101-98-4

Basic information

• Product Name: N-Benzyl-N-methylethanolamine
• Synonyms: 2-[methyl(phenylmethyl)amino]-ethano;Ethanol, 2-(benzylmethylamino)-;N-Benzyl-N-methylethanolamine,99%;N-Benzyl-N-Methyl;2-[benzyl(Methyl)aMino]ethan-1-ol;2-[BENZYL(METHYL)AMINO]ACETALDEHYDE;N-Benzyl-N-MethylethanolaMine technical grade, 90%;2-( N-methyl-N-benzyl)ethanolamine
• CAS NO: 101-98-4
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 202-994-3
• Product Categories: Aromatic alcohols and diols;Hydroxyethylamines
• Mol File: 101-98-4.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 95-105 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellowish liquid
• Density: 1.017 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00788mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.75±0.10(Predicted)
• BRN: 366412
• CAS DataBase Reference: N-Benzyl-N-methylethanolamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-N-methylethanolamine(101-98-4)
• EPA Substance Registry System: N-Benzyl-N-methylethanolamine(101-98-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 101-98-4(Hazardous Substances Data)

Usage

Chemical Properties

clear yellowish liquid

Uses

2-[Methyl(phenylmethyl)amino]ethanol is used in the preparation of dihydropyrimidinones as sodium iodide symporter inhibitors used to regulate the accumulation of iodide in the thyroid gland. Also used in the synthesis of new class of pseudopeptides as potential inhibitors of β-sheet aggregation.

General Description

N-Benzyl-N-methylethanolamine is a tertiary benzylamine. Electrochemical alkoxylation of N-benzyl-N-methylethanolamine is reported. Rate of proton exchange of N-benzyl-N-methylethanolamine in aqueous HCl has been reported.

InChI:InChI=1/C10H15NO/c1-11(7-8-12)9-10-5-3-2-4-6-10/h2-6,12H,7-9H2,1H3/p+1

Synthetic route

benzyl-methyl-amine (103-67-3) + 2-chloro-ethanol (107-07-3) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
In acetonitrile Heating;	100%
With potassium carbonate; potassium iodide In acetonitrile for 48h; Heating / reflux;	63%
With toluene
at 110℃; im Rohr;

(2-hydroxyethyl)(methyl)amine (109-83-1) + benzoyl chloride (98-88-4) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Stage #1: (2-hydroxyethyl)(methyl)amine; benzoyl chloride With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Further stages.;	98%

(2-hydroxyethyl)(methyl)amine (109-83-1) + benzyl chloride (100-44-7) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 1h;	95.5%
With triethylamine In acetonitrile at 0 - 20℃; for 1h;	95.5%
With tetrabutylammomium bromide; triethylamine In benzene for 48h; Heating;	79%

(2-hydroxyethyl)(methyl)amine (109-83-1) + benzyl bromide (100-39-0) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 1.5h;	90%

methanol (67-56-1) + N-Benzylethanolamine (104-63-2) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With 5percent silver supported on titanium oxide at 25℃; for 10h; Inert atmosphere; Sealed tube; UV-irradiation;	87%

(2-hydroxyethyl)(methyl)amine (109-83-1) + benzaldehyde (100-52-7) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Stage #1: (2-hydroxyethyl)(methyl)amine; benzaldehyde With titanium(IV) isopropylate In ethanol at 20℃; for 6h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; Inert atmosphere; Cooling with ice;	86%

formaldehyd (50-00-0) + N-Benzylethanolamine (104-63-2) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With formic acid In methanol for 20h; Heating;	84%
With formic acid In water at 105℃; Eschweiler-Clarke Methylation;	61%
With formic acid

N-benzyl-N-methyl-2-fluoroethylamine → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With tris(bis(trimethylsilyl)amido)lanthanum(III); water In dichloromethane at 20℃; for 1h; Inert atmosphere;	70%

benzyl-methyl-amine (103-67-3) + 2-bromoethanol (540-51-2) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 9h;	58%

oxirane (75-21-8) + benzyl-methyl-amine (103-67-3) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With zinc dibromide In tetrahydrofuran at 0 - 20℃;	55%

