14044-65-6

Basic information

• Product Name: Borane-tetrahydrofuran complex
• Synonyms: borane-tetrahydrofurancomplex,bthf-1m;borane-tetrahydrofurancomplex,bthf-2m;TETRAHYDROFURAN BORANE;BORON HYDRIDE-TETRAHYDROFURAN COMPLEX;BORANE;BORANE-TETRAHYDROFURAN;BORANE TETRAHYDROFURAN COMPLEX;Borane tetrahydrofuran complex solution
• CAS NO: 14044-65-6
• Molecular Formula: C₄H₁₁BO
• Molecular Weight: 82.91672
• EINECS: 237-881-8
• Product Categories: B (Classes of Boron Compounds);Boranes;Reduction;Synthetic Organic Chemistry;Synthetic Reagents;organoboron and borato-metal complexes;25mL Sure/Seal Reagents;Chemical Synthesis;Organometallic Reagents;Synthetic Reagents
• Mol File: 14044-65-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: -17 °C
• Boiling Point: 35 °C
• Flash Point: 1 °F
• Appearance: Colorless/Liquid
• Density: 0.898 g/mL at 25 °C
• Vapor Pressure: 152mmHg at 25°C
• Storage Temp.: 2-8°C
• Water Solubility: REACTS
• Sensitive: Air & Moisture Sensitive
• Stability: Stable, but may form explosive peroxides in contact with air. Incompatible with acids, acid chlorides, acid anhydrides, oxidizin
• BRN: 3668402
• CAS DataBase Reference: Borane-tetrahydrofuran complex(CAS DataBase Reference)
• NIST Chemistry Reference: Borane-tetrahydrofuran complex(14044-65-6)
• EPA Substance Registry System: Borane-tetrahydrofuran complex(14044-65-6)

Safety Data

• Hazard Codes: F,Xn,Xi
• Statements: 14/15-19-22-36/37/38-41-37/38-11-67-66-40-36/37
• Safety Statements: 16-33-36/37/39-7/9-7/8-43-37/39-26-36-29-36/37
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 3
• F: 1-10-13-34
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: I
• Hazardous Substances Data: 14044-65-6(Hazardous Substances Data)

Usage

Description

Borane tetrahydrofuran complex (BH3-THF) is widely used as a reducing agent in organic synthesis. It is also used as a reagent in hydroboration reactions.It is a charge-transfer complex that is a useful surrogate for diborane1 in organic synthesis. It can be used to reduce carboxylic acids to alcohols or nitriles to primary amines. It reacts with olefins to add the BH2 functional group. Alkyl- or arylboranes formed in this way can further react with unsaturated compounds such as olefins, imines, ketones, and alkynes (the hydroboration reaction) to make useful boron-containing intermediates.

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 14044-65-6 differently. You can refer to the following data:
1. Borane-tetrahydrofuran complex is used to reduce Nylon surface amide groups to secondary amines.It is an important reagent used in the reduction of certain functional groups viz. aldehyde, ketone, carboxylic acid, amide, oxime, imine and nitrile. It is also used as hydro borating agent. It acts as a borane source for oxazaborolidine catalyzed asymmetric reductions.
2. Borane-tetrahydrofuran complex is an important reagent used in the reduction of certain functional groups viz. aldehyde, ketone, carboxylic acid, amide, oxime, imine and nitrile. It is also used as hydro borating agent. It acts as a borane source for oxazaborolidine catalyzed asymmetric reductions. It is utilized to reduce nylon surface amide groups to secondary amines.

Application

New, Safer, NIMBA-Stabilized BH3 THF SolutionsBH3-THF can be used as a reducing agent for the reduction of various functional groups such as carboxylic acids, aldehydes, ketones, esters, acid chlorides, nitriles, epoxides, amides, lactones, oximes, and imines into corresponding alcohols and amines. Grignard reagents, arylmercury, arylthalium, and allyl and propargyllithium compounds react with BH3?THF to give organoboranes, which can be oxidized to the corresponding alcohols, phenols, and 1,3-diols.It can also be used:To synthesize the chiral borane catalyst, which is used in the enantioselective halo-aldol reaction.To prepare 9-unsubstituted acridines by reduction of corresponding acridones.To reduce nylon surface amide groups to secondary amines.

