693-05-0

Basic information

• Product Name: 3-Methylaminopropionitrile
• Synonyms: (2-Cyanoethyl)methyl amine;(2-cyanoethyl)methylamine;(Methylamino)propionitrile;3-(methylamino)-propanenitril;3-(Methylamino)propanenitrile;3-(methylamino)-propionitril;3-(n-methylamino)propionitrile;ai3-26057
• CAS NO: 693-05-0
• Molecular Formula: C₄H₈N₂
• Molecular Weight: 84.12
• EINECS: 211-740-0
• Product Categories: Industrial/Fine Chemicals;Building Blocks;C1 to C5;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 693-05-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 49-50 °C
• Boiling Point: 182-186 °C
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 0.899 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.883mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• PKA: 8.27±0.10(Predicted)
• BRN: 1699160
• CAS DataBase Reference: 3-Methylaminopropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylaminopropionitrile(693-05-0)
• EPA Substance Registry System: 3-Methylaminopropionitrile(693-05-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21-36/37/38
• Safety Statements: 26-36/37-37/39
• WGK Germany: 3
• RTECS: TZ4910000
• HazardClass: IRRITANT
• Hazardous Substances Data: 693-05-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW LIQUID

Uses

(3-MethylaMinopropionitrile) Aminoproponitriles can be used as inhibitors of oxidase enzymes and as a reagent for aminomethylphosphine ligands or the synthesis of aminobenzothiazoles.

InChI:InChI=1/C4H8N2/c1-6-4-2-3-5/h6H,2,4H2,1H3/p+1

Synthetic route

acrylonitrile (107-13-1) + methylamine (74-89-5) → N-(2-cyanoethyl)-N-methylamine (693-05-0)

Conditions	Yield
With C12H18NO3S(1+)*HO4S(1-) at 25℃; for 0.0666667h; Ionic liquid; Neat (no solvent); chemoselective reaction;	99%
In methanol a) 0 deg C, 1 h, b) RT, overnight;	84%
In ethanol at 15℃; under 760.051 Torr;	83.5%

3-methyl-2-oxo-1,3-oxazolidine (19836-78-3) → N-(2-cyanoethyl)-N-methylamine (693-05-0)

Conditions	Yield
With potassium cyanide; 18-crown-6 ether at 100℃; for 8h; Neat (no solvent);	50%

methanol (67-56-1) + acrylonitrile (107-13-1) + methylamine (74-89-5) → N-(2-cyanoethyl)-N-methylamine (693-05-0)

Conditions	Yield
unter Kuehlung;
unter Kuehlung;

N-(2-cyanoethyl)-N-methylamine (693-05-0) → 3-(methylamino)propanamidoxime (16750-50-8)

Conditions	Yield
With hydroxylamine In ethanol; water at 20 - 50℃; for 27h;	99.5%
With hydroxylamine

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 1-chloro-2,4-dinitro-benzene (97-00-7) → 2,4-dinitro-N-methyl-N-β-cyanoethylaniline (81676-70-2)

Conditions	Yield
at 20℃; for 7h;	99%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + di-tert-butyl dicarbonate (24424-99-5) → t-butyl N-(2-cyanoethyl)-N-methylcarbamate (128304-84-7)

Conditions	Yield
In dichloromethane	99%
In dichloromethane at 20℃; for 2h;	90%
In dichloromethane at 20℃; for 2h;	90%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + p-tolyl isoselenocyanate (14223-45-1) → 1-(2-cyanoethyl)-1-methyl-3-(4-tolyl)selenourea (1332566-42-3)

Conditions	Yield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;	99%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + [4S-[4α,5β,6β(S*)]]-4-methyl-3-[[[(2-methylpropoxy)carbonyl]oxy]methyl]-7-oxo-6-[1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hepten-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester (246848-23-7) → C28H40N4O6Si

Conditions	Yield
With 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In N,N-dimethyl-formamide at 20℃; for 12 - 36h;	98%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + p-chlorphenylisocyanate (104-12-1) → 3-(4-chlorophenyl)-1-(2-cyanoethyl)-1-methylurea (91090-02-7)

Conditions	Yield
In benzene	96%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 2,3-epoxy-2-methyl-1-phenylpropan-1-one (49837-27-6) → 2-Hydroxy-2-methyl-3--1-phenyl-1-propanone (108440-19-3)

