenylmercury(II)
587-85-9

diphenylmercury(II)

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
byproducts: H2O; distn.;;
iodobenzene
591-50-4

iodobenzene

boron trichloride
10294-34-5

boron trichloride

phenylborondichloride
873-51-8

phenylborondichloride

Conditions
ConditionsYield
Irradiation (UV/VIS);
Irradiation (UV/VIS);
boron trichloride
10294-34-5

boron trichloride

phenylmercury(II) chloride
100-56-1

phenylmercury(II) chloride

phenylborondichloride
873-51-8

phenylborondichloride

phenylborondichloride
873-51-8

phenylborondichloride

dimethyl amine
124-40-3

dimethyl amine

Bis-(dimethylamino)-phenylboran
1201-45-2

Bis-(dimethylamino)-phenylboran

Conditions
ConditionsYield
In pentane at -78 - 20℃; Inert atmosphere;100%
In hexane87%
In hexane87%
nitrido(tetra-tert-butylphthalocyaninato)rhenium(V)
158789-52-7

nitrido(tetra-tert-butylphthalocyaninato)rhenium(V)

phenylborondichloride
873-51-8

phenylborondichloride

((CH3)3CC8H3NN)4ReNBCl2C6H5
582295-88-3

((CH3)3CC8H3NN)4ReNBCl2C6H5

Conditions
ConditionsYield
In dichloromethane Re compd. dissolved in CH2Cl2 and cooled to -5°C, electrophile added dropwise to this soln., stirred for 6 h at -5°C; solvent removed at -5°C, elem. anal.;100%
4-phenyl-1,2,3-selenadiazole
25660-64-4

4-phenyl-1,2,3-selenadiazole

phenylborondichloride
873-51-8

phenylborondichloride

4-phenyl-1,2,3-selenadiazole phenyldichloroborane complex
1047719-64-1

4-phenyl-1,2,3-selenadiazole phenyldichloroborane complex

Conditions
ConditionsYield
In benzene at 20℃; for 1h;100%
5,5-dimethyl-5H-dibenzo[b,f]stannepine
1189139-25-0

5,5-dimethyl-5H-dibenzo[b,f]stannepine

phenylborondichloride
873-51-8

phenylborondichloride

5-phenyl-5H-dibenzo[b,f]borepin
1237745-14-0

5-phenyl-5H-dibenzo[b,f]borepin

Conditions
ConditionsYield
In toluene at -78 - 20℃; for 18h; Inert atmosphere;100%
In toluene Schlenk air-free techniques; react. of Sn compound and PhBCl2 at -78°C;99%
phenylborondichloride
873-51-8

phenylborondichloride

5,5-dimethyl-5H-dibenzo[b,d]stannole
5565-85-5

5,5-dimethyl-5H-dibenzo[b,d]stannole

5-phenyl-5H-dibenzo[b,d]borole
14010-93-6

5-phenyl-5H-dibenzo[b,d]borole

Conditions
ConditionsYield
In toluene byproducts: Me2SnCl2; (Ar); using Schlenk techniques; vac. transferring of toluene into flask with C12H8SnMe2 at -78°C; addn. dropwise via syringe of soln. of C6H5BCl2 at -78°C, slowly warming to room temp., stirring overnight; removal of solvent under vac., transferring to a sublimator, removal of Me2SnCl2 under static vac. at 40°C for 2 days, elem. anal.;99%
In water; toluene at -78 - 20℃; for 12h; Inert atmosphere; Schlenk technique;
In toluene at -78 - 20℃; Inert atmosphere;
Tl(C5H3(Si(CH3)3)2)

