3288-80-0

Basic information

• Product Name: 1,1,1-TRIMETHYLHYDRAZINIUM IODIDE
• Synonyms: 1,1,1-TRIMETHYLHYDRAZINIUM IODIDE;1,1,1-TRIMETHYLHYDRAZONIUM IODIDE;1,1,1-trimethyl-hydraziniuiodide;1,1,1-trimethyl-hydrazoniuiodide;1,1,1-triMethylhydrazin-1-iuM iodide;1,1,1-TriMethylhydraziniuM iodide 97%;Mildronate Impurity 1;amino(trimethyl)azanium:iodide
• CAS NO: 3288-80-0
• Molecular Formula: C₃H₁₁N₂*I
• Molecular Weight: 202.04
• Product Categories: Hydrazines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 3288-80-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 225-230 °C (dec.)(lit.)
• Appearance: /
• CAS DataBase Reference: 1,1,1-TRIMETHYLHYDRAZINIUM IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-TRIMETHYLHYDRAZINIUM IODIDE(3288-80-0)
• EPA Substance Registry System: 1,1,1-TRIMETHYLHYDRAZINIUM IODIDE(3288-80-0)

Safety Data

• Hazard Codes: T
• Statements: 61-36/37/38
• Safety Statements: 53-36/37/39-45
• WGK Germany: 3
• RTECS: MW0349100
• Hazardous Substances Data: 3288-80-0(Hazardous Substances Data)

Usage

Uses

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

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).

InChI:InChI=1/C3H11N2/c1-5(2,3)4/h4H2,1-3H3/q+1

Upstream product

• 57-14-7 N,N-Dimethylhydrazine 
• 74-88-4 methyl iodide 
• 75-50-3 trimethylamine 

Downstream Products

• 75-58-1 tertamethylammonium iodide 
• 472999-07-8 1-methyl-2-para-methoxyphenyl-4-isobutylsulphonyl-6-nitro-7-aminoindole 
• 960590-24-3 [5-(3-amino-5-chloro-4-nitrophenyl)-10,15,20-tris(3-chlorophenyl)-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]copper 
• 960590-26-5 [5-(3-amino-4-nitrophenyl)-10-(4-nitrophenyl)-15,20-diphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]copper 
• 960590-29-8 [5,10-bis(3-amino-4-nitrophenyl)-15,20-diphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]copper 
• 960590-25-4 [5-(3-amino-4-nitrophenyl)-10-(4-nitrophenyl)-15,20-diphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc 
• 960590-27-6 [5,10-bis(3-amino-4-nitrophenyl)-15,20-diphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc 
• 960590-34-5 [5-[4-amino-3-(tert-butoxy)phenyl]-10-(4-nitrophenyl)-15,20-diphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc 
• 960590-22-1 [5-(3-amino-4-nitrophenyl)-10,15,20-triphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]nickel 
• 960590-21-0 [5-(3-amino-4-nitrophenyl)-10,15,20-triphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]copper 
• 960590-20-9 [5-(3-amino-4-nitrophenyl)-10,15,20-triphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc 
• 960590-31-2 [5-[4-amino-3-(tert-butoxy)phenyl]-10,15,20-triphenyl-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc 
• 627531-37-7 3-Amino-2-hydroxy-4-nitro-benzonitrile 

Relevant articles and documents

1,1-Dimethyl-1-(trialkoxysilylmethyl)hydrazinium and 1,1-dimethyl-1-(silatranylmethyl)hydrazinium Halides

Formerly unknown 1,1-dimethyl-1-(trialkoxysilylmethyl)- and 1,1-dimethyl-1-(silatranylmethyl)hydrazinium halides were prepared by reaction of 1,1-dimethylhydrazine with (halomethyl)trialkoxysilanes XCH 2Si(OR)3 (X = Cl, I; R=Me, Et) and 1-(halomethyl)silatranes XCH2Si(OCH2CH2) 3N (X = Cl, Br). 1,1-Dimethyl-1-(silatranylmethyl)hydrazinium chloride and iodide were also obtained by transetherification of corresponding 1,1-dimethyl-1-(trimethoxysilylmethyl)hydrazinium halides with tris(2-hydroxyethyl)amine.

Hypergolic N,N,-Dimethylhydraznium ionic liquids

N,N-Dimethylhydrazinium dicyanamide and nitrocyanamide ionic liquids (ILs) were prepared by quaterization of N,N-dimethylhydrazine with alkyl halides followed by metathesis reactions with silver dicyanamide or silver nitrocyanamide. The key physicochemical properties, such as melting point and decomposition temperatures, density, viscosity, heat of formation, detonation pressure and velocity, and specific impulse were measured/calculated. The impact of anions and alkyl substituted cations on these properties is demonstrated. Droplet tests with white-fuming nitric acid (WFNA) as an oxidizer were utilized to show that the 14 new N,N-dimethylhydrazinium salts are hypergolic with ignition delay (ID) times ranging from 22 to 1642 ms, thereby suggesting that some may have potential as bipropellants.

(Butylsulfanyl)ethanal and 3-(organylsulfanyl)butanal 1,1-dimethylhydrazones

Previously unknown (butylsulfanyl)ethanal and 3-(organylsulfanyl)butanal 1,1-dimethylhydrazones were synthesized. Their reactivity toward methyl iodide was studied.