Tributylamine

Base Information

• Chemical Name: Tributylamine
• CAS No.: 102-82-9
• Deprecated CAS: 168153-19-3
• Molecular Formula: C12H27N
• Molecular Weight: 185.353
• Hs Code.: 29211.99 Oral rat LD50: 114 mg/kg
• European Community (EC) Number: 203-058-7
• ICSC Number: 1048
• UN Number: 2542
• UNII: C3TZB2W0R7
• DSSTox Substance ID: DTXSID4026183
• Nikkaji Number: J35.156C
• Wikipedia: Tributylamine
• Wikidata: Q905558
• Metabolomics Workbench ID: 56068
• ChEMBL ID: CHEMBL1877658
• Mol file: 102-82-9.mol

Synonyms:Tributylamine(7CI,8CI);N,N-Dibutyl-1-butanamine;Tri-n-butylamine;Tris-n-butylamine;Tributylamine;

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Chemical Property of Tributylamine

Chemical Property:

• Appearance/Colour: pale yellow liquid with an amine odour
• Vapor Pressure: 0.3 mm Hg ( 20 °C)
• Melting Point: -70 °C(lit.)
• Refractive Index: 1.4283
• Boiling Point: 215.3 °C at 760 mmHg
• PKA: 9.99±0.50(Predicted)
• Flash Point: 63.3 °C
• PSA: 3.24000
• Density: 0.792 g/cm³
• LogP: 3.68870
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: sparingly soluble in water; soluble in most organic solvents; soluble in acetone and benzene; very soluble in alcohol and ether
• Water Solubility.: 0.386 g/L (25 ºC)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 185.214349865
• Heavy Atom Count: 13
• Complexity: 72.1
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N,T+
• Statements: 22-23/24-38-51/53-23/24/25-26-24
• Safety Statements: 26-36/37-45-61-36/37/39-28A-28

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aliphatic
• Canonical SMILES: CCCCN(CCCC)CCCC
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the skin. The substance is mildly irritating to the eyes.
• Uses: Solvent, inhibitor in hydraulic fluids, intermediate. Tributylamine is used as a solvent, an inhibitor in hydraulic fluids, a dental cement, and in isoprene polymerization. Tri-n-butylamine is an important intermediate in the production of phase transfer catalysts like tributylmethylammonium chloride and tributylbenzylammonium chloride. It is also used in pharmaceuticals, agrochemicals, surfactants, lubricant additives, vulcanization accelerators and dyes. It acts as a catalyst and as a solvent in organic syntheses and polymerization reactions. It serves as a strong base anion exchanger, acid acceptor, inhibitor in hydraulic fluids and an emulsifying agent. Further, it is used to prepare photographic chemicals.

Technology Process of Tributylamine

There total 151 articles about Tributylamine 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: 80.5%

→ tributyl-amine (102-82-9) + chloro(cyclopropyl)methane (5911-08-0)

Guidance literature:

Reference yield: 77.0%

tetra-(n-butyl)ammonium iodide (311-28-4) → 1-iodo-butane (542-69-8) + tributyl-amine (102-82-9)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In acetone; at 320 ℃; Product distribution; in a gas chromatograph; other temperature; various concentration of reagent;

DOI:10.1021/ac00240a064

Reference yield: 68.0%

1,4-dibromobicyclo<2.2.1>heptane (40950-22-9) + mercury → tributyl-amine (102-82-9) + norbornene (279-23-2) + 1-bromonorbornane (13474-70-9) + bis(1-norbornyl)mercury (67773-54-0)

Guidance literature:

With tetra-n-butylammonium perchlorate; In N,N-dimethyl-formamide; Electrolysis; at 25°C, at mercury cathode, at -1.9 V;

DOI:10.1021/ja00532a024

upstream raw materials:

1-bromo-butane

propyl cyanide

tetra-(n-butyl)ammonium iodide

1-iodo-butane

Downstream raw materials:

dibutylamine

butyraldehyde

tetrabutylammomium bromide

(4-ethoxy-phenyl)-[2]pyridyl-carbamoyl chloride

Refernces

• 1、 de Carli,Galimberti. "-". . . Retrieved 1940.
• 2、 Sim, Tae Bo,Ahn, Jin Hee,Yoon, Nung Min. "Selective deoxygenation of amine N-oxides using borohydride exchange resin-copper sulfate in methanol". . p. 324 - 326. Retrieved 1996.
• 3、 Moore, W. Michael. "Simultaneous Determination of Chloride, Bromide, and Iodide by Gas Chromatography". . p. 602 - 604. Retrieved 1982.
• 4、 Shigemori, Keisuke,Watanabe, Momoka,Kong, Julie,Mitsudo, Koichi,Wakamiya, Atsushi,Mandai, Hiroki,Suga, Seiji. "Iodide-mediated or iodide-catalyzed demethylation and friedel-crafts C-H borylative cyclization leading to thiophene-fused 1,2-oxaborine derivatives". . p. 2171 - 2175. Retrieved 2019.
• 5、 Pavlov,Nazin. "Decomposition mechanism of dinitramide onium salts". . p. 1848 - 1850. Retrieved 1997.
• 6、 Carroll, William F.,Peters, Dennis G.. "Electrolytic Reduction of 1,4-Dihalonorbornanes at Mercury Electrodes in Dimethylformamide. Evidence for Propellane as an Intermediate". . p. 4127 - 4134. Retrieved 1980.
• 7、 Mizuta, Tomoya,Sakaguchi, Satoshi,Ishii, Yasutaka. "Catalytic reductive alkylation of secondary amine with aldehyde and silane by an iridium compound". . p. 2195 - 2199. Retrieved 2005.
• 8、 Kielland, Nicola,Vicente-Garcia, Esther,Reves, Marc,Isambert, Nicolas,Arevalo, Maria Jose,Lavilla, Rodolfo. "Scope and post-transformations for the borane-isocyanide multicomponent reactions: Concise access to structurally diverse heterocyclic compounds". . p. 3273 - 3284. Retrieved 2013.
• 9、 Segobia,Trasarti,Apesteguía. "Hydrogenation of nitriles to primary amines on metal-supported catalysts: Highly selective conversion of butyronitrile to n-butylamine". . p. 69 - 75. Retrieved 2012.
• 10、 Kostera,Wyrzykiewicz,Pawlu?,Marciniec. "Ruthenium-catalyzed deaminative redistribution of primary and secondary amines". . p. 11552 - 11555. Retrieved 2017.