Tl(C5H3(Si(CH3)3)2)

phenylborondichloride
873-51-8

phenylborondichloride

bis(bis(trimethylsilyl)cyclopentadienyl)phenylborane
192649-53-9

bis(bis(trimethylsilyl)cyclopentadienyl)phenylborane

Conditions
ConditionsYield
In pentane byproducts: TlCl; Ar-atmosphere; dropwise addn. of B-compd. to 2 equiv. of Tl-compd. at room temp., stirring overnight; filtration off of TlCl, washing (pentane), slow evapn. (below 30°C), solidified on cooling, recrystn. (pentane);99%
phenylborondichloride
873-51-8

phenylborondichloride

1-ethyl-2-aminonaphthalene

1-ethyl-2-aminonaphthalene

2‐phenyl‐1,2‐dihydro‐1‐aza‐2‐boraphenanthrene

2‐phenyl‐1,2‐dihydro‐1‐aza‐2‐boraphenanthrene

Conditions
ConditionsYield
With triethylamine In chlorobenzene at 130℃; for 12h; Glovebox;99%
phenylborondichloride
873-51-8

phenylborondichloride

1‐vinylnaphthalen‐2‐amine

1‐vinylnaphthalen‐2‐amine

2‐phenyl‐1,2‐dihydro‐1‐aza‐2‐boraphenanthrene

2‐phenyl‐1,2‐dihydro‐1‐aza‐2‐boraphenanthrene

Conditions
ConditionsYield
With triethylamine In chlorobenzene at 130℃; for 14h; Inert atmosphere;99%
phenylborondichloride
873-51-8

phenylborondichloride

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

{((C6H5)2Si)4(B(C6H5))(CH2)5}

{((C6H5)2Si)4(B(C6H5))(CH2)5}

Conditions
ConditionsYield
With sodium; 1,2-dibromomethane In xylene Ar; to suspension of Na were added at 138°C during 1.5 h silane and borane (4:1) and CH2Br2; 30 min reflux; filtration; evapn. of solvent and drying at 100°C for 20 h (vacuo); elem. anal.;98.8%
phenylborondichloride
873-51-8

phenylborondichloride

2,4,6-triphenylborazine
976-28-3

2,4,6-triphenylborazine

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 55℃; for 240h;98%
With ammonia96%
With NH396%
phenylborondichloride
873-51-8

phenylborondichloride

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

2,4,6-triphenylborazine
976-28-3

2,4,6-triphenylborazine

Conditions
ConditionsYield
In dichloromethane (Ar), (Me3Si)2NH in CH2Cl2 cooled to -78°C, treated with PhBCl2 under stirring, kept at 55°C for 10 d; evapd.(vac.), crystd.(Et2O);98%
In benzene byproducts: Me3SiCl; absence of moisture; addn. of silylamine to borane derivative (during 4h, cooling in ice/EtOH, stirring), slow warming to room temp. (overnight); distn. of Me3SiCl (50-55°C, atmospheric pressure), repeated fractional distn.;78%
1,1-chloro(methyl)-1-sila-[1]ferrocenophane
174872-97-0

1,1-chloro(methyl)-1-sila-[1]ferrocenophane

phenylborondichloride
873-51-8

phenylborondichloride

(C5H4B(C6H5)Cl)Fe(C5H4SiCl2(CH3))
627099-07-4

(C5H4B(C6H5)Cl)Fe(C5H4SiCl2(CH3))

Conditions
ConditionsYield
In hexane under Ar; Fe complex dissolved in hexane; added dropwise at 0°C to soln. of PhBCl2 (5 equiv.) in hexane; stirred at room temp. for 3 h; volatiles removed in vac.; taken up in hexane; soln. filtered over Na2SO4; solvent removed; detd. by (1)H NMR spectra;98%
bis-valine N,N'-sulfone
1104867-77-7

bis-valine N,N'-sulfone

phenylborondichloride
873-51-8

phenylborondichloride

C22H26B2N2O6S
1104867-78-8

C22H26B2N2O6S

Conditions
ConditionsYield
Stage #1: bis-valine N,N'-sulfone; phenylborondichloride In toluene for 0.5h;
Stage #2: With polymer-bound 2,6-di-tert-butylpyridine In toluene for 0.25h;
98%
8-((trimethylsilyl)oxy)quinoline
23111-13-9

