benzyltrimethylazanium; dichloroiodanuide

• ChemBase ID: 151247
• Molecular Formular: C10H16Cl2IN
• Molecular Mass: 348.05121
• Monoisotopic Mass: 346.97045288
• SMILES: C[N+](C)(C)Cc1ccccc1.Cl[I-]Cl
• Canonical SMILES: C[N+](Cc1ccccc1)(C)C.Cl[I-]Cl
• InChI: InChI=1S/C10H16N.Cl2I/c1-11(2,3)9-10-7-5-4-6-8-10;1-3-2/h4-8H,9H2,1-3H3;/q+1;-1
• InChIKey: PPDJNZTUDFPAHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyltrimethylazanium; dichloroiodanuide
• IUPAC Traditional name: benzyltrimethylazanium; dichloroiodanuide
• Synonyms: BTMA-ICl2; Benzyltrimethylammonium dichloroiodide; Benzyltrimethylammonium dichloroiodate; Benzyltrimethylammonium dichloroiodate; 苄基三甲基二氯碘化铵; 苄基三甲基二氯碘酸铵

Database IDs

• CAS Number: 114971-52-7
• MDL Number: MFCD00075259
• Beilstein Number: 4611949
• PubChem SID: 162245403; 24848435; 24861152
• PubChem CID: 2724680

CALCULATED PROPERTIES

• Acid pKa: 18.822325
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -2.247694
• LogD (pH = 7.4): -2.247694
• Log P: -2.247694
• Molar Refractivity: 60.5143 cm^3
• Polarizability: 19.203337 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 124-126 °C; 124-126 °C(lit.); ca. 125°C

Safety Information

• Storage Warning: Light Sensitive & Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (RT); 95%; 95+%; 97%
• Grade: purum
• Linear Formula: C6H5CH2N(ICl2)(CH3)3

DETAILS

Sigma Aldrich - 343366

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 13983

Other Notes
Reagent for the selective iodination of aromatic alcohols, ethers and amines1,2; α-Chlorination of carbonyl compounds3

REFERENCES

• Under mild conditions in the presence of MeOH, iodinates phenols: Chem. Lett., 2109 (1987), or arylamines: Bull. Chem. Soc. Jpn., 61, 597 (1988); J. Med. Chem., 35, 2231 (1992), also trans-chloroiodinates alkenes: Bull Chem. Soc. Jpn., 63, 3033 (1990), and ɑ-chlorinates acetophenones: Synthesis, 545 (1988); 212 (1990). In the presence of ZnCl₂, iodinates aromatic ethers: Chem. Lett., 795 (1988), alkylarenes, acetanilides, or thiophenes: Bull. Chem. Soc. Jpn., 62, 439, 1349 (1989); 64, 2566 (1991), respectively.