7422-78-8

Usage

Uses

Used in Pharmaceutical Industry:
Allylhydrazine is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its reactivity and ability to form different chemical structures make it a valuable component in the development of new drugs and medications.
Used in Dye Industry:
In the dye industry, allylhydrazine is utilized as a chemical intermediate for the production of various dyes. Its unique chemical properties allow for the creation of a wide range of colors and hues, contributing to the diversity of dyes available for various applications.
Used in Agricultural Chemical Industry:
Allylhydrazine is employed as a chemical intermediate in the manufacturing of agricultural chemicals, such as pesticides and herbicides. Its ability to form explosive materials and its reactivity make it a useful component in the development of effective and efficient agricultural products.

InChI:InChI=1/C3H8N2/c1-2-3-5-4/h2,5H,1,3-4H2

Synthetic route

1-amino-2-propene (107-11-9) → allylhydrazine (7422-78-8)

Conditions	Yield
With sodium hydroxide; chloroamine In water at 35 - 45℃;	80%
With chloroamine

3-chloroprop-1-ene (107-05-1) → allylhydrazine (7422-78-8)

Conditions	Yield
With hydrazine hydrate at 100℃;

C15H17N2OP (70629-56-0) → allylhydrazine (7422-78-8)

Conditions	Yield
With hydrogenchloride Heating;

α-Allyl-Nβ-isopropyliden-hydrazino>-triphenyl-phosphoniumiodid → allylhydrazine (7422-78-8)

Conditions	Yield
(i) aq. Na2CO3, (ii) AcOH, PhCHO; Multistep reaction;

1,2-propanediene (463-49-0) → acetone hydrazone (5281-20-9) + allylhydrazine (7422-78-8)

Conditions	Yield
With C24H20B(1-)*C27H39AuClN*K(1+); hydrazine at 130℃; for 14h; Inert atmosphere;

N'-[(tert-butoxy)carbonyl]-N'-(prop-2-en-1-yl)(tert-butoxy)carbohydrazide (202980-98-1) → allylhydrazine (7422-78-8)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1h;

4,6-dichloropyrimidine (1193-21-1) + allylhydrazine (7422-78-8) → 4,6-bis[1-(prop-2-enyl)hydrazino]pyrimidine

Conditions	Yield
for 3h; Heating;	100%

allylhydrazine (7422-78-8) + p-fluorobenzoylacetone (29681-98-9) → 1-allyl-5-(4-fluorophenyl)-3-methyl-1H-pyrazole (1221503-18-9)

Conditions	Yield
With triethylamine; trifluoroacetic acid In isopropyl alcohol at 80℃; for 1h;	95%

allylhydrazine (7422-78-8) + β-naphthaldehyde (66-99-9) → 1-allyl-2-(naphthalen-2-ylmethylene)hydrazine (1097191-46-2)

Conditions	Yield
In ethanol; water at 20℃; for 12h; Inert atmosphere;	94%

allylhydrazine (7422-78-8) + ethyl acetate (141-78-6) → 1-acetyl-2-allylhydrazide (64632-82-2)

Conditions	Yield
at 150℃; for 19h; sealed tube;	92%
In water

(3Z)-3-(4-methoxyphenylmethylidene)-2-benzofuran-1(3H)-one (71126-50-6) + allylhydrazine (7422-78-8) → 2-allyl-4-(4-methoxy-benzyl)-2H-phthalazin-1-one

Conditions	Yield
	90%

(Z)-3-(4-chlorophenyl)methylidenephthalide (105279-16-1) + allylhydrazine (7422-78-8) → 2-allyl-4-(4-chlorobenzyl)phthalazin-1(2H)-one

Conditions	Yield
	89%

allylhydrazine (7422-78-8) + ethyl bromoacetate (105-36-2) → ethyl 2-(1-allylhydrazinyl)acetate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 25h; Reflux;	87%

(Z)-3-(4-methylsulfanylbenzylidene)isobenzofuran-1-one + allylhydrazine (7422-78-8) → 2-allyl-4-(4-methylsulfanyl-benzyl)-2H-phthalazin-1-one

Conditions	Yield
	85%

(Z)-3-(3,4-dimethoxybenzylidene)isobenzofuran-1(3H)-one (148345-07-7) + allylhydrazine (7422-78-8) → 2-allyl-4-(3,4-dimethoxy-benzyl)-2H-phthalazin-1-one

Conditions	Yield
	70%

allylhydrazine (7422-78-8) + benzyl isothiocyanate (3173-56-6) → 4-benzyl-2-allylsemicarbazide

Conditions	Yield
In chloroform at 0℃; for 2h;	70%

allylhydrazine (7422-78-8) + methyl N-4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl-N'-(2-(4-fluorophenyl)pent-4-enoyl)carbamimidothioate (1235493-42-1) → 1-allyl-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5-(1-(4-fluorophenyl)but-3-enyl)-1H-1,2,4-triazol-3-amine (1235493-43-2)

Conditions	Yield
In ethanol; water at 80℃; for 3h;	69%

allylhydrazine (7422-78-8) + 1,4-di(benzyloxy)-5,8-dichloro-9,10-dihydro-9,10-anthracenedione (91440-79-8) → 2-Allyl-7,10-bis-benzyloxy-5-chloro-2H-dibenzo[cd,g]indazol-6-one (111425-44-6)

Conditions	Yield
With potassium fluoride; potassium hydrogencarbonate In dimethyl sulfoxide at 80℃; for 18h;	53%

allylhydrazine (7422-78-8) + propargyl bromide (106-96-7) → N-Allyl-N-prop-2-ynyl-hydrazine (54362-42-4)

Conditions	Yield
In diethyl ether	45%

2-chloropyrimidine (1722-12-9) + allylhydrazine (7422-78-8) → 2-(1-allylhydrazinyl)pyrimidine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 75℃; for 12h;	38%

allylhydrazine (7422-78-8) + (S)-1-(1-((4-fluorophenyl)sulfonyl)-6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-1,2,3,4-tetrahydroquinolin-2-yl)but-3-yn-2-one → (S)-2-(2-((1-allyl-1H-pyrazol-5-yl)methyl)-1-((4-fluorophenyl)sulfonyl)-1,2,3,4-tetrahydroquinolin-6-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol + (S)-2-(2-((1-allyl-1H-pyrazol-3-yl)methyl)-1-((4-fluorophenyl)sulfonyl)-1,2,3,4-tetrahydroquinolin-6-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Conditions	Yield
In methanol at 20℃; for 1h;	A 21% B 21%

6-bromo-1-benzopyran-4(4H)-one (51483-92-2) + allylhydrazine (7422-78-8) → 2-(1-allyl-1H-pyrazol-3-yl)-4-bromophenol

Conditions	Yield
In dimethyl sulfoxide at 100℃;	21%
In dimethyl sulfoxide at 100℃; for 36h;	50 mg

allylhydrazine (7422-78-8) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → 1-Allyl-5-methylsulfanyl-1H-[1,2,4]triazol-3-ylamine (84827-81-6) + 1-allyl-5-amino-3-methylthio-1,2,4-triazole (84827-80-5)

Conditions	Yield
In ethanol for 3h; Heating;	A 8% B 16%

3-oxabicyclo[3.1.0]hexane-2,4-dione (5617-74-3) + allylhydrazine (7422-78-8) → (1S,6R)-3-Allyl-3,4-diaza-bicyclo[4.1.0]heptane-2,5-dione

Conditions	Yield
In ethanol for 12h; Heating;	16%

allylhydrazine (7422-78-8) + phenyl isothiocyanate (103-72-0) → 2-allyl-4-phenyl thiosemicarbazide (21076-33-5)

Conditions	Yield
In diethyl ether

potassium cyanate (590-28-3) + furan-2-yl-oxo-acetic acid (1467-70-5) + allylhydrazine (7422-78-8) → 2-allyl-6-furan-2-yl-2H-[1,2,4]triazine-3,5-dione (26216-81-9)

Conditions	Yield
(i) aq. HCl, (ii) /BRN= 115630/; Multistep reaction;

formaldehyd (50-00-0) + allylhydrazine (7422-78-8) → N-Allyl-N'-methylene-hydrazine (36214-52-5)

Conditions	Yield

tert-butyl isothiocyanate (590-42-1) + allylhydrazine (7422-78-8) → 4-tert.-Butyl-2-allyl-thiosemicarbazid (21076-15-3)

Conditions	Yield
In diethyl ether

allylhydrazine (7422-78-8) + S-Methyl-monothiokohlensaeure-tert.-butylester (29518-83-0) → (tert-butoxy)-N-(prop-2-en-1-yl)carbohydrazide (21075-86-5)

