Borane-tetrahydrofuran complex

Borane-tetrahydrofuran complex Basic information
Product Name:Borane-tetrahydrofuran complex
Synonyms:borane-tetrahydrofurancomplex,bthf-1m;BORAN-TETRAHYDROFURANCOMPLEX;BORANE-TETRAHYDROFURANCOMPLEX,1MSOLUTIONINTETRAHYDROFURAN;Borane tetrahydrofuran complex 1.0 molar in THF;Borane-tetrahydrofuran complex, 1M soln. in THF, stab. with 5mmol NaBH4;Borane-tetrahydrofuran complex, 1M soln. in THF, packaged under Argon in resealable ChemSealTM bottles;Borane - Tetrahydrofuran Complex (8.5% in Tetrahydrofuran, ca. 0.9mol/L) (stabilized with Sodium Borohydride);Borane, 1M in tetrahydrofuran
CAS:14044-65-6
MF:C4H11BO
MW:85.94
EINECS:237-881-8
Product Categories:Synthetic Reagents;B (Classes of Boron Compounds);Boranes;Reduction;Synthetic Organic Chemistry;25mL Sure/Seal Reagents;organoboron and borato-metal complexes;Chemical Synthesis;Organometallic Reagents;Synthetic Reagents;14044-65-6
Mol File:14044-65-6.mol
Borane-tetrahydrofuran complex Structure
Borane-tetrahydrofuran complex Chemical Properties
Melting point -17 °C
Boiling point 35 °C
density 0.898 g/mL at 25 °C
Fp 1 °F
storage temp. Store at <= 20°C.
form Liquid
color Colorless
Water Solubility REACTS
Sensitive Air & Moisture Sensitive
BRN 3668402
Exposure limitsACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
Stability:Stable, but may form explosive peroxides in contact with air. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents, alcohols. Reacts violently with water. Highly flammable. Store under inert gas.
CAS DataBase Reference14044-65-6(CAS DataBase Reference)
EPA Substance Registry SystemBoron, trihydro(tetrahydrofuran)-, (T-4)- (14044-65-6)
Safety Information
Hazard Codes F,Xn,Xi
Risk 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
1-10-13-34
TSCA Yes
HazardClass 4.3
PackingGroup I
HS Code 29321900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Borane-tetrahydrofuran complex Usage And Synthesis
DescriptionBorane 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 Propertiescolourless liquid
UsesBorane-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.
UsesBorane-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.
ApplicationNew, Safer, NIMBA-Stabilized BH3 THF Solutions
BH3-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.
ReactionsBorane-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.
Borane-tetrahydrofuran complex reaction
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 DescriptionBorane tetrahydrofuran complex (BH3-THF) is widely used as a reducing agent in organic synthesis. It is also used as a reagent in hydroboration reactions.
PrecautionsAir 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.
Borane-tetrahydrofuran complex Preparation Products And Raw materials
Preparation Products1-(4-(Pyrrolidin-1-yl)butyl)hydrazine-->6-bromo-1,2,3,4-tetrahydroisoquinoline-->1-(4-Morpholinobutyl)hydrazine-->1-(3-(pyrrolidin-1-yl)propyl)hydrazine-->1-Methyl-3-phenylpiperazine-->CATECHOLBORANE-->1,1,2-Trimethylpropylborane-->BORANE-DIISOPROPYLAMINE-->Dicyclohexylborane-->Borane - 5-Ethyl-2-Methylpyridine CoMplex-->Trimethoxyboroxine-->9-BBN DIMER-->1-Octylboronic acid-->METHYLDIPHENYLPHOSPHINE-->BORANE-N,N-DIETHYLANILINE COMPLEX-->Borane-triethylamine complex
BODIPY(R) 515/530 GTP-GAMMA-S, THIOESTER, SODIUM SALT Borane-dimethylsulfide DIETHANOLAMINE-(3R)-(+)-TETRAHYDROFURANYLBORONATE BODIPY(R) FL-14-DUTP BODIPY(R) TR GTP-GAMMA-S, THIOESTER, SODIUM SALT POLY(TETRAHYDROFURAN) STANDARD 20000 CHROMATIDE(TM) BODIPY(R) 630/650-14-DUTP aplasmomycin ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), BODIPY(R) FL THIOETHER, TRISODIUM SALT BODIPY(R) TMR-14-DUTP CHROMATIDE(TM) BODIPY(R) 650/665-14-DUTP BODIPY(R) FL GTP-GAMMA-S, THIOETHER, TRISODIUM SALT CALCIUM BOROHYDRIDE BIS(TETRAHYDROFURAN) BODIPY(R) TR-X THAPSIGARGIN BODIPY(R) TMR-14-UTP INTERMEDIATES BODIPY(R) FL GTP-GAMMA-NH, AMIDE, SODIUM SALT BORANE, [3H]-THF COMPLEX

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