8-((trimethylsilyl)oxy)quinoline

phenylborondichloride
873-51-8

phenylborondichloride

2-chloro-2-phenyl-2H-2l4,3l4-[1,3,2]oxazaborolo[5,4,3-ij]quinoline

2-chloro-2-phenyl-2H-2l4,3l4-[1,3,2]oxazaborolo[5,4,3-ij]quinoline

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;98%
In dichloromethane98%
N-(1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-2(3H)-ylidene)-1,1,1-trimethylsilanamine

N-(1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-2(3H)-ylidene)-1,1,1-trimethylsilanamine

phenylborondichloride
873-51-8

phenylborondichloride

C33H41BClN3

C33H41BClN3

Conditions
ConditionsYield
In toluene at -35 - 20℃; for 1.5h;98%
(trimethylsilyl)(trimethylstannyl)cyclopentadiene

(trimethylsilyl)(trimethylstannyl)cyclopentadiene

phenylborondichloride
873-51-8

phenylborondichloride

bis(trimethylsilylcyclopentadienyl)phenylborane

bis(trimethylsilylcyclopentadienyl)phenylborane

Conditions
ConditionsYield
In toluene Ar-atmosphere; refluxing (overnight); evapn. (vac.);97.7%
1,1-dichloro-1-sila-[1]ferrocenophane

1,1-dichloro-1-sila-[1]ferrocenophane

phenylborondichloride
873-51-8

phenylborondichloride

(C5H4B(C6H5)Cl)Fe(C5H4SiCl3)
627099-29-0

(C5H4B(C6H5)Cl)Fe(C5H4SiCl3)

Conditions
ConditionsYield
In hexane under Ar; Fe complex dissolved in hexane; added dropwise at 0°C to soln. of PhBCl2 (5 equiv.) in hexane; stirred at room temp. for 3 h; volatiles removed in vac.; taken up in hexane; soln. filtered over Na2SO4; solvent removed; detd. by (1)H NMR spectra;97%
phenylborondichloride
873-51-8

phenylborondichloride

2,6-di(prop-1-en-2-yl)aniline

2,6-di(prop-1-en-2-yl)aniline

C18H18BN

C18H18BN

Conditions
ConditionsYield
In toluene at 0℃; for 2.5h; Inert atmosphere; Reflux;97%
trimethylsilylazide
4648-54-8

trimethylsilylazide

phenylborondichloride
873-51-8

phenylborondichloride

diazido(phenyl)borane
168281-51-4

diazido(phenyl)borane

Conditions
ConditionsYield
In benzene byproducts: Me3SiCl; cooling (0°C), stirring (12 h, room temp.); evapn. (vac.), distn. (50°C, 1 torr);96.5%
phenylborondichloride
873-51-8

phenylborondichloride

Bis-(dimethylamino)-phenylboran
1201-45-2

Bis-(dimethylamino)-phenylboran

chloro(dimethylamino)phenylborane
1196-44-7

chloro(dimethylamino)phenylborane

Conditions
ConditionsYield
(dichloro)phenylborane was added to bis(dimethylamino)phenylborane keeping the temp. at 60-70°C, stirred for 30 min; destn.;96%
In neat (no solvent) mixed and set aside for 3 h; distd. in vac.;90%
phenylborondichloride
873-51-8

phenylborondichloride

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

C6H5BCl2N(C6H11)CN(C6H11)
874162-18-2

C6H5BCl2N(C6H11)CN(C6H11)

Conditions
ConditionsYield
In hexane PhBCl2 in hexane treated with equiv. of ligand at ambient temp.; isolated, crystd.;96%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

phenylborondichloride
873-51-8

phenylborondichloride

1-(1,2,4-triazol-4-yl)-2,4,6-trimethylbenzene
54893-29-7

1-(1,2,4-triazol-4-yl)-2,4,6-trimethylbenzene

tris(1-mesityl-1,3,4-triazolium)phenylborane bis(triflate)

tris(1-mesityl-1,3,4-triazolium)phenylborane bis(triflate)

