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471623 Sigma-Aldrich

1,1,1-Trimethylhydrazinium iodide

97%

  • CAS Number 3288-80-0

  • Linear Formula H2NN(CH3)3I

  • Molecular Weight 202.04

  •  MDL number MFCD00464984

  •  PubChem Substance ID 24870749

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Hydrazines, Nitrogen Compounds - Organic Building Blocks, Organic Building Blocks More...
Quality Level   100
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.

Packaging

50 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
MW0349100
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles
Peer-Reviewed Papers
15

References

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