Reactions

Borane-tetrahydrofuran complex (BTHF) is a valuable reagent for the reduction of functional groups and for hydroboration reactions with carbon-carbon double and triple bonds. Functional groups that are readily reduced by BTHF include aldehyde, ketone, carboxylic acid, amide, oxime, imine, and nitrile. The carboxylic acid group is reduced at a faster rate than most groups including non-conjugated alkene. Conjugated α,β-unsaturated carboxylic acids give saturated alcohols as the major products.Ketones and the carbonyl of enones are effectively reduced with borane-tetrahydrofuran. The addition of borohydride to the reaction solution is advantageous for accelerated reduction as well as higher selectivity towards carbonyl reduction in conjugated and non-conjugated enones.Asymmetric ketone reduction using chiral oxazaborolidine catalysts was recently reviewed. Work at Callery with BTHF improved on reaction conditions to provide consistent results in the reduction.

General Description

Borane tetrahydrofuran complex (BH3-THF) is widely used as a reducing agent in organic synthesis. It is also used as a reagent in hydroboration reactions.

Precautions

Air and moisture sensitive. Forms explosive peroxides in contact with air. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents and alcohols. On hydrolysis, it forms hydrogen and boric acid.

InChI:InChI=1/C4H8O.BH3/c1-2-4-5-3-1;/h1-4H2;1H3

Synthetic route

tetrahydrofuran (109-99-9) → borane-THF (14044-65-6)

Conditions	Yield
With dimethylsulfide borane complex for 0.5h; Heating / reflux;

lithium borohydride + methanesulfonic acid (75-75-2) → borane-THF (14044-65-6)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran byproducts: LiO3SMe, H2; N2-atmosphere, 25°C, 0.25 h, stirring; not isolated, reaction followed by (11)B-NMR spectroscopy and H2-volumetry;

lithium borohydride + aluminium trichloride (7446-70-0) → borane-THF (14044-65-6) + hydridoaluminium bis(tetrahydroborate)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran molar ratio B:Al=1:1 to 7.2:1; not isolated, detd. by (11)B-NMR spectroscopy;

lithium borohydride + aluminium bromide (7727-15-3) → borane-THF (14044-65-6) + hydridoaluminium bis(tetrahydroborate)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran molar ratio B:Al=2.8:1 to 1:2; not isolated, detd. by (11)B-NMR spectroscopy;

lithium borohydride → borane-THF (14044-65-6)

Conditions	Yield
With tetrahydrofuran; aluminium trichloride In tetrahydrofuran addn. of AlCl3 to LiBH4 (molar ratio B:Al=1.2:1 to 1.7:1); not isolated, detd. by (11)B-NMR spectroscopy;
With tetrahydrofuran; aluminum tri-bromide; aluminium trichloride In tetrahydrofuran addn. of LiBH4 to AlBr3 (molar ratio B:Al=4:1), 1 h; not isolated, detd. by (11)B-NMR spectroscopy;
With tetrahydrofuran; aluminum tri-bromide In tetrahydrofuran molar ratio B:Al=1:1 to 7.4:1; not isolated, detd. by (11)B-NMR spectroscopy;

lithium borohydride + bis(trimethylsilyl)sulphate (18306-29-1) → borane-THF (14044-65-6)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran byproducts: Li2SO4; N2-atmosphere, 25°C, 0.25 h, stirring; not isolated, reaction followed by (11)B-NMR spectroscopy;

lithium borohydride + trimethylsilyl methanesulfonate (10090-05-8) → borane-THF (14044-65-6)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran byproducts: LiO3SMe, HSiMe3; N2-atmosphere, 25°C, 0.25 h, stirring; not isolated, reaction followed by (11)B-NMR spectroscopy;

triborane(7)*tetrahydrofuran + trimethylphosphine-borane (1898-77-7) → borane-THF (14044-65-6) + pentaborane(9) (19624-22-7) + trimethylphosphine-triborane adduct (97012-38-9) + diborane (19287-45-7)

Conditions	Yield
In tetrahydrofuran soln. of educts in THF allowed to stand at room temp. for 8 months; NMR anal.;

tetraborane (18283-93-7) + trimethylphosphane (594-09-2) → borane-THF (14044-65-6) + octahydrotriborate(1-) + trimethylphosphine-triborane adduct (97012-38-9) + triborane(7)*tetrahydrofuran + trimethylphosphine-borane (1898-77-7)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran; dichloromethane B4H10 dissolved in THF at -80°C, kept at 0°C for 4 h, treated with PMe3 in CH2Cl2 at 25°C; NMR anal.;

tetraborane (18283-93-7) + trimethylphosphane (594-09-2) → borane-THF (14044-65-6) + triborane(7)*tetrahydrofuran + H2B[P(CH3)3]2(1+)*B3H8(1-)=H2B[P(CH3)3]2B3H8 + trimethylphosphine-borane (1898-77-7)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran B4H10 dissolved in THF at -80°C, kept at -63°C for 3 h, treated with PMe3, kept at -10 to 25°C; NMR anal.;

aluminium trichloride (7446-70-0) + tetrabutylammonium borohydride → borane-THF (14044-65-6) + (CH3CH2CH2CH2)4N(1+)*Al(3+)*2BH4(1-)*2Cl(1-)=(CH3CH2CH2CH2)4N[Al(BH4)2Cl2]

Conditions	Yield
In tetrahydrofuran addn. of AlCl3 to Bu4NBH4 (molar ratio B:Al=1:2 or 1:3); or addn. of Bu4NBH4 to AlCl3 (molar ratio B:Al=5:1 to 2:1); not isolated, detd. by (11)B-NMR spectrocopy;

tetraborane (18283-93-7) + phosphan (7803-51-2) → borane-THF (14044-65-6) + triborane(7)*tetrahydrofuran + phosphine-triborane(7) + phosphine-borane (19121-56-3)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran B4H10 dissolved in THF at -80°C, kept at 0°C for 4 h, treated with PH3 at -60°C, allowed to warm to 0°C, stored for67 h; NMR anal.;
With tetrahydrofuran In tetrahydrofuran B4H10 dissolved in THF at -80°C, kept at -63°C for 3 h, treated with PH3 at -80 to -50°C, warmed slowly to 0°C; NMR anal.;

aluminium trichloride (7446-70-0) + tetrabutylammonium borohydride → borane-THF (14044-65-6) + (CH3CH2CH2CH2)4N(1+)*Al(3+)*2BH4(1-)*2Cl(1-)=(CH3CH2CH2CH2)4N[Al(BH4)2Cl2] + tetrabutylammonium diborohydride (40001-25-0)

Conditions	Yield
In tetrahydrofuran addn. of AlCl3 to Bu4NBH4 (molar ratio B:Al=1:1); not isolated, detd. by (11)B-NMR spectrocopy;

tetrahydrofuran (109-99-9) + triphenylmethane hydrodisulfide (3492-71-5) → borane-THF (14044-65-6) + triphenylmethanethiol (3695-77-0) + hydrosulfide anion (15035-72-0)

Conditions	Yield
With tetrabutylammonium borohydride In dichloromethane-d2 Inert atmosphere; Glovebox;

tetrahydrofuran (109-99-9) + sodium tetrahydroborate (16940-66-2) → borane-THF (14044-65-6)

Conditions	Yield
With dimethyl sulfate at -10℃;
With chloro-trimethyl-silane at 20℃; for 24h; Reagent/catalyst; Temperature;
With iodine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique;
With iodine at 0℃; for 1h; Inert atmosphere;

tetrahydrofuran (109-99-9) + diborane (19287-45-7) → borane-THF (14044-65-6)

Conditions	Yield
at 0 - 5℃; for 0.75h; Inert atmosphere;

tetrahydrofuran (109-99-9) + BH4(1-)*BH6N2(1-)*2H(1+) → borane-THF (14044-65-6)

Conditions	Yield
With dimethyl amine at -40 - 20℃; for 0.166667h; Inert atmosphere;

ammonia borane complex (10043-11-5) + H2BCl * tetrahydrofuran (55606-72-9) → borane-THF (14044-65-6) + ammonia chloroborane (71648-05-0)

Conditions	Yield
In tetrahydrofuran at 0℃; Equilibrium constant; Schlenk technique;

benzophenone (119-61-9) + borane-THF (14044-65-6) → tris(diphenylmethoxy)borane (29002-71-9)

Conditions	Yield
In tetrahydrofuran (N2); 0°C, 5 min; removal of volatiles, recrystn. (hot toluene); elem. anal.;	100%

borane-THF (14044-65-6) + [disodium(2+)][1,2-diselena-diboranate(2-)] → Na(1+)*H3BSe(B2H5)(1-)=Na[H3BSeB2H5] (131636-29-8)

