140-69-2

Basic information

• Product Name: (4-METHOXYBENZYL)HYDRAZINEDIHYDROCHLORIDE
• Synonyms: hydrazine, [(4-methoxyphenyl)methyl]-;(4-methoxybenzyl)hydrazine(SALTDATA: HCl);[(4-Methoxyphenyl)Methyl]hydrazine;Hydrazine,[(4-methoxyphenyl)methyl]- 2hcl
• CAS NO: 140-69-2
• Molecular Formula: C₈H₁₂N₂O
• Molecular Weight: 152.19368
• Mol File: 140-69-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 34-36 °C
• Boiling Point: 311.9 °C at 760 mmHg
• Flash Point: 142.5 °C
• Appearance: /
• Density: 1.069 g/cm³
• Vapor Pressure: 7.4E-06mmHg at 25°C
• PKA: 7.46±0.70(Predicted)
• CAS DataBase Reference: (4-METHOXYBENZYL)HYDRAZINEDIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHOXYBENZYL)HYDRAZINEDIHYDROCHLORIDE(140-69-2)
• EPA Substance Registry System: (4-METHOXYBENZYL)HYDRAZINEDIHYDROCHLORIDE(140-69-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 140-69-2(Hazardous Substances Data)

Usage

General Description

(4-Methoxybenzyl)hydrazinedihydrochloride is a chemical compound with the molecular formula C8H12N2O and a molecular weight of 188.19 g/mol. It is commonly used in organic synthesis and pharmaceutical research as a versatile building block for the preparation of various organic compounds. This chemical is a hydrazine derivative and is typically found in the form of a white or off-white crystalline powder. It is known for its ability to undergo various chemical reactions such as reduction, acylation, and alkylation, making it a valuable tool in the field of organic chemistry. Additionally, it has been investigated for its potential medical applications, particularly in the field of cancer treatment.

InChI:InChI=1/C8H12N2O.2ClH/c1-11-8-4-2-7(3-5-8)6-10-9;;/h2-5,10H,6,9H2,1H3;2*1H

Synthetic route

p-methoxybenzyl chloride (824-94-2) → 4-methoxybenzylhydrazine (140-69-2)

Conditions	Yield
With potassium carbonate; hydrazine hydrate at 10 - 30℃; Inert atmosphere;	69%
With hydrazine In methanol for 2h; Ambient temperature;	54%
With hydrazine hydrate In methanol at 20℃; for 2h;	52%

2-((4-methoxybenzyl)amino)isoindoline-1,3-dione (345928-21-4) → 2,3-dihydrophthalazine-1,4-dione (1445-69-8) + 4-methoxybenzylhydrazine (140-69-2)

Conditions	Yield
With hydrazine hydrate In ethanol; water Heating;	A n/a B 65%
With hydrazine hydrate In ethanol; water for 2.5h; Heating;	A n/a B 65%

p-anisaldehyde hydrazone (5953-85-5) → 4-methoxybenzylhydrazine (140-69-2)

Conditions	Yield
With ethanol; acetic acid; platinum Hydrogenation;

4-methoxy-benzaldehyde-(4-methoxy-benzylhydrazone) (33708-60-0) → 4-methoxybenzylhydrazine (140-69-2)

Conditions	Yield
With hydrogenchloride

N-(p-methoxybenzylidene)aminophthalimide (85468-48-0) → 4-methoxybenzylhydrazine (140-69-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / hydrogen, / 5percent palladium on charcoal / dimethylformamide / 20 h / 2585.7 Torr 2: 65 percent / 64percent NH2NH2*H2O / H2O; ethanol / 2.5 h / Heating View Scheme

4-methoxy-benzaldehyde (123-11-5) → 4-methoxybenzylhydrazine (140-69-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / ethanol / 1.) reflux, 2.5 h; 2.) room temp., overnight 2: 79 percent / hydrogen, / 5percent palladium on charcoal / dimethylformamide / 20 h / 2585.7 Torr 3: 65 percent / 64percent NH2NH2*H2O / H2O; ethanol / 2.5 h / Heating View Scheme

ethyl 4-(3,5-dichlorophenoxy)-3-oxobutanoate (1226145-00-1) + 4-methoxybenzylhydrazine (140-69-2) → C18H16Cl2N2O3 (1412896-04-8)

