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1885-29-6

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1885-29-6 Usage

Chemical Properties

Yellow Solid

Uses

2-Aminobenzonitrile is used for induction of nitrilase activity in Arthrobacter and for radioprotective agent.

Preparation

2-Aminobenzamide was dehydrated to 2-aminobenzonitrile without protection of the amino group in the presence of phenylphosphonyl dichloride and pyridine. Other structural isomers (3-aminobenzamide and 4-aminobenzamide) did not give corresponding aminobenzonitriles.In this paper, the dehydration reactions of 2-aminobenzamide (1a) to 2-aminobenzonitrile (3a) using phosphoryl chloride (2a), phenyl phosphoryl dichloride (2b), 4-chlorophenyl phosphoryl dichloride (2c) or phenylphosphonic dichloride (2d) in pyridine are reported.The chemical yield and melting point of 2-aminobenzonitrile (3a) obtained by four dehydrating reagents (2a-d) are listed in Table-1. 2-Aminobenzamide was dehydrated by reagents 2a-c to give 2-aminobenzonitrile in the yield lower than 60 %, while the reaction by reagent (2d) gave the highest yield, 96 %. On the other hand, benzamide (1b) without amino groups afforded benzonitrile (3a) in the yield of 43 %.synthesis of aminobenzonitrile by dehydration of aminobenzamide using phenylphosphonic dichloