40851-65-8

Basic information

• Product Name: 2-Aminomethylphenylacetic acid
• Synonyms: Benzeneacetic acid, 2-(aMinoMethyl)-;2-(AMinoMethyl)benzeneacetic acid;2-(2-(AMinoMethyl)phenyl)acetic acid;2-AMINOMETHYL-PHENYLACETIC ACID;2-AMINOMETHYL-PHENYLACETIC ACID 98%;2-aminomethylphenylacetic acid (intermediate of ceforanide);2-Aminomethylphenyl Acetic Acid(2-Ampa);2-aminomethylphenylaceti
• CAS NO: 40851-65-8
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.19
• EINECS: 255-110-3
• Product Categories: Organic acids;(intermediate of ceforanide);pharmacetical
• Mol File: 40851-65-8.mol

Chemical Properties

• Boiling Point: 328 °C at 760 mmHg
• Flash Point: 152.2 °C
• Appearance: /
• Density: 1.206 g/cm³
• Vapor Pressure: 7.86E-05mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Water (Slightly)
• PKA: 4.12±0.10(Predicted)
• CAS DataBase Reference: 2-Aminomethylphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminomethylphenylacetic acid(40851-65-8)
• EPA Substance Registry System: 2-Aminomethylphenylacetic acid(40851-65-8)

Safety Data

• Hazardous Substances Data: 40851-65-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Aminomethylphenylacetic acid is used as an intermediate in the synthesis of Ceforanide (C242930), a cephalosporin-based antibiotic. It plays a crucial role in the production of this antibiotic, which is utilized for sterilization in various medical procedures. 2-Aminomethylphenylacetic acid's presence in the synthesis process contributes to the development of effective treatments for bacterial infections.

InChI:InChI=1/C9H11NO2.ClH/c10-6-8-4-2-1-3-7(8)5-9(11)12;/h1-4H,5-6,10H2,(H,11,12);1H

Synthetic route

sodium 2-(1-ethoxycarbonyl-1-propen-2-ylaminomethyl)phenylacetate (52786-77-3) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
With hydrogenchloride In water pH=2; Cooling with ice;	79%

2-(tert-butoxycarbonylaminomethyl)phenylacetic acid (40851-66-9) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
With trifluoroacetic acid In diethyl ether at 20℃;	78%

[2-(benzoylamino-methyl)-phenyl]-acetonitrile (170306-38-4) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
With hydrogenchloride at 115℃; im Rohr;

2-(2-(azidomethyl)phenyl)acetic acid (40851-64-7) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal

o-chloromethylbenzylamine (38379-25-8) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH-solution / unter Kuehlung 2: diluted alcohol 3: concentrated hydrochloric acid / 115 °C / im Rohr View Scheme

N-(2-chloromethyl-benzyl)-benzamide (28837-90-3) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diluted alcohol 2: concentrated hydrochloric acid / 115 °C / im Rohr View Scheme

bis-(2-ethoxymethyl-benzyl)-amine (861338-62-7) → 2-Aminomethylphenylacetic acid (40851-65-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: alcohol; hydrogen chloride 2: NaOH-solution / unter Kuehlung 3: diluted alcohol 4: concentrated hydrochloric acid / 115 °C / im Rohr View Scheme
Multi-step reaction with 4 steps 2: NaOH-solution / unter Kuehlung 3: diluted alcohol 4: concentrated hydrochloric acid / 115 °C / im Rohr View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → 2-[2-(aminomethyl)cyclohexyl]acetic acid

Conditions	Yield
With 5wt.% Rh on activated alumina; hydrogen In water at 100℃; under 13501.4 Torr; for 24h; Autoclave;	92%

di-tert-butyl dicarbonate (24424-99-5) + 2-Aminomethylphenylacetic acid (40851-65-8) → 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid (40851-66-9)

Conditions	Yield
With water In 1,4-dioxane at 0 - 20℃; for 3.16667h;	88.1%

2-Aminomethylphenylacetic acid (40851-65-8) + ethyl acetoacetate (141-97-9) → sodium 2-(1-ethoxycarbonyl-1-propen-2-ylaminomethyl)phenylacetate (52786-77-3)

Conditions	Yield
With sodium In ethanol Reflux;	82.3%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 2-Aminomethylphenylacetic acid (40851-65-8) → 2-(2-(((((9H-fluoren-9-yl)methoxy)carbonyl)amino)methyl)phenyl)acetic acid

Conditions	Yield
With potassium carbonate In 1,4-dioxane; water at 20℃; for 2h;	25%
Yield given;
With sodium carbonate In 1,4-dioxane; water at 20℃;

2-Aminomethylphenylacetic acid (40851-65-8) + 2-(4-((1H-pyrazol-1-yl)methyl)benzyl)-4-chloro-2H-pyrazolo[3,4-d]pyrimidine → 2-(2-((2-(4-((1H-pyrazol-1-yl)methyl)benzyl)-2H-pyrazolo[3,4-d]pyrimidin-4-ylamino)methyl)phenyl)acetic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃;	2%

2-Aminomethylphenylacetic acid (40851-65-8) → 1,4-dihydro-3(2H)-isoquinolinone (24331-94-0)

Conditions	Yield
unter vermindertem Druck;
Multi-step reaction with 2 steps 1: aqueous alkaline solution 2: soda lime / 200 - 250 °C View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) + acetic anhydride (108-24-7) → [2-(acetylamino-methyl)-phenyl]-acetic acid (112072-92-1)