Conditions	Yield
In ethanol at 20℃; for 7h;	97%

(4-chlorophenyl)(2-isothiocyanatothiophen-3 -yl)methanone + 4-methoxybenzylhydrazine (140-69-2) → N-(3-(4-chlorobenzoyl)thiophen-2-yl)-1-(4-methoxybenzyl)hydrazine-1-carbothioamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 5h;	80%

3-(1,4-Dioxa-spiro[4.4]non-7-yl)-3-oxo-N-(3-trifluoromethyl-phenyl)-thiopropionamide + 4-methoxybenzylhydrazine (140-69-2) → [5-(1,4-Dioxa-spiro[4.4]non-7-yl)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-(3-trifluoromethyl-phenyl)-amine

Conditions	Yield
With acetic acid In ethanol	79%

4-methoxybenzylhydrazine (140-69-2) → 5-Cyclobutyl-2-(4-methoxy-benzyl)-2H-pyrazol-3-ylamine + β-Cyclobutyl-β-oxopropionitrile (118431-89-3)

Conditions	Yield
In ethanol; ethyl acetate	A 77% B n/a

tert-butyl ((1-(6-chloro-5-cyanopyrazin-2-yl)-4-methylpiperidin-4-yl)methyl)carbamate + 4-methoxybenzylhydrazine (140-69-2) → tert-butyl ((1-(3-amino-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyrazin-6-yl)-4-methylpiperidin-4-yl)methyl)carbamate

Conditions	Yield
With triethylamine In ethanol at 90℃; for 12h;	77%

diethyl 2-ethoxymethylenemalonate (87-13-8) + 4-methoxybenzylhydrazine (140-69-2) → ethyl 5-hydroxy-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (821016-23-3)

Conditions	Yield
With potassium carbonate for 3h; Heating;	75%

ethyl acetoacetate (141-97-9) + 4-methoxybenzylhydrazine (140-69-2) → 2-(4-methoxybenzyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one (33555-99-6)

Conditions	Yield
at 0℃; for 0.5h;	75%

acetylacetone (123-54-6) + 4-methoxybenzylhydrazine (140-69-2) → 1-p-methoxybenzyl-3,5-dimethylpyrazole

Conditions	Yield
With hydrogenchloride In ethanol for 1h; Heating;	73%

(6-bromo-indol-3-yl)-oxo-acetic acid ethyl ester (17826-12-9) + 4-methoxybenzylhydrazine (140-69-2) → 7-bromo-2-[(4-methoxyphenyl)methyl]-2H,4H,5H-pyrazolo[3,4-c]quinolin-4-one

Conditions	Yield
With acetic acid In ethanol at 80℃;	68%

malonaldehydebis(dimethylacetal) (102-52-3) + 4-methoxybenzylhydrazine (140-69-2) → 1-(p-methoxyphenyl)methyl-pyrazole (145162-51-2)

Conditions	Yield
With hydrogenchloride In ethanol for 1h; Heating;	64%

methyl 2-chloro-6-(2-furyl)-5-pyrimidin-4-ylnicotinate (868360-50-3) + 4-methoxybenzylhydrazine (140-69-2) → 6-(2-furyl)-1-(4-methoxybenzyl)-5-pyrimidin-4-yl-1,2-dihydro-3H-pyrazolo[3,4-b]pyridin-3-one (868360-65-0)

Conditions	Yield
In ethanol at 65℃;	63%

4-methoxybenzylhydrazine (140-69-2) + ethyl (ethoxymethylene)cyanoacetate (94-05-3) → ethyl 5-amino-1-[(4-methoxyphenyl)methyl]pyrazole-4-carboxylate (384835-92-1)

Conditions	Yield
In ethanol Reflux;	63%
In ethanol Reflux;	63%
In ethanol Reflux;	63%

(4-hydroxyphenyl)carbonohydrazonoyl dicyanide + 4-methoxybenzylhydrazine (140-69-2) → 4-((3,5-diamino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)diazenyl)phenol (1374431-85-2)

Conditions	Yield
In methanol at 65℃; for 4h;	62%

(E)-2-(1-(dimethylamino)-3-oxo-3-phenylprop-1-en-2-yl)isoindoline-1,3-dione + 4-methoxybenzylhydrazine (140-69-2) → 2-(3-phenyl-1H-pyrazol-4-yl)isoindoline-1,3-dione (216854-27-2)

