41965-95-1

Basic information

• Product Name: 3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE
• Synonyms: BIO-FARMA BF004393;3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE;4-AMINOMETHYL-2-CHLOROANISOLE HCL;4-AMINOMETHYL-2-CHLOROANISOLE HYDROCHLORIDE;3-chloro-4-methoxybenzylamineHCl;3-Chloro-4-methoxybenzylamineHCl95%;3-Chloro-4-methoxybenzylaminehydrochloride95%;3-Chloro-4-methoxybenzylamine hydrochloride 95%
• CAS NO: 41965-95-1
• Molecular Formula: C₈H₁₀ClNO*ClH
• Molecular Weight: 208.09
• EINECS: 1308068-626-2
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;pharmacetical;Anilines, Amides & Amines;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Benzene derivatives;Amine Salts;Nitrogen Compounds;Organic Building Blocks
• Mol File: 41965-95-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 250-255 °C(lit.)
• Boiling Point: 263.5 °C at 760 mmHg
• Flash Point: 113.2 °C
• Appearance: /Solid
• Vapor Pressure: 0.0102mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE(41965-95-1)
• EPA Substance Registry System: 3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE(41965-95-1)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-36/37-45-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 41965-95-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder solid

InChI:InChI=1/C8H10ClNO.ClH/c1-11-8-3-2-6(5-10)4-7(8)9;/h2-4H,5,10H2,1H3;1H

Synthetic route

N-(3-chloro-4-methoxybenzyl)formamide (212576-67-5) → (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	95%

3-Chloro-4-methoxybenzonitrile (102151-33-7) → (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1)

Conditions	Yield
Stage #1: 3-Chloro-4-methoxybenzonitrile With potassium tert-butylate In tetrahydrofuran at 70℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; Glovebox; Inert atmosphere; Sealed tube; Stage #3: With hydrogenchloride In methanol; diethyl ether at 20℃; for 0.333333h; Inert atmosphere;	90%

4-methoxy-benzylamine (2393-23-9) → (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1)

Conditions	Yield
With sulfuryl dichloride; acetic acid In diethyl ether at 20℃;	80%
With sulfuryl dichloride In acetic acid at 20℃; for 5h; Chlorination;	78.7%
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In tetrahydrofuran; diethyl ether at 0℃; for 0.333333h; Stage #2: With sulfuryl dichloride; acetic acid at 20 - 70℃;	44%

4-methoxybenzylamine hydrochloride (17061-61-9) → (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1)

Conditions	Yield
With chlorine In acetic acid at 20℃; for 0.333333h;	71%
With hydrogenchloride; dihydrogen peroxide In water at 63℃; for 11h;	26.5 g

3-chloro-4-methoxy-benzaldehyde (4903-09-7) + aqueous sodium cyanacetate → (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / HCOOH / 6 h / 130 °C 2: 95 percent / conc. HCl / 3 h / Heating View Scheme

4-methoxy-benzaldehyde (123-11-5) + (+-)-2-cyano-3-m-tolyl-propionic acid hydrazide → (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / SO2Cl2, pyridine / 1.) RT, 0.5 h, 2.) 70 deg C, 4 h 2: 64 percent / HCOOH / 6 h / 130 °C 3: 95 percent / conc. HCl / 3 h / Heating View Scheme

9-chloro-2-ethyl-7-(trifluoromethyl)-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → 9-((3-chloro-4-methoxybenzyl)amino)-2-ethyl-7-(trifluoromethyl)-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 90℃; for 2h; Inert atmosphere;	99%
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 90℃; for 1h;

(3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) + 4-chloro-6-cyanoquinoline-3-carboxylic acid ethyl ester (403841-76-9) → ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-6-cyanoquinoline-3-carboxylate (403838-46-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In propan-1-ol	97%
With N-ethyl-N,N-diisopropylamine In propan-1-ol for 2h; Heating;

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate (330785-81-4)

Conditions	Yield
Stage #1: (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester In tetrahydrofuran at 20℃; Cooling with ice;	88.3%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 4h; Temperature; Cooling with ice;	78%
Stage #1: (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride With triethylamine In tetrahydrofuran at 20℃; for 0.25h; Cooling with ice; Stage #2: 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester In tetrahydrofuran at 20℃;	74.2%
With sodium carbonate In water at 25 - 30℃; for 4h;	90 g

4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxamide + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → C14H15ClN4O2S

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 40℃; for 2.5h; Reagent/catalyst; Temperature; Solvent;	87.37%

(3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) + 1-(9-chloro-3-ethyl-3H-pyrazolo[4',3':5,6]pyrido-[3,4-d]pyridazin-6-yl)-4-methylimidazolecarboxamide (296250-65-2) → 1-[9-[[(3-chloro-4-methoxyphenyl)methyl]amino]-3-ethyl-3H-pyrazolo[4',3':5,6]pyrido[3,4-d]pyridazin-6-yl]-N-methyl-1H-imidazole-4-carboxamide (296250-53-8)

