593-82-8

Basic information

• Product Name: 1,1-DIMETHYLHYDRAZINE HYDROCHLORIDE
• Synonyms: Hydrazine, 1,1-dimethyl-, hydrochloride;1,1-DiMethylhydrazine HCl;N,N-DiMethylhydrazine (hydrochloride);1,1-dimethyl-hydrazinhydrochloride;1,1-DIMETHYLHYDRAZINE HYDROCHLORIDE;Dimethylhydrazinehydrochloride;1,1-dimethylhydrazine monohydrochloride;asym-DimethylhydrazineHCl
• CAS NO: 593-82-8
• Molecular Formula: C₂H₉N₂*Cl
• Molecular Weight: 96.56
• EINECS: 209-811-6
• Mol File: 593-82-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 85°C
• Boiling Point: 63.9°Cat760mmHg
• Flash Point: 1.1°C
• Appearance: /
• Density: 0.829g/cm³
• Vapor Pressure: 168mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: almost transparency
• Merck: 14,3247
• CAS DataBase Reference: 1,1-DIMETHYLHYDRAZINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DIMETHYLHYDRAZINE HYDROCHLORIDE(593-82-8)
• EPA Substance Registry System: 1,1-DIMETHYLHYDRAZINE HYDROCHLORIDE(593-82-8)

Safety Data

• Statements: 20/21-28
• Safety Statements: 22-36/37/39-45
• RIDADR: 2811
• RTECS: MV2900000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 593-82-8(Hazardous Substances Data)

Usage

Uses

1,1-Dimethylhydrazine Hydrochloride is a toxic volatile hydrazine found in rocket fuel systems.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl and NOx

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

Synthetic route

1,2-dichlorovinyl propyl ketone (882037-58-3) + 1,1-dimethylhydrazine (57-14-7) → N,N-dimethylhydrazine hydrochloride (593-82-8)

Conditions	Yield
In diethyl ether	89%

N,N-dimethylammonium chloride (506-59-2) → N,N-dimethylhydrazine hydrochloride (593-82-8)

Conditions	Yield
Stage #1: N,N-dimethylammonium chloride With sodium nitrite In water at 20℃; Cooling with ice; Stage #2: With zinc In water at 20℃; Cooling with ice;	63.2%

1-(2-carbamylethyl)-1,1-dimethylhydrazinium chloride (6439-49-2) → N,N-dimethylhydrazine hydrochloride (593-82-8) + 3-hydroxypropanoic acid sodium salt (6487-38-3)

Conditions	Yield
With sodium hydroxide for 1.5h; Heating;	A 54% B n/a

N-Nitrosodimethylamine (62-75-9) → N,N-dimethylhydrazine hydrochloride (593-82-8)

Conditions	Yield
With acetic acid; zinc at 25 - 30℃; Dampfdestillation und nachfolgendes Abdampfen mit Salzsaeure;

dibutylchloroborane (1730-69-4) + 1,1-dimethylhydrazine (57-14-7) → (n-C4H9)2BNHN(CH3)2 (14575-27-0) + N,N-dimethylhydrazine hydrochloride (593-82-8)

2-(prop-2-ynyloxy)-1-naphthaldehyde (58758-48-8) + N,N-dimethylhydrazine hydrochloride (593-82-8) → 2,2-Dimethyl-1,2,4,11c-tetrahydro-5-oxa-1-aza-2-azonia-cyclopenta[c]phenanthrene; chloride (108120-55-4)

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

2-allyloxy-1-naphthaldehyde (19530-43-9) + N,N-dimethylhydrazine hydrochloride (593-82-8) → 2,2-dimethyl-1,2,3,3a,4,11c-hexahydronaphtho<1',2':5,6>pyrano<4,3-c>pyrazolium chloride (108120-49-6)

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

N,N-dimethylhydrazine hydrochloride (593-82-8) + (E)-ethyl 4-(1-formyl-2-naphthoxy)but-2-enoate (96601-25-1) → 3-Ethoxycarbonyl-2,2-dimethyl-1,2,3,3a,4,11c-hexahydro-5-oxa-1-aza-2-azonia-cyclopenta[c]phenanthrene; chloride (108120-53-2)

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

N,N-dimethylhydrazine hydrochloride (593-82-8) + 2-<2-(benzyloxy)ethyl>cyclopentanone (131685-20-6) → C16H24N2O (1488133-66-9)

