35205-54-0

Basic information

• Product Name: 1-METHYL-2-PHENOXYETHYLAMINE
• Synonyms: 1-methyl-2-phenoxy-ethylamin;1-phenoxy-2-propanamin;1-Phenoxy-2-propanamine;1-Phenoxy-2-propylamine;2-Amino-1-phenoxypropane;2-Phenoxy-1-methylethylamine;2-Phenoxyisopropylamine;2-Propanamine, 1-phenoxy-
• CAS NO: 35205-54-0
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.20562
• EINECS: 252-434-7
• Mol File: 35205-54-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 147-148 °C
• Boiling Point: 240.5°Cat760mmHg
• Flash Point: 99.5°C
• Appearance: /
• Density: 1.004g/cm³
• Vapor Pressure: 0.0378mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform; Dichloromethane; Methanol
• PKA: 8.22±0.10(Predicted)
• CAS DataBase Reference: 1-METHYL-2-PHENOXYETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-PHENOXYETHYLAMINE(35205-54-0)
• EPA Substance Registry System: 1-METHYL-2-PHENOXYETHYLAMINE(35205-54-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 35205-54-0(Hazardous Substances Data)

Usage

Description

1-METHYL-2-PHENOXYETHYLAMINE, also known as 1-Phenoxypropan-2-amine, is an organic compound with the molecular formula C9H13NO. It is a derivative of phenethylamine, featuring a phenoxy group attached to the second carbon and a methyl group on the first carbon. 1-METHYL-2-PHENOXYETHYLAMINE serves as a key intermediate in the synthesis of various pharmaceuticals and has significant applications in the medical field.

Uses

1-METHYL-2-PHENOXYETHYLAMINE is used as an intermediate in the pharmaceutical industry for the synthesis of various medications.
Used in Pharmaceutical Industry:
1-METHYL-2-PHENOXYETHYLAMINE is used as a building block for the development of antihistaminics, which are medications that help alleviate symptoms of allergies and colds by blocking the action of histamine, a compound released by the immune system during an allergic reaction.
1-METHYL-2-PHENOXYETHYLAMINE is also used as a precursor in the synthesis of cardiovascular agents, which are drugs that affect the heart and blood vessels, helping to treat conditions such as high blood pressure, heart failure, and arrhythmias.

InChI:InChI=1/C9H13NO/c1-8(10)7-11-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

Synthetic route

3-phenoxy-2-propanone (621-87-4) → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
Stage #1: 3-phenoxy-2-propanone With ammonium formate In methanol at 80℃; for 0.166667h; Inert atmosphere; Stage #2: With formic acid; C29H32ClIrNO; triethylamine In methanol at 80℃;	87%
With 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; ammonium formate In methanol at 80℃; for 12h; Inert atmosphere; chemoselective reaction;	87%
Stage #1: 3-phenoxy-2-propanone With ammonium formate In methanol at 80℃; for 0.166667h; Inert atmosphere; Stage #2: With formic acid; 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; triethylamine In methanol at 80℃; Inert atmosphere;	87%

1-Phenoxy-propan-2-one oxime → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
With hydrogen; nickel In isopropyl alcohol at 60℃; under 3102.9 Torr; 20-24 h;	81%

2-(1-methyl-2-phenoxyethyl)-1H-isoindole-1,3(2H)-dione → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
With hydrazine hydrate; acetic acid In methanol for 4h; Reflux;	56%
With hydrazine hydrate In ethanol

1-phenoxy-2-propanol (770-35-4) → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
Stage #1: 1-phenoxy-2-propanol In dichloromethane cooling; Stage #2: With dibenzyl azodicarboxylate In dichloromethane cooling; Stage #3: With trifluoroacetic acid In dichloromethane Further stages.;	55%

phenoxyacetone oxime (30263-61-7) → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
With nickel; benzene at 45℃; under 73550.8 Torr; Hydrogenation;
With diethyl ether; cyclohexane; nickel at 45℃; under 73550.8 Torr; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In diethyl ether for 12h; Heating;
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux;

