3677-81-4

Basic information

• Product Name: Borane, chlorodiphenyl-
• Synonyms: diphenylchloroboron;BPh2Cl;chlorodiphenylborane;(c-Hex)2BCl;BClPh2;diphenyl boron chloride
• CAS NO: 3677-81-4
• Molecular Formula: C12H10BCl
• Molecular Weight: 200.475
• Mol File: 3677-81-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Borane, chlorodiphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Borane, chlorodiphenyl-(3677-81-4)
• EPA Substance Registry System: Borane, chlorodiphenyl-(3677-81-4)

Safety Data

• Hazardous Substances Data: 3677-81-4(Hazardous Substances Data)

Usage

General Description

Borane, chlorodiphenyl- is a chemical compound that consists of a boron atom bonded to two phenyl (C6H5) groups and one chlorine atom. It is commonly used as a reducing agent in organic synthesis reactions, particularly in the reduction of carbonyl compounds to alcohols. Borane, chlorodiphenyl- is a highly reactive and versatile chemical that can also be used in the synthesis of various organoboron compounds and as a catalyst in various chemical reactions. Due to its reactivity, it requires careful handling and storage to prevent accidents and ensure safety in laboratory and industrial settings.

Synthetic route

diphenyl(diethylamino)borane (7397-50-4) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4) + Diethylaminodichloroborane (868-30-4)

Conditions	Yield
distn. of BCl3 into (C6H5)2BN(C2H5)2 at -50°C; distn.;	A 94% B n/a
distn. of BCl3 into (C6H5)2BN(C2H5)2 at -50°C; distn.;	A 94% B n/a

triphenylborane (960-71-4) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With octene-1; Bis(borolane) In xylene introduction of BCl3 into soln. of B(C6H5)3 and bis(borolane), stirring at 120°C for 15 min (cooler at -78°C), addn. of octene-1; vac. distn; further product obtained by adding bis(borolane) to unified residue and predistillate and repeating procedure;	77%

tetraphenyltin(IV) (595-90-4) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4)

Conditions	Yield
In benzene pouring BCl3 in soln. of Sn(C6H5)4 at 10°C, boiling under reflux (cooler at -78°C) for 3 h, with water temp. cooler for further 48 h; removing benzene by distn., twofold fractionated distn. of product at reduced pressure;	75%
In benzene pouring BCl3 in soln. of Sn(C6H5)4 at 10°C, boiling under reflux (cooler at -78°C) for 3 h, with water temp. cooler for further 48 h; removing benzene by distn., twofold fractionated distn. of product at reduced pressure;	75%

dimethyldiphenyltin (1080-43-9) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4)

Conditions	Yield
In n-heptane byproducts: dimethyltin dichloride; glovebox; addn. of 1 equiv. of BCl3 as 1 M soln. in heptane to a flask contg. dimethyldiaryltin and heptane at room temp., sealing, stirring at room temp. for 30 min, heating at 100°C in oil bath for 24-48 h; cooling, decantation, removal of volatiles, recrystn. from petroleum ether at -35°C;	72.8%
In n-heptane

oxybis(diphenylborane) (4426-21-5) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With phosphorus pentachloride at 150℃; Inert atmosphere;	63%
With boron trichloride at -80℃;
With phosphorus pentachloride

diphenylborinic acid butyl ester (15323-04-3) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With boron trichloride at -80℃;

diphenyl-propoxy-borane (98882-69-0) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With phosphorus pentachloride

phenylborondichloride (873-51-8) + diphenylmercury(II) (587-85-9) → diphenylboronchloride (3677-81-4)

Conditions	Yield
at 300 - 320℃; extrahiert das Produkt mit Petrolaether;

iodobenzene (591-50-4) + phenylborondichloride (873-51-8) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With silver Irradiation;
photolysis;

triphenylborane (960-71-4) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With di-n-butylborane; phenylborondichloride

phenylborondichloride (873-51-8) + bromo(phenyl)mercury (1192-89-8) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With bis(trimethylsilyl)mercury In benzene

isobutyl diphenylborinate (23147-97-9) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With phosphorus pentachloride

boron trichloride (10294-34-5) + diphenyltin(IV) dichloride (1135-99-5) → phenylborondichloride (873-51-8) + diphenylboronchloride (3677-81-4) + phenyltin trichloride (1124-19-2)

