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4-(1H-1,2,4-Triazol-1-ylmethyl)aniline is an organic compound with the molecular structure featuring a triazole ring and an aniline group. It is characterized as a brown solid and is known for its role as an intermediate in various chemical processes and organic synthesis.

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  • 119192-10-8 Structure
  • Basic information

    1. Product Name: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline
    2. Synonyms: 1-(4-Aminobenzyl)-1H-1,2,4-triazole;4-(1H-1,2,4-Triazol-1-ylmethyl)aniline 97%;4-(1H-1,2,4-triazol-1-ylmethyl)-benzenamine( For Rizatriptan );4-[1H-1,2,4-TRIAZOLE-1-YL METHYL]BENZENE AMINE (FOR RIZATRIPTAN);1-(4-Aminophenyl)methyl-1,2,4-Triazole see also 4-(1H-1,2,4-Triazol-1-yl-Methyl)Benzenamine;1-(4-AMINOBENZYL)-1,2,4-TRIAZOL;Benzenamine, 4-(1H-1,2,4-triazol-1-ylmethyl);AIDS339154
    3. CAS NO:119192-10-8
    4. Molecular Formula: C9H10N4
    5. Molecular Weight: 174.2
    6. EINECS: 1806241-263-5
    7. Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;Chemical Amines;Intermediates of Rizatriptan;Amine;Aromatics;Heterocycles;Phenyls & Phenyl-Het
    8. Mol File: 119192-10-8.mol
  • Chemical Properties

    1. Melting Point: 124 °C
    2. Boiling Point: 402.1 °C at 760 mmHg
    3. Flash Point: 197 °C
    4. Appearance: White to pale yellow/Powder
    5. Density: 1.26 g/cm3
    6. Vapor Pressure: 1.12E-06mmHg at 25°C
    7. Refractive Index: 1.663
    8. Storage Temp.: -20°C Freezer
    9. Solubility: Chloroform (Slightly), Methanol (Slightly)
    10. PKA: 4.42±0.10(Predicted)
    11. CAS DataBase Reference: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(119192-10-8)
    13. EPA Substance Registry System: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(119192-10-8)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 20/21/22-36/37/38-41-37/38
    3. Safety Statements: 22-26-36/37/39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: 6.1
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 119192-10-8(Hazardous Substances Data)

119192-10-8 Usage

Uses

Used in Pharmaceutical Industry:
4-(1H-1,2,4-Triazol-1-ylmethyl)aniline is used as an intermediate for the synthesis of Rizatriptan, which is a medication primarily used to treat migraine headaches. It helps alleviate the symptoms by narrowing the blood vessels around the brain and reducing the release of substances that cause inflammation, pain, and other migraine symptoms.
Used in Organic Synthesis:
4-(1H-1,2,4-Triazol-1-ylmethyl)aniline is also utilized as an intermediate in organic synthesis for the production of various other chemicals and compounds. Its unique structure allows it to be a valuable building block in the creation of a wide range of molecules with different applications in the chemical and pharmaceutical industries.

Check Digit Verification of cas no

The CAS Registry Mumber 119192-10-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,1,9 and 2 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 119192-10:
(8*1)+(7*1)+(6*9)+(5*1)+(4*9)+(3*2)+(2*1)+(1*0)=118
118 % 10 = 8
So 119192-10-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H10N4/c10-9-3-1-8(2-4-9)5-13-7-11-6-12-13/h1-4,6-7H,5,10H2

119192-10-8 Well-known Company Product Price

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  • Alfa Aesar

  • (H66620)  1-(4-Aminobenzyl)-1H-1,2,4-triazole, 98%   

  • 119192-10-8

  • 25g

  • 882.0CNY

  • Detail
  • Alfa Aesar

  • (H66620)  1-(4-Aminobenzyl)-1H-1,2,4-triazole, 98%   

  • 119192-10-8

  • 100g

  • 2822.0CNY

  • Detail

119192-10-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline

1.2 Other means of identification

Product number -
Other names 4-(1,2,4-triazol-1-ylmethyl)aniline

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:119192-10-8 SDS

119192-10-8Synthetic route

1-(4-nitrophenyl)methyl-1,2,4-triazole
119192-09-5

1-(4-nitrophenyl)methyl-1,2,4-triazole

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Conditions
ConditionsYield
With hydrogenchloride; palladium-carbon In ethanol; water; ethyl acetate100%
With hydrogenchloride; palladium-carbon In ethanol; water; ethyl acetate100%
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;96%
aniline hydrochloride
142-04-1