Conditions
ConditionsYield
Stage #1: phenylborondichloride; 1-(1,2,4-triazol-4-yl)-2,4,6-trimethylbenzene In toluene for 8h;
Stage #2: trimethylsilyl trifluoromethanesulfonate In toluene at 110℃; for 24h;
96%
phenylborondichloride
873-51-8

phenylborondichloride

C25H30BFePSn

C25H30BFePSn

A

(methyl)(phenyl)chloroborane
13272-66-7

(methyl)(phenyl)chloroborane

C24H27BClFePSn

C24H27BClFePSn

Conditions
ConditionsYield
Stage #1: phenylborondichloride; C25H30BFePSn In benzene-d6 at 20℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: In benzene-d6 at 50℃; Inert atmosphere; Schlenk technique; Glovebox;
A n/a
B 96%
phenylborondichloride
873-51-8

phenylborondichloride

N-methyl-N,N-di(3-thienyl)amine

N-methyl-N,N-di(3-thienyl)amine

4-methyl-8-phenyl-4,8-dithieno[3,2-b:2',3'-e][1,4]azaborine

4-methyl-8-phenyl-4,8-dithieno[3,2-b:2',3'-e][1,4]azaborine

Conditions
ConditionsYield
With triethylamine In chlorobenzene at 135℃; for 48h;96%
phenylborondichloride
873-51-8

phenylborondichloride

2,2’-(2,5-dimethoxy-1,4-phenylene)dithiophene

2,2’-(2,5-dimethoxy-1,4-phenylene)dithiophene

C26H16B2O2S2

C26H16B2O2S2

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; triethylamine In chlorobenzene at 135℃; for 24h;96%
phenylborondichloride
873-51-8

phenylborondichloride

2,2'-(4,6-dimethoxy-1,3-phenylene)dithiophene

2,2'-(4,6-dimethoxy-1,3-phenylene)dithiophene

C26H16B2O2S2

C26H16B2O2S2

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; triethylamine In chlorobenzene at 135℃; for 24h;96%
phenylborondichloride
873-51-8

phenylborondichloride

dimethyl amine
124-40-3

dimethyl amine

({(CH3)2NH}2B(Cl)C6H5)(1+)*Cl(1-)=({(CH3)2NH}2B(Cl)C6H5)Cl
94947-35-0

({(CH3)2NH}2B(Cl)C6H5)(1+)*Cl(1-)=({(CH3)2NH}2B(Cl)C6H5)Cl

Conditions
ConditionsYield
In benzene95.5%
In benzene95.5%
6,16-dimesityl-11-phenyl-subpyriporphyrin

6,16-dimesityl-11-phenyl-subpyriporphyrin

phenylborondichloride
873-51-8

phenylborondichloride

[6,16-dimesityl-11-phenyl-subpyriporphyrin-phenylboron] tetrafluoroborate

[6,16-dimesityl-11-phenyl-subpyriporphyrin-phenylboron] tetrafluoroborate

Conditions
ConditionsYield
Stage #1: 6,16-dimesityl-11-phenyl-subpyriporphyrin; phenylborondichloride In toluene for 1.5h;
Stage #2: With silver tetrafluoroborate In toluene Further stages.;
95%
1,1-di-n-butyl-2,3,4,5-tetraphenylstannol
75632-74-5

1,1-di-n-butyl-2,3,4,5-tetraphenylstannol

phenylborondichloride
873-51-8

phenylborondichloride

A

dibutyltin chloride
683-18-1

dibutyltin chloride

B

1,2,3,4,5-pentaphenyl-1H-borole
20195-59-9

1,2,3,4,5-pentaphenyl-1H-borole

Conditions
ConditionsYield
In toluene To a cooled toluene soln. of stannol was added PhBCl2, stirred for 3 h at room temp. (inert atm.);; filtered, ppt. was washed with toluene, dried in high vac.; elem. anal.;;A n/a
B 95%

873-51-8Relevant articles and documents

Organoboranes. 55. Improved procedure for the conversion of representative achiral and chiral alkyl-, (E)-1-alkenyl, (Z)-1-alkenyl-, and arylboronates into the corresponding organyldichloroboranes

Brown, Herbert C.,Salunkhe, Ashok M.,Argade, Ankush B.