Conditions	Yield
In dichloromethane sealed tube, room temp.; Sn:B molar ratio >1:1;

boron trichloride (10294-34-5) + phenyl sodium (1623-99-0) → triphenylborane (960-71-4) + diphenylboronchloride (3677-81-4)

oxybis(diphenylborane) (4426-21-5) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4)

diphenylborinic acid butyl ester (15323-04-3) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4)

boron trichloride (10294-34-5) + phenylmercury(II) chloride (100-56-1) → diphenylboronchloride (3677-81-4)

diphenyl(diethylamino)borane (7397-50-4) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4)

tetraphenyltin(IV) (595-90-4) + boron trichloride (10294-34-5) → phenylborondichloride (873-51-8) + diphenylboronchloride (3677-81-4) + phenyltin trichloride (1124-19-2)

Conditions	Yield
In dichloromethane sealed tube, room temp.; Sn:B molar ratio 1:2;

tetraphenyltin(IV) (595-90-4) + boron trichloride (10294-34-5) → diphenylboronchloride (3677-81-4) + diphenyltin(IV) dichloride (1135-99-5)

phosphorus pentachloride (10026-13-8, 874483-75-7) + oxybis(diphenylborane) (4426-21-5) → diphenylboronchloride (3677-81-4)

tetrachloromethane (56-23-5) + triphenylborane (960-71-4) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With chromium chloride
With CrCl3

tetrachloromethane (56-23-5) + [Cr(η-benzene)2](BPh4) (11136-23-5) → diphenylboronchloride (3677-81-4)

phosphorus pentachloride (10026-13-8, 874483-75-7) + B,B-diphenyl-boranylamine (13188-39-1) → diphenylboronchloride (3677-81-4)

phosphorus pentachloride (10026-13-8, 874483-75-7) + diphenyl-propoxy-borane (98882-69-0) → diphenylboronchloride (3677-81-4)

triphenylborane (960-71-4) + phenylborondichloride (873-51-8) → diphenylboronchloride (3677-81-4)

Diphenylthioborsaeure (27485-00-3) → sulfur (10544-50-0) + diphenylboronchloride (3677-81-4) + hydrogen sulfide (7783-06-4)

Conditions	Yield
With chlorine

dibutoxy-chloro-borane (18379-65-2) + Butyl-diphenyl-borat (10220-76-5) → boric acid tributyl ester (688-74-4) + diphenylboronchloride (3677-81-4)

phenylhydrazinodiphenylborane (31263-73-7) → diphenylboronchloride (3677-81-4)

Conditions	Yield
With hydrogenchloride byproducts: C6H5NHNH2*HCl;
With HCl byproducts: C6H5NHNH2*HCl;

[2,2]bipyridinyl (366-18-7) + diphenylboronchloride (3677-81-4) → (C5H4N)2B(C6H5)2(1+)*Cl(1-)={(C5H4N)2B(C6H5)2}Cl (14075-86-6)

Conditions	Yield
In benzene	100%
In nitrobenzene	78%
In not given
In not given

N,N,N,N,-tetramethylethylenediamine (110-18-9) + trimethylphosphine-borane (1898-77-7) + diphenylboronchloride (3677-81-4) → [(phenyl)2B(CH2P(methyl)2(BH3))2][Li(N,N,N',N'-tetramethylethylenediamine)] (591216-09-0)

Conditions	Yield
With n-butyllithium In diethyl ether; toluene N2; dissolving P(CH3)3(BH3) in ether, cooling to -78°C, addn. of 1.6 M soln. of butyllithium dropwise, warming to room temp. with stirring over 12 h, cooling to -78°C, addn. of (C6H5)2BCl in toluene dropwise, warming over 4 h with stirring; volatiles removal under reduced pressure, washing the solid with diethylether;	97.8%