aniline hydrochloride

1-(hydroxymethyl)-1,2,4-triazole
74205-82-6

1-(hydroxymethyl)-1,2,4-triazole

A

4,4'-diamino diphenyl methane
101-77-9

4,4'-diamino diphenyl methane

B

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Conditions
ConditionsYield
With acetic acid for 0.0833333h; Heating;A 10%
B 59%
4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

SO2

SO2

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / sodium ethoxide / ethanol / room temp. 4 h, reflux, 1 h
2: 96 percent / hydrogen / 5percent Pd/C / ethanol / Ambient temperature
View Scheme
4-amino-1-(4-nitrobenzyl)-1,2,4-triazolium bromide
6085-99-0

4-amino-1-(4-nitrobenzyl)-1,2,4-triazolium bromide

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / 10percent aq NaNO2 / aq. HCl / 0 °C
2: 80 percent / H2 / 10percent Pd-C / ethyl acetate / 60 °C / 760 Torr
View Scheme
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / ethanol / 4 h / Heating
2: 65 percent / 10percent aq NaNO2 / aq. HCl / 0 °C
3: 80 percent / H2 / 10percent Pd-C / ethyl acetate / 60 °C / 760 Torr
View Scheme
4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

1-(tetrazol-2-ylmethyl)-4-nitrobenzene
144035-43-8

1-(tetrazol-2-ylmethyl)-4-nitrobenzene

2-(4-Aminophenyl)methyl-1,2,3,4-tetrazole

2-(4-Aminophenyl)methyl-1,2,3,4-tetrazole

Conditions
ConditionsYield
100%
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(4-(trifluoromethyl)phenyl)thiazolidin-4-one
1388155-36-9

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(4-(trifluoromethyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 4h;97%
2-formyl oxine
14510-06-6

2-formyl oxine

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

C19H15N5O

C19H15N5O

Conditions
ConditionsYield
With acetic acid In toluene Molecular sieve; Reflux; Inert atmosphere;96%
4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

A

4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine
160194-26-3

4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine

B

3,5-diiodo-4-aminobenzyltriazole

3,5-diiodo-4-aminobenzyltriazole

Conditions
ConditionsYield
With Iodine monochloride; calcium carbonate In methanol; waterA 91%
B 3%
4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine
160194-26-3

4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate In water for 30h;90%
With Iodine monochloride; calcium carbonate
With Iodine monochloride; calcium carbonate
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

4-((1H-1,2,4-triazol-1-yl)methyl)-2-(perfluorohexyl)aniline

4-((1H-1,2,4-triazol-1-yl)methyl)-2-(perfluorohexyl)aniline

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;90%
4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

1-(p-hydroxybenzyl)-1,2,4-triazole
119192-11-9

1-(p-hydroxybenzyl)-1,2,4-triazole

Conditions
ConditionsYield
With sodium nitrate; sulfuric acid In water room temp., 20 min, 85 deg C, 35 min;88%
1-chloro-7-hydroxy-4-nitro-9(10H)-acridinone
99009-49-1

1-chloro-7-hydroxy-4-nitro-9(10H)-acridinone

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

1-((4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)amino)-7-hydroxy-4-nitroacridin-9(10H)-one

1-((4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)amino)-7-hydroxy-4-nitroacridin-9(10H)-one

Conditions
ConditionsYield
With caesium carbonate In 1,4-dioxane for 9h; Heating;87.6%
phthalic anhydride
85-44-9

phthalic anhydride

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

2-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}carbamoyl)benzoic acid

2-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}carbamoyl)benzoic acid

Conditions
ConditionsYield
In acetone at 20℃; for 1h;86%
In acetone at 20℃; for 1h;
Togni's reagent II
887144-94-7

