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Tetrabutylammonium iodide

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Name

Tetrabutylammonium iodide

EINECS 206-220-5
CAS No. 311-28-4 Density 1.20 g/mL at 25 °C
PSA 0.00000 LogP 2.00760
Solubility acetonitrile: 0.1 g/mL, clear, colorless Melting Point 141-143 °C(lit.)
Formula C16H36IN Boiling Point 145.3℃[at 101 325 Pa]
Molecular Weight 369.373 Flash Point 100oC
Transport Information N/A Appearance white or tan powder
Safety 26-36-37/39 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 311-28-4 (Tetrabutylammonium iodide) Hazard Symbols HarmfulXn
Synonyms

1-Butanaminium,N,N,N-tributyl-, iodide (9CI);Ammonium, tetrabutyl-, iodide (8CI);N,N,N-Tributyl-1-butanaminium iodide;

Article Data 24

Tetrabutylammonium iodide Synthetic route

102-82-9

tributyl-amine

6214-23-9

methyl (2Z)-3-iodoprop-2-enoate

A

311-28-4

tetra-(n-butyl)ammonium iodide

B

methyl (E)-3-(N,N-dibutylamino)-2-propenoate

Conditions
ConditionsYield
In toluene Heating;A 96%
B 94%

{PdCl[Ind(Ph2P=S)2]}(nBu4N)

74-88-4

methyl iodide

A

74-87-3

methylene chloride

{PdI[Ind(Me)(Ph2P=S)2]}

C

311-28-4

tetra-(n-butyl)ammonium iodide

Conditions
ConditionsYield
In dichloromethane at 40℃; for 24h; Inert atmosphere;A n/a
B 95%
C n/a
542-69-8

1-iodo-butane

102-82-9

tributyl-amine

311-28-4

tetra-(n-butyl)ammonium iodide

Conditions
ConditionsYield
With butanone
at 170℃;
at 100 - 110℃;
In ethyl acetate
542-69-8

1-iodo-butane

111-92-2

dibutylamine

311-28-4

tetra-(n-butyl)ammonium iodide

Conditions
ConditionsYield
at 100 - 110℃;
102-82-9

tributyl-amine

111-92-2

dibutylamine

109-73-9

N-butylamine

311-28-4

tetra-(n-butyl)ammonium iodide

Conditions
ConditionsYield
With ethanol at 110℃; Edukt 4: Butyljodid;
108-85-0

1-bromocyclohexane

90826-86-1

Tetra-n-butylammonium-phenylcyanphosphid

A

311-28-4

tetra-(n-butyl)ammonium iodide

B

90826-93-0

C13H16NP

Conditions
ConditionsYield
In tetrahydrofuran
74-96-4

ethyl bromide

90826-86-1

Tetra-n-butylammonium-phenylcyanphosphid

A

74626-63-4

ethylphenylphosphinous cyanide

B

311-28-4

tetra-(n-butyl)ammonium iodide

Conditions
ConditionsYield
In tetrahydrofuran
75-09-2

dichloromethane

90826-86-1

Tetra-n-butylammonium-phenylcyanphosphid

A

311-28-4

tetra-(n-butyl)ammonium iodide

B

90826-97-4

C8H7ClNP

Conditions
ConditionsYield
In tetrahydrofuran
109-69-3

n-Butyl chloride

90826-86-1

Tetra-n-butylammonium-phenylcyanphosphid

A

311-28-4

tetra-(n-butyl)ammonium iodide

B

90826-92-9

C11H14NP

Conditions
ConditionsYield
In tetrahydrofuran
1923-70-2

tetrabutylammonium perchlorate

4636-73-1

triethylammonium iodide

A

311-28-4

tetra-(n-butyl)ammonium iodide

B

14999-75-8

Triethylammonium perchlorate

Conditions
ConditionsYield
In chloroform at 25℃; Equilibrium constant;

Tetrabutylammonium iodide Specification

The IUPAC name of Tetrabutylammonium iodide is tetrabutylazanium iodide. With the CAS registry number 311-28-4, it is also named as N,N,N-Tributyl-1-butanaminium iodide. The product's categories are Quarternary Ammonium Salts; Ammonium Iodides (Quaternary); Quaternary Ammonium Compounds. Besides, it is white or tan powder, which should be stored in sealed, dry and dark place. It is stable and incompatible with strong oxidizing agents. In addition, its molecular formula is C16H36IN and molecular weight is 369.37.

The other characteristics of this product can be summarized as: (1)EINECS: 206-220-5; (2)H-Bond Donor: 0; (3)H-Bond Acceptor: 1; (4)Rotatable Bond Count: 12; (5)Exact Mass: 369.189243; (6)MonoIsotopic Mass: 369.189243; (7)Topological Polar Surface Area: 0; (8)Heavy Atom Count: 18; (9)Complexity: 116; (10)Density: 1.20 g/mL at 25 °C; (11)Melting point: 141-150 °C; (12)Solubility: Acetonitrile: 0.1 g/mL.

Preparation of Tetrabutylammonium iodide: this chemical can be prepared by the reaction of Tributylamine with (Z)-3-Iodpropensaeure-methylester.



This reaction needs Toluene by heating. The yield is 94 %.

Uses of Tetrabutylammonium iodide: this chemical is ued as phase transfer catalyst, and reagent for polarographic analysis. Similarly, it can react with Diacetoxy-phenyl-l3-iodane to get Tetrabutylammonium diacetoxyiodate(I).



This reaction needs CHCl3. The yield is 85 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. It is also harmful if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: [I-].CCCC[N+](CCCC)(CCCC)CCCC
(2)InChI: InChI=1/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
(3)InChIKey: DPKBAXPHAYBPRL-REWHXWOFAZ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo oral 1600mg/kg (1600mg/kg)   Journal of Pharmaceutical Sciences. Vol. 69, Pg. 327, 1980.
rat LD50 oral 1990mg/kg (1990mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 489, 1986.

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