3-phenoxy-2-propanone (621-87-4) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
Kochen des Reaktionsprodukts mit konz. wss. HCl;

phenol (108-95-2) → 1-methyl-2-phenoxyethylamine (35205-54-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium iodide; potassium carbonate / N,N-dimethyl-formamide 2: hydroxylamine hydrochloride; sodium hydroxide / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.5 h / 20 °C 1.2: 3 h / Reflux 2.1: formamide / water / 4 h / 185 °C View Scheme

1-methyl-2-phenoxyethylamine (35205-54-0) + (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one (54750-12-8) → ((2R,4S,5R)-3,4-Dimethyl-5-phenyl-2-thioxo-2λ5-[1,3,2]oxazaphospholidin-2-yl)-(1-methyl-2-phenoxy-ethyl)-amine

Conditions	Yield
With triethylamine In tetrahydrofuran RT, 24 h, 65 deg C, 24 h;	100%

1-methyl-2-phenoxyethylamine (35205-54-0) + acetic anhydride (108-24-7) → N-(1-methyl-2-phenoxyethyl)acetamide (68157-86-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; Inert atmosphere;	93%

1-methyl-2-phenoxyethylamine (35205-54-0) + (2S)-4-methyl-2-isopropoxycarbonylaminopentanoic acid → (2S)-N-(1-methyl-2-phenoxyethyl)-4-methyl-2-(isopropoxycarbonylamino)pentanamide

Conditions	Yield
Stage #1: (2S)-4-methyl-2-isopropoxycarbonylaminopentanoic acid With isopropyl chloroformate; triethylamine In tetrahydrofuran at -3℃; for 1.5h; Stage #2: 1-methyl-2-phenoxyethylamine In tetrahydrofuran at 20℃; for 5.5h;	83.2%

(2S)-3-methyl-2-isopropoxycarbonylaminopentanoic acid + 1-methyl-2-phenoxyethylamine (35205-54-0) → (2S)-N-(1-methyl-2-phenoxyethyl)-3-methyl-2-(isopropoxycarbonylamino)pentanamide

Conditions	Yield
Stage #1: (2S)-3-methyl-2-isopropoxycarbonylaminopentanoic acid With isopropyl chloroformate; triethylamine In tetrahydrofuran at -3℃; for 1.5h; Stage #2: 1-methyl-2-phenoxyethylamine In tetrahydrofuran at 20℃; for 5.5h;	82.6%

1-methyl-2-phenoxyethylamine (35205-54-0) + (S)-2-((isopropoxycarbonyl)amino)-3-methylbutanoic acid derivative → C18H28N2O4

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 10h;	78.5%

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (3056-18-6) + 1-methyl-2-phenoxyethylamine (35205-54-0) → NNC 21-0041

Conditions	Yield
With sodium; triethylamine In 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate	76%

1-methyl-2-phenoxyethylamine (35205-54-0) + methyl L-(-)-3-chloroacetylthioazolidine-4-carboxylate (188561-33-3) → 7-(1-Methyl-2-phenoxy-ethyl)-tetrahydro-thiazolo[3,4-a]pyrazine-5,8-dione (95110-27-3)

Conditions	Yield
With triethylamine In 2-ethoxy-ethanol Heating;	73%

1-methyl-2-phenoxyethylamine (35205-54-0) + 4-chloro-2-(pyridin-3-yl)quinazoline (98296-25-4) → N-(1-phenoxypropan-2-yl)-2-(pyridin-3-yl)quinazolin-4-amine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	60%

Os(NH3)4(N2)2(2+)*2O3SCF3(1-)=[Os(NH3)4(N2)2](O3SCF3)2 + 1-methyl-2-phenoxyethylamine (35205-54-0) → cis-[Os(NH3)4(N2)((+/-)-1-phenoxy-2-propylamine)](OTf)2

Conditions	Yield
In not given N2-atmosphere; in dimethylacetamide or DME/dimethylacetamide=4:1 (not specified); excess amine, sealed tube, 80°C, 5 h; cooling, pptn. on dropwise addn. to stirred CH2Cl2 or CH2Cl2/Et2O (not specified), collection (filtration), washing (Et2O), drying (vac.); elem.anal.;	53%