Conditions	Yield
In further solvent(s) byproducts: H2; Ar atm.; triglyme or diglyme, room temp., heating (50°C); evapn. (vac.), followed by NMR;	100%

sodium tetrahydroborate (16940-66-2) + borane-THF (14044-65-6) + diphosphane-borane (186336-54-9) → sodium 1,1,2-tris(borane)-1,2,2-trihydrogendiphosphide (186336-57-2)

Conditions	Yield
In tetrahydrofuran byproducts: H2, Na2[P2H2(BH3)4]; N2 atm.; molar ratio P2H4BH3:NaBH4 1:1, cooling (-78 to -196°C), stirring (4 h), heating (-78°C, 3 h), stirring (room temp., 6 h); crystn. (-78°C, several d);	100%

borane-THF (14044-65-6) + ((CH3)3Si)2NHBH3 (186796-04-3) → N,N-bis(trimethylsilyl)-μ-aminodiborane (186796-05-4)

Conditions	Yield
In tetrahydrofuran byproducts: H2; N2 atm.; equimolar ratio, stirring (room temp., 12 h); solvent removal (vac.);	100%

borane-THF (14044-65-6) + tris(3,5-dibromo-2-hydoxyphenyl)methane (1289219-86-8) → C23H15BBr6O4 (1289219-91-5)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 2h; Inert atmosphere;	100%

borane-THF (14044-65-6) + tris(5-bromo-2-hydroxyphenyl)methane (1289219-87-9) → C23H18BBr3O4 (1289219-92-6)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 2h; Inert atmosphere;	100%

borane-THF (14044-65-6) + tris(5-fluoro-2-hydroxyphenyl)methane (1289219-88-0) → C23H18BF3O4 (1289219-94-8)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 2h; Inert atmosphere;	100%

borane-THF (14044-65-6) + tris(2-hydroxy-3-phenylphenyl)methane (1289219-89-1) → C41H33BO4 (1289219-95-9)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 2h; Inert atmosphere;	100%

borane-THF (14044-65-6) + tris(2-hydroxy-3-(1-naphthyl)phenyl)methane (1289219-90-4) → C53H39BO4 (1289219-96-0)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 3h; Inert atmosphere;	100%

borane-THF (14044-65-6) + N2,N6-bis(diisopropylphosphino)pyridine-2,6-diamine (885665-51-0) → N,N′-bis(diisopropylphosphino-borane)-2,6-diaminopyridine (1433219-02-3)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	100%

borane-THF (14044-65-6) + o-anisyl(hydroxymethyl)phenylphosphine oxide → o-anisyl(hydroxymethyl)phenylphosphine borane

Conditions	Yield
In tetrahydrofuran at 20℃; for 4.03h; Inert atmosphere; Schlenk technique; regioselective reaction;	100%

borane-THF (14044-65-6) + C34H30N2 → C34H36B2N2

Conditions	Yield
In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere;	100%

borane-THF (14044-65-6) + (η5-C5H4PCy2)Re(CO)2CO → C20H29BO3PRe

Conditions	Yield
In tetrahydrofuran	100%

borane-THF (14044-65-6) + (η5-C5H4PPh2)Re(CO)2PMe3 (1241904-55-1) → C22H26BO2P2Re

Conditions	Yield
In tetrahydrofuran	100%

borane-THF (14044-65-6) + (η5-C5H4PPh2)Re(CO)2P(OMe)3 (1241904-56-2) → C22H26BO5P2Re

Conditions	Yield
In tetrahydrofuran	100%

borane-THF (14044-65-6) + tricarbonyl(η5-diphenylphosphinocyclopentadienyl)rhenium → C20H17BO3PRe

Conditions	Yield
In tetrahydrofuran	100%

3,5-dibromopyridine (625-92-3) + borane-THF (14044-65-6) + tris[{S}-1-{2-hydroxy-3-(1-naphthyl)naphthyl}]methane → C66H40BBr2NO3

Conditions	Yield
Stage #1: borane-THF; tris[{S}-1-{2-hydroxy-3-(1-naphthyl)naphthyl}]methane In dichloromethane at 60℃; for 8h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: 3,5-dibromopyridine In dichloromethane for 0.0833333h; Glovebox; Inert atmosphere; Sealed tube;	100%

borane-THF (14044-65-6) + tris[{S}-1-{2-hydroxy-3-(1-naphthyl)naphthyl}]methane → C65H45BO4

