tetrabutylazanium iodide

• ChemBase ID: 74452
• Molecular Formular: C16H36IN
• Molecular Mass: 369.36821
• Monoisotopic Mass: 369.18924816
• SMILES: [N+](CCCC)(CCCC)(CCCC)CCCC.[I-]
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[I-]
• InChI: InChI=1S/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
• InChIKey: DPKBAXPHAYBPRL-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabutylazanium iodide
• IUPAC Traditional name: tetrabutylammonium ion iodide; tetrabutylammonium iodide
• Synonyms: Tetrabutylammonium iodide; TETRA-N-BUTYLAMMONIUM HYDROXIDE, 25% AQUEOUS SOLUTION; Tetra-n-butylammonium iodide; TBAI; Tetra(but-1-yl)ammonium iodide; TETRABUTYLAMMONIUM IODIDE; 四丁基碘化铵; 四正丁基碘化铵

Database IDs

• CAS Number: 311-28-4; 2052-49-5
• EC Number: 206-220-5
• MDL Number: MFCD00011636
• Beilstein Number: 3916152
• PubChem SID: 24848477; 162039371; 24888817; 24888809; 24888824
• PubChem CID: 67553

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.3234289
• LogD (pH = 7.4): 1.3234289
• Log P: 1.3234289
• Molar Refractivity: 91.3961 cm^3
• Polarizability: 31.734425 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble0.1 g/mL, clear, colorless
• Melting Point: 141-143 °C(lit.); 141-150°C; 142-148°C; 143-147 °C; 144-146 °C; 145-148°C
• Absorption Wavelength: λ: 290 nm Amax: 0.1; λ: 300 nm Amax: 0.05; λ: 320 nm Amax: 0.02; λ: 500 nm Amax: 0.02

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Protect from light
• Storage Warning: Harmful/Irritant/Light Sensitive/Hygroscopic; Light Sensitive & Hygroscopic
• RTECS: BS5450000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; R:22
• Safety Statements: 26-36; 26-36/37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); ≥99%; ≥99.0%; ≥99.0% (AT); 98%
• Grade: for electrochemical analysis; for ion pair chromatography; purum; reagent grade
• Suitability: corresponds to standard for filter test
• λ: 10 % in acetonitrile
• Linear Formula: (CH3CH2CH2CH2)4N(I)

DETAILS

MP Biomedicals - 02156768

Crystalline

MP Biomedicals - 05219216

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 140775

Packaging
25, 100, 500 g in glass bottle

Sigma Aldrich - 86890

Other Notes
Catalyst used in the synthesis of ethers1,2
Packaging
25, 100, 500 g in poly bottle

Sigma Aldrich - 86912

General description
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REFERENCES

• Catalyst for the high-yield methylation of alcohols with dimethyl sulfate: Angew. Chem., 85, 868; Angew. Chem. Int. Ed., 12, 846 (1973), or the benzylation of alcohols with benzyl bromide in organic solvents: Org. Synth. Coll., 8, 34 (1993); 9, 52 (1998).
• Useful source of I^- for nucleophilic displacements, e.g. in the formation of neopentyl iodides from the triflates: J. Org. Chem., 45, 4387 (1980).
• Aliphatic and aromatic sulfonic acids are reduced to thiols in the presence of trifluoroacetic anhydride, followed by hydrolysis of the resulting trifluoroacetates: Tetrahedron Lett., 21, 1235 (1980).
• In combination with Boron trifluoride diethyl etherate, A15275, has been used in a mild, versatile cleavage of ethers: Synthesis, 274 (1985).