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

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

Uses

Used in Pharmaceutical Industry:
3-Methylaminopropionitrile is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile intermediate in the development of new drugs, particularly those targeting oxidase enzymes.
Used in Chemical Research:
In the field of chemical research, 3-Methylaminopropionitrile serves as a reagent for the synthesis of aminomethylphosphine ligands. These ligands are essential in various chemical reactions, particularly in catalysis, where they can improve the efficiency and selectivity of the process.
Used in Synthesis of Aminobenzothiazoles:
3-Methylaminopropionitrile is also utilized in the synthesis of aminobenzothiazoles, which are important compounds in the development of new pharmaceuticals and agrochemicals. These compounds exhibit a wide range of biological activities, making them valuable in the creation of novel therapeutic agents.
Overall, 3-Methylaminopropionitrile is a valuable compound with diverse applications in the pharmaceutical and chemical research industries. Its unique structure and reactivity make it an essential component in the development of new drugs and chemical processes.

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

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

Downstream Products

• 2213-08-3 ethyl 3-methylaminopropionate 
• 6291-84-5 N-Methyl-1,3-propanediamine 
• 6640-05-7 N-methyl-N-phenylcarbamoyl-β-alanine nitrile 
• 52317-87-0 3-(4-Bromo-2-methyl-phenyl)-1-(2-cyano-ethyl)-1-methyl-thiourea 
• 59049-62-6 N-(2-Benzoyl-4-nitro-phenyl)-2-[(2-cyano-ethyl)-methyl-amino]-N-methyl-acetamide 
• 52317-50-7 3-(4-Chloro-2-methyl-phenyl)-1-(2-cyano-ethyl)-1-methyl-thiourea 
• 686-56-6 1-(2-Cyanoethyl)-1-methylurea 
• 19946-51-1 cis-N-Methyl-N-(2-cyanoethyl)-3-benzyloxycarbonylamino-cyclopentan-carbonamid 
• 13181-82-3 3-({5-[1-(4-Isopropyl-phenyl)-meth-(Z)-ylideneaminooxy]-2,4-dinitro-phenyl}-methyl-amino)-propionitrile 
• 60153-49-3 β-methyl-nitrosaminopropionitrile 
• 2679-14-3 n-methyl-β-alanine 
• 16283-58-2 1--cyclohexen-(1) 
• 20749-62-6 3-[(2-Chloro-benzyl)-methyl-amino]-propionitrile 
• 25675-94-9 (2-Cyano-ethyl)-methyl-dithiocarbamic acid 2,4-dinitro-phenyl ester 

Relevant articles and documents

Improved method used for preparing quinazoline drugs

The invention relates to an improved method used for preparing quinazoline drugs, and provides a synthesis route taking 2-chloro-4-amino-6,7-dimethoxyquinazoline as an intermediate. The synthesis route comprises following steps: acrylonitrile and a methylamine alcohol solution are subjected to amination reaction so as to obtain intermediate (I); triethylamine is taken as an acid binding agent, andbenzyl chloride is taken as a protective group so as to obtain an intermediate (II); a metal hydride is adopted so as to obtain an intermediate (III) through reduction; acylation with tetrahydro-2-furancarbonylchloride is carried out so as to obtain an intermediate (IV); the intermediate (IV) and ammonium formate are subjected to hydrogenolysis under catalytic effect of palladium on carbon so asto obtain an intermediate (V); and at least condensation reaction with 2-chloro-4-amino-6,7-dimethoxyquinazoline is carried out so as to obtain quinazoline drug Alfuzosin Hydrochloride (VI). Comparedwith the prior art, the improved method possesses following advantages: operation is simple and safe; reaction conditions are convenient to control; energy consumption is low; yield is stable; and industrialized application prospect is promising.

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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