1-methyl-2-phenoxyethylamine (35205-54-0) + quinuiclidine-2-carbonyl chloride hydrochloride (66073-49-2) → 1-Aza-bicyclo[2.2.2]octane-2-carboxylic acid (1-methyl-2-phenoxy-ethyl)-amide

Conditions	Yield
With triethylamine In benzene at 55 - 80℃; for 1.75h;	50%

7-chloro-6-(2-chloroethyl)-5-methyl-1,2,4-triazolo<1,5-a>pyrimidine (62053-05-8) + 1-methyl-2-phenoxyethylamine (35205-54-0) → 7,8-dihydro-5-methyl-8-(1-methyl-2-phenoxyethyl)6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine (74258-45-0)

Conditions	Yield
With sodium carbonate In ethanol for 2h; Heating;	45%

1-methyl-2-phenoxyethylamine (35205-54-0) + 1,2-epoxy-3-(3-hydroxyphenoxy)propane (4870-90-0) → 1-(1-methyl-2-phenoxyethylamino)-3-(3-hydroxyphenoxy)-2-propanol + 4-chloro-α-methylbenzenepropanamine (74697-68-0)

Conditions	Yield
	A 38% B n/a

1-methyl-2-phenoxyethylamine (35205-54-0) + 4-(2,3-epoxypropoxy)carbazole (51997-51-4) → 1-[carbazolyl-(4)-oxy]-3-[1-phenoxypropyl-(2)-amino]-propan-2-ol

Conditions	Yield
	31%

1-methyl-2-phenoxyethylamine (35205-54-0) + oxalic acid (144-62-7) + 1-[2-(cyclopropyl-methoxy)-ethyl]-4-(2,3-epoxypropoxy)-benzene (63659-17-6) → 1-[4-(2-Cyclopropylmethoxy-ethyl)-phenoxy]-3-(1-methyl-2-phenoxy-ethylamino)-propan-2-ol; compound with oxalic acid

Conditions	Yield
In ethanol for 12h; Heating;	25%

formaldehyd (50-00-0) + 1-methyl-2-phenoxyethylamine (35205-54-0) → N,N-dimethyl-1-phenoxypropan-2-amine (100054-51-1)

Conditions	Yield
With formic acid

1-methyl-2-phenoxyethylamine (35205-54-0) → β-iodo-isopropylamine

Conditions	Yield
With hydrogen iodide Heating;

1-methyl-2-phenoxyethylamine (35205-54-0) → S-(+)-1-phenoxy-2-propanamine (45972-73-4)

1-methyl-2-phenoxyethylamine (35205-54-0) → R-(-)-1-phenoxy-2-propanamine (45972-74-5)

3H-1,2-benzodithiole-3-thione (3354-42-5) + 1-methyl-2-phenoxyethylamine (35205-54-0) → 2-(1-Methyl-2-phenoxy-ethyl)-benzo[d]isothiazole-3-thione

Conditions	Yield
In ethanol for 2h; Heating;

1-methyl-2-phenoxyethylamine (35205-54-0) + 3,7-Dichlor-2H-1,2,4-benzothiadiazin-1,1-dioxid (59943-32-7) → (7-Chloro-1,1-dioxo-1,2-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-(1-methyl-2-phenoxy-ethyl)-amine (71259-62-6)

Conditions	Yield
With triethylamine In isopropyl alcohol at 20℃; for 2h;

1-methyl-2-phenoxyethylamine (35205-54-0) + (R,S)-cyanopyridiloxymethyloxirane (66781-34-8) → 2-[2-Hydroxy-3-(1-methyl-2-phenoxy-ethylamino)-propoxy]-nicotinonitrile

Conditions	Yield
at 60 - 70℃;

(4-hydroxylphenyl)glyoxal (24645-80-5) + 1-methyl-2-phenoxyethylamine (35205-54-0) → 4-Hydroxy-ω-(1-methyl-2-phenoxy-ethylamino)-acetophenon (1519-76-2, 1519-95-5, 93407-37-5)

