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6011-14-9

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6011-14-9 Usage

Chemical Properties

White to light brown solid

Uses

Used as pharmaceutical intermediates, organic synthetic raw material transportation.

Application

Aminoacetonitrile is a useful synthetic intermediate. It is a reagent used to synthesize dipeptide nitriles as reversible and potent cathepsin S inhibitors. It can also used to prepare substituted cyclic ureas as possible HIV protease inhibitors.

Preparation

Synthesis of Aminoacetonitrile Hydrochloride by Reaction of Aminoacetonitrile with Hydrogen Chloride in Methanol: mixing the aminoacetonitrile with hydrogen chloride methanol solution, reacting at 45-50°C for 1-2 hours, cooling to below 5°C, filtering, and centrifugalizing to obtain the aminoacetonitrile hydrochloride, wherein in the hydrogen chloride methanol solution, the content of hydrogen chloride is 30-50 wt%, and the water content is less than or equal to 1%.Preparation method of aminoacetonitrile hydrochloride

Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and HCl.

Purification Methods

The salt recrystallises from dilute EtOH as hygroscopic leaflets. It is best to crystallise it from absolute EtOH/Et2O (1:1) and then recrystallise it from absolute EtOH. The melting point recorded ranges from 144o to 174o. The free base has b 58o/15mm with partial decomposition. [Klages J Prakt Chem [2] 65 189 1902, Mange J Am Chem Soc 56 2197 1934, Goldberg & Kelly J Chem Soc 1371 1947, Beilstein 4 H 344, 4 I 468, 4 II 783, 4 III 1120, 4 IV 2363.]

Check Digit Verification of cas no

The CAS Registry Mumber 6011-14-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,0,1 and 1 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 6011-14:
(6*6)+(5*0)+(4*1)+(3*1)+(2*1)+(1*4)=49
49 % 10 = 9
So 6011-14-9 is a valid CAS Registry Number.
InChI:InChI=1/C2H4N2.ClH/c3-1-2-4;/h1,3H2;1H

6011-14-9 Well-known Company Product Price

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  • Alfa Aesar

  • (41984)  Aminoacetonitrile hydrochloride, 98+%   

  • 6011-14-9

  • 25g

  • 656.0CNY

  • Detail

6011-14-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Aminoacetonitrile Hydrochloride

1.2 Other means of identification

Product number -
Other names Acetonitrile, amino-, monohydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6011-14-9 SDS

6011-14-9Synthetic route

2-aminoacetonitrile
540-61-4

2-aminoacetonitrile

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 20 - 30℃; for 2h; Temperature;82.8%
sodium cyanide
773837-37-9

sodium cyanide

formaldehyd
50-00-0

formaldehyd

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

Conditions
ConditionsYield
Stage #1: sodium cyanide; formaldehyd With ammonium hydroxide
Stage #2: With hydrogenchloride
phthalic anhydride
85-44-9

phthalic anhydride

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

N-(cyanomethyl)phthalimide
3842-20-4

N-(cyanomethyl)phthalimide

Conditions
ConditionsYield
With triethylamine In chloroform for 6h; Heating;100%
With triethylamine In chloroform at 10℃; for 12.5h; Temperature; Reflux;98.6%
With triethylamine In chloroform for 18h; Reflux;75%
N-(t-butoxycarbonyl)-isoleucine
13139-16-7

N-(t-butoxycarbonyl)-isoleucine

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-tert-Butyloxycarbonylamino-3-methyl-pentanoic acid cyanomethyl-amide

2-tert-Butyloxycarbonylamino-3-methyl-pentanoic acid cyanomethyl-amide

Conditions
ConditionsYield
With benzotriazol-1-ol In DMF (N,N-dimethyl-formamide); water at 20℃; for 1h;100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

N-(cyanomethyl)isonicotinamide
1184796-18-6

N-(cyanomethyl)isonicotinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

(2-hydroxy-3-methoxybenzylideneamino)acetonitrile
1279019-01-0

(2-hydroxy-3-methoxybenzylideneamino)acetonitrile

Conditions
ConditionsYield
With sodium acetate In methanol at 20℃; for 2h;99%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

p-chlorobenzyl cyanide
140-53-4

p-chlorobenzyl cyanide

Conditions
ConditionsYield
With sodium nitrite In water; toluene at 50℃; for 24h; Schlenk technique;99%
ethyl 2-(allylthio)acetate
15224-05-2

ethyl 2-(allylthio)acetate

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

ethyl 2-((1-cyanobut-3-en-1-yl)thio)acetate

ethyl 2-((1-cyanobut-3-en-1-yl)thio)acetate

Conditions
ConditionsYield
With meso-tetraphenylporphyrin iron(III) chloride; sodium nitrite In dichloromethane; water at 20℃; for 15h; Inert atmosphere; diastereoselective reaction;99%
N-benzyl-N-(4-methylphenyl)amine
5405-15-2