Conditions	Yield
In dichloromethane at 60℃; for 8h; Glovebox; Inert atmosphere; Sealed tube;	100%

borane-THF (14044-65-6) + [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]diphenylphosphine (1250258-94-6) → diphenyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]phosphine borane (1417911-71-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	100%

borane-THF (14044-65-6) + tris(3-bromo-2-hydroxyphenyl)(methyl)silane → C23H20BBr3O4Si

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Glovebox;	100%

borane-THF (14044-65-6) + tris(2-hydroxy- [1,1'-biphenyl]-3-yl)(methyl)silane → C41H35BO4Si

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Glovebox;	100%

borane-THF (14044-65-6) + (4-hydroxyphenyl)(methyl)(phenyl)phosphine → (4-hydroxyphenyl)(methyl)(phenyl)phosphine borane

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	100%

borane-THF (14044-65-6) + bis(di-tert-butylphosphanyl)amine (97049-90-6) → C16H43B2NP2

Conditions	Yield
In tetrahydrofuran; toluene for 0.166667h;	100%

borane-THF (14044-65-6) + Tri-(tert-butyl)-phosphinmethylen (64286-40-4) → trihydro(tri-tert-butylphosphoniomethyl)borate (73946-50-6)

Conditions	Yield
In tetrahydrofuran byproducts: THF; under N2, mixt. decompd. at -20°C, then stirring at 20°C for 2 h; solvent removed, recrystd. from toluene/pentane, elem. anal.;	99%

borane-THF (14044-65-6) + 4,5-dihydro-3H-dinaphtho[2.1-c:1',2'-e]phosphepine (218767-47-6) → Fe(CO)4(4,5-dihydro-3H-dinaphtho[2.1-c:1',2'-e]phosphepine), borane adduct (524941-61-5, 218767-81-8, 1092063-99-4)

Conditions	Yield
In tetrahydrofuran inert atmosphere; equimolar amts., stirring for 12 h; solvent removal (20°C, 0.05 mbar); elem. anal.;	99%

borane-THF (14044-65-6) + arachno-9-1,1'-bis(diphenylphosphino)ferrocene-6-SB9H11 → arachno-9-1,1'-bis(diphenylphosphino)ferrocene(BH3)-6-SB9H11

Conditions	Yield
In tetrahydrofuran; toluene byproducts: THF; N2-atmosphere; addn. of borane (in THF) to Fe-complex (in PhMe), standing for 2 h; in air; filtration (SiO2), evapn. (vac.), chromy. (SiO2, CH2Cl2/hexane=1:1); elem. anal.;	99%

borane-THF (14044-65-6) + [(η6-p-cymeme)RuCl2(η1-PPh2CCPPh2)] (913821-47-3) → [(η6-p-cymeme)RuCl2(η1-PPh2CCPPh2BH3)] (913821-48-4)

Conditions	Yield
In tetrahydrofuran under N2; 1.2 M soln. of BH3*THF (0.01 ml) added dropwise to soln. of Rucomplex (0.01 ml) in THF (2 ml, -78°C); stirred (1 h); solvent removed (vac., room temp.);	99%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + borane-THF (14044-65-6) + methylphenylphosphine (6372-48-1) → 2,2'-oxybis(ethane-2,1-diyl)bis(methylphenylphosphine-borane) (1147564-62-2, 1147564-78-0)

Conditions

Yield

With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-DIFLUORPHOS)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate), NMR and MS;

99%

borane-THF (14044-65-6) + 4,6-bis(chloromethyl)dibenzofuran (1147564-68-8) + methylphenylphosphine (6372-48-1) → C12H6O(CH2P(Me)(Ph)(BH3))2 (1147564-48-4, 1147564-70-2)

Conditions

Yield

With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-MeO-BiPHEP)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate);

99%

borane-THF (14044-65-6) + (CH3)2C13H6O(CH2Cl)2 (1147564-67-7) + methylphenylphosphine (6372-48-1) → (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(methylene)bis(methylphenylphosphine-borane) (1147564-34-8, 1147564-69-9)

Conditions	Yield
With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-MeO-BiPHEP)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate);	99%
With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-MeO-BiPHEP)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at -30°C; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate);

