Product Name

  • Name

    Tetrabutylurea

  • EINECS 224-929-8
  • CAS No. 4559-86-8
  • Article Data22
  • CAS DataBase
  • Density 0.886 g/cm3
  • Solubility 4.3mg/L at 20℃
  • Melting Point <-50oC
  • Formula C17H36N2O
  • Boiling Point 379.8 °C at 760 mmHg
  • Molecular Weight 284.486
  • Flash Point 132 °C
  • Transport Information
  • Appearance
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 4559-86-8 (Tetrabutylurea)
  • Hazard Symbols
  • Synonyms Urea,1,1,3,3-tetrabutyl- (6CI,7CI);Urea, tetrabutyl- (8CI,9CI);1,1,3,3-Tetrabutylurea;NSC 3892;
  • PSA 23.55000
  • LogP 4.91080

Synthetic route

Tetrabutyl-selenourea
160594-75-2

Tetrabutyl-selenourea

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

dibutylamine
111-92-2

dibutylamine

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
In water at 0 - 5℃; for 2h; Temperature;92.4%
dibutylamine
111-92-2

dibutylamine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
With sodium methylate In methanol at 30 - 60℃; for 5h; Temperature; Solvent; Reagent/catalyst; Reflux;90.9%
phosgene
75-44-5

phosgene

dibutylamine
111-92-2

dibutylamine

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
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

carbon dioxide

dibutylamine
111-92-2

dibutylamine

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
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

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

diethylamine
109-89-7

diethylamine

A

N,N-diethyl-1,1,1-trifluoromethanesulfonamide
357-39-1

N,N-diethyl-1,1,1-trifluoromethanesulfonamide

B

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

C

diethylammonium trifluoromethanesulfonate
60933-18-8

diethylammonium trifluoromethanesulfonate

Conditions
ConditionsYield
In chloroform at 4℃; for 72h;A 55%
B 74%
C n/a
...Expand
carbon monoxide
201230-82-2

carbon monoxide

dibutylamine
111-92-2

dibutylamine

A

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

B

N,N,N',N'-Tetrabutyl-2-oxo-malonamide
132279-00-6

N,N,N',N'-Tetrabutyl-2-oxo-malonamide

C

N,N-dibutylglyoxylamide hemihydrate
83862-73-1

N,N-dibutylglyoxylamide hemihydrate

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
...Expand
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

dibutylamine
111-92-2

dibutylamine

A

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

B

1,1'-dibutyl-3-phenylurea
2589-21-1

1,1'-dibutyl-3-phenylurea

Conditions
ConditionsYield
With zeolite HSZ-360 at 180℃; for 3h; Condensation;
...Expand
O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

diisopropylamine
108-18-9

diisopropylamine

A

C7H14F3NO2S

C7H14F3NO2S

B

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

C

diisopropylammonium trifluoromethanesulfonate
77534-66-8

diisopropylammonium trifluoromethanesulfonate

Conditions
ConditionsYield
In chloroform at 4℃; for 72h;
...Expand
O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

dibutylamine
111-92-2

dibutylamine

A

C9H18F3NO2S

C9H18F3NO2S

B

dibutylammonium trifluoromethanesulfonate

dibutylammonium trifluoromethanesulfonate

C

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
In chloroform at 4℃; for 72h;
...Expand
dibutylamine
111-92-2

dibutylamine

2-bromo-1-<7-chloro-naphthyl-(1)>-ethanol-(1)

2-bromo-1-<7-chloro-naphthyl-(1)>-ethanol-(1)

N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

bis(tetrabutylamidinio) ether bis(trifluoromethanesulfonate)

bis(tetrabutylamidinio) ether bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
In dichloromethane for 12h; Heating;84%
N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

N-butyl-N-(chloro(dibutylamino)methylene)butan-1-aminium chloride
81363-13-5

N-butyl-N-(chloro(dibutylamino)methylene)butan-1-aminium chloride

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

O-trifluoromethanesulfonyl-N,N,N',N'-tetrabutyluronium triflate

Conditions
ConditionsYield
In chloroform at 0℃;
N,N,N',N'-Tetrabutylurea
4559-86-8

