4559-86-8

Basic information

• Product Name: Tetrabutylurea
• Synonyms: TETRA-N-BUTYLUREA;TETRABUTYL UREA;N,N,N',N'-TETRABUTYLUREA;N,N,N',N'-TETRA-N-BUTYLUREA;1,1,3,3-tetrabutyl-ure;tetrabutyl-ure;1,1,3,3-TETRABUTYLUREA;Tetra Butyl Ureas ( TBU )
• CAS NO: 4559-86-8
• Molecular Formula: C₁₇H₃₆N₂O
• Molecular Weight: 284.48
• EINECS: 224-929-8
• Product Categories: Phosgene Derivatives
• Mol File: 4559-86-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: <-50°C
• Boiling Point: 163 °C / 12mmHg
• Flash Point: 93 °C
• Appearance: /
• Density: 0.88
• Vapor Pressure: 5.7E-06mmHg at 25°C
• Refractive Index: 1.4520-1.4560
• PKA: -0.61±0.70(Predicted)
• Water Solubility: 4.3mg/L at 20℃
• CAS DataBase Reference: Tetrabutylurea(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabutylurea(4559-86-8)
• EPA Substance Registry System: Tetrabutylurea(4559-86-8)

Safety Data

• Safety Statements: 22-24/25
• RTECS: YU2080000
• TSCA: Yes
• Hazardous Substances Data: 4559-86-8(Hazardous Substances Data)

Usage

Uses

Plasticizer.

InChI:InChI=1/C17H36N2O/c1-5-9-13-18(14-10-6-2)17(20)19(15-11-7-3)16-12-8-4/h5-16H2,1-4H3

Synthetic route

Tetrabutyl-selenourea (160594-75-2) → N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h;	100%

bis(trichloromethyl) carbonate (32315-10-9) + dibutylamine (111-92-2) → N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
In water at 0 - 5℃; for 2h; Temperature;	92.4%

dibutylamine (111-92-2) + carbonic acid dimethyl ester (616-38-6) → N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
With sodium methylate In methanol at 30 - 60℃; for 5h; Temperature; Solvent; Reagent/catalyst; Reflux;	90.9%

phosgene (75-44-5) + dibutylamine (111-92-2) → N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
With sodium hydroxide In H20 at 75 - 85℃; for 5.75 - 7h; pH=10 - 11; Product distribution / selectivity;	88%
With potassium carbonate
With potassium carbonate In benzene

carbon dioxide (124-38-9) + dibutylamine (111-92-2) → N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
Stage #1: carbon dioxide; dibutylamine In dimethyl sulfoxide at 20℃; Stage #2: dibutylamine With triphenylphosphine; diethylazodicarboxylate In dimethyl sulfoxide at 20℃; for 3h; chemoselective reaction;	84%
With potassium hydroxide at 149.84℃; under 60006 Torr; for 10h; Autoclave;	36.7%
Stage #1: carbon dioxide; dibutylamine With 1,8-dimethylaminonaphthalene In tetrahydrofuran at 20℃; under 750.075 Torr; for 1h; Stage #2: dibutylamine In tetrahydrofuran; tetrachloromethane at 60℃; for 23h; Further stages.;	99 % Spectr.

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate + diethylamine (109-89-7) → N,N-diethyl-1,1,1-trifluoromethanesulfonamide (357-39-1) + N,N,N',N'-Tetrabutylurea (4559-86-8) + diethylammonium trifluoromethanesulfonate (60933-18-8)

Conditions	Yield
In chloroform at 4℃; for 72h;	A 55% B 74% C n/a

carbon monoxide (201230-82-2) + dibutylamine (111-92-2) → N,N,N',N'-Tetrabutylurea (4559-86-8) + N,N,N',N'-Tetrabutyl-2-oxo-malonamide (132279-00-6) + N,N-dibutylglyoxylamide hemihydrate (83862-73-1)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

N-phenylacetoacetamide (102-01-2) + dibutylamine (111-92-2) → N,N,N',N'-Tetrabutylurea (4559-86-8) + 1,1'-dibutyl-3-phenylurea (2589-21-1)

Conditions	Yield
With zeolite HSZ-360 at 180℃; for 3h; Condensation;

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate + diisopropylamine (108-18-9) → C7H14F3NO2S + N,N,N',N'-Tetrabutylurea (4559-86-8) + diisopropylammonium trifluoromethanesulfonate (77534-66-8)

Conditions	Yield
In chloroform at 4℃; for 72h;

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate + dibutylamine (111-92-2) → C9H18F3NO2S + dibutylammonium trifluoromethanesulfonate + N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
In chloroform at 4℃; for 72h;

dibutylamine (111-92-2) + 2-bromo-1-<7-chloro-naphthyl-(1)>-ethanol-(1) → N,N,N',N'-Tetrabutylurea (4559-86-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 22 percent / Se, NaH, HMPA / 0.5 h / 80 °C 2: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 0 °C View Scheme

N,N,N',N'-Tetrabutylurea (4559-86-8) + trifluoromethylsulfonic anhydride (358-23-6) → bis(tetrabutylamidinio) ether bis(trifluoromethanesulfonate)

Conditions	Yield
In dichloromethane for 12h; Heating;	84%

N,N,N',N'-Tetrabutylurea (4559-86-8) → N-butyl-N-(chloro(dibutylamino)methylene)butan-1-aminium chloride (81363-13-5)

Conditions	Yield
With COCl2 at 80℃; for 2h;	83%
With phosgene In acetonitrile 1.) 6 h, -5 deg C, 2.) 24 h, room temp.;
With phosgene In acetonitrile 1) 6 h, -5 deg C, 2) 24 h, room temperature;
With oxalyl dichloride In dichloromethane at 60℃; for 18h; Inert atmosphere;
With oxalyl dichloride In toluene at 60℃; for 20h; Inert atmosphere; Cooling with ice;

