14044-65-6 Usage
Description
Borane-tetrahydrofuran complex (BH3-THF) is a colorless liquid that serves as a reducing agent in organic synthesis and is also used as a reagent in hydroboration reactions. It is a charge-transfer complex that acts as a useful surrogate for diborane in organic synthesis, enabling the reduction of various functional groups and the formation of boron-containing intermediates.
Uses
1. Used in Organic Synthesis:
Borane-tetrahydrofuran complex is used as a reducing agent for the reduction of various functional groups such as aldehyde, ketone, carboxylic acid, amide, oxime, imine, and nitrile. It facilitates the conversion of these groups into corresponding alcohols and amines.
2. Used in Hydroboration Reactions:
Borane-tetrahydrofuran complex acts as a hydro borating agent and a borane source for oxazaborolidine catalyzed asymmetric reductions, making it an essential component in these types of reactions.
3. Used in Nylon Surface Modification:
Borane-tetrahydrofuran complex is used to reduce nylon surface amide groups to secondary amines, which can enhance the properties of nylon for various applications.
4. Used in the Synthesis of Chiral Borane Catalysts:
It is utilized to synthesize the chiral borane catalyst, which is used in the enantioselective halo-aldol reaction, a significant process in the production of enantiomerically pure compounds.
5. Used in the Preparation of 9-Unsubstituted Acridines:
Borane-tetrahydrofuran complex is employed in the reduction of corresponding acridones to prepare 9-unsubstituted acridines, which are important compounds in the field of pharmaceuticals and dyes.
6. Used in the Production of Organoboranes:
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, further expanding the utility of this complex in organic synthesis.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 14044-65-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,0,4 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 14044-65:
(7*1)+(6*4)+(5*0)+(4*4)+(3*4)+(2*6)+(1*5)=76
76 % 10 = 6
So 14044-65-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O.BH3/c1-2-4-5-3-1;/h1-4H2;1H3
14044-65-6Relevant 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
T?nase, Constantin I.,Cocu, Florea G.,C?proiu, Miron Teodor,Dr?ghici, Constantin,Shova, Sergiu
, (2017)
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
Chen, Xi-Meng,Liu, Si-Cong,Xu, Cong-Qiao,Jing, Yi,Wei, Donghui,Li, Jun,Chen, Xuenian
, p. 12239 - 12242 (2019)
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
Guo, Yu,Wang, Xinghua,Ma, Nana,Cao, Yilin,Hussain, Sajjad,Zhang, Jie,Wei, Donghui,Chen, Xuenian
, p. 4994 - 4999 (2019/12/24)
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.