Upstream product

• 7727-15-3 aluminium bromide 
• 18306-29-1 bis(trimethylsilyl)sulphate 
• 10090-05-8 trimethylsilyl methanesulfonate 
• 10043-11-5 borane-ammonia complex 
• 55606-72-9 H₂BCl * tetrahydrofuran 
• 109-99-9 tetrahydrofuran 
• 19287-45-7 diborane 
• 16940-66-2 sodium tetrahydroborate 
• 3492-71-5 triphenylmethane hydrodisulfide 
• 7446-70-0 aluminium trichloride 
• 18283-93-7 tetraborane 
• 7803-51-2 phosphan 
• 594-09-2 trimethylphosphane 
• 1898-77-7 trimethylphosphine-borane 

Downstream Products

• 141850-54-6 (2R,4R)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 141334-24-9 B(C₆H₉O(CH₃)(CH(CH₃)2))2H 
• 635-20-1 B(O-d,l-menthyl)3 
• 131392-39-7 N-isobutyltriphenylphosphoranimine borane 
• 131441-55-9 N-methyltriphenylphosphoranimine borane 
• 131392-42-2 N-phenylaminotriphenylphosphoranimine borane 
• 131441-56-0 N-ethyltriphenylphosphoranimine borane 
• 131441-57-1 N-n-propyltriphenylphosphoranimine borane 
• 131392-41-1 N-dimethylaminotriphenylphosphoranimine borane 
• 131441-58-2 N-isopropyltriphenylphosphoranimine borane 
• 131392-43-3 N-methylphenylaminotriphenylphosphoranimine borane 
• 131392-40-0 N-t-butyltriphenylphosphoranimine borane 
• 127686-64-0 (3-butenyl)diphenylphosphine-borane complex 
• 1289219-95-9 C₄₁H₃₃BO₄ 

Relevant articles and documents

Hydroboration-oxidation of (±)-(1α,3α,3aβ,6aβ) -1,2,3,3a,4,6a-hexahydro-1,3-pentalenedimethanol and its O-protected derivatives: Synthesis of new compounds useful for obtaining (iso)carbacyclin analogues and X-ray analysis of the products

Hydroboration-oxidation of 2α,4α-dimethanol-1β,5β-bicyclo[3.3.0]oct-6-en dibenzoate (1) gave alcohols 2 (symmetric) and 3 (unsymmetric) in ~60% yield, together with the monobenzoate diol 4a (37%), resulting from the reduction of the closer benzoate by the

Unravelling a general mechanism of converting ionic B/N complexes into neutral B/N analogues of alkanes: H: δ +?Hδ - ydrogen bonding assisted dehydrogenation

Long-sought mechanisms for the conversion of diammoniate of diborane ([NH3BH2NH3]+[BH4]-) into NH3BH3 and [NH2BH2]n as well as ammonium aminodiborane ([NH4]+[BH3NH2BH3]-) into a butane analogue, NH3BH2NH2BH3, have been elucidated on the basis of extensive experimental and theoretical studies. The [NH4]+ ammonium cation and the (η2-H2)BH2R moiety are found to be critical in B/N chain expansion.

Mechanisms of the Reactions of B-Substituted Amine Boranes with THF·BH3

The reactions of NH3BH2R (R = Me, Ph and Cl) with THFBH3 have been investigated and it was found that different substituents on the B atom help to proceed the reactions in different ways. The expected doubly-bridged B-substituted aminodiborane products, similar to aminodiborane (ADB, BH2(μ-H)(μ-NH2)BH2) via the reaction of ammonia borane (AB, NH3BH3) and tetrahydrofuran borane (THFBH3), are not obtained. Two competitive reactions occurred with the change of R = Me or Ph. When R is a Me group, an “open“ version of B-substituted μ-aminodiborane, THFBH(Me)(μ-NH2)BH3, is formed as a major product; when R is a Ph group, AB and THFBH2Ph are formed as main products via the intermolecular NH3–THF exchange reaction. However, if R is Cl, then NH3BH2Cl reacts with THFBH3 through reversible intermolecular Cl–H exchange mechanism. Furthermore, DFT calculations are performed to elucidate the formation mechanism of THFBH(Me)(μ-NH2)BH3 via the reaction of NH3BH2Me and THFBH3 as well as the exchange mechanism of Cl–H in the reaction of NH3BH2Cl and THFBH3.