| Identification | More | [Name]
Tetrabutylammonium iodide | [CAS]
311-28-4 | [Synonyms]
TBAI
TETRABUTYLAMMONIUM IODIDE
TETRA-N-BUTYLAMMONIUM IODIDE
1-Butanaminium,N,N,N-tributyl-,iodide
n,n,n-tributyl-1-butanaminiuiodide
n,n,n-tributyl-1-butanaminiumiodide
tetrabutyl-ammoniuiodide
tetra-n-butylammoniumjodid
Tetrabutylammonium Iodid
TETRABUTYLAMMONIUM IODIDE, FOR IPC
TETRABUTYLAMMONIUM IODIDE, ELECTRO-CHEMI CAL GRADE
TetraN-ButylammoniumIodideA.R.
TetrabutylAmmoniumIodideGr
TETRABUTYLAMMONIUM IODIDE REAGENT
TETRABUTYLAMMONIUM IODIDE extrapure AR
Tetrabutylazanium iodide
Tetrabutylammonium iodide ,99%
Tetrabutylaminium·iodide | [EINECS(EC#)]
206-220-5 | [Molecular Formula]
C16H36IN | [MDL Number]
MFCD00011636 | [Molecular Weight]
369.37 | [MOL File]
311-28-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white or tan powder | [Melting point ]
141-143 °C(lit.)
| [Boiling point ]
145.3℃[at 101 325 Pa] | [density ]
1.20 | [vapor pressure ]
0Pa at 25℃ | [storage temp. ]
Store below +30°C. | [solubility ]
acetonitrile: 0.1 g/mL, clear, colorless
| [form ]
Crystalline Powder | [color ]
White to cream | [Odor]
Amine like | [Stability:]
Stable. Incompatible with strong oxidizing agents. Light-sensitive. | [Water Solubility ]
Soluble in water and methanol. Insoluble in benzene. | [Sensitive ]
Light Sensitive & Hygroscopic | [λmax]
λ: 290 nm Amax: 0.1
λ: 300 nm Amax: 0.05
λ: 320 nm Amax: 0.02
λ: 500 nm Amax: 0.02 | [Detection Methods]
T,NMR,TITR | [BRN ]
3916152 | [Exposure limits]
ACGIH: TWA 0.01 ppm | [InChIKey]
DPKBAXPHAYBPRL-UHFFFAOYSA-M | [LogP]
0.869 at 25℃ | [CAS DataBase Reference]
311-28-4(CAS DataBase Reference) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
311-28-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
BS5450000
| [F ]
8 | [TSCA ]
Yes | [HS Code ]
29239000 | [Toxicity]
LD50 orally in Rabbit: 1990 mg/kg |
| Hazard Information | Back Directory | [Description]
Tetrabutylammonium iodide is a organic ammonium compound, for which all four valences of a nitrogen atom are bonded organically. It is often used as phase-transfer catalysts and ion pair reagents. | [Chemical Properties]
white or tan powder | [Uses]
Tetrabutylammonium iodide is used in the preparation of novel quaternary amines to serve as antibacterial agents in the rise of drug-resistant bacteria,it is also used in phosphonium reversible inhibitors of cholinesterases.
| [Application]
Tetrabutylammonium iodide may be used as a mobile phase additive in ion-pair high-performance liquid chromatography (IP-HPLC) assay of 4-aminopyridine in serum. It may also be used as a mobile phase additive in the analysis of tetracycline by reversed-phase IPC. The addition of tetrabutylammonium iodide regulates the retention of tetracyclines.
Tetrabutylammonium iodide can be used:
As an additive in the synthesis of fused triazole derivatives using palladium catalyst.
To prepare allyl-PEG-allyl, which is a key intermediate polymer used to synthesize fluorinated amphiphilic copolymers.
As a catalyst used in the synthesis of ethers. | [Reactions]
Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:
Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.
Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.
Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.
Other reactions where TBAI can be used as a catalyst:
TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.
Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.
Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate. | [General Description]
Tetrabutylammonium iodide is a quaternary ammonium salt used in phase-transfer reactions. It is also used in regioselective ether cleavage reactions and as a source of iodide for nucleophilic displacement reactions. | [Flammability and Explosibility]
Notclassified | [Purification Methods]
Crystallise the iodide from toluene/pet ether (see entry for the corresponding bromide), acetone, ethyl acetate, EtOH/diethyl ether, nitromethane, aqueous EtOH or water. Dry it at room temperature under a vacuum. It has also been dissolved in MeOH/acetone (1:3, 10mL/g), filtered and allowed to stand at room temperature to evaporate to ca half its original volume. Distilled water (1mL/g) is then added, and the precipitate is filtered off and dried. It can also be dissolved in acetone, precipitated by adding ether and dried in a vacuum at 90o for 2 days. It has also been recrystallised from CH2Cl2/pet ether or hexane, or anhydrous methanol and stored in a vacuum desiccator over H2SO4. [Chau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 558.] |
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