Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A10249 Tetra-n-butylammonium bromide, 98+%

CAS Number
1643-19-2
Synonyms
TBAB
Aliquat 100

Stock No. Size Price ($) Quantity Availability
A10249-22 100g 45.40
A10249-36 500g 133.00
A10249-0E 2500g 533.00
Add to Cart Bulk/Specialty Print Quote View Item

Tetra-n-butylammonium bromide, 98+%

MDL
MFCD00011633
EINECS
216-699-2

Chemical Properties

Formula
C16H36BrN
Formula Weight
322.38
Melting point
101-105°
Density
1.15
Storage & Sensitivity
Hygroscopic. Store under Argon. Ambient temperatures.
Solubility
Soluble in water and ethanol.

Applications

Phase transfer catalyst Tetra-n-butylammonium bromide is used as a phase transfer catalyst for the preparation of lactones by cyclization of potassium salt of µ-bromocarboxylic acids and beta-lactones from beta-bromoacid by cyclization. It is also involved in the Curtius rearrangement, N-alkylation of aromatic carboxamides. It plays an important role as an ionic liquid in the regioselective O-alkylation reactions. It is also used in the preparation of polymer solar cells and single component green-light emitting electrochemical cells.

Notes

Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literature References

Phase-transfer catalyst of wide application. Some illustrative examples are given below. See also Appendix 2.

K salts of ω-bromocarboxylic acids can be cyclized to lactones under effectively "high-dilution" conditions by extracting into toluene in the presence of a small amount of catalyst. The 16-membered ring lactone was formed in 92% yield: J. Org. Chem., 48, 1533 (1983).

Primary alkyl chlorides can be converted to alcohols in excellent yield by phase-transfer reaction with sodium formate and hydrolysis of the resulting formate esters: Synthesis, 763 (1986).

ß-Lactones are formed by the cyclization of ß-bromoacids under phase-transfer conditions: Chem. Pharm. Bull., 29, 1063 (1981).

An improved procedure for the Curtius rearrangement involves reaction of acid chlorides with azide ion under phase-transfer conditions: Synthesis, 38 (1983).

Aromatic carboxamides undergo N-alkylation with alkyl halides using KOH under solvent-free conditions: Synth. Commun., 22, 1661 (1992).

Has been used as an "ionic liquid" in the regioselective O-alkylation of ambident nucleophiles: Tetrahedron Lett., 33, 4435 (1992). A method is described whereby the "solvent" can be recovered quantitatively. A semi-molten mixture with KF or CsF has been found to be an effective system for fluorodehalogenation of, e.g., benzyl bromide: J. Fluorine Chem., 73, 185 (1995).

Effective catalyst for amination reactions of alkyl or activated aryl halides, by increasing the solubility of ammonia in organic media: J. Chem. Soc., Chem. Commun., 267 (1987).

Tzirakis, F.; Stringari, P.; Von Solms, N.; Coquelet, C.; Kontogeorgis, G. Hydrate equilibrium data for the CO2+ N2 system with the use of Tetra-n-butylammonium bromide (TBAB), cyclopentane (CP) and their mixture. Fluid Phase Equilib. 2015, 408, 240-247.

Akiba, H.; Ueno, H.; Ohmura, R. Crystal Growth of Ionic Semiclathrate Hydrate Formed at the Interface between CO2 Gas and Tetra-n-butylammonium Bromide Aqueous Solution. Cryst. Growth Des. 2015, 15 (8), 3963-3968.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3570983
Harmonized Tariff Code
2923.90
TSCA
Yes

Recommended

  • A10221

    Imidazole, 99%
  • A11766

    Allyl bromide, 99%, stab. with 300-1000ppm Propylene oxide
  • A13268

    Benzyltriethylammonium chloride, 99%
  • A15484

    Tetra-n-butylammonium iodide, 98%
  • 33337

    Magnesium sulfate, anhydrous, 99.5% min

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware