471623

1,1,1-Trimethylhydrazinium iodide

97%

• Synonym(s): 1,1,1-Trimethylhydrazine iodide, N,N,N-Trimethylhydrazinium iodide, Trimethylhydrazonium iodide (6CI)
• Linear Formula: H₂NN(CH₃)₃I
• CAS Number: 3288-80-0
• Molecular Weight: 202.04
• MDL number: MFCD00464984
• UNSPSC Code: 12352100
• PubChem Substance ID: 24870749
• NACRES: NA.22

Properties

• Assay: 97%
• mp: 225-230 °C (dec.) (lit.)
• SMILES string: [I-].C[N+](C)(C)N
• InChI: 1S/C3H11N2.HI/c1-5(2,3)4;/h4H2,1-3H3;1H/q+1;/p-1
• InChI key: HLNPDVKKRBWQAA-UHFFFAOYSA-M

Description

General description

1,1,1-Trimethylhydrazinium iodide ([(CH₃)₃N-NH₂]I, TMHI) is widely employed as a vicarious nucleophilic substitution (VNS) reagent for various aromatic amination reactions. On reaction with silver salt, it affords the following salts: nitrate (([(CH₃)₃N-NH₂][NO₃]), perchlorate ([(CH₃)₃N-NH₂][ClO₄]), azide ([(CH₃)₃N-NH₂][N₃]), 5-amino-1H-tetrazolate ([(CH₃)₃N-NH₂][H₂N-CN₄]) and sulfate ([(CH₃)₃N-NH₂]₂[SO₄].2H₂O).

Application

1,1,1-Trimethylhydrazinium iodide (TMHI) may be employed for the amination of 1-X-3,5-dinitrobenzenes.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H315,H319,H335,H360
• Precautionary Statements: P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves