122-56-5

Basic information

• Product Name: TRIBUTYLBORANE
• Synonyms: TRIBUTYLBORANE;Tributylboron;TRI-N-BUTYLBORON;Borane, tributyl-;Tributylborane, 1.0 M solution in THF, SpcSeal;Tributylborane solution 1.0 M in THF;Tributylborane, 1M Solution in Tetrahydrofuran;Borane,tributyl-
• CAS NO: 122-56-5
• Molecular Formula: C₁₂H₂₇B
• Molecular Weight: 182.15
• EINECS: 204-554-6
• Product Categories: Boranes;Reduction;Synthetic Reagents
• Mol File: 122-56-5.mol

Chemical Properties

• Melting Point: -34 °C
• Boiling Point: 109 °C20 mm Hg(lit.)
• Flash Point: 1 °F
• Appearance: Clear colorless to light yellow/Solution
• Density: 0.834 g/mL at 25 °C
• Vapor Pressure: 0.3mmHg at 25°C
• Refractive Index: 1.4285
• Storage Temp.: Flammables area
• Solubility: Benzene, Tetrahydrofuran
• Water Solubility: Not miscible or difficult to mix with water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: TRIBUTYLBORANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIBUTYLBORANE(122-56-5)
• EPA Substance Registry System: TRIBUTYLBORANE(122-56-5)

Safety Data

• Hazard Codes: F,Xn,C
• Statements: 17-34-40-36/37/38-20/21/22-11-22-19-37
• Safety Statements: 7-23-26-36/37/39-43-45-16
• RIDADR: UN 2845 4.2/PG 1
• WGK Germany: 1
• RTECS: ED1850000
• TSCA: Yes
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 122-56-5(Hazardous Substances Data)

Usage

Uses

Used in Petrochemical Industry:
Tributylborane is used as a reducing agent in the controlled radical polymerization of alkyl acrylates, which is an important process in the petrochemical industry. Its reducing properties enable the production of polymers with specific characteristics, such as controlled molecular weight and narrow molecular weight distribution.
Used in Organic Reactions:
In the field of organic chemistry, tributylborane is employed as a reagent in various reactions, such as hydroboration, which involves the addition of a borane compound to an alkene. This reaction is useful for the synthesis of complex organic molecules and the formation of new chemical bonds.
Used as a Catalyst:
Tributylborane also serves as a catalyst in certain chemical reactions, promoting the formation of desired products and increasing the efficiency of the reaction. Its ability to act as a Lewis acid and accept electron pairs makes it a versatile catalyst in various organic transformations.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 427, 1986 DOI: 10.1021/jo00354a002Tetrahedron Letters, 26, p. 4311, 1985 DOI: 10.1016/S0040-4039(00)98721-5

Hazard

Flammable, dangerous fire risk, store and use in inert atmosphere, ignites spontaneously in air.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. A very dangerous fire hazard when exposed to heat or flame; can ignite spontaneously. When heated to decomposition it emits acrid smoke and irritating fumes. See also BORANES.

InChI:InChI=1/C12H27B/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 60-29-7 diethyl ether 
• 7359-98-0 tri-n-butylboroxine 
• 121-43-7 Trimethyl borate 
• 16500-38-2 tris(isobutyloxy) boroxine 
• 1095-03-0 triphenylborane 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 5674-70-4 bromo-dibutyl-borane 
• 109-72-8 n-butyllithium 
• 1116-70-7 tri(n-butyl)aluminium 
• 17381-60-1 diiodophenylborane 
• 7637-07-2 boron trifluoride 
• 1767-37-9 (amino)di-n-butylborane 
• 41830-29-9 tetra-n-butyldiborane 

Downstream Products

• 507-20-0 tertiary butyl chloride 
• 109-69-3 n-Butyl chloride 
• 513-88-2 1,1-Dichloroacetone 
• 75-65-0 tert-butyl alcohol 
• 32429-86-0 Dibutan-1-borinsaeure-ethylester 
• 14090-22-3 butyl-dichloro-borane 
• 1730-68-3 (n-C₄H₉)2BNH-n-C₄H₉ 
• 32705-36-5 dibutyl-phenoxy-borane 
• 615-96-3 Ethyl 2-bromohexanoate 
• 58190-83-3 2-phenylacetyl-hexanoic acid ethyl ester 
• 24744-99-8 Ethyl-β-phenyl-α-butyl-hydroacrylat 
• 6134-71-0 ethyl 2-butyl-3-oxo-3-phenylpropanoate 
• 42480-09-1 2-(1-Hydroxy-1-phenyl-propyl)-hexanoic acid ethyl ester 
• 1540-29-0 ethyl 2-butylacetoacetate 

Relevant articles and documents

Preparation of tributylborane from butyllithium and boron trifluoride etherate

A convenient laboratory synthesis of tributylborane from commercially available n-butyllithium and boron trifluoride etherate is developed.

