71271-61-9

Basic information

• Product Name: 1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE
• Synonyms: 4-PHENYL-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE;1-METHYL-2-PYRIDIN-3-YL-ETHYLAMINE;CHEMBRDG-BB 4002035;RARECHEM AN KC 0155;RARECHEM AN KC 0157;(1-methyl-2-pyridin-3-ylethyl)amine(SALTDATA: FREE);a-Methyl-3-PyridineethanaMine
• CAS NO: 71271-61-9
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• EINECS: 604-604-1
• Mol File: 71271-61-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 237.4 °C at 760 mmHg
• Flash Point: 118 °C
• Appearance: /
• Density: 1.001 g/cm³
• Vapor Pressure: 0.0449mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: 1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE(71271-61-9)
• EPA Substance Registry System: 1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE(71271-61-9)

Safety Data

• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 71271-61-9(Hazardous Substances Data)

Usage

General Description

1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE, also known as 2-Pyridin-4-ylethanamine, N-methyl, is a chemical compound with the molecular formula C9H12N2. It is a clear colorless to light yellow liquid with a faint amine odor and is soluble in organic solvents. 1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE is commonly used as an intermediate in the synthesis of pharmaceutical compounds and agrochemicals. It is also used in the production of UV-curable polymers, corrosion inhibitors, and as a chemical intermediate in the manufacture of other chemicals. 1-METHYL-2-PYRIDIN-4-YL-ETHYLAMINE is considered to be a potential skin irritant and may cause eye irritation, and should be handled with proper care and precautions.

InChI:InChI=1/C8H12N2/c1-7(9)5-8-3-2-4-10-6-8/h2-4,6-7H,5,9H2,1H3

Synthetic route

(E)-3-(2-nitroprop-1-en-1-yl)pyridine (106508-04-7) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	33%

1-(pyridin-3-yl)-2-propanone (6302-03-0) + ammonium formate (540-69-2) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
at 160 - 170℃; Erhitzen des Reaktionsgemisches mit verd. wss. HCl;

[3]pyridyl-acetone oxime (34672-31-6) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2-nitro-1-(3-pyridinyl)-1-propene (3156-53-4) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9) + [3]pyridyl-acetone oxime (34672-31-6)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

3-pyridinecarboxaldehyde (500-22-1) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: butylamine 2: LiAlH4; diethyl ether View Scheme
Multi-step reaction with 3 steps 1: butylamine 2: LiAlH4; diethyl ether 3: LiAlH4; diethyl ether View Scheme
Multi-step reaction with 3 steps 1: butylamine 2: lithium alanate; diethyl ether 3: LiAlH4; diethyl ether View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / 6 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Inert atmosphere; Reflux View Scheme

2-nitro-1-(3-pyridinyl)-1-propene (3156-53-4) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: LiAlH4; diethyl ether View Scheme
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: LiAlH4; diethyl ether View Scheme
With lithium aluminium tetrahydride In diethyl ether at 20℃; Heating / reflux;

3-pyridinylacetonitrile (6443-85-2) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanolic sodium ethylate solution 2: hydrobromic acid; water 3: 160 - 170 °C / Erhitzen des Reaktionsgemisches mit verd. wss. HCl View Scheme

pyridyl-3-yl-acetic acid (501-81-5) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate 2: 160 - 170 °C / Erhitzen des Reaktionsgemisches mit verd. wss. HCl View Scheme

pyridin-3-yl-acetic acid ethyl ester (39931-77-6) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: concentrated aqueous NH3 2: POCl3; NaCl; 1,2-dichloroethane 3: ethanolic sodium ethylate solution 4: hydrobromic acid; water 5: 160 - 170 °C / Erhitzen des Reaktionsgemisches mit verd. wss. HCl View Scheme

2-[3]pyridyl-acetoacetonitrile (90417-12-2) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrobromic acid; water 2: 160 - 170 °C / Erhitzen des Reaktionsgemisches mit verd. wss. HCl View Scheme

2-(pyridin-3-yl)acetamide (3724-16-1) → (+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: POCl3; NaCl; 1,2-dichloroethane 2: ethanolic sodium ethylate solution 3: hydrobromic acid; water 4: 160 - 170 °C / Erhitzen des Reaktionsgemisches mit verd. wss. HCl View Scheme

(+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9) + ethyl 2-methoxyacetate (3938-96-3) → (S)-1-(3-pyridyl)propan-2-amine (1292798-88-9) + (R)-N-[1-(3-pyridyl)propan-2-yl]-2-methoxyacetamide (1292798-85-6)

Conditions	Yield
With lipase B from Candida antarctica In tetrahydrofuran at 30℃; for 4h; Inert atmosphere; Enzymatic reaction; optical yield given as %ee;	A 36% B 96%

(+/-)-1-(3-pyridyl)propan-2-amine (71271-61-9) + 2-isopropyl-5-methylcyclohexanecarbonyl chloride (39668-87-6) → (1R,2S,5R)-2-isopropyl-5-methyl-N-(1-(pyridin-3-yl)propan-2-yl)cyclohexanecarboxamide (1254731-71-9)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 16h;

Upstream product

• 6302-03-0 1-(pyridin-3-yl)-2-propanone 
• 540-69-2 ammonium formate 
• 34672-31-6 [3]pyridyl-acetone oxime 
• 3156-53-4 2-nitro-1-(3-pyridinyl)-1-propene 
• 500-22-1 3-pyridinecarboxaldehyde 
• 6443-85-2 3-pyridinylacetonitrile 
• 501-81-5 pyridyl-3-yl-acetic acid 
• 39931-77-6 pyridin-3-yl-acetic acid ethyl ester 
• 90417-12-2 2-[3]pyridyl-acetoacetonitrile 
• 3724-16-1 2-(pyridin-3-yl)acetamide 
• 106508-04-7 (E)-3-(2-nitroprop-1-en-1-yl)pyridine 

Downstream Products

• 1254731-71-9 (1R,2S,5R)-2-isopropyl-5-methyl-N-(1-(pyridin-3-yl)propan-2-yl)cyclohexanecarboxamide 

Relevant articles and documents

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