306-37-6

Usage

Uses

1,2-Dimethylhydrazine dihydrochloride is used as a potent carcinogen for [application type] in [application reason] as a DNA alkylating agent. It is particularly utilized to induce colon tumors in experimental animals, which aids in the study and understanding of cancer development and progression.
Used in Pharmaceutical Industry:
1,2-Dimethylhydrazine dihydrochloride is used as a reagent for the preparation of spiroisoquinolinedione aldose reductase inhibitors. These inhibitors are essential in the development of drugs targeting various diseases and conditions, including diabetes and its complications.
Used in Research and Development:
In the field of research and development, 1,2-dimethylhydrazine dihydrochloride is used as a tool to study the effects of carcinogens on DNA and cellular processes. This helps scientists understand the mechanisms behind cancer development and design more effective treatments and preventive measures.

Air & Water Reactions

Extremely hygroscopic. Water soluble.

Reactivity Profile

1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE is a reducing agent. Incompatible with oxidizing agents and bases.

Fire Hazard

Flash point data for 1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE are not available; however, 1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE is probably combustible.

Biochem/physiol Actions

Induces colon cancer in rats and mice.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion and subcutaneous routes. Experimental reproductive effects. Mutation data reported. A rocket fuel. When heated to decomposition it emits very toxic fumes of HCl and NOx

InChI:InChI=1/C2H8N2.2ClH/c1-4(2)3;;/h3H2,1-2H3;2*1H

Synthetic route

hydrogenchloride (7647-01-0) + C44H82N6Sc2 → C42H76Cl2N4Sc2 + N,N'-Dimethylhydrazine dihydrochloride (306-37-6)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78 - 20℃; for 1h; Inert atmosphere; Schlenk technique;	A 48% B 89%

2-(allyloxy)benzaldehyde (28752-82-1) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → (3aS,9bR)-1,2-Dimethyl-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-c]pyrazole (108120-71-4)

Conditions	Yield
In ethanol for 3h; Heating;	100%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (3E)-1,1,1-trifluoro-4-methoxy-pent-3-en-2-one (135351-20-1) → 1,2,5-trimethyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	100%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-trichloro-4-methoxypent-3-en-2-one (135351-18-7) → 3-methyl-5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chloride

Conditions	Yield
In toluene at 80℃; for 0.2h; microwave irradiation;	98%
With hydrogenchloride In ethanol for 4h; Heating;	90%

(E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (59938-06-6) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → 1,2-dimethyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	97%

N-Cbz-L-Phe (1161-13-3) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → (S)-benzyl (1-(1,2-dimethylhydrazinyl)-1-oxo-3-phenylpropan-2-yl)carbamate (1043922-50-4)

Conditions	Yield
Stage #1: N-Cbz-L-Phe With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -25℃; Stage #2: N,N'-Dimethylhydrazine dihydrochloride With sodium hydroxide In tetrahydrofuran; water at -25 - 20℃; for 2h;	97%
Stage #1: N-Cbz-L-Phe With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.833333h; Stage #2: N,N'-Dimethylhydrazine dihydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 28h;	83%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → C2H8N2*2HNO3

Conditions	Yield
With silver nitrate In water at 20℃; for 2h; Darkness;	97%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → C2H8N2*2ClHO4

Conditions	Yield
With silver perchlorate In water at 20℃; for 0.5h; Darkness;	96%

(3E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one (59938-07-7) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → 5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chloride

Conditions	Yield
With hydrogenchloride In ethanol for 4h; Heating;	95%
In toluene at 80℃; for 0.166667h; microwave irradiation;	80%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trichloro-4-methoxy-hept-3-en-2-one (438537-10-1) → 3-propyl-5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chloride

Conditions	Yield
In toluene at 80℃; for 0.2h; microwave irradiation;	95%
With hydrogenchloride In ethanol for 4h; Heating;	76%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trifluoro-4-(4-fluoro-phenyl)-4-methoxy-but-3-en-2-one → 5-(4-fluoro-phenyl)-1,2-dimethyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	95%

1-Adamantylmalonaldehyd (52086-98-3) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → 4-(Adamantan-1-yl)-1,2-dimethylpyrazolium-perchlorat

Conditions	Yield
With perchloric acid In methanol for 16h; Ambient temperature;	94%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trichloro-4-methoxy-3-methyl-but-3-en-2-one → 1,2,4-trimethyl-3-trichloromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
In toluene at 80℃; for 0.2h; microwave irradiation;	94%
With hydrogenchloride In ethanol for 4h; Heating;	90%