Conditions	Yield

allylhydrazine (7422-78-8) + 4-Butyloxy-dithiobenzoesaeure-(carboxy-methylester) (60246-54-0) → 4-Butyloxy-thiobenzoesaeure-(N1-allyl-hydrazid) (98528-41-7)

Conditions	Yield
With sodium hydroxide

allylhydrazine (7422-78-8) + 3-formylrifamycin SV (13292-22-3) → 3-(allylhydrazono-methyl)-rifamycin (39976-77-7)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;

allylhydrazine (7422-78-8) + methyl thioisocyanate (556-61-6) → 4-Methyl-2-allyl-thiosemicarbazid (21198-39-0)

Conditions	Yield
In diethyl ether

Upstream product

• 107-05-1 3-chloroprop-1-ene 
• 202980-98-1 N'-[(tert-butoxy)carbonyl]-N'-(prop-2-en-1-yl)(tert-butoxy)carbohydrazide 
• 463-49-0 1,2-propanediene 
• 70629-56-0 C₁₅H₁₇N₂OP 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 21076-33-5 2-allyl-4-phenyl thiosemicarbazide 
• 192725-90-9 tert-butyl 2-(prop-2-en-1-yl)hydrazinecarboxylate 
• 21075-86-5 (tert-butoxy)-N-(prop-2-en-1-yl)carbohydrazide 
• 671198-40-6 ethyl 2-(1-allylhydrazinyl)acetate 
• 1221503-18-9 1-allyl-5-(4-fluorophenyl)-3-methyl-1H-pyrazole 
• 1235493-43-2 1-allyl-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5-(1-(4-fluorophenyl)but-3-enyl)-1H-1,2,4-triazol-3-amine 
• 1072138-70-5 C₁₉H₁₄Br₃ClN₆O₂ 
• 1072138-71-6 C₁₉H₁₄Br₃ClN₆O₂ 
• 1072138-74-9 C₂₀H₁₇BrCl₂N₆O₂ 
• 1072138-75-0 C₂₀H₁₇BrCl₂N₆O₂ 
• 1097191-49-5 1-allyl-2-(3-methylbenzylidene)hydrazine 
• 1097191-53-1 1-allyl-2-(2-methoxybenzylidene)hydrazine 
• 1097191-52-0 1-allyl-2-(3-methoxybenzylidene)hydrazine 
• 1097191-50-8 1-allyl-2-(2-methylbenzyliene)hydrazine 

Relevant academic research and scientific papers

Gold-catalyzed hydroamination of alkynes and allenes with parent hydrazine

A diverse array of nitrogen-containing compounds were formed by the addition of hydrazine to alkynes, diynes, enynes, and allenes in the presence of cationic gold(I) complexes with a cyclic (alkyl)(amino)carbene ligand (see scheme; the X-ray crystal structure of the gold-hydrazine complex is shown). This hydroamination is an ideal initial step for the preparation of acyclic and heterocyclic bulk chemicals. Dipp=2,6-diisopropylphenyl. Copyright

Method for the continuous synthesis of monoalkyl-hydrazines with a functionalised alkyl group

The invention relates to a method for the continuous synthesis of monoalkyl-hydrazines with a functionalised alkyl group. The inventive method is characterised in that it comprises a step consisting in demixing a solution containing the synthesised monoalkyl hydrazine, by reacting an anhydrous amine with monochloramine, in an organic phase and an aqueous phase with the addition of anhydrous sodium hydroxide. The invention can he used to obtain perfect selectivity in relation to monoalkyl-hydrazine without the presence of the di- and tri-substituted forms thereof. According to the invention, the starting amine which has not reacted is collected and reused directly without any additional treatment.

Method for treating multiple sclerosis

Provided is a method of treating multiple sclerosis employing certain aryl-substituted rhodanines.

Aryl-substituted rhodanine derivatives

Provided are certain aryl-substituted rhodanine derivatives, treatment methods and pharmaceutical formulations thereof.

Method of treating inflammatory bowel disease

Provided is a method of treating inflammatory bowel disease in mammals utilizing certain benzyl-substituted rhodanine derivatives. Also provided are novel benzyl-substituted rhodanine derivatives and pharmaceutical compositions thereof, as well as a novel process for selectively isolating in substantially pure enantiomeric form the enantiomers of certain racemic benzyl-substituted rhodanine derivatives.

Method of treating type I diabetes

Provided is a method for treating Type I diabetes in mammals utilizing certain aryl-substituted rhodanine derivatives.