Togni's reagent II

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

4-((1H-1,2,4-triazol-1-yl)methyl)-2-(trifluoromethyl)aniline
1558046-39-1

4-((1H-1,2,4-triazol-1-yl)methyl)-2-(trifluoromethyl)aniline

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation;82%
With tris[2-phenylpyridinato-C2,N]iridium(III) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation; Schlenk technique;80%
benzaldehyde
100-52-7

benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-phenylthiazolidin-4-one
1388155-35-8

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-phenylthiazolidin-4-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 7h;81%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-p-tolylthiazolidin-4-one
1388155-37-0

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-p-tolylthiazolidin-4-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 11h;80%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(4-chlorophenyl)thiazolidin-4-one
1388155-38-1

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(4-chlorophenyl)thiazolidin-4-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 7h;79%
mercaptoacetic acid
68-11-1

mercaptoacetic acid

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(3-chlorophenyl)thiazolidin-4-one
1388155-39-2

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(3-chlorophenyl)thiazolidin-4-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 7h;78%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(2-chlorophenyl)thiazolidin-4-one
1388155-40-5

3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(2-chlorophenyl)thiazolidin-4-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 7h;76%
salicylaldehyde
90-02-8

salicylaldehyde

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

2-[2-(4-[1,2,4]triazol-1-ylmethylphenyl)iminomethylphenol]

2-[2-(4-[1,2,4]triazol-1-ylmethylphenyl)iminomethylphenol]

Conditions
ConditionsYield
With acetic acid In ethanol at 65 - 70℃; for 6h;76%
Ethyl bromodifluoroacetate
667-27-6

Ethyl bromodifluoroacetate

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

5-((1H-1,2,4-triazol-1-yl)methyl)-3,3-difluoroindolin-2-one

5-((1H-1,2,4-triazol-1-yl)methyl)-3,3-difluoroindolin-2-one

Conditions
ConditionsYield
Stage #1: Ethyl bromodifluoroacetate; 4-(1H-1,2,4-triazol-1-ylmethyl)aniline With tris[2-phenylpyridinato-C2,N]iridium(III); sodium carbonate In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; Sealed tube;
Stage #2: With ethanol at 60℃; for 6h;
74%
1-(1H-benzo[f]chromen-2-yl)-2,2,2-trifluoroethan-1-one

1-(1H-benzo[f]chromen-2-yl)-2,2,2-trifluoroethan-1-one

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

(E)-1,1,1-trifluoro-3-[(2-hydroxynaphth-1-yl)methyl]-4-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}amino)but-3-en-2-one

(E)-1,1,1-trifluoro-3-[(2-hydroxynaphth-1-yl)methyl]-4-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}amino)but-3-en-2-one

Conditions
ConditionsYield
In methanol at 20℃; for 4h; stereoselective reaction;74%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

(4-nitrobenzylidene)-(4-[1,2,4]triazol-1-ylmethylphenyl)amine
127988-32-3

(4-nitrobenzylidene)-(4-[1,2,4]triazol-1-ylmethylphenyl)amine

Conditions
ConditionsYield
With acetic acid In ethanol at 65 - 70℃; for 6h;72%
In ethanol; benzene for 24h; Heating;58%
cadmium(II) perchlorate hexahydrate

cadmium(II) perchlorate hexahydrate

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

{[Cd(1-(4-aminobenzyl)-1H-1,2,4-triazole)2(H2O)2]*(ClO4)2*H2O}n

{[Cd(1-(4-aminobenzyl)-1H-1,2,4-triazole)2(H2O)2]*(ClO4)2*H2O}n

Conditions
ConditionsYield
In methanol; water for 0.5h;69%
C24H17NO4

C24H17NO4

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

4'-{2-oxo-3-[(4-[1,2,4]triazol-1-ylmethyl-phenyl-imino)-methyl]-2H-quinolin-1-ylmethyl}-biphenyl-2-carboxylic acid
1599479-42-1

4'-{2-oxo-3-[(4-[1,2,4]triazol-1-ylmethyl-phenyl-imino)-methyl]-2H-quinolin-1-ylmethyl}-biphenyl-2-carboxylic acid