, p. 3094 - 3097 (1992)

Diethyl alkylboronates, R*B(OEt)2, of essentially 100% enantiomeric purity, prepared by asymmetric hydroboration of readily available prochiral alkenes, were effectively converted into the corresponding chiral alkyldichloroboranes, R*BC12, by treatment with boron trichloride (1 M solution in dichloromethane) in the presence of a catalytic amount of anhydrous ferric chloride (3 mol %). This reaction is quite general, proceeds well without detectable racemization, and is applicable to essentially optically pure boronic esters of widely varied structural requirements. The reaction is also applicable to achiral boronates, such as 1-hexyl, and hindered alkyl, such as tert-butyl. It is also applicable to the conversion of (E)- and (Z)-1-hezenylboronates, representative of the 1-alkenyl derivatives, and to phenylboronates, representative of aryl derivatives. Consequently, this procedure appears to be broadly applicable to the conversion of organylboronates, RB(OR′)2, into the corresponding organyldichloroboranes, RBCl2.

PROCESS FOR REDUCING THE CONTENT OF BORON COMPOUNDS IN HALOSILANE-CONTAINING COMPOSITIONS

-

Paragraph 0030; 0059, (2022/01/24)

The content of boron compounds in a composition containing at least one halosilane is reduced by bringing the composition into contact with at least one phenylsilane and removing the at least one halosilane. The invention further relates to the use of phenylsilanes for removing boron compounds from halosilane-containing compositions.

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.].

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.

Synthesis of Boron-Halogenated Diborylamines and Diborylhydrazines by Cleavage of Stannazanes

Diemer, Stefan,Noeth, Heinrich,Storch, Wolfgang

, p. 1765 - 1780 (2007/10/03)

The diborylamines R'-N(BRX)2 (3; X=Cl, Br) are obtained by stannazane cleavage of distannylorganylamines R'-N(SnMe3)2 (4) with alkyldihaloboranes RBX2 in a 1:2 molar ratio. The presence of the sterically demanding substituents R and R' also causes carbon-tin bond cleavage, resulting in low yields of 3. However, carbon-tin bond cleavage can be suppressed by the use of bis(dimethylchlorostannyl)organylamines 5 as the nitrogen source for the synthesis of diborylamines. This results in almost quantitative yields of the compounds 3. Treatment of the distannylhydrazines R2N-N(SnMe3)2 (7) with RBX2 in a 1:2 molar ratio leads to the formation of N,N-bis(alkylhaloboryl)hydrazines 8 under mild conditions and in good yield. The molecular structures of 3 and 8 were determined by multinuclear magnetic resonance spectra in solution as well as by X-ray structure analysis in the case of 8d. A typical structural feature of 8d is the intramolecular BN adduct formation. Support for the constitutions of compounds 8c comes from MS fragmentation patterns as well as from IR spectra.

Activation of the BCO unit in the ketenylidene analogue (μ-H)3Os3(CO)9(μ3-BCO) by electrophiles: Syntheses of vinylidene and alkyne analogues

Workman, David P.,Jan, Deng-Yang,Shore, Sheldon G.

, p. 3518 - 3525 (2008/10/08)