[(CO)5CrC(OC2H5)(CC(C5H4)Fe(C5H5))] + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → pentacarbonyl[1,2-dimethyl-5-ferrocenyl-1,2-pyrazolin-3-ylidene]chromium

Conditions	Yield
With NaOH In tetrahydrofuran; water byproducts: C2H5OH; using Schlenk techniques; addn. dropwise soln. of NaOH in water at 0°C to soln. of 1,2-dimethylhydrazine dihydrochloride in H2O; stirringfor 15 min; addn. of to (CO)5Cr(OEt)CC(C5H4)Fe(C5H5) in THF for 1 min; removal of solvent in vac., chromy. on silica gel at -20°C using petrol ether/CH2Cl2 as the eluent; elem. anal.;	94%

4,4-dimethoxycyclohexa-2,5-dienone (935-50-2) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → 8,8-dimethoxy-6,7-dimethyl-6,7-diazabicyclo[3.2.1]octan-3-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In isopropyl alcohol for 3h; Reflux; regioselective reaction;	94%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + 1,1,1-trifluoro-4-methoxy-4-(4-methylphenyl)-3-buten-2-one → 1,2-dimethyl-5-p-tolyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	92%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trifluoro-4-methoxy-dec-3-en-2-one → 5-hexyl-1,2-dimethyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	92%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + 1,1,1-trifluoro-4-methoxy-4-phenyl-3-buten-2-one → 1,2-dimethyl-5-phenyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	91%

pentacarbonyl[3-(dimethylamino)-3-phenyl-1,2-propadienylidene]chromium + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → pentacarbonyl(1,2-dimethyl-5-phenyl-2,3-dihydropyrazol-3-ylidene)chromium + pentacarbonyl(1,3-bis(dimethylamino)-3-phenylprop-2-en-1-ylidene)chromium

Conditions	Yield
With NaOH In tetrahydrofuran; water (under inert atm., Schlenk); soln. of ligand reacted with NaOH in H2O atroom temp., added to soln. of Cr-complex in THF, warmed to 50°C; solvent removed in vacuo, silica gel column chromy. with pentane/CH2Cl2 2:1-1:2 at -20°C, collected, solvent removed in vacuo;	A 91% B 4%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trichloro-4-methoxy-hex-3-en-2-one (233272-56-5) → 3-ethyl-5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chloride

Conditions	Yield
In toluene at 80℃; for 0.2h; microwave irradiation;	90%
With hydrogenchloride In ethanol for 4h; Heating;	81%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trifluoro-4-methoxy-hept-3-en-2-one → 1,2-dimethyl-5-propyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	90%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-4-(4-Chloro-phenyl)-1,1,1-trifluoro-4-methoxy-but-3-en-2-one → 5-(4-chloro-phenyl)-1,2-dimethyl-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	90%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-1,1,1-Trifluoro-4-methoxy-4-(4-nitro-phenyl)-but-3-en-2-one → 1,2-dimethyl-5-(4-nitro-phenyl)-3-trifluoromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 5h; Heating;	90%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + (E)-10,10,10-Trichloro-7-methoxy-9-oxo-dec-7-enoic acid ethyl ester → 5-(5-ethoxycarbonyl-pentyl)-1,2-dimethyl-3-trichloromethyl-2H-pyrazol-1-ium; chloride

Conditions	Yield
With hydrogenchloride In ethanol for 12h; Heating;	89%

3,4-bis(5-chloro-2-methylthiophen-3-yl)furan-2,5-dione + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → 3,4-bis(5-chloro-2-methylthiophen-3-yl)-1-methyl-1H-pyrrole-2,5-dione

Conditions	Yield
With PEG400 at 160℃; for 12h;	86%

((C6H5(CH3(CH2)5)2(CH3)2C10HN2)2)RhI(CH3OH) (340722-24-9) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → ((C6H5(CH3(CH2)5)2(CH3)2C10HN2)2)RhI(CH3NH)2 (351496-49-6)

Conditions	Yield
With NaOH In dichloromethane; water slight excess of hydrazine in water added to a soln. of Rh(III) porphyrin in CH2Cl2; 10% NaOH added; mixt. shaken; org. layer sepd., dried over MgSO4 and evapd.;	85%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + benzoyl chloride (98-88-4) → N'-benzoyl-N,N'-dimethylbenzohydrazide (1226-43-3)

Conditions	Yield
Stage #1: N,N'-Dimethylhydrazine dihydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.333333h; Stage #2: benzoyl chloride In dichloromethane at 0 - 20℃;	85%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + 1,1,1-trichloro-4-methoxy-4-phenyl-3-buten-2-one → 3-phenyl-5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chloride

