2842-44-6

Basic information

• Product Name: N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE
• Synonyms: N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE;2-(N-methyl-p-toluidino)ethanol;N-Methyl-N-hydroxyethyl-P-toluidine;N-(2-Hydroxyethyl)-N-methyl-p-toluidine;2-[Methyl(4-methylphenyl)amino]ethanol;2-(N-Methyl-N-4-tolylamino)ethanol;FirstCure MHPT;N-Methyl-N-(2-hydroxyethyl)-p-toluidine
• CAS NO: 2842-44-6
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 220-638-5
• Mol File: 2842-44-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 298.1°Cat760mmHg
• Flash Point: 148.8°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 0.00058mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.69±0.10(Predicted)
• CAS DataBase Reference: N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE(2842-44-6)
• EPA Substance Registry System: N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE(2842-44-6)

Safety Data

• Hazardous Substances Data: 2842-44-6(Hazardous Substances Data)

Usage

Uses

N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE is an amine organic compound, which can be used as intermediate in organic synthesis.

Synthesis

Add reactant (0.2 mmol, 1.0 equiv), THF (2.0 mL) and CH2Br2?(0.6 mmol, 3.0 equiv) to a flame-dried 10 mL Schlenk tube in a glove box. Seal and take out of the glove box. Cool the reaction mixture to -78°C. Add nBuLi (0.56 mmol, 2.8 equiv) dropwise under N2?atmosphere within 3minutes. Stir the reaction at -78°C for 30 minutes and add ZnCl2?(0.1 mL, 0.5equiv, 1.0 M in Et2O). Allow the mixture to warm to room temperature and stir for 1 hour. Cool the mixture to 0°C. Add a premixture of H2O2?(30% in H2O, 0.5 mL) and NaOH (2.0 M, 1.0 mL). Stir the mixture at room temperature for another 1 hour and dilute with water (20 mL). Extract with DCM (30 mL x 2) and dry over Na2SO4. Filter and concentrate under vacuum. Purify the crude product by silica gel flash column chromatography to obtain product.?1H NMR (CDCl3, 500 MHz) δ 7.08 (d, J = 8.4 Hz, 2H), 6.78 (d, J = 8.4 Hz,2H), 3.80 (t, J = 5.6 Hz, 2H), 3.43 (t, J = 5.4 Hz, 2H), 2.93 (s, 3H), 2.28 (s, 3H), 2.01 (brs, 1H).?13C NMR (CDCl3, 125 MHz) δ 148.3, 129.8, 127.1, 114.0, 60.1, 56.2, 39.1, 20.4. Fig The synthetic method of N-(2-hydroxyethyl)-N-methyl-4-toluidine

InChI:InChI=1/C10H15NO/c1-9-3-5-10(6-4-9)11(2)7-8-12/h3-6,12H,7-8H2,1-2H3

Synthetic route

N-methyl-p-toluidine (623-08-5) + glycerol (56-81-5) → 2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6)

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;	91%

(2-hydroxyethyl)(methyl)amine (109-83-1) + 4-tolyl iodide (624-31-7) → 2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6)

Conditions	Yield
With copper(l) iodide; sodium hydroxide In water; dimethyl sulfoxide at 90℃; for 16h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	82%

D-Xylose (87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2) + N-methyl-p-toluidine (623-08-5) → 2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6)

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); acetic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 150℃; for 16h; Inert atmosphere; Glovebox; chemoselective reaction;	75%

hydriodide of methyl-<β-oxy-ethyl>-p-toluidine → 2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6)

Conditions	Yield
With potassium carbonate

N-(4-methylphenyl)-N-methylglycine ethyl ester (120547-24-2) → 2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6)

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

3-{2-[methyl(4'-methylphenyl)amino]ethyl}-4-oxo-3H,4H-imidazo[1,5-d][1,2,3,5]tetrazine-8-carboxamide → C10H14NO4P(2-) + 2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6) + 5-Aminoimidazole-4-carboxamide (360-97-4)

Conditions	Yield
With disodium hydrogenphosphate; citric acid In dimethyl sulfoxide at 37℃; Kinetics; pH-value;

2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6) → N-(2-iodoethyl)-N-methyl-4-methylaniline

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In toluene at 100℃; for 28h; Inert atmosphere;	79%

2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6) + benzyl bromide (100-39-0) → N-(2-(benzyloxy)ethyl)-N-methyl-p-toluidine (1262227-05-3)

Conditions	Yield
Stage #1: 2-(methyl(p-tolyl)amino)ethan-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;

2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6) → diethyl 2-(2-((4-tolyl)methylamino)ethyl)malonate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 28 h / 100 °C / Inert atmosphere 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.08 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 80 °C / Inert atmosphere View Scheme

2-(methyl(p-tolyl)amino)ethan-1-ol (2842-44-6) → diethyl 1,6-dimethyl-2,3-dihydroquinoline-4,4(1H)-dicarboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 28 h / 100 °C / Inert atmosphere 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.08 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 80 °C / Inert atmosphere 3.1: copper(II) 2-ethylhexanoate; N-ethyl-N,N-diisopropylamine / toluene / 19 h / 120 °C View Scheme

Upstream product

• 120547-24-2 N-(4-methylphenyl)-N-methylglycine ethyl ester 
• 87-72-9 D-Xylose 
• 623-08-5 N-methyl-p-toluidine 
• 56-81-5 glycerol 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 1262227-05-3 N-(2-(benzyloxy)ethyl)-N-methyl-p-toluidine 

Relevant articles and documents

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