Conditions	Yield
With alkaline solution

2-Aminomethylphenylacetic acid (40851-65-8) + butyryl chloride (141-75-3) → [2-(butyrylamino-methyl)-phenyl]-acetic acid (100609-65-2)

Conditions	Yield
With alkaline solution

2-Aminomethylphenylacetic acid (40851-65-8) + (S)-1-((R)-3-tert-Butoxycarbonylamino-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid (775354-22-8) → [2-({[(S)-1-((R)-3-tert-Butoxycarbonylamino-4-phenyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-methyl)-phenyl]-acetic acid

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane

2-Aminomethylphenylacetic acid (40851-65-8) + (S)-1-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-pyrrolidine-2-carboxylic acid (775354-21-7) → [2-({[(S)-1-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-phenyl]-acetic acid

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane

2-Aminomethylphenylacetic acid (40851-65-8) → [2-({[(S)-1-((R)-3-Amino-4-phenyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-methyl)-phenyl]-acetic acid; compound with trifluoro-acetic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: EDC; HOBt; DIEA / CH2Cl2 2: CH2Cl2 View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → [2-({[(S)-1-((S)-2-Amino-2-cyclohexyl-acetyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-phenyl]-acetic acid; compound with trifluoro-acetic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: EDC; HOBt; DIEA / CH2Cl2 2: CH2Cl2 View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → 3-methylisoquinoline (1125-80-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous alkaline solution 2: soda lime / 250 °C / mehrtaegiges Aufbewahren der bei 94-96grad/5 Torr siedenden Fraktion des Rktprod. View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → 3-n-propylisoquinoline (76039-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous alkaline solution 2: soda lime / 250 °C View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → 3-methyl-1,2-dihydro-isoquinoline (59816-89-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous alkaline solution 2: soda lime / 200 - 250 °C View Scheme

triethylamine (TEA) hydrochloride + 4,4,4-trichloro-2-butanone (112605-39-7) + 2-Aminomethylphenylacetic acid (40851-65-8) → α-(2-aminomethyl-1,4-cyclohexadienyl)acetic acid (56167-90-9)

Conditions	Yield
With lithium In P2 O5; methanol hydrate

2-Aminomethylphenylacetic acid (40851-65-8) → (9H-fluoren-9-yl)methyl (2-(2-((2-hydroxyethyl)amino)-2-oxoethyl)benzyl)carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane; water / 2 h / 20 °C 2: 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → (9H-fluoren-9-yl)methyl (2-(2-oxo-2-((2-oxoethyl)amino)ethyl)benzyl)carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / 1,4-dioxane; water / 2 h / 20 °C 2: 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → (9H-fluoren-9-yl)methyl (2-(oxazol-2-ylmethyl)benzyl)carbamate

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / 1,4-dioxane; water / 2 h / 20 °C 2: 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: Burgess Reagent / tetrahydrofuran / 12 h / 65 °C View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → (2-(oxazol-2-ylmethyl)phenyl)methanamine

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium carbonate / 1,4-dioxane; water / 2 h / 20 °C 2: 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: Burgess Reagent / tetrahydrofuran / 12 h / 65 °C 5: piperidine / 1,4-dioxane / 1 h / 50 °C View Scheme

2-Aminomethylphenylacetic acid (40851-65-8) → 6-methyl-N-(2-(oxazol-2-ylmethyl)benzyl)-4-oxo-3,4-dihydrofuro[2,3-d]pyrimidine-5-carboxamide

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium carbonate / 1,4-dioxane; water / 2 h / 20 °C 2: 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: Burgess Reagent / tetrahydrofuran / 12 h / 65 °C 5: piperidine / 1,4-dioxane / 1 h / 50 °C 6: 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine / dichloromethane / 12 h / 20 °C View Scheme

Upstream product

• 170306-38-4 [2-(benzoylamino-methyl)-phenyl]-acetonitrile 
• 38379-25-8 o-chloromethylbenzylamine 
• 28837-90-3 N-(2-chloromethyl-benzyl)-benzamide 
• 40851-66-9 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid 
• 52786-77-3 sodium 2-(1-ethoxycarbonyl-1-propen-2-ylaminomethyl)phenylacetate 
• 861338-62-7 bis-(2-ethoxymethyl-benzyl)-amine 
• 40851-64-7 2-(2-(azidomethyl)phenyl)acetic acid 

Downstream Products

• 24331-94-0 1,4-dihydro-3(2H)-isoquinolinone 
• 112072-92-1 [2-(acetylamino-methyl)-phenyl]-acetic acid 
• 100609-65-2 [2-(butyrylamino-methyl)-phenyl]-acetic acid 
• 882847-15-6 2-(2-(((((9H-fluoren-9-yl)methoxy)carbonyl)amino)methyl)phenyl)acetic acid 
• 56167-90-9 α-(2-aminomethyl-1,4-cyclohexadienyl)acetic acid 
• 40851-66-9 2-(tert-butoxycarbonylaminomethyl)phenylacetic acid 
• 52786-77-3 sodium 2-(1-ethoxycarbonyl-1-propen-2-ylaminomethyl)phenylacetate 
• 1125-80-0 3-methylisoquinoline 

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