Conditions	Yield
In ethanol at 20℃; for 15h;	59%

4-methoxybenzylhydrazine (140-69-2) + 2-chloro-3-cyanopyrazine (55557-52-3) → 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyrazine-3-amine (1432112-13-4)

Conditions	Yield
With potassium carbonate In ethanol for 6h; Reflux;	56%
With potassium carbonate In ethanol for 6h; Reflux;	56%

Benzoylacetonitrile (614-16-4) + 4-methoxybenzylhydrazine (140-69-2) → 1-(4-methoxybenzyl)-3-phenyl-1H-pyrazol-5-amine

Conditions	Yield
With acetic acid In ethanol at 85℃;	52%
With acetic acid In ethanol at 85℃;	14.4 g

ethyl acetoacetate (141-97-9) + 4-methoxybenzylhydrazine (140-69-2) → 1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-5-ol (326488-07-7)

Conditions	Yield
In acetic acid at 100℃;	46%

3-oxabicyclo[3.1.0]hexane-2,4-dione (5617-74-3) + 4-methoxybenzylhydrazine (140-69-2) → (+/-)-3-(4-methoxybenzyl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione (154186-47-7)

Conditions	Yield
In acetonitrile for 15h; cyclocondensation; Heating;	34%
In acetonitrile Reflux;	25.5%

4-bromo-2-chlorobenzamide (426265-73-8) + 1,1-dimethoxyethane (534-15-6) + 4-methoxybenzylhydrazine (140-69-2) → 3-(4-bromo-2-chlorophenyl)-1-(4-methoxybenzyl)-1H-1,2,4-triazole

Conditions	Yield
In Petroleum ether	27%

(E)-3-(dimethylamino)-2-phenylacrylonitrile (70515-61-6) + 4-methoxybenzylhydrazine (140-69-2) → 1-(4-methoxybenzyl)-4-phenyl-1H-pyrazol-3-amine + 4-phenyl-1H-pyrazol-3-ylamine (5591-70-8)

Conditions	Yield
In ethanol at 20℃; for 12h;	A 12.3% B 21.6%

4-methoxybenzylhydrazine (140-69-2) → sodium (E)-(4-methoxyphenyl)methanediazoate

Conditions	Yield
With n-Butyl nitrite; sodium ethanolate In diethyl ether; ethanol for 16h;

Glyoxal (131543-46-9) + 4-methoxybenzylhydrazine (140-69-2) → 2-(4-Methoxy-benzyl)-2H-[1,2,3]triazole 1-oxide

Conditions	Yield
With pyridine; hydroxylamine hydrochloride; sodium carbonate; copper(II) sulfate 1.) water, methanol, r.t., 0.5 h, 2.) water, methanol, reflux, 0.5 h; Yield given. Multistep reaction;

(2-amino-4-methyl-phenyl)-cyclohexyl-methanone (528884-49-3) + bis(trichloromethyl) carbonate (32315-10-9) + 4-methoxybenzylhydrazine (140-69-2) → C23H29N3O3

Conditions	Yield
Stage #1: (2-amino-4-methyl-phenyl)-cyclohexyl-methanone; bis(trichloromethyl) carbonate With triethylamine In dichloromethane at -40℃; for 0.833333h; Stage #2: 4-methoxybenzylhydrazine In dichloromethane at -40 - 20℃; Further stages.;

thiophosgene (463-71-8) + 2-aminoacetophenone (551-93-9) + 4-methoxybenzylhydrazine (140-69-2) → C17H19N3O2S

Conditions	Yield
Stage #1: thiophosgene; 2-aminoacetophenone With triethylamine In dichloromethane at -20 - 20℃; Stage #2: 4-methoxybenzylhydrazine In dichloromethane at 20℃; for 16h; Further stages.;

Upstream product

• 5953-85-5 p-anisaldehyde hydrazone 
• 824-94-2 p-methoxybenzyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 345928-21-4 2-((4-methoxybenzyl)amino)isoindoline-1,3-dione 
• 33708-60-0 4-methoxy-benzaldehyde-(4-methoxy-benzylhydrazone) 
• 85468-48-0 N-(p-methoxybenzylidene)aminophthalimide 

Downstream Products

• 118431-89-3 β-Cyclobutyl-β-oxopropionitrile 
• 154186-47-7 (+/-)-3-(4-methoxybenzyl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione 
• 34586-54-4 diisopropyl (4-methoxybenzyl)phosphonate 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 

Relevant articles and documents

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