Syntheses and structures of benzo-bis(1,3,2-diazaboroles) and acenaphtho-1,3,2-diazaboroles

Colorless crystalline 2,6-dibromo-4,8-dimethyl-1,3,5,7-tetraphenylbenzobis(diazaborole) 4 resulted from the cyclocondensation of 3,6-dimethyl-1,2,4,5-tetraphenylaminobenzene 3d with two equivalents of boron tribromide in the presence of calcium hydride. Synthesis of the dark-red crystalline 2-bromo-N,N′-bis(diisopropylphenyl)acenaphtho-1,3,2-diazaborole 7 was effected by the cyclocondensation of 1,2-bis(N-2′,6′-diisopropylphenylimino)acenaphthene (5) and boron tribromide with subsequent sodium amalgam reduction of the initially formed burgundy red diazaborolium salt 6. Compounds 4, 6 and 7 are characterised by elemental analyses, 1H, 11B and 13C NMR spectroscopy, as well as by single X-ray diffraction studies. The electronic structures of 4, 6 and 7 are subject to DFT calculations.

Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.

Controlled radical polymerization of alkyl acrylates in the presence of the tri-n-butylborane–p-quinone system

The reactivities of different p-quinones in the radical polymerization of methyl and tert-butyl acrylates were studied. The inhibitory effect of p-quinones decreases witn an increase in the volume and number of substituents. The radical polymerization of alkyl acrylates in the presence of tri-n-butylborane and p-quinones proceeds without gel effect by the “living” polymerization mechanism. UV spectroscopy showed that the reaction between the growth radical and p-quinone proceeds with different regioselectivity and depends on the nature of the latter. The obtained polyacrylates possess the capability of reinitiating polymerization. The reinitiation mechanism was studied by mass spectrometry (MALDI-TOF) and ESR spectroscopy. Gel permeation chromatography showed that, depending on the nature of p-quinone, macroinitiator polymers exhibit different activity in post-polymerization.

METHOD FOR PRODUCING TRIHYDROCARBYLBORANE

The present invention provides a method for industrial production of trihydrocarbylborane which method is excellent both in quality and in cost. The present invention is concerned with production of trihydrocarbylborane, comprising a reaction synthesizing the trihydrocarbylborane and aluminum oxide from trihydrocarbylboroxine and trihydrocarbylaluminum, characterized in that the reaction is allowed to proceed so that the trihydrocarbylaluminum is present at the end of the reaction in an amount of 0.5 moles or more per mole of the aluminum oxide produced in the reaction.

Reaction of Metal and Metalloid Compounds with Polyfunctional Molecules, XXXVI. New Syntheses of Open-Chain and Cyclic N-Borylureas and -thioureas

N,N,N'-Triorganylureas and thioureas react either in lithiated or not lithiated form with bromodimethylborane.In the first case, the monomeric N-borylureas and -thioureas 1 - 7 are obtained; in the second case, by-products are 1,3,5,2-triazaborine-4,6-diones (8, 13), 1,3,5,2,6-oxadiazaborin-4-one (10), and 1,3,5,7,2-tetraazaborocine-4,6,8-trione derivatives (9, 12).With N,N'-diorganylureas and -thioureas, resp., the following paths of synthesis were investigated: 1.Lithiation with n-butyllithium (mol ratio 1 : 2) and subsequent reaction with dihalogenoorganylboranes, 2. reaction of the N,N'-bis(trimethylsilyl) derivatives with dihalogenoorganylboranes, 3. reaction with tris(dimethylamino)borane, 4. reaction with halogenodiorganylboranes, 5. reaction with triorganylboranes.In 1. - 4. 1,3,5,2,6-oxa-(thia)diazadiborin-4-one and -thione, resp., (10, 14 - 25, 31 - 36), 1,3,5,2,4-triazadiborin-6-one and -thione derivatives, resp., (26 - 30, 37, 42), and 1,3,5,2-triazaborine-4,6-dione (38) are formed.Path 4. yields also the 1,3,5,2,4-thiadiazadiborin-6-imine 43.By synthesis 5. the N,O-bis(diorganylboryl)isobiuret derivatives, 44 and 45 are accessible.N,N',N''-triorganyl-N,N''-bis(trimethylsilyl)biuret reacts with dihalogenoorganylboranes to give the 1,3,5,2-triazaborine-4,6-diones 11, 39 - 41 and the 1,3,5,2,6-oxadiazadiborin-4-one 40.The compounds were characterized analytically and spectroscopically.

REACTION OF METHYL AND PHENYL PICRATES WITH NUCLEOPHILES

The reactions of 2,4,6-trinitroanisole with various nucleophiles Me3SnM, Me3SiLi, BuLi, Me4NBBu4, PhMgI, CN-, lithium (potassium) succinimide, F-, Cl-, Br-, SCN-, NO2-, NO3-, HCO3-, PhSO2-,AcO-, S2- were investigated.It was found that the final products are the picrate and the corresponding methyl derivatives.The formation of intermediate ? complexes was detected in a series of the reactions (Me3SnLi, potassium succinimide, Bu4B-, CN-, NO2-, PhSO2-).Possible mechanisms for the reaction are examined.Reactions of 2,4,6-tricyanoanisole and phenyl picrate with certain nucleophiles were also investigated.