Conditions	Yield
With triethylamine In ethanol for 16h; Inert atmosphere; Reflux;	98%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 3-oxo-2-(phenylhydrazono)-3-(2-thienyl)propanal → (2Z,3Z)-3-(2,2-dimethylhydrazono)-2-(2-phenylhydrazono)-1-(thiophen-2-yl)propan-1-one

Conditions	Yield
With sodium acetate In methanol at 25℃; Inert atmosphere;	97%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 3-oxo-3-phenyl-2-(2-phenylhydrazono)propanal → (2Z,3Z)-3-(2,2-dimethylhydrazono)-1-phenyl-2-(2-phenylhydrazono)propan-1-one

Conditions	Yield
With sodium acetate In methanol at 25℃; Inert atmosphere;	96%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 3-(2-furyl)-3-oxo-2-(phenylhydrazono)propanal → (2Z,3Z)-3-(2,2-dimethylhydrazono)-1-(furan-2-yl)-2-(2-phenylhydrazono)propan-1-one

Conditions	Yield
With sodium acetate In methanol at 25℃; Inert atmosphere;	94%

N,N-dimethylhydrazine hydrochloride (593-82-8) + (E)-4-(1-Formyl-naphthalen-2-yloxy)-but-2-enenitrile (108120-33-8) → 3-Cyano-2,2-dimethyl-1,2,3,3a,4,11c-hexahydro-5-oxa-1-aza-2-azonia-cyclopenta[c]phenanthrene; chloride (108120-52-1)

Conditions	Yield
In ethanol for 3h; Heating;	90%

N,N-dimethylhydrazine hydrochloride (593-82-8) + cyclopentanone (120-92-3) → 2-cyclopentylidene-1,1-dimethylhydrazine (14090-60-9)

Conditions	Yield
With triethylamine In ethanol for 3.5h; Inert atmosphere; Reflux;	89%

N,N-dimethylhydrazine hydrochloride (593-82-8) + N-(2-n-octyldodecyl)-2-pyrrolecarbaldehyde → C27H51N3

Conditions	Yield
With sodium acetate In tetrahydrofuran; methanol at 85℃; for 8h; Inert atmosphere;	82%

trinitroacetonitrile (630-72-8) + N,N-dimethylhydrazine hydrochloride (593-82-8) → dimethylhydrazinium salt of dinitroacetonitrile

Conditions	Yield
In methanol; tetrachloromethane for 2h;	80%

pentacyanonitrosylferrate(III) + N,N-dimethylhydrazine hydrochloride (593-82-8) → pentacyano(1,1-dimethylhydrazine)ferrate(II)(3-)

Conditions	Yield
With NaOH; NaCl In water Kinetics; byproducts: Me2NH, N2O; hydrazine soln. contg. buffer and solid Fe complex mixed at 25.0°C, pH 6-10, ionic strength 0.1 M (NaCl); not isolated; monitored spectrophotometrically;	80%

(15)N-pentacyanonitrosylferrate(II)(2-) (687970-88-3) + N,N-dimethylhydrazine hydrochloride (593-82-8) → pentacyano(1,1-dimethylhydrazine)ferrate(II)(3-)

Conditions	Yield
With NaOH; NaCl In water byproducts: Me2NH, N(15)NO; hydrazine soln. contg. buffer and solid Fe complex mixed at 25.0°C, pH 9.4, ionic strength 0.1 M (NaCl); not isolated; monitored spectrophotometrically;	80%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 2-[((E)-but-2-enyl)oxy]-naphthalene-1-carbaldehyde (108120-31-6) → 2,2,3-Trimethyl-1,2,3,3a,4,11c-hexahydro-5-oxa-1-aza-2-azonia-cyclopenta[c]phenanthrene; chloride (108120-50-9)

Conditions	Yield
In ethanol for 3h; Heating;	79%

5-nitrofurane-2-carboxaldehyde (698-63-5) + N,N-dimethylhydrazine hydrochloride (593-82-8) → 5-nitro-2-furancarboxaldehyde dimethylhydrazone (69819-71-2)

Conditions	Yield
In methanol; water at 20℃; Darkness;	75%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 2-((E)-3-phenyl-allyloxy)-naphthalene-1-carbaldehyde (108120-32-7) → 2,2-Dimethyl-3-phenyl-1,2,3,3a,4,11c-hexahydro-5-oxa-1-aza-2-azonia-cyclopenta[c]phenanthrene; chloride (108120-51-0)