N-Benzylethanolamine (104-63-2) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With tetrafluoroboric acid; sodium chloride In hexane; dichloromethane at 0℃; for 30h;	38%

3-methyl-2-phenyl-oxazolidine (1630-62-2, 121998-66-1) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate
With potassium In tetrahydrofuran for 24h; Ambient temperature; Yield given;
Stage #1: 3-methyl-2-phenyl-oxazolidine With naphthalene; lithium In tetrahydrofuran at -20℃; for 2h; reductive lithiation; Stage #2: With water In tetrahydrofuran at -20℃; for 0.166667h; Substitution;
With hydrogen; {Rh[1,4-bis(diphenylphosphino)butane]COD}B4 In methanol at 20℃; under 37503 - 39003.1 Torr; for 0.3h;

Benzyl-bis-(2-hydroxy-aethyl)-methyl-ammonium (96731-97-4) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With ammonia; potassium amide

3-methyl-2-phenyl-oxazolidine (1630-62-2, 121998-66-1) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + 2-({2-[(2-Hydroxy-ethyl)-methyl-amino]-1,2-diphenyl-ethyl}-methyl-amino)-ethanol

Conditions	Yield
With lithium In tetrahydrofuran for 24h; Ambient temperature; Yield given. Yields of byproduct given;

3-benzyl-1,3-oxazolidine (13657-16-4) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With hydrogen; [1,4-bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 20℃; under 37503 - 39003.1 Torr; for 3h;

benzaldehyde (100-52-7) + (C5H5)2(Cl)Zr{trans-CH=CH[CH2]4OSi(CH3)2(t-Bu)} → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-TsOH*H2O / benzene / Heating 2: H2 / {Rh[1,4-bis(diphenylphosphino)butane]COD}B4 / methanol / 0.3 h / 20 °C / 37503 - 39003.1 Torr View Scheme

benzaldehyde (100-52-7) + polymer-PPh2(1+)-CH2-Ph*Br(1-) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH4Cl / benzene / Heating 2: Li / tetrahydrofuran / 24 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: NH4Cl / benzene / Heating 2: K / tetrahydrofuran / 24 h / Ambient temperature View Scheme

N-benzyl-diethanolamine (101-32-6) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: KNH2, liq. NH3 View Scheme

benzyl chloride (100-44-7) + sodium compound of α-naphthol → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Multi-step reaction with 3 steps 2: diethyl ether 3: KNH2, liq. NH3 View Scheme

(2-hydroxyethyl)(methyl)amine (109-83-1) + benzyl bromide (100-39-0) → 2-›N-(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl)-N[-methylamino]ethanol + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

methanol (67-56-1) + formaldehyd (50-00-0) + benzyl-methyl-amine (103-67-3) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With tert.-butylhydroperoxide; titanium(III) chloride at 20℃; for 0.5h; Acidic aq. solution; Inert atmosphere;

nicardipine hydrochloride (54527-84-3, 69441-18-5, 118705-95-6, 118934-78-4) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + C16H15N2O6(1-)*Na(1+) (1259327-68-8)

Conditions	Yield
With water; sodium hydroxide at 100℃; pH=4.5; Kinetics; pH-value; Concentration; Temperature; Reagent/catalyst; aq. buffer;

benzyl-methyl-amine (103-67-3) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 60 °C 2: tris(bis(trimethylsilyl)amido)lanthanum(III); water / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

methyl bromide (74-83-9) + N-Benzylethanolamine (104-63-2) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With potassium carbonate In acetonitrile

N-methyl-N-benzylglycine (37429-48-4) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;

benzyl-methyl-amine (103-67-3) + glycerol (56-81-5) → 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4)

Conditions	Yield
With N-methyl-1-(thiophen-2-yl)methanamine; tris(triphenylphosphine)ruthenium(II) chloride; 1,1'-bis(dicyclohexylphosphinocyclopentadienyl)iron; potassium tert-butylate In 1,4-dioxane at 150℃; for 20h;	61 %Chromat.