N,N,N',N'-Tetrabutylurea (4559-86-8) + trifluoromethylsulfonic anhydride (358-23-6) → O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

Conditions	Yield
In chloroform at 0℃;

N,N,N',N'-Tetrabutylurea (4559-86-8) → 1,1,2,2-Tetrabutyl-3,3-dipropylguanidiniumchlorid (89609-85-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1) 6 h, -5 deg C, 2) 24 h, room temperature 2: 83 percent / triethylamine / 1 h / Ambient temperature View Scheme

N,N,N',N'-Tetrabutylurea (4559-86-8) → 1,1-Dially-2,2,3,3-tetrabutylguanidiniumchlorid (89609-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1) 6 h, -5 deg C, 2) 24 h, room temperature 2: 82 percent / triethylamine / 1 h / Ambient temperature View Scheme

N,N,N',N'-Tetrabutylurea (4559-86-8) → 1-pyrrolidiniumchlorid

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1) 6 h, -5 deg C, 2) 24 h, room temperature 2: 85 percent / triethylamine / 1 h / Ambient temperature View Scheme

N,N,N',N'-Tetrabutylurea (4559-86-8) → 1-piperidiniumchlorid

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1) 6 h, -5 deg C, 2) 24 h, room temperature 2: 82 percent / triethylamine / 1 h / Ambient temperature View Scheme

N,N,N',N'-Tetrabutylurea (4559-86-8) → 1-morpholiniumchlorid

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1) 6 h, -5 deg C, 2) 24 h, room temperature 2: 87 percent / triethylamine / 1 h / Ambient temperature View Scheme

N,N,N',N'-Tetrabutylurea (4559-86-8) → 1,1,2,2,3,3-Hexabutylguanidiniumchlorid (89450-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1) 6 h, -5 deg C, 2) 24 h, room temperature 2: 88 percent / triethylamine / 1 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: phosgene / acetonitrile / 1.) 6 h, -5 deg C, 2.) 24 h, room temp. 2: triethylamine / acetonitrile / 1 h / Ambient temperature View Scheme

Upstream product

• 75-44-5 phosgene 
• 111-92-2 dibutylamine 
• 13358-73-1 N,N-dibutylcarbamoyl chloride 
• 650-51-1 sodium trichloroacetate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 616-38-6 carbonic acid dimethyl ester 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 109-89-7 diethylamine 
• 108-18-9 diisopropylamine 
• 124-38-9 carbon dioxide 
• 102-01-2 N-phenylacetoacetamide 
• 160594-75-2 Tetrabutyl-selenourea 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 128838-18-6 4-Phenyl-1,1,3,3-tetrabutylguanidine 
• 114591-53-6 1,1,3,3,4-Pentabutylguanidine 

Relevant articles and documents

Method for preparing tetrabutylurea by oil-water two-phase reaction system

The invention discloses a method for preparing tetrabutylurea by using an oil-water two-phase reaction system, which is characterized in that bis (trichloromethyl) carbonate and dibutylamine are used as raw materials, the oil-water two-phase reaction system is designed and provided, a solvent capable of effectively dissolving bis (trichloromethyl) carbonate and dibutylamine is adopted, meanwhile, a water phase is added into the reaction system to perform liquid seal on the reaction system, can absorb hydrogen chloride gas generated by the reaction at the same time, and promotes the forward proceeding of the whole reaction, and the method has the characteristics of high conversion rate, high selectivity and the like. The method for preparing tetrabutylurea by using the oil-water two-phase reaction system comprises the following steps: dissolving bis (trichloromethyl) carbonate in an organic solvent, placing the solution in a reactor, and simultaneously adding water into the reactor to perform liquid seal on the reaction system; and dissolving dibutylamine in an organic solvent, slowly injecting the dibutylamine into the organic solution of bis (trichloromethyl) carbonate through a micro-injection pump, carrying out chemical reaction, and carrying out refining treatment to obtain the product tetrabutylurea.

Synthesis method of tetrabutylurea

The invention provides a synthesis method of tetrabutylurea. The synthesis method comprises the following steps: dissolving an organic strong base catalyst and dimethyl carbonate into a solvent; raising temperature to 30 DEG C to 50 DEG C to obtain mixed liquid; dropwise adding dibutylamine into the mixed liquid at 50 DEG C to 80 DEG C; after dropwise adding, heating to reflux and keeping the heat and reacting for 5h to 8h to obtain reaction liquid; rectifying the reaction liquid under normal pressure to obtain condensed liquid containing the solvent and residual liquid; decompressing and rectifying the residual liquid to obtain a tetrabutylurea product and residues. According to the synthesis method of the tetrabutylurea, provided by the invention, a toxic raw material, namely phosgene, is not used and hydrogen chloride gas is not generated, so that equipment is not corroded and requirements on the equipment are relatively low; meanwhile, three wastes are avoided; the mass content of the tetrabutylurea in an obtained tetrabutylurea product is 99 percent or more and the yield is 75 percent or more.

Palladium-Catalyzed Oxidative N-Dealkylation/Carbonylation of Tertiary Amines with Alkynes to α,β-Alkynylamides

The first highly effective Pd/C-catalyzed oxidative N-dealkylation/carbonylation of various aliphatic as well as cyclic tertiary amines with alkynes has been described. The selective sp3 C-N bond activation of tertiary amines at the less steric side using O2 as a sole oxidant and a plausible reaction pathway for the reaction are discussed. The general and operationally simple methodology provides an alternative for the synthesis of a wide range of alk-2-ynamide derivatives under mild conditions. The present protocol is ecofriendly and practical, and it shows significant recyclability.