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471623

Sigma-Aldrich

1,1,1-Trimethylhydrazinium iodide

97%

Synonym(s):

1,1,1-Trimethylhydrazine iodide, N,N,N-Trimethylhydrazinium iodide, Trimethylhydrazonium iodide (6CI)

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About This Item

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

Assay

97%

mp

225-230 °C (dec.) (lit.)

functional group

amine

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

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR3795
MKCP2855
MKCL3925
MKCK2753
MKCG1339

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Vladimir V Rozhkov et al.
The Journal of organic chemistry, 68(6), 2498-2501 (2003-03-15)
The amination of 1-X-3,5-dinitrobenzenes via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK or NaOMe in DMSO was studied. It was observed (when X = OMe, OCH(2)CF(3), OCH(2)CF(2)CF(2)H, OPh) that the amination
Carles Miró Sabaté et al.
Chemistry, an Asian journal, 7(9), 2080-2089 (2012-06-29)
1,1,1-Trimethylhydrazinium iodide ([(CH(3))(3)N-NH(2)]I, 1) was reacted with a silver salt to form the corresponding nitrate ([(CH(3))(3)N-NH(2)][NO(3)], 2), perchlorate ([(CH(3))(3)N-NH(2)][ClO(4)], 3), azide ([(CH(3))(3)N-NH(2)][N(3)], 4), 5-amino-1H-tetrazolate ([(CH(3))(3)N-NH(2)][H(2)N-CN(4)], 5), and sulfate ([(CH(3))(3)N-NH(2)](2)[SO(4)]·2H(2)O, 6·2H(2)O) salts. The metathesis reaction of compound 6·2H(2)O with barium salts

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