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → 2-(N-benzyl-N-methylamino)ethyl chloride hydrochloride (23510-18-1)

Conditions	Yield
With thionyl chloride at 35℃; for 16h;	100%
With thionyl chloride	95%
With thionyl chloride for 3h; Heating;	94%

propyl benzoate (2315-68-6) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → 1-benzoyloxy-2-(benzyl-methyl-amino)-ethane

Conditions	Yield
With potassium hydroxide	98.1%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + methanesulfonyl chloride (124-63-0) → C11H17NO3S (379267-43-3)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1.5h;	94%
With sodium hydroxide; tetrabutyl-ammonium chloride In dichloromethane; water at -10℃; for 0.916667h;
With sodium hydroxide; tetrabutyl-ammonium chloride In dichloromethane; water at -10℃; for 0.916667h;

(E)-1-Bromo-2-butene (4784-77-4, 39616-19-8, 29576-14-5) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → N-benzyl-N-[but-(2E)-en-1-yl]-N-(2-hydroxyethyl)-N-methylammonium bromide

Conditions	Yield
In acetonitrile at 20℃; for 2h;	92%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + Cinnamyl bromide (4392-24-9) → N-benzyl-N-(2-hydroxyethyl)-N-[methyl-N-3-phenyprop-(2E)-en-1-yl]ammonium bromide

Conditions	Yield
In acetonitrile at 20℃;	90%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → benzyl-(2-{4,6-bis-[2-(benzyl-methyl-amino)-ethoxy]-[1,3,5]triazin-2-yloxy}-ethyl)-methyl-amine

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 14h;	88%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + acetic anhydride (108-24-7) → 2-(benzyl(methyl)amino)ethyl acetate (491878-76-3)

Conditions	Yield
With triethylamine; dmap In dichloromethane at 20℃; for 3h;	87%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → benzyl-(2-chloro-ethyl)-methyl-amine (17542-47-1)

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 3h; Reagent/catalyst; Time; Temperature;	85.6%
With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 3h;	85.6%
With thionyl chloride In chloroform for 15h; Ambient temperature;
With sodium hydroxide; thionyl chloride In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether; dichloromethane; toluene
With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 0.75h;

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → (2-hydroxyethyl)(methyl)amine (109-83-1)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 0.166667h; Heating;	83%
With hydrogen; Pd/C (5percent) In ethanol at 20℃; for 2h;	67%
With hydrazine hydrate; palladium on activated charcoal In ethanol for 2h; Heating;	42%

benzothiophene-3-carbonyl chloride (39827-12-8) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → Benzo[b]thiophene-3-carboxylic acid 2-(benzyl-methyl-amino)-ethyl ester; hydrochloride

Conditions	Yield
In benzene Heating;	80%

1-Chloropropane (540-54-5) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → N-benzyl-N-methyl-2-propoxyethan-1-amine hydrochloride

Conditions	Yield
Stage #1: 2-(N-benzyl-N-methyl)amino-1-ethanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: 1-Chloropropane In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #3: With hydrogenchloride In diethyl ether	80%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + methyl iodide (74-88-4) → benzyl(2-methoxyethyl)methylamine (136705-83-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 1.5h; Heating;	78%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + acetic acid (64-19-7) → 2-(benzyl(methyl)amino)ethyl acetate (491878-76-3)

Conditions	Yield
With tetrabutylammomium bromide; oxygen; sodium nitrite at 70℃; for 4h; Green chemistry;	78%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → 2-(Benzylmethylamino)ethyl benzoylacetate (129108-61-8)

Conditions	Yield
In benzene Heating;	77%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + acrylonitrile (107-13-1) → 3-<2-(N-benzyl-N-methylamino)ethoxy>propionitrile (101264-59-9)

Conditions	Yield
With sodium ethanolate at 80℃; for 7h;	76.7%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + benzyl tetraethylphosphorodiamidite (66954-57-2) → O-(N-methyl-N-benzylaminoethyl) O-benzyl diethylaminophosphite (82878-43-1)

Conditions	Yield
	75.2%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester (50586-80-6) → N-benzyl-2-(2-(2-methoxyethoxy)ethoxy)ethyl-N-methylamine (1351960-19-4)