Conditions	Yield
In isopropyl alcohol for 15h; Heating;	96%

2,4-dichlorothieno[3,2-d]pyrimidine (16234-14-3) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → 3-((2-chlorothieno-[3,2-d]pyrimidin-4-yl)(methyl)amino)propanenitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃;	95%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + sodium 4-methylbenzenesulfinate (824-79-3) → N-(2-cyanoethyl)-N,4-dimethylbenzenesulfonamide (21230-34-2)

Conditions	Yield
With iodine In water at 20℃; for 3h; Green chemistry;	93%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 1-nitroanthraquinone (82-34-8) → 1-(methylamino)anthraquinone (82-38-2)

Conditions	Yield
In butan-1-ol at 118℃; for 135h;	92%
In methanol at 130℃; for 13h; Rate constant; other solvent;

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4) → N-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-N-methyl-2-cyanoethyl-amine (76362-28-2)

Conditions	Yield
With toluene-4-sulfonic acid In butan-1-ol for 3h; Heating / reflux;	92%
In i-Amyl alcohol at 135 - 140℃; for 4h;	78%
In i-Amyl alcohol

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 3-nitrosalicylic aldehyde (5274-70-4) → 3-((2-hydroxy-3-nitrobenzyl)amino)propanenitrile

Conditions	Yield
Stage #1: N-(2-cyanoethyl)-N-methylamine; 3-nitrosalicylic aldehyde In tetrahydrofuran for 0.25h; Stage #2: With sodium diacetoxy(acetyl)boranuide In tetrahydrofuran at 20℃; for 16h;	92%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-fluorobenzoyl chloride (403-43-0) → N-(2-cyanoethyl)-4-fluoro-N-methylbenzamide

Conditions	Yield
With triethylamine In water; toluene at 20℃; for 1.5h;	92%

N-(2-cyanoethyl)-N-methylamine (693-05-0) → n-methyl-β-alanine (2679-14-3)

Conditions	Yield
With sulfuric acid for 3h; Heating;	91%
With barium dihydroxide

2-acetyl-2-methyloxirane (4587-00-2) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → 4--3-hydroxy-3-methyl-2-butanone (78563-49-2)

Conditions	Yield
In isopropyl alcohol for 15h; Heating;	91%

Cyclopentanecarboxylic acid chloride (4524-93-0) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → N-(3-cyanopropyl)-N-methylcyclopentanecarboxamide (72104-46-2)

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;	91%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → 3-[(4-Methanesulfonyl-2-nitro-phenyl)-methyl-amino]-propionitrile (81689-46-5)

Conditions	Yield
In butan-1-ol at 118℃; for 2h;	91%

(η(5)-pentadienyl)Fe(CO)3(+) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → [(((2-5-η)-2,4-pentadienyl)methylamino)propionitrile]tricarbonyliro (166832-71-9)

Conditions	Yield
With triethylamine In tetrahydrofuran N2-atmosphere; stirring (-40°C, 20 min, 25°C, 30 min); 50% EtOAc / hexanes addn., washing (H2O, brine), drying (MgSO4), concg.,chromy. (SiO2, 15% EtOAc / hexanes);	91%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride (80745-07-9) → N-(2-Cyanoethyl)-4-methoxy-N,2,3,6-tetramethylbenzenesulfonamide (1073697-24-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 16h;	91%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + Fmoc-Glu(OH)-OtBu → tert-butyl (2S)-4-[(2-cyanoethyl)(methyl)carbamoyl]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;	91%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + ethyl bromoacetate (105-36-2) → [(2-cyanoethyl)methylamino]acetic acid ethyl ester (24286-82-6)

Conditions	Yield
With potassium carbonate In butanone Heating;	88.9%
With potassium carbonate In butanone Heating;

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl isocyanate (142010-50-2) → 1-(2-Cyano-ethyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-1-methyl-urea

Conditions	Yield
In diethyl ether for 2h; Ambient temperature;	88%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + dimedone (126-81-8) → 3-<2-cyanoethyl(methyl)amino>-5,5-dimethylcyclohex-2-enone (90043-98-4)

Conditions	Yield
In xylene for 3h; Heating;	87%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 5'-tosyladenosine (5135-30-8) → 5'-<(2-cyanoethyl)methylamino>-5'-deoxyadenosine (72648-38-5)