1,8-bis[(trimethylstannyl)ethynyl]anthracene + diphenylboronchloride (3677-81-4) → 1,8-bis[(diphenylboranyl)ethynyl]anthracene

Conditions	Yield
In hexane at 0 - 20℃; Inert atmosphere;	96%

N,N-diisorpopylformamide (2700-30-3) + diphenylboronchloride (3677-81-4) → C-(diphenylboryloxy)-N,N-diisopropylaldiminium chloride

Conditions	Yield
In diethyl ether at 20℃; for 12h;	95%
In diethyl ether under Ar, Schlenk techniques; soln. of ligand at -78°C added to soln. of boron compd. (1:1), suspn. stirred at room temp. for 12 h, pptd.; filtered off, washed (Et2O), NMR;	95%

diphenylboronchloride (3677-81-4) + 1,8-bis[(trimethylstannyl)ethynyl]anthracene → 1,8-bis[(diphenylboranyl)ethynyl]anthracene

Conditions	Yield
In hexane at 0 - 20℃; for 48h;	95%

diphenylboronchloride (3677-81-4) + 2-(diisopropylphosphino)phenyl bromide → o-iPr2P(C6H4)BPh2 (1198074-97-3)

Conditions	Yield
With n-C4H9Li In diethyl ether; hexane; toluene byproducts: LiCl; (Ar); to siln. of o-oPr2(C6H4)Br in ether was added 1.6 M BuLi in hexaneat -40°C, stirred for 20 min, filtered, dissolved in toluene, so ln. of Ph2BCl in toluene was added aT -78°C, warmed to room temp.; filtered, evapd.;	94%

diphenylboronchloride (3677-81-4) + 2-(diisopropylphosphino)phenyl bromide → o-iPr2P(C6H4)BPh2 (1198075-03-4)

Conditions	Yield
Stage #1: 2-(diisopropylphosphino)phenyl bromide With n-butyllithium In diethyl ether; hexane at -40℃; for 0.333333h; Inert atmosphere; Stage #2: diphenylboronchloride In toluene at -78 - 20℃; Inert atmosphere;	94%

C56H54Br2N6O2 (1314518-64-3) + diphenylboronchloride (3677-81-4) → C80H72B2Br2N6O2 (1314518-80-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene Reflux;	94%

diphenylboronchloride (3677-81-4) + (lithiomethyl)bis(tert-butyl)phosphane (64065-07-2) → (tBu)2PCH2BPh2 (1353248-56-2)

Conditions	Yield
In not given	94%
In hexane; n-heptane at -78 - 20℃; for 18 - 20h; Inert atmosphere;

1-(trimethylsilyl)-1-hexyne (3844-94-8) + diphenylboronchloride (3677-81-4) → 1-(chlorophenylboryl)-1-phenyl-2-(trimethylsilyl)-1-hexene (86429-24-5)

Conditions	Yield
In neat (no solvent) 5 °C; crystn. by coolign to -20 °C, crystn. from pentane; elem. anal.;	93%

C22H18BN2(1+)*ClO4(1-) (13985-97-2) + diphenylboronchloride (3677-81-4) → 2,2'-bipyridyldiphenylboronium(dichloro)diphenylborate (108037-84-9)

Conditions	Yield
In benzene	92.5%

di-p-tolylcarbodiimide (726-42-1) + diphenylboronchloride (3677-81-4) → ClB{N(C6H4CH3)(C((NC6H4CH3))C6H5)}2 (13471-16-4)

Conditions	Yield
	90.5%
	90.5%

sodium azide + diphenylboronchloride (3677-81-4) → diphenylazidoborane pyridine adduct (94541-40-9)

