Tributylborane

Base Information

• Chemical Name: Tributylborane
• CAS No.: 122-56-5
• Deprecated CAS: 31259-85-5
• Molecular Formula: C12H27B
• Molecular Weight: 182.157
• Hs Code.: 29310099
• European Community (EC) Number: 204-554-6
• DSSTox Substance ID: DTXSID9059543
• Nikkaji Number: J55.477D
• Wikidata: Q72509961
• Mol file: 122-56-5.mol

Synonyms:tri-n-butylborane;tributylborane

Chemical Property of Tributylborane

Chemical Property:

• Appearance/Colour: colorless to pale yellow liquid
• Vapor Pressure: 0.3mmHg at 25°C
• Melting Point: -34 °C
• Refractive Index: 1.4285
• Boiling Point: 209 °C at 760 mmHg
• Flash Point: 94.9 °C
• PSA: 0.00000
• Density: 0.732 g/cm³
• LogP: 4.88150
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: Benzene, Tetrahydrofuran
• Water Solubility.: Not miscible or difficult to mix with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 9
• Exact Mass: 182.2205810
• Heavy Atom Count: 13
• Complexity: 72.1

Purity/Quality:

99% ^*data from raw suppliers

Tributylborane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; F; C
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B(CCCC)(CCCC)CCCC
• Uses: Petrochemical industry, organic reactions, catalyst. Tributylborane is a reducing agent used in the controlled radical polymerization of alkyl acrylates.

Technology Process of Tributylborane

There total 42 articles about Tributylborane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.7%

tri-n-butylboroxine (7359-98-0) + tri(n-butyl)aluminium (1116-70-7) → tributyl borane (122-56-5)

Guidance literature:

at 100 - 140 ℃; for 5h; Product distribution / selectivity;

Reference yield: 79.0%

dibromomethylborane (17933-16-3) + N,N'-diethylurea (623-76-7) → tributyl borane (122-56-5) + 3,5-Diethyl-2,3,5,6-tetrahydro-2,6-dimethyl-4H-1,3,5,2,6-oxadiazadiborin-4-on (81233-27-4)

Guidance literature:

With n-butyllithium; In hexane; Petroleum ether; byproducts: butane, LiBr; the urea in petroleum ether was refluxed under N2 with n-BuLi in hexanefor 48 h; the solvents were removed in vac., the residue was fractional distd.; elem. anal.;

Reference yield: 70.0%

n-butyllithium (109-72-8,29786-93-4) → tributyl borane (122-56-5)

Guidance literature:

With 2,6-dibromo-4,8-dimethyl-1,3,5,7-tetraphenylbenzobis(diazaborole); In hexane; toluene; at -78 ℃; for 1h;

DOI:10.1039/c9dt03818c

upstream raw materials:

n-butyl magnesium bromide

diethyl ether

tri-n-butylboroxine

Trimethyl borate

Downstream raw materials:

Dibutan-1-borinsaeure-ethylester

dibutyl-phenoxy-borane

Ethyl 2-bromohexanoate

2-(2-Hydroxyhexyl)-1-cyclohexanol

Refernces

• 1、 Johnson, J. R.,Snyder, H. R.,Campen, M. G. van. "-". . p. 115 - 121. Retrieved 1938.
• 2、 Pasto,Timony. "". . p. 222,239. Retrieved 1975.
• 3、 Wu,Shen. "Preparation of tributylborane from butyllithium and boron trifluoride etherate". . p. 2939 - 2942. Retrieved 2001.
• 4、 Horino, Yoshikazu,Murakami, Miki,Aimono, Ataru,Lee, Jun Hee,Abe, Hitoshi. "Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols". supporting information. p. 476 - 480. Retrieved 2019/01/14.
• 5、 -. "METHOD FOR PRODUCING TRIHYDROCARBYLBORANE". Page/Page column 6. . Retrieved 2008/06/13.