Conditions	Yield
Stage #1: 2-(N-benzyl-N-methyl)amino-1-ethanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In N,N-dimethyl-formamide at 20℃; Cooling with ice;	74%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → N-benzyl N-methyl ethanolamine N-oxide (15831-63-7)

Conditions	Yield
With dihydrogen peroxide Oxidation;	72%
With α-D-glucose 6-phosphate; oxygen; NADP; cyclohexanone monooxygenase In dichloromethane for 48h; pH=8.6; Oxidation; Enzymatic reaction;	58%

4-(benzyloxy)-1-(4-hydroxyphenyl)pyridin-2(1H)-one (864757-74-4) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → 1-(4-(2-[benzyl(methyl)amino]ethoxy)phenyl)-4-(benzyloxy)pyridin-2(1H)-one

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h; Mitsunobu reaction;	70%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + 5-cyclo-propylmethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyrimidine (98050-83-0) + trichloromethyl chloroformate (503-38-8) → 3-{2-(N-benzyl-N-methylamino)ethoxycarbonyl}-5-cyclopropylmethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-3,4-dihydropyrimidine

Conditions	Yield
With sodium chloride; triethylamine In tetrahydrofuran	68%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + (S)-1,1-Dibenzyl-3-[(R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-piperidinium; bromide → Nicardipine (55985-32-5)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 25℃; for 24h;	67%

4-methyleneoxetan-2-one (674-82-8) + 2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) → acetoacetic acid [2-(N-methyl-N-benzylamino)-ethyl]-ester (54527-65-0)

Conditions	Yield
With triethylamine In chloroform for 10h; Ambient temperature;	63.6%

Upstream product

• 75-21-8 oxirane 
• 103-67-3 benzyl-methyl-amine 
• 96731-97-4 Benzyl-bis-(2-hydroxy-aethyl)-methyl-ammonium 
• 13657-16-4 3-benzyl-1,3-oxazolidine 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 54527-84-3 nicardipine hydrochloride 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 100-52-7 benzaldehyde 
• 56-81-5 glycerol 
• 104-63-2 N-Benzylethanolamine 
• 37429-48-4 N-methyl-N-benzylglycine 
• 74-83-9 methyl bromide 
• 100-39-0 benzyl bromide 

Downstream Products

• 108930-83-2 4-Methyl-6-(3-nitro-phenyl)-2-oxo-3,6-dihydro-2H-pyrimidine-1,5-dicarboxylic acid 1-[2-(benzyl-methyl-amino)-ethyl] ester 5-ethyl ester 
• 143874-16-2 2-(4-Isobutyl-phenyl)-propionic acid 2-(benzyl-methyl-amino)-ethyl ester 
• 121484-71-7 6-Methyl-4-(2-nitro-phenyl)-2-oxo-3,4-dihydro-2H-pyrimidine-1,5-dicarboxylic acid 1-[2-(benzyl-methyl-amino)-ethyl] ester 5-cyclopropylmethyl ester 
• 2133-10-0 Schefelsaeure-mono-<2-(benzyl-methyl-amino)-aethylester> 
• 55985-32-5 Nicardipine 
• 17542-47-1 benzyl-(2-chloro-ethyl)-methyl-amine 
• 7026-00-8 benzyl-methyl-vinyl-amine 
• 379267-43-3 C₁₁H₁₇NO₃S 
• 108932-19-0 2-[[(4-methoxyphenyl)methyl]thio]-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, 5-(1-methylethyl) 1-[2-[methyl(phenylmethyl)amino]ethyl]ester 
• 154018-19-6 3-Phenyl-4-(2-(N-benzyl-N-methylamino)ethoxy)-1,2,5-oxadiazole-2-oxide hydrochloride 
• 116643-69-7 1-(1-methylvinyl)-3-[2-(N-benzyl-N-methylamino)ethyl]-2-benzimidazolinone 
• 1351960-19-4 N-benzyl-2-(2-(2-methoxyethoxy)ethoxy)ethyl-N-methylamine 
• 54527-65-0 acetoacetic acid [2-(N-methyl-N-benzylamino)-ethyl]-ester 

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