Conditions	Yield
at 20℃; for 120h;	87%
at 20℃; for 120h;	87%
for 120h; Ambient temperature;	80%
for 168h; Ambient temperature;	42%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + benzoic acid anhydride (93-97-0) → N-methyl-N-cyanoethyl benzamide (23873-66-7)

Conditions	Yield
With sodium hydroxide In dichloromethane	87%

N-methylmaleimide (930-88-1) + N-(2-cyanoethyl)-N-methylamine (693-05-0) + benzyl thiosulphate (6313-36-6) → 3-((4-(benzylthio)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)(methyl)amino)propanenitrile

Conditions	Yield
With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; for 24h; Schlenk technique;	86%
With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; for 24h;	86%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 6-(tert-butyl)-2,4-dichlorothieno[3,2-d]pyrimidine → 3-((6-(tert-butyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)(methyl)amino)propanenitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	86%

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-bromonaphthalene-1,8-dicarboximide (52559-36-1) → 4-N-methylaminonaphthalimide (89393-98-6)

Conditions	Yield
In methanol at 130℃; Rate constant; Kinetics; Thermodynamic data; sealed tube; other temperature;	85%
In methanol at 130℃; for 18h; sealed tube;	85%

1,2,3,4-tetrahydroquinoxaline (3476-89-9) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → 3,3'-(quinoxaline-2,6-diylbis(methylazanediyl))dipropanenitrile

Conditions	Yield
With pyridine; N-hydroxyphthalimide; oxygen; copper dichloride In N,N-dimethyl-formamide at 30℃; for 2h; chemoselective reaction;	85%

Upstream product

• 67-56-1 methanol 
• 107-13-1 acrylonitrile 
• 74-89-5 methylamine 
• 19836-78-3 3-methyl-2-oxo-1,3-oxazolidine 

Downstream Products

• 2213-08-3 ethyl 3-methylaminopropionate 
• 6291-84-5 N-Methyl-1,3-propanediamine 
• 30380-98-4 N'-Phenyl-N-methyl-N-(2-cyanaethyl)thioharnstoff 
• 20749-62-6 3-[(2-Chloro-benzyl)-methyl-amino]-propionitrile 
• 30388-44-4 methyl 4-methyl-amino-3-nitrophenyl sulfone 
• 81689-46-5 3-[(4-Methanesulfonyl-2-nitro-phenyl)-methyl-amino]-propionitrile 
• 85020-87-7 2-cyano-4-nitro-N-methylaniline 
• 81676-74-6 2-cyano-4-nitro-N-methyl-N-β-cyanoethylaniline 
• 82-38-2 1-(methylamino)anthraquinone 
• 68528-28-9 3-Nitro-4-methylamino-benzolsulfonsaeure-dimethylamid 
• 81676-73-5 4-[(2-Cyano-ethyl)-methyl-amino]-N,N-dimethyl-3-nitro-benzenesulfonamide 
• 2382-08-3 N-methylnaphthalimide 
• 54229-22-0 4-methylamino-N-methyl-1,8-naphthalic imide 
• 90043-98-4 3-<2-cyanoethyl(methyl)amino>-5,5-dimethylcyclohex-2-enone 

Relevant articles and documents

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A process for the preparation of alfuzosin hydrochloride method (by machine translation)

The invention relates to a process for the preparation of alfuzosin hydrochloride method, method comprises the following steps: (1) 15 °C following, acrylonitrile into the the methylamine is mellow solution to stir, by distillation to obtain (I); (2) to (I) is dripped reducing agent in an organic solvent, heating to reflux, then slowly sequentially into the 25% sodium hydroxide solution and distilled water, by the distillation treatment to obtain the (II); (3) under dry condition, the thionyl chloride is slowly dripped into the 2 - tetrahydrofuran formic acid, a 2 - tetrahydrofuran chloride; (4) the temperature control in the 5 - 15 °C conditions, will be 2 - tetrahydrofuran formyl the chlorine drips into containing acid, organic solvent and (II) of the mixed solution, then completing the stirring 3 hours, for 25% sodium hydroxide solution to neutralize, by organic solvent extraction, (III) be; (5) to (III) with 2 - chloro - 4 - amino - 6, 7 - dimethoxy quinazoline in presence of organic solvent, reflux stirring 4 - 10 hours, cooling and filtering, and steaming and removing the organic solvent, acetone dispersed precipitate solid, then re-crystallizing mixed solvent, to get the alfuzosin hydrochloride (IV). (by machine translation)

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