Conditions	Yield
With pyridine 25°C, stirring for several days; recrystn. from benzene/hexane;	90%
With pyridine 25°C, stirring for several days; recrystn. from benzene/hexane;	90%
With pyridine 70°C in suspn., 12 h under N2; recrystn. from benzene/hexane;

N,N-diethyl-N'-phenyl-N'-trimethylsilyl urea (1146-59-4) + diphenylboronchloride (3677-81-4) → N',N'-Diethyl-N-phenyl-N-diphenylureidoboran (77091-44-2)

Conditions	Yield
In Petroleum ether byproducts: (CH3)3SiCl; to the soln. of urea/petroleum ether the soln. of borane/petroleum ether was added dropwise under N2, refluxed for 5 h; evapd. in vac., distn.; elem. anal.;	90%

N-methyl-1,1,2,2,3,3,4,4-nonafluoro-N-(2-hydroxyethyl)butane-1-sulphonamide (34454-97-2) + diphenylboronchloride (3677-81-4) → C4F9SO2N(CH3)CH2CH2OB(C6H5)2 (74948-29-1)

Conditions	Yield
In tetrachloromethane byproducts: HCl; (N2); to soln. of sulfonamide was dropped soln. of boranederiv. and mixt. was refluxed for 12 h; solvent was removed and residue sublimated in vac.; elem. anal.;	90%

perfluoro-n-butane sulfonamide (30334-69-1) + diphenylboronchloride (3677-81-4) → C4F9SO2NHB(C6H5)2 (74941-53-0)

Conditions	Yield
In tetrachloromethane byproducts: HCl; (N2); to soln. of sulfonamide was dropped soln. of boranederiv. and mixt. was refluxed for 12 h; solvent was removed and residue distd. in vac.; elem. anal.;	90%

1,1,2,2,3,3,4,4,4-Nonafluoro-butane-1-sulfonic acid (2-hydroxy-ethyl)-amide (34454-99-4) + diphenylboronchloride (3677-81-4) → C4F9SO2N(B(C6H5)2)CH2CH2OB(C6H5)2 (74941-57-4)

Conditions	Yield
In tetrachloromethane byproducts: HCl; (N2); to soln. of sulfonamide was dropped soln. of boranederiv. (1:2 mol) and mixt. was refluxed for 12 h; solvent was removed and residue distd. in vac.; elem. anal.;	90%

diphenylboronchloride (3677-81-4) + 1-tert-butylimidazole (45676-04-8) → [H2BIM(tBu)BPh2]Cl (1160462-16-7)

Conditions	Yield
In toluene under Ar; to a soln. of N-tert-butylimidazole (49.2 mmol) in abs. toluene at 0°C was added slowly a soln. of Ph2BCl (18.9 mmol) in abs. toluene; stirring at room temp. for 15 min and then at 110°C for 48 h; the suspn. was filtered under Ar; the ppt. was washed with dry toluene and hexane and then dried at 1E-3 mbar; elem. anal.;	89.5%

diphenylboronchloride (3677-81-4) + sodium 1-butinyl triethylborate (15170-87-3) → (Z)-3-(diethylboryl)-4-(diphenylboryl)-3-hexene (138517-72-3)

Conditions

Yield

In diethyl ether byproducts: NaCl; dropping soln. of ClB(C6H5)2 in diethyl ether to soln. of Na-salt in diethyl ether within 3.5 h under Ar, rise in temp. to 30°C; refluxing for 4 h; after method of R. Koester, Pure Appl. Chem. 1977, 49, 765-789 and 6 further publications;; filtration; removal of solvent under atmospheric pressure; removal of remaining volatile products in vac. at <=60°C; elem. anal.;;

89%

diphenylboronchloride (3677-81-4) + (S)-4-(tert-butyl)-4,5-dihydrooxazole (132377-00-5) → lithium diphenyl-bis[(S)-4-tert-butyloxazolin-2-yl]borate