The Lewis acids BX3 (X = Cl, Br), BH3, B-Cl-9-BBN, and PhBCl2 react with (μ-H)3Os3(CO)9(μ3-BCO) (I), a ketenylidene analogue, apparently through electrophilic attack at the oxygen of the unique carbonyl. Reactions of I with BX3 (X = Cl, Br) result in an exchange of B and C atom positions in the BCO unit to form a vinylidene analogue, (μ-H)3Os3(CO)9(μ3-CBX 2). Boron-10-labeling experiments indicate that this transformation occurs through an intramolecular interchange of the boron and carbon atom positions. The ketenylidene analogue (μ-H)3Os3(CO)8(PPh3)(μ 3-BCO) reacts similarly with BCl3 to produce (μ-H)3Os3(CO)8(PPh3)(μ 3-CBCl2). The nucleophiles PMe3, PPh3, and NMe3 add to the tricoordinate boron of (μ-H)3Os3-(CO)9(μ3-CBCl 2). Above -10°C the NMe3 adduct is converted to the salt [NMe3H][(μ-H)2Os3(CO)9(μ 3-CBCl2)] and the PMe3 adduct dissociates. The PPh3 adduct decomposes above 30°C. The reaction of (μ-H)3Os3(CO)9(μ3-BCO) with THF·BH3 produces (μ-H)3Os3(CO)9(μ3-BCH 2), a second type of vinylidene analogue. In this case the boron and carbon atoms do not change positions. Alkyne analogues, (μ-H)3Os3(CO)9[μ3-η 2-C(OBC8H14)B(Cl)] and (μ-H)3Os3(CO)9[μ3-η 2-C{OB(Ph)Cl}B(Cl)] are obtained from reactions of (μ-H)3Os3(CO)9(μ3-BCO) with B-Cl-9-BBN and PhBCl2. These compounds react with BCl3 to produce (μ-H)3Os3(CO)9(μ3-CBCl 2). They also react with HCl to produce (μ-H)3Os3(CO)9(μ3-CH).

Borylation of Arylsilanes, I. - A General, Easy, and Selective Access to Phenyldihaloboranes

Kaufmann, Dieter

, p. 853 - 854 (2007/10/02)

Upon treatment with trihaloboranes 2b-d the phenyltrimethylsilanes 1,6,8, and 10 yield the corresponding phenyldihaloboranes 3, 7, 9, and 11 with high selectivity.Benzylsilanes are not attacked.

Novel Organoboron-Oxygen-Halogenaluminium Compounds from Triorganoboroxins with Aluminium Trihalides

Koester, Roland,Angermund, Klaus,Serwatowski, Janusz,Sporzynski, Andrzej

, p. 1301 - 1314 (2007/10/02)

4 mol of triorganoboroxins (RBO)3 (1) react with 6 mol of aluminium trihalides AlHal3 (2) under cleavage of 4 mol dihalogenoorganoboranes RBHal2 (3) leading in high yields to 2 mol of compounds 4 having the composition R4Al3B4Hal5O6 (MS analyses) .The structure of 4aa, 4ba, 4ca, and 4bb in solution is deduced from spectroscopic data (IR; 1H, 11B, 17O and 27Al NMR).The molecular structure of the solid (C6H5)4Al3B4Cl5O6 (4da) with two (AlOBOBO)-rings bonded through one penta-coordinated aluminium atom was determined by X-ray diffraction analysis.

Darstellung von Arylhalogenboranen

Haubold, Wolfgang,Herdtle, Joerg,Gollinger, Walter,Einholz, Wolfgang

, p. 1 - 8 (2007/10/02)

In a ligand-exchange reaction between aryltrimethylsilanes, (ArSiMe3) and halogenboranes, (BX3 or ArBX2), arylhalogenboranes (ArBX2, ArAr'BX or Ar2BX) and halogentrimethylsilane are formed.This transfer of substituted aromatic groups from a silicon to a boron atom is an efficient synthetic pathway for the preparation of the corresponding arylhalogenboranes and diarylhalogenboranes with different aryl groups.Physical properties and spectroscopical data of the new arylhalogenboranes are given.

A New Borylation Method for Alkylbenzene and Polystyrene

Paetzold, Peter,Hoffmann, Juergen

, p. 3724 - 3733 (2007/10/02)

The borylation of alkylbenzenes by Hal2BH (Hal = F, Cl, Br) gives H2 and a mixture of m- and p-alkyl(dihaloboryl)benzenes.In the case of bulky alkyl groups, such as isopropyl, tert-butyl, these are partially split off as R - H and RBHal2.The phenyl groups in polystyrene-divinylbenzene copolymers undergo borylation with Br2BH in a 55percent yield.

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