Conditions	Yield
With N-isopropylethylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 3h;	85%

7,9-dichloro-2-ethyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → 7-chloro-9-((3-chloro-4-methoxybenzyl)amino)-2-ethyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 90℃; for 2h; Inert atmosphere;	85%
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 90℃; for 2h;

ethyl 8-bromo-4-chloro-6-(trifluoromethyl)quinoline-3-carboxylate + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → ethyl 8-bromo-4-[(3-chloro-4-methoxybenzyl)amino]-6-(trifluoromethyl)quinoline-3-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In propan-1-ol for 16h; Reflux;	85%

methyl 2,4-dichloro-6-cyanoquinoline-3-carboxylate (1448419-17-7) + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → methyl 2-chloro-4-[(3-chloro-4-methoxybenzyl)amino]-6-cyanoquinoline-3-carboxylate (1448419-18-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	80%
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	80%
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	80%

9-chloro-2-ethyl-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-b]-quinoline-7-carbonitrile + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → 9-((3-chloro-4-methoxybenzyl)amino)-2-ethyl-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline-7-carbonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 90℃; for 2h; Inert atmosphere;	79%
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 90℃; for 1h;

tert-butyl 2,4-dichloro-5-pyrimidinecarboxylic acid + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate

Conditions	Yield
Stage #1: tert-butyl 2,4-dichloro-5-pyrimidinecarboxylic acid; (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride With triethylamine In dichloromethane at 0℃; for 2h; Stage #2: (S)-1-Pyrrolidin-2-yl-methanol In dichloromethane for 2h;	75%

ethyl 2,4-dichloropyrimidine-5-carboxylate (51940-64-8) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate

Conditions	Yield
Stage #1: ethyl 2,4-dichloropyrimidine-5-carboxylate; (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride With triethylamine In dichloromethane at 0℃; for 2h; Stage #2: (S)-1-Pyrrolidin-2-yl-methanol In dichloromethane for 2h;	70%

Upstream product

• 4196-58-1 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dimethyl- 
• 41965-80-4 2-[(3-chloro-4-methoxy-phenyl)methyl]isoindoline-1,3-dione 
• 41965-71-3 2-Propenoyl chloride, 2-broMo- 
• 41965-60-0 1,3-bis(4-chlorophenoxy)propan-2-yl acetate 
• 41964-93-6 2(1H)-Pyridinone,6-ethyl-3-(1-methylethyl)-(9CI) 
• 41964-65-2 2-BROMO-N-(3-CHLORO-PHENYL)-ACETAMIDE 
• 41964-63-0 [5-(TERT-BUTYL)-2-HYDROXYPHENYL](PHENYL)METHANONE OXIME 
• 41964-44-7 6-(METHYLAMINO)-2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDIN-5-YLFORMAMIDE 
• 41964-42-5 6-(methylamino)-5-nitropyrimidine-2,4(1H,3H)-dione 
• 41964-07-2 Tolimidone 
• 41964-04-9 1-Chloro-4-(2,2-diethoxyethoxy)benzene 
• 4196-36-5 2,3,4,6-tetra-O-benzyl-1-O-(4-nitrobenzoyl)hexopyranose 
• 4196-35-4 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide 
• 41963-20-6 4-BROMO-3-METHYLBENZONITRILE 

Downstream Products

• 41966-09-0 N-(3-CHLORO-4-METHOXYBENZYL)-N'-PHENYLTHIOUREA 
• 41966-25-0 2,2-bis(hydroxymethyl)butanal 
• 41966-75-0 1,3-Butadiyn-1-amine,N,N-diethyl-(9CI) 
• 41966-94-3 (3,3-dimethylbutyl)triethoxysilane 
• 41967-34-4 3-(acetyloxy)-1-(diphenylmethyl)-1-azoniabicyclo[2.2.2]octane 
• 41967-35-5 3-(acetyloxy)-1-benzyl-1-azoniabicyclo[2.2.2]octane 
• 41967-36-6 3-(acetyloxy)-1-(2-phenylethyl)-1-azoniabicyclo[2.2.2]octane 
• 41968-40-5 Cyanamide, (1-methyl-1H-benzimidazol-2-yl)- (9CI) 
• 41968-62-1 3-bromo-4,8-dimethylquinolin-2(1H)-one 
• 4196-86-5 PENTAERYTHRITOL TETRABENZOATE 
• 4196-87-6 2-[(benzoyloxy)methyl]-2-methylpropane-1,3-diyl dibenzoate 
• 4196-89-8 NEOPENTYL GLYCOL DIBENZOATE 
• 41969-16-8 2-ethylquinoline-3-carbonitrile 
• 41969-25-9 2-(2-nitro-2-phenylethenyl)thiophene 

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• 403841-76-9  4-chloro-6-cyanoquinoline-3-carboxylic acid ethyl ester 
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