Conditions
ConditionsYield
In methanol Reflux;65.2%
C24H17N5OS

C24H17N5OS

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

{2-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethylsulphanyl]-quinolin-3-ylmethylene}-(4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine
1599479-49-8

{2-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethylsulphanyl]-quinolin-3-ylmethylene}-(4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine

Conditions
ConditionsYield
In methanol Reflux;63.7%
cyclohexanone
108-94-1

cyclohexanone

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

4-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-1-thia-4-azaspiro[4.5]decan-3-one
1388155-31-4

4-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-1-thia-4-azaspiro[4.5]decan-3-one

Conditions
ConditionsYield
In polypropylene glycol-2000 at 110℃; for 11h;60%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

N-(4-chlorobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine
127988-30-1

N-(4-chlorobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine

Conditions
ConditionsYield
In ethanol; benzene for 24h; Heating;59%
2,4,6-triphenylpyrylium tetrafluoroborate
448-61-3

2,4,6-triphenylpyrylium tetrafluoroborate

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

1-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate

1-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate

Conditions
ConditionsYield
In ethanol at 85 - 90℃; for 4h; Schlenk technique;57%
silver perchlorate

silver perchlorate

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

[Ag2(μ2-1-(4-aminobenzyl)-1,2,4-triazole)(μ3-1-(4-aminobenzyl)-1,2,4-triazole)(perchlorate)].(perchlorate)

[Ag2(μ2-1-(4-aminobenzyl)-1,2,4-triazole)(μ3-1-(4-aminobenzyl)-1,2,4-triazole)(perchlorate)].(perchlorate)

Conditions
ConditionsYield
In methanol; water at 160℃; for 12.5h; Autoclave;53%
water
7732-18-5

water

silver nitrate

silver nitrate

4-(1H-1,2,4-triazol-1-ylmethyl)aniline
119192-10-8

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

C9H10N4*Ag(1+)*NO3(1-)*0.125H2O

C9H10N4*Ag(1+)*NO3(1-)*0.125H2O

Conditions
ConditionsYield
In methanol at 160℃; for 12h; Autoclave;53%

119192-10-8Relevant articles and documents

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Gallou, Fabrice,Li, Xiaohan,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.

supporting information, p. 8114 - 8118 (2021/10/25)

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

“TPG-lite”: A new, simplified “designer” surfactant for general use in synthesis under micellar catalysis conditions in recyclable water

Thakore, Ruchita R.,Takale, Balaram S.,Hu, Yuting,Ramer, Selene,Kostal, Jakub,Gallou, Fabrice,Lipshutz, Bruce H.

, (2021/04/22)

Using the oxidized, carboxylic acid-containing form of MPEG-750, esterification with racemic vitamin E affords a new surfactant (TPG-lite) that functions as an enabling, nanoreactor-forming amphiphile for use in many types of important reactions in synthesis. The presence of a single ester bond is suggestive of simplified treatment as a component of (eventual) reaction waste water, after recycling. Many types of reactions, including aminations, Suzuki-Miyaura, SNAr, and several others are compared directly with TPGS-750-M, leading to the conclusion that TPG-lite can function as an equivalent nanomicelle-forming surfactant in water. Prima facie evidence amassed via DLS and cryo-TEM analyses support these experimental observations. In silico evaluations of the aquatic toxicity and carcinogenicity of TPG-lite indicate that it is safe to use.

PROCESS FOR THE LARGE SCALE PRODUCTION OF RIZATRIPTAN BENZOATE

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Page/Page column 4; 8-9, (2008/06/13)

The present invention provides a method for preparing pure Rizatriptan benzoate having purity more than 99.5% and dimer impurity less than 0.1% comprises, i) Condensation of 1,2,4-Triazole with 4-Nitro benzyl bromide to yield l-(4-nitrophenyl) methyl-1,2,4- triazole ii) Reducing the l-(4-nitrophenyl) methyl-1,2,4-triazole to give l-(4- aminophenyl) methyl-1,2,4-triazole iii) Converting l-(4-aminophenyl) methyl-1,2,4-triazole to l-(4-hydrazinophenyl) methyl-1,2,4-triazole hydrochloride iv) Condensing the hydrazine derivative with 4-(Dimethylamino) butanal diethylacetal to get Rizatriptan and v) Salification of Rizatriptan to Rizatriptan benzoate.

