306-37-6

Basic information

• Product Name: 1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE
• Synonyms: 1,2-dimethyl-hydrazindihydrochloride;1,2-dimethylhydraziniumdichloride;1,2-DIMETHYLHYDRAZINE 2HCL;1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE;N,N'-DIMETHYLHYDRAZINE DI HCL (SYM);N,N'-DIMETHYLHYDRAZINE DIHYDROCHLORIDE;SYM-DIMETHYLHYDRAZINE DIHYDROCHLORIDE;N,N'-Dimethylhydrazine (sym.) dihydrochloride
• CAS NO: 306-37-6
• Molecular Formula: C₂H₁₀N₂*2Cl
• Molecular Weight: 133.02
• EINECS: 206-183-5
• Mol File: 306-37-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 167-169 °C (dec.)(lit.)
• Boiling Point: 81.5 °C at 760 mmHg
• Flash Point: 1.1°C
• Appearance: White to light yellow/Crystalline Flakes or Powder
• Vapor Pressure: 168mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: almost transparency
• Merck: 14,3248
• BRN: 3905684
• CAS DataBase Reference: 1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE(306-37-6)
• EPA Substance Registry System: 1,2-DIMETHYLHYDRAZINE DIHYDROCHLORIDE(306-37-6)

Safety Data

• Hazard Codes: T,N
• Statements: 45-23/24/25-51/53
• Safety Statements: 53-45-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: MV2800000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 306-37-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 306-37-6 differently. You can refer to the following data:
1. carcinogen
2. 1,2-Dimethylhydrazine is a potent carcinogen that acts as a DNA alkylating agent. It is used to induce colon tumors in experimental animals. It was also used in preparation of spiroisoquinolinedione aldose reductase inhibitors.

Definition

ChEBI: A hydrochloride resulting from the reaction of 1,2,dimethylhydrazine with 2 mol eq. of hydrogen chloride.

General Description

Prisms (from water) or white crystalline powder. Distinct amine fishy or ammonia-like odor.

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

• 22527-64-6 2,3-dimethyl-1,2,3,4-tetrahydrophthalazine-1,4-dione 
• 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 
• 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 
• 63282-45-1 N-(2-nitro-4-trifluoromethylphenyl)-N,N'-dimethylhydrazine 
• 132401-05-9 N,N'-dimethyl-N,N'-di(3-phenylpropionyl)hydrazine 
• 4143-41-3 trans-dimethyl-diazene 

Relevant articles and documents

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.