Conditions	Yield
Stage #1: (S)-4-(tert-butyl)-4,5-dihydrooxazole With tert.-butyl lithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: diphenylboronchloride In tetrahydrofuran; hexane; toluene	88%
Stage #1: (S)-4-(tert-butyl)-4,5-dihydrooxazole With tert.-butyl lithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: diphenylboronchloride In tetrahydrofuran; hexane; toluene at -78 - 20℃;

diphenylboronchloride (3677-81-4) + ammonia (7664-41-7) → (C6H5)2BCl*2NH3

Conditions	Yield
In further solvent(s) with anhydrous NH3 at 0°C;	87.2%

diphenylboronchloride (3677-81-4) + tert-butylamine (75-64-9) → (C6H5)2BNH-t-C4H9 (17520-34-2)

Conditions	Yield
With triethylamine	87%
With (C2H5)3N	87%
With triethylamine In benzene byproducts: triethylammonium chloride; Ph2BCl dissolved in benzene, mixt. cooled in ice bath, benzene soln. oft-BuNH2 added dropwise with stirring, mixt. allowed to attain room temp., triethylamine in benzene was added slowly then mixt. refluxed for 3 h; cooling, filration, removal of benzene under vac., distn. of residue; elem. anal.;	65%

heptamethyldisilazane (920-68-3) + diphenylboronchloride (3677-81-4) → diphenylboran (27151-87-7)

Conditions	Yield
100°C for 3 h under N2;	85%
100°C for 3 h under N2;	85%

trimethylsilylazide (4648-54-8) + diphenylboronchloride (3677-81-4) → (azido)diphenyl borane

Conditions	Yield
In hexane byproducts: (CH3)3SiCl; at 0°C; stirred at room temp. for 50 h; distn. at 75°C/1E-5 Torr; elem. anal.;	84%

diphenylboronchloride (3677-81-4) + sodium diphenylphosphide (4376-01-6) → (diphenylphosphino)diphenylborane (3053-72-3)

Conditions	Yield
In tetrahydrofuran byproducts: NaCl;	84%

diphenylboronchloride (3677-81-4) + lead(II) ethyl sulfide (28420-40-8, 32812-83-2, 40597-30-6) → (C6H5)2BSC2H5 (31179-14-3)

Conditions	Yield
	84%
	84%

diphenylboronchloride (3677-81-4) + 5-azoniaspiro<4.4>nonane bromide (16450-38-7) + (lithiomethyl)diphenylphosphane (62263-69-8) → 5-azonia-spiro[4.4]nonane bis(diphenylphosphinomethyl)diphenylborate (350480-00-1)

Conditions	Yield
Stage #1: diphenylboronchloride; (lithiomethyl)diphenylphosphane With N,N,N,N,-tetramethylethylenediamine In diethyl ether; toluene at -78 - 20℃; for 14h; Stage #2: 5-azoniaspiro<4.4>nonane bromide In ethanol for 0.166667h;	83.1%

(n-C4H9)2BNHN(CH3)2 (14575-27-0) + diphenylboronchloride (3677-81-4) → (N',N'-dimethylhydrazino)-diphenylborane (14579-48-7)

Conditions	Yield
	83%
	83%

diphenylboronchloride (3677-81-4) + ortho-lithio-N,N-dimethylaniline (22608-37-3) → C20H20BN

Conditions	Yield
In toluene at -85 - 20℃; Schlenk technique; Inert atmosphere;	82%

Upstream product

• 873-51-8 phenylborondichloride 
• 587-85-9 diphenylmercury(II) 
• 10294-34-5 boron trichloride 
• 1135-99-5 diphenyltin(IV) dichloride 
• 1080-43-9 dimethyldiphenyltin 
• 1623-99-0 phenyl sodium 
• 4426-21-5 oxybis(diphenylborane) 
• 15323-04-3 diphenylborinic acid butyl ester 
• 100-56-1 phenylmercury(II) chloride 
• 7397-50-4 diphenyl(diethylamino)borane 
• 960-71-4 triphenylborane 
• 595-90-4 tetraphenyltin(IV) 
• 10026-13-8 phosphorus pentachloride 
• 13188-39-1 B,B-diphenyl-boranylamine 