N-benzyl-N-(4-methylphenyl)amine

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

[N-benzyl-(4-methylphenyl)amino]acetonitrile

[N-benzyl-(4-methylphenyl)amino]acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With FeCl(tiprp); sodium nitrite In toluene at 55℃; Inert atmosphere; Flow reactor;
Stage #2: N-benzyl-N-(4-methylphenyl)amine In toluene at 20℃; Inert atmosphere;
99%
N-benzyl-3-methylaniline
5405-17-4

N-benzyl-3-methylaniline

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

3-(benzyl(m-tolyl)amino)acetonitrile

3-(benzyl(m-tolyl)amino)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With FeCl(tiprp); sodium nitrite In toluene at 55℃; Inert atmosphere; Flow reactor;
Stage #2: N-benzyl-3-methylaniline In toluene at 20℃; Inert atmosphere;
99%
2-fluorothiophenol
2557-78-0

2-fluorothiophenol

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-((2-fluorophenyl)thio)acetonitrile
61081-27-4

2-((2-fluorophenyl)thio)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With FeCl(tiprp); sodium nitrite In toluene at 55℃; Inert atmosphere; Flow reactor;
Stage #2: 2-fluorothiophenol In toluene at 20℃; for 3h; Inert atmosphere;
99%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

1-(2-methylphenyl)-1H-indole
210162-61-1

1-(2-methylphenyl)-1H-indole

2-(1-(2-methylphenyl)-1H-indol-3-yl)acetonitrile

2-(1-(2-methylphenyl)-1H-indol-3-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With sodium nitrite In water at 55℃;
Stage #2: 1-(2-methylphenyl)-1H-indole With meso-tetraphenylporphyrin iron(III) chloride In dichloromethane; water at 20℃; for 2.16h; Inert atmosphere;
99%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

N-(p-tolyl)indole
167283-32-1

N-(p-tolyl)indole

2-(1-(p-tolyl)-1H-indol-3-yl)acetonitrile
1632196-77-0

2-(1-(p-tolyl)-1H-indol-3-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With sodium nitrite In water at 55℃;
Stage #2: N-(p-tolyl)indole With meso-tetraphenylporphyrin iron(III) chloride In dichloromethane; water at 20℃; for 2.16h; Inert atmosphere;
99%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

1-(3-methylphenyl)-1H-indole
210162-62-2

1-(3-methylphenyl)-1H-indole

2-(1-(3-methylphenyl)-1H-indol-3-yl)acetonitrile

2-(1-(3-methylphenyl)-1H-indol-3-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With sodium nitrite In water at 55℃;
Stage #2: 1-(3-methylphenyl)-1H-indole With meso-tetraphenylporphyrin iron(III) chloride In dichloromethane; water at 20℃; for 2.16h; Inert atmosphere;
99%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

N-(cyanomethyl)isobutyramide

N-(cyanomethyl)isobutyramide

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;99%
2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

N-(cyanomethyl)thiophe ne-2-carboxamide
349097-56-9

N-(cyanomethyl)thiophe ne-2-carboxamide

Conditions
ConditionsYield
With pyridine at 0℃; for 12h;99%
With pyridine at 0℃; for 12h;90%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(4-chlorobenzylideneamino)acetonitrile
95730-58-8

2-(4-chlorobenzylideneamino)acetonitrile

Conditions
ConditionsYield
With sodium acetate In methanol at 20℃; for 2h;98%
Stage #1: 2-aminoacetonitrile hydrochloride With triethylamine In ethanol at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4-chlorobenzaldehyde In ethanol Inert atmosphere;
3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

3-methoxyphenylacetonitrile
19924-43-7

3-methoxyphenylacetonitrile

Conditions
ConditionsYield
With sodium nitrite In water; toluene at 50℃; for 24h; Schlenk technique;98%
1-methyl-2-prop-2-enylsulfanylbenzene
24309-31-7

1-methyl-2-prop-2-enylsulfanylbenzene

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-((2-methylphenyl)thio)pent-4-enenitrile

2-((2-methylphenyl)thio)pent-4-enenitrile

Conditions
ConditionsYield
With meso-tetraphenylporphyrin iron(III) chloride; sodium nitrite In dichloromethane; water at 20℃; for 15h; Inert atmosphere;98%
(S)-(α,α-dimethylallyl)-p-chlorothiophenol
1173006-79-5

(S)-(α,α-dimethylallyl)-p-chlorothiophenol

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-((4-chlorophenyl)thio)-3,3-dimethylpent-4-enenitrile

2-((4-chlorophenyl)thio)-3,3-dimethylpent-4-enenitrile

Conditions
ConditionsYield
With meso-tetraphenylporphyrin iron(III) chloride; sodium nitrite In dichloromethane; water at 20℃; for 15h; Inert atmosphere;98%
4-methylphenyl prop-2'-ynyl sulfide
33597-89-6

4-methylphenyl prop-2'-ynyl sulfide

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-((4-methylphenyl)thio)-4λ5-penta-3,4-dienenitrile