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol

1-methyl-2-phenoxyethylamine (35205-54-0) + 4-methoxyphenylacetone (770-39-8) → 4-[(S)-2-((R)-1-Methyl-2-phenoxy-ethylamino)-propyl]-phenol + rac. Allo-1.1'-dimethyl-2-phenoxy-2'-(4-hydroxy-phenyl)-diaethylamin

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid

1-methyl-2-phenoxyethylamine (35205-54-0) + 2-[4-(benzyloxy)benzyl]acetic acid (6547-53-1) → 2-(4-Benzyloxy-phenyl)-N-(1-methyl-2-phenoxy-ethyl)-acetamide

Conditions	Yield
(i) SOCl2, benzene, (ii) /BRN= 2045304/, Et2O; Multistep reaction;

Upstream product

• 30263-61-7 phenoxyacetone oxime 
• 621-87-4 3-phenoxy-2-propanone 
• 77287-34-4 formamide 
• 770-35-4 1-phenoxy-2-propanol 
• 108-95-2 phenol 

Downstream Products

• 100054-51-1 N,N-dimethyl-1-phenoxypropan-2-amine 
• 45972-73-4 S-(+)-1-phenoxy-2-propanamine 
• 45972-74-5 R-(-)-1-phenoxy-2-propanamine 
• 74258-45-0 7,8-dihydro-5-methyl-8-(1-methyl-2-phenoxyethyl)6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 
• 95110-27-3 7-(1-Methyl-2-phenoxy-ethyl)-tetrahydro-thiazolo[3,4-a]pyrazine-5,8-dione 
• 71259-62-6 (7-Chloro-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-(1-methyl-2-phenoxy-ethyl)-amine 
• 1519-76-2 4-Hydroxy-ω-(1-methyl-2-phenoxy-ethylamino)-acetophenon 
• 66022-31-9 (2-Benzhydryloxy-ethyl)-(1-methyl-2-phenoxy-ethyl)-amine 
• 16258-43-8 3-(2-Aethyl-phenoxy)-1-(1-phenoxy-2-propylamino)-propanol-⁽²⁾ 
• 157736-23-7 (1-Methyl-2-phenoxy-ethyl)-trimethylsilanyl-amine 
• 157736-03-3 C₁₂H₂₀ClNOSSi 
• 157736-14-6 2-(1-Methyl-2-phenoxyethyl)-4,5-dimethyl-3,6-dihydro-2H-1,2-thiazine 

Relevant articles and documents

A (different) bright ammonia amide carbamate derivative and application thereof (by machine translation)

The invention belongs to the field of plant, relates to a general formula (I) is shown in a (different) bright ammonia amide carbamate derivatives and their pharmaceutically acceptable salt, wherein substituent R has the definition given in the specification, the invention also relates to the general formula (I) preparation of compounds of the, specifically for the preparation of the intermediate of its development and application of plant disease control. (by machine translation)

Design, synthesis and effect of the introduction of a propargyloxy group on the fungicidal activities of 1-substituted phenoxypropan-2-amino valinamide carbamate derivatives

The cell walls of oomycetes are composed of cellulose, making cellulose synthase enzymes good targets for carboxylic acid amide fungicides. Valinamide carbamates are amino acid fungicides that represent excellent alternatives to conventional synthetic pesticides in terms of their ability to reduce the negative impacts of these compounds on human health and the environment. In a continuation of our research towards the development of new cellulose synthase inhibitors, we have developed a series of "stretched" analogues of iprovalicarb by the introduction of an additional OCH2 linker. The bioassay results indicated that compounds containing a small group at the para-position of phenyl gave excellent fungicidal activities with EC50 values ranging from 0.59 to 2.06 μmol L-1. Most notably, the introduction of a propargyloxy group led to a pronounced increase in the fungicidal activity. Furthermore, compound 7o bearing a propargyloxy group was identified as the most promising candidate because of its excellent fungicidal potency against oomycete diseases and good fungicidal activity against non-oomycete diseases.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.