Downstream Products

• 3826-41-3 diphenyl-trifluoroacetoxy-borane 
• 958-03-2 isobutyl diphenylborate 
• 27151-87-7 diphenylboran 
• 19374-74-4 6-phenyl-6H-dibenzo[c,e][1,2]thiaborinine 
• 47143-63-5 Ph₂BCCPh 
• 86429-10-9 (n-C₄H₉)(C₆H₅)CCHBClC₆H₅ 
• 15325-54-9 (Z)-hex-1-en-1-ylbenzene 
• 6111-82-6 (E)-1-phenyl-1-hexene 
• 20826-80-6 2-phenylhex-1-ene 
• 942-92-7 caprophenone 
• 73083-29-1 α-butylbenzeneacetaldehyde 
• 35887-50-4 N-(2-biphenyl)aniline 
• 86-74-8 9H-carbazole 
• 1007852-27-8 (tBuP(Ph)2)2 

Relevant articles and documents

Four-coordinate triarylborane synthesis: Via cascade B-Cl/C-B cross-metathesis and C-H bond borylation

To develop a simple and efficient synthetic method for four-coordinate triarylboranes, we herein describe a tandem highly selective B-Cl/C-B cross-metathesis of two of the same or different arylboranes and C-H bond borylation to synthesize four-coordinate triarylboranes with a broad substrate scope. By switching substituent groups of the target molecules, different emission wavelengths can be achieved from 467 nm to 583 nm with aggregation-induced emission (AIE) properties.

Bis(phosphino)borates: A new family of monoanionic chelating phosphine ligands

The reaction of dimethyldiaryltin reagents Me2SnR2 (R = Ph (1), p-MePh (2), m,m-Me2Ph (3), p-tBuPh (4), p-MeOPh (5), p-CF3Ph (6)) with BCl3 provided a high-yielding, simple preparative route to the corresponding diarylchloroboranes R2BCl (R = Ph (10), p-MePh (11), m,m-Me2Ph (12), p-tBuPh (13), p-MeOPh (14), p-CF3Ph (15)). In some cases, the desired diarylchloroborane was not formed from an appropriate tin reagent Me 2SnR2 (R = o-MeOPh (7), o,o-(MeO)2Ph (8), o-CF3Ph (9)). The reaction of lithiated methyldiaryl- or methyldialkylphosphines with diarylchloroboranes or dialkylchloroboranes is discussed. Specifically, several new monoanionic bis(phosphino)borates are detailed: [Ph2B(CH2PPh2)2] (25); [(p-MePh)2B(CH2PPh2)2] (26); [(p-tBuPh)2B(CH2PPh2)2] (27); [(p-MeOPh)2B-(CH2PPh2)2] (28) ; [(p-CF3Ph)2B(CH2PPh2) 2] (29); [Cy2B(CH2PPh2) 2] (30); [Ph2B(CH2P{p-tBuPh} 2)2] (31);[(p-MeOPh)2B-(CH2P{p- tBuPh}2)2] (32); [Ph2B(CH 2P{p-CF3Ph}2)2] (33); [Ph 2B(CH2P(BH3)(Me)2)2] (34); [Ph2B(CH2P(S)(Me)2)2] (35); [Ph2B(CH2P1Pr2)2] (36); [Ph2B(CH2PtBu2)2] (37); [(m,m-Me2Ph)2B(CH2PtBu 2)2] (38). The chelation of diarylphosphine derivatives 25-33 and 36 to platinum was examined by generation of a series of platinum dimethyl complexes. The electronic effects of substituted bis(phosphino)borates on the carbonyl stretching frequency of neutral platinum alkyl carbonyl complexes were studied by infrared spectroscopy. Substituents remote from the metal center (i.e. on boron) have minimal effect on the electronic nature of the metal center, whereas substitution close to the metal center (on phosphorus) has a greater effect on the electronic nature of the metal center.