N,N,N',N'-Tetrabutylurea

1,1,2,2-Tetrabutyl-3,3-dipropylguanidiniumchlorid
89609-85-8

1,1,2,2-Tetrabutyl-3,3-dipropylguanidiniumchlorid

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

1,1-Dially-2,2,3,3-tetrabutylguanidiniumchlorid
89609-86-9

1,1-Dially-2,2,3,3-tetrabutylguanidiniumchlorid

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

1-pyrrolidiniumchlorid

1-pyrrolidiniumchlorid

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

1-piperidiniumchlorid

1-piperidiniumchlorid

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

1-morpholiniumchlorid

1-morpholiniumchlorid

Conditions
ConditionsYield
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

N,N,N',N'-Tetrabutylurea

1,1,2,2,3,3-Hexabutylguanidiniumchlorid
89450-31-7

1,1,2,2,3,3-Hexabutylguanidiniumchlorid

Conditions
ConditionsYield
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

Tetrabutylurea Specification

The Tetrabutylurea, with the CAS registry number 4559-86-8, is also known as Urea, 1,1,3,3-tetrabutyl-. It belongs to the product category of Phosgene Derivatives. Its EINECS registry number is 224-929-8. This chemical's molecular formula is C17H36N2O and molecular weight is 284.48054. Its IUPAC name is called Tetrabutylurea. This chemical's classification code is Reproductive Effect. When you are using this chemical, please be cautious about it. You should not breathe its dust. What's more, you must avoid contact with skin and eyes. Tetrabutylurea is mainly used as solvents in production of hydrogen peroxide via AQ reaction. It also can be used as the products instead of trioctyl phosphate.

Physical properties of Tetrabutylurea: (1)ACD/LogP: 6.57; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.57; (4)ACD/LogD (pH 7.4): 6.57; (5)ACD/BCF (pH 5.5): 57585.23; (6)ACD/BCF (pH 7.4): 57585.3; (7)ACD/KOC (pH 5.5): 88922.63; (8)ACD/KOC (pH 7.4): 88922.73; (9)#H bond acceptors: 3; (10)#Freely Rotating Bonds: 12; (11)Index of Refraction: 1.462; (12)Molar Refractivity: 88.27 cm3; (13)Molar Volume: 320.7 cm3; (14)Surface Tension: 32.3 dyne/cm; (15)Density: 0.886 g/cm3; (16)Flash Point: 132 °C; (17)Enthalpy of Vaporization: 62.79 kJ/mol; (18)Boiling Point: 379.8 °C at 760 mmHg; (19)Vapour Pressure: 5.7E-06 mmHg at 25°C.

Preparation of Tetrabutylurea: this chemical can be prepared by carbonochloridic acid ethyl ester and Dibutyl-lithiumamid. This reaction will need solvent tetrahydrofuran. The reaction time is 1 day at ambient temperature. The yield is about 30%.

Tetrabutylurea can be prepared by carbonochloridic acid ethyl ester and Dibutyl-lithiumamid

Uses of Tetrabutylurea: it can be used to produce N,N,N'N'-Tetrabutylchloroamidinium chloride at temperature of 80 °C. This reaction will need reagent COCl2 with reaction time of 2 hours. The yield is about 83%.

Tetrabutylurea can be used to produce N,N,N'N'-Tetrabutylchloroamidinium chloride

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCN(CCCC)C(=O)N(CCCC)CCCC
(2)InChI: InChI=1S/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
(3)InChIKey: SNDGLCYYBKJSOT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LCLo inhalation 700mg/m3/4H (700mg/m3)   Food and Chemical Toxicology. Vol. 25, Pg. 173, 1987.
rat LD50 oral 17gm/kg (17000mg/kg)   Food and Chemical Toxicology. Vol. 25, Pg. 173, 1987.

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