2-((4-methylphenyl)thio)-4λ5-penta-3,4-dienenitrile

Conditions
ConditionsYield
With meso-tetraphenylporphyrin iron(III) chloride; sodium nitrite In dichloromethane; water at 20℃; for 15h; Inert atmosphere;98%
N-Benzylaniline
758640-21-0

N-Benzylaniline

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-(benzyl(phenyl)amino)acetonitrile
36271-19-9

2-(benzyl(phenyl)amino)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-aminoacetonitrile hydrochloride With FeCl(tiprp); sodium nitrite In toluene at 55℃; Inert atmosphere; Flow reactor;
Stage #2: N-Benzylaniline In toluene at 20℃; for 1h; Catalytic behavior; Solvent; Inert atmosphere;
98%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

propionic acid anhydride
123-62-6

propionic acid anhydride

N-(cyanomethyl)propionamide
36801-37-3

N-(cyanomethyl)propionamide

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;98%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

N-(cyanomethyl)-4-iodobenzamide
177724-09-3

N-(cyanomethyl)-4-iodobenzamide

Conditions
ConditionsYield
With pyridine at 0℃; for 12h;98%
With pyridine at 0℃; for 12h;97%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

acetic anhydride
108-24-7

acetic anhydride

acetylaminoacetonitrile
4814-80-6

acetylaminoacetonitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane; water at 5 - 20℃; for 3h;97.94%
With pyridine at 20℃; for 12h;70%
With pyridine for 48h; Ambient temperature;60%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

(2R)-2-(3-bromophenyl)-4-methylpentanoic acid
513246-79-2

(2R)-2-(3-bromophenyl)-4-methylpentanoic acid

(2R)-2-(3-bromophenyl)-N-(cyanomethyl)-4-methylpentanamide
513246-85-0

(2R)-2-(3-bromophenyl)-N-(cyanomethyl)-4-methylpentanamide

Conditions
ConditionsYield
Stage #1: (2R)-2-(3-bromophenyl)-4-methylpentanoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 2-aminoacetonitrile hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2.5h;
97.5%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

tert-butyl cyanomethylcarbamate
85363-04-8

tert-butyl cyanomethylcarbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane; water at 20℃; for 15h; Cooling with ice;97.1%
With sodium hydroxide In 1,4-dioxane; water for 24h; Ambient temperature;96%
With triethylamine In dichloromethane for 16h; Ambient temperature;95%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

(2-hydroxy-5-methoxybenzylideneamino)acetonitrile
1279019-07-6

(2-hydroxy-5-methoxybenzylideneamino)acetonitrile

Conditions
ConditionsYield
With sodium acetate In methanol at 20℃; for 2h;97%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

salicylaldehyde
90-02-8

salicylaldehyde

(2-hydroxy-benzylideneamino)acetonitrile
122373-28-8

(2-hydroxy-benzylideneamino)acetonitrile

Conditions
ConditionsYield
With sodium acetate In methanol at 20℃; for 2h;97%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

5-chlorosalicyclaldehyde
635-93-8

5-chlorosalicyclaldehyde

(2-hydroxy-5-chlorobenzylideneamino)acetonitrile
1279019-02-1

(2-hydroxy-5-chlorobenzylideneamino)acetonitrile

Conditions
ConditionsYield
With sodium acetate In methanol at 20℃; for 2h;97%
2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4-tert-butylbenzyl cyanide
3288-99-1

4-tert-butylbenzyl cyanide

Conditions
ConditionsYield
With sodium nitrite In water; toluene at 50℃; for 24h; Schlenk technique;97%
phenyl propargyl sulfide
5651-88-7

phenyl propargyl sulfide

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

2-(phenylthio)-4λ5-penta-3,4-dienenitrile

2-(phenylthio)-4λ5-penta-3,4-dienenitrile

Conditions
ConditionsYield
With meso-tetraphenylporphyrin iron(III) chloride; sodium nitrite In dichloromethane; water at 20℃; for 15h; Inert atmosphere;97%

6011-14-9Relevant articles and documents

Enabling iron catalyzed Doyle-Kirmse rearrangement reactions with: In situ generated diazo compounds

Hock, Katharina J.,Mertens, Lucas,Hommelsheim, Renè,Spitzner, Robin,Koenigs, Rene M.

, p. 6577 - 6580 (2017)

Slow addition of sodium nitrite allows the in situ preparation of highly explosive diazo compounds and enables their safe and scalable application in iron catalyzed rearrangement reactions of allylic and propargylic sulfides. With catalyst loadings as low as 0.1 mol% an effective entry into α-mercapto-nitriles, α-mercapto-esters and α-trifluoromethyl-sulfides on a gram-scale is achieved.

Fluorobenzamides and uses thereof

-

, (2008/06/13)

The invention relates to fluorobenzamide derivatives of the formula wherein R1, R2, R3 R4, R5, R6 and R7 are as defined herein. =, The compounds of the invention are selective monoamine oxidase B inhibitors and therefore they are suitable for the treatment of diseases mediated by monoamine oxidase B, such as Alzheimer's disease or senile dementia.

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