Conditions	Yield
In toluene at 80℃; for 0.2h; microwave irradiation;	84%
With hydrogenchloride In ethanol for 12h; Heating;	70%

N,N'-Dimethylhydrazine dihydrochloride (306-37-6) + benzoyl chloride (98-88-4) → Benzoesaeure-1,2-dimethylhydrazid (80791-41-9)

Conditions	Yield
Stage #1: N,N'-Dimethylhydrazine dihydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: benzoyl chloride In dichloromethane at 0℃; for 0.75h;	82%
With sodium hydroxide In 1,4-dioxane; water for 1h; Ambient temperature;	39%

2-(4-chloro-2-methylsulfanylpyrimidin-5-yl)-1-(2,6-dichlorophenyl)ethanone (909095-75-6) + N,N'-Dimethylhydrazine dihydrochloride (306-37-6) → 1-(2,6-dichloro-phenyl)-2-[4-(N,N'-dimethyl-hydrazino)-2-methylsulfanyl-pyrimidin-5-yl]-ethanone (909095-76-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Heating;	82%

Upstream product

• 7647-01-0 hydrogenchloride 
• 74-89-5 methylamine 

Downstream Products

• 4143-42-4 (Z)-azomethane 
• 52341-81-8 2,3-dimethyl-1,1-dioxo-6-phenyl-1λ⁶-[1,2,3,7]thiatriazepan-4-one 
• 3478-74-8 tris(1,2-dimethylhydrazino)diphosphane 
• 106376-59-4 1,2-di-n-pentyldimethylhydrazine 
• 81436-64-8 1,2-Dimethyl-4-acetyl-1,2,4-triazolidin 
• 82490-90-2 N¹,N²-dimethylformohydrazide phenylimide 
• 108120-69-0 (3R,3aS,11cR)-1,2-Dimethyl-3-phenyl-1,2,3,3a,4,11c-hexahydro-5-oxa-1,2-diaza-cyclopenta[c]phenanthrene 
• 21939-23-1 1,2-dimethyl-cis-3,5-diphenylpyrazolidine 
• 21939-23-1 1,2-dimethyl-trans-3,5-diphenylpyrazolidine 
• 108120-72-5 1,2-dimethyl-4-(methoxycarbonyl)-3-phenylpyrazolidine 
• 108120-73-6 1,2-dimethyl-5-(methoxycarbonyl)-3-phenylpyrazolidine 
• 80791-41-9 Benzoesaeure-1,2-dimethylhydrazid 
• 23337-88-4 1,2-Dipropyl-1,2-dimethylhydrazin 
• 116149-14-5 1,2-di-n-butyldimethylhydrazine 

Relevant academic research and scientific papers

Stabilization of Azapeptides by Namide···H-NamideHydrogen Bonds

An unusual Namide···H-Namide hydrogen bond (HB) was previously proposed to stabilize the azapeptide β-Turns. Herein we provide experimental evidence for the Namide···H-Namide HB and show that this HB endows a stabilization of 1-3 kcal·mol-1 and enforces the trans-cis-Trans (t-c-T) and cis-cis-Trans (c-c-T) amide bond conformations in azapeptides and N-methyl-Azapeptides, respectively. Our results indicate that these Namide···H-Namide HBs can have stabilizing contributions even in short azapeptides that cannot fold to form β-Turns.

Scandium-Promoted Direct Conversion of Dinitrogen into Hydrazine Derivatives via N-C Bond Formation

Direct conversion of dinitrogen (N2) into organic compounds, not through ammonia (NH3), is of great significance both fundamentally and practically. Here we report a highly efficient scandium-mediated synthetic cycle affording hydrazine derivatives (RMeN-NMeR′) directly from N2 and carbon-based electrophiles. The cycle includes three main steps: (i) reduction of a halogen-bridged discandium complex under N2 leading to a (N2)3--bridged discandium complex via a (N2)2- intermediate; (ii) treatment of the (N2)3- complex with methyl triflate (MeOTf), affording a (N2Me2)2--bridged discandium complex; and (iii) further reaction of the (N2Me2)2- complex with the carbon-based electrophile, producing the hydrazine derivative and regenerating the halide precursor. Furthermore, insertion of a CO molecule into one Sc-N bond in the (N2Me2)2--scandium complex was observed. Most notably, this is the first example of rare-earth metal-promoted direct conversion of N2 to organic compounds; the formation of C-N bonds by the reaction of these (N2)3- and (N2Me2)2- complexes with electrophiles represents the first case among all N2-metal complexes reported.