IMPROVED PROCESS FOR THE PREPARATION OF RIZATRIPTAN BENZOATE

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Abstract, (2010/11/25)

Present invention discloses an improved and commercially viable process for the preparation of rizatriptan benzoate of formula (I). According to the present process the hydrazone intermediate derived from the phenylhydrazine of formula- (III) and 4- dimethylaminobutyraldehyde diethyl acetal is gradually heated to 60-70 °C in aqueous sulfuric acid medium and maintained for 3-4hr to get rizatriptan with less dimeric impurity of formula (X). The resultant rizatriptan is isolated and converted into the pharmaceutically acceptable benzoate salt. Present process produces less percentage of dimeric (less than 3 %) or polymeric impurities compared to the prior art process and more yield of rizatriptan. Rizatriptan benzoate produced according to the present process has more than 99.5 % purity with less than 0.1% dimeric impurity of formula (X) by HPLC. Rizatriptan benzoate is useful for the treatment of migraine.

IMIDAZOQUINOLINES AS LIPID KINASE INHIBITORS

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Page/Page column 92, (2008/06/13)

The invention relates to novel organic compounds of formula (I) processes for the preparation thereof, the application thereof in a process for the treatment of the human or animal body, the use thereof - alone or in combination with one or more other pharmaceutically active compounds - for the treatment of an inflammatory or obstructive airway disease, such as asthma, disorders commonly occurring in connection with transplantation, or a proliferative disease, such as a tumor disease.

Substituted indolines which inhibit receptor tyrosine kinases

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Page column 51, (2008/06/13)

Indolinones of the formula having an inhibitory effect on receptor tyrosine kinases and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumor cells. Exemplary are: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone, and (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-metboxycarbonyl-2-indolinone.

Imidazole, Triazole and tetrazole derivatives

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, (2008/06/13)

Imidazole, triazole and tetrazole derivatives of formula (I) are selective agonists of 5-HT1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated, wherein the broken circle represents two non-adjacent double bonds in any position in the five-membered ring; two, three or four of V, W, X, Y and Z represent nitrogen and the remainder represent carbon provided that, when two of V, W, X, Y and Z represent nitrogen and the remainder represent carbon, then the said nitrogen atoms are in non-adjacent positions within the five-membered ring; E represents a bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms; F represents a group of formula (a); U represents nitrogen or C--R2 ; B represents oxygen, sulphur or N--R3 ; R1 represents a group of formula (i), (ii) or (iii).

Process for preparing indole derivatives containing a 1,2,4-triazol-1-yl substituent

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, (2008/06/13)

A process for preparing tryptamine derivatives and related compounds having a 1,2,4-triazol-1-yl moiety within the molecule comprises reacting 4-amino-1,2,4-triazol with a nitrobenzene derivative containing a readily displaceable group; deaminating the aminotriazolium salt thereby obtained by treatment with nitrous acid followed by neutralisation; reducing the triazolyl-nitrobenzene derivative thereby obtained by transfer hydrogenation; treating the triazolyl-aniline derivative thereby obtained with nitrous acid and then with an alkali metal sulphate, followed by acidification; and subsequently reacting the triazolyl-hydrazine derivative thereby obtained in situ with a suitable carbonyl compound, to obtain the required triazolyl-indole derivative.

Sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy

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, (2008/06/13)

The sulphate salt of N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine is a selective agonist of 5-HT 1 -like receptors and is therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

A Novel and Convenient Route to (1H-1,2,4-Triazol-1-ylmethyl)phenols, Anilines, N-Alkylanilines and N,N-Dialkylanilines

Katritzky, Alan R.,El-Zemity, Saad,Lang, Hengyuan

, p. 1813 - 1822 (2007/10/02)

Phenols, naphthols, anilines, N-alkylanilines and N,N-dialkylanilines are readily alkylated by 1-hydroxymethyl-1,2,4-triazole to afford the corresponding triazole derivatives in good yields.

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