Triethylammonium formate

Base Information

• Chemical Name: Triethylammonium formate
• CAS No.: 585-29-5
• Molecular Formula: C7H17NO3
• Molecular Weight: 147.217
• Hs Code.: 29151200
• European Community (EC) Number: 629-594-5
• UNII: UN4T038P8M
• Wikidata: Q27291157
• Mol file: 585-29-5.mol

Synonyms:triethylamine;triethylamine acetate;triethylamine dinitrate;triethylamine hydrobromide;triethylamine hydrochloride;triethylamine maleate (1:1);triethylamine phosphate;triethylamine phosphate (1:1);triethylamine phosphonate (1:1);triethylamine sulfate;triethylamine sulfate (2:1);triethylamine sulfite (1:1);triethylamine sulfite (2:1);triethylammonium formate

Chemical Property of Triethylammonium formate

Chemical Property:

• Refractive Index: n20/D 1.355
• PSA: 44.57000
• Density: 1.02 g/mL at 25 °C(lit.)
• LogP: -1.06700
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 147.125928785
• Heavy Atom Count: 10
• Complexity: 35.9

Purity/Quality:

99% ^*data from raw suppliers

FORMIC ACID:TRIETHYLAMINE 2:1 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34-42-10-35-20/21/22
• Safety Statements: 23-26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CC.C(=O)O
• Uses: In syntheses employing the Leuckart reaction.

Technology Process of Triethylammonium formate

There total 6 articles about Triethylammonium formate 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: 90.0%

formic acid (64-18-6) + triethylamine (121-44-8) → triethylammonium formate (585-29-5)

Guidance literature:

at 25 - 60 ℃; for 4h;

DOI:10.1039/c1cp21817d

Reference yield: 76.0%

→ triethylammonium formate (585-29-5)

Guidance literature:

Reference yield: 16.0%

→ 1,1,1-tri(hydroxymethyl)propane (77-99-6) + triethylammonium formate (585-29-5)

Guidance literature:

upstream raw materials:

formic acid

triethylamine

carbon dioxide

methanol

Downstream raw materials:

7-Methyl-3-phenyl-8,9-dihydro-3H,7H-imidazo[4,5-f]quinoline-6-carbaldehyde

(E)-2-Formyloxymethyl-3-phenyl-acrylic acid ethyl ester

Formic acid (E)-2-cyano-3-(4-trifluoromethyl-phenyl)-allyl ester

5-bromo-3,4-dihydroquinoline-1(2H)-carbaldehyde

Refernces

PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES. A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS

10.1016/S0040-4039(00)85262-4

The study presents a novel and selective method for the deoxygenation of phenols through the reduction of aryl triflates. The key chemicals involved are aryl triflates, which are the substrates to be reduced; triethylammonium formate, which acts as the hydrogen donor; and a homogeneous palladium catalyst, typically palladium acetate, which facilitates the reaction. Triethylamine is also used as a base, and phosphine ligands, such as triphenylphosphine or 1,1'-bis(diphenylphosphino)ferrocene (DPPF), are employed to stabilize the palladium catalyst and enhance its activity. The reaction is carried out in DMF solvent, with formic acid added to generate the active hydrogen donor species. The study demonstrates that this method is highly chemoselective, tolerating various functional groups like nitro, ketones, esters, and olefins, and it provides high yields of aromatic hydrocarbons. The mechanism likely involves oxidative addition of the aryl triflate to the palladium catalyst, displacement of the triflate by formate ion, loss of carbon dioxide to form an arylpalladium(II) hydride, and subsequent reductive elimination to yield the aromatic hydrocarbon and regenerate the active palladium species.