Conditions	Yield
In ethanol for 3h; Heating;	70%

N,N-dimethylhydrazine hydrochloride (593-82-8) + benzaldehyde (100-52-7) + acrylic acid methyl ester (292638-85-8) → 1,1-dimethyl-4-(methoxycarbonyl)-3-phenylpyrazolidinium chloride (108120-67-8)

Conditions	Yield
With hydroquinone In methanol for 4h; Heating;	66%

4-formyl-3-methyl-2-butenyl phenyl sulfide (69690-06-8) + N,N-dimethylhydrazine hydrochloride (593-82-8) → (E)-1,1-dimethyl-2-((E)-2-methyl-4-(phenylthio)but-2-enylidene)hydrazine (1606991-83-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	63%

trinitromethyladamantane (59987-69-8) + N,N-dimethylhydrazine hydrochloride (593-82-8) → N'-[1-Adamantan-1-yl-1-nitro-meth-(Z)-ylidene]-N,N-dimethyl-hydrazine

Conditions	Yield
In methanol for 120h;	59%

ferrocenecarboxaldehyde (12093-10-6) + N,N-dimethylhydrazine hydrochloride (593-82-8) → C10H9FeCHNN(CH3)2

Conditions	Yield
In ethanol boiling;	56%
In ethanol boiling;	56%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 7-diethylaminocoumarine-3-aldehyde (57597-64-5) → (E)-7-(diethylamino)-3-((2,2-dimethylhydrazineylidene)methyl)-2H-chromen-2-one

Conditions	Yield
In ethanol at 20℃; for 36h;	56%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 2-Adamantan-1-yl-N-(2,2,2-trinitro-ethyl)-acetamide (74605-73-5) → 2-Adamantan-1-yl-N-[2-(dimethyl-hydrazono)-2-nitro-ethyl]-acetamide

Conditions	Yield
In methanol for 120h;	54%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 3-Bromo-adamantane-1-carboxylic acid (2,2,2-trinitro-ethyl)-amide → 3-Bromo-adamantane-1-carboxylic acid [2-(dimethyl-hydrazono)-2-nitro-ethyl]-amide

Conditions	Yield
In methanol for 120h;	53%

N,N-dimethylhydrazine hydrochloride (593-82-8) + Adamantane-1-carboxylic acid (2,2,2-trinitro-ethyl)-amide (74605-68-8) → Adamantane-1-carboxylic acid [2-(dimethyl-hydrazono)-2-nitro-ethyl]-amide

Conditions	Yield
In methanol for 120h;	52%

2-(3-methylbut-2-enyloxy)naphthalene-1-carbaldehyde (58758-47-7) + N,N-dimethylhydrazine hydrochloride (593-82-8) → 2,2,3,3-Tetramethyl-1,2,3,3a,4,11c-hexahydro-5-oxa-1-aza-2-azonia-cyclopenta[c]phenanthrene; chloride (108120-54-3)

Conditions	Yield
In ethanol for 3h; Heating;	51%

trinitromethane (517-25-9) + N,N-dimethylhydrazine hydrochloride (593-82-8) → dinitroformaldehyde dimethylhydrazone (6421-08-5)

Conditions	Yield
In methanol at 20℃;	47%

N,N-dimethylhydrazine hydrochloride (593-82-8) + 3-Hydroxy-adamantane-1-carboxylic acid (2,2,2-trinitro-ethyl)-amide (74605-69-9) → 3-Hydroxy-adamantane-1-carboxylic acid [2-(dimethyl-hydrazono)-2-nitro-ethyl]-amide

Conditions	Yield
In methanol for 120h;	47%

Upstream product

• 1730-69-4 dibutylchloroborane 
• 57-14-7 N,N-Dimethylhydrazine 
• 506-59-2 N,N-dimethylammonium chloride 
• 882037-58-3 1,2-dichlorovinyl propyl ketone 
• 6439-49-2 1-(2-carbamylethyl)-1,1-dimethylhydrazinium chloride 
• 62-75-9 N-Nitrosodimethylamine 

Downstream Products

• 17239-58-6 (C₆H₅)₂PN(NMe₂)P(C₆H₅)₂ 
• 1606991-83-6 (E)-1,1-dimethyl-2-[(E)-2-methyl-4-(phenylthio)but-2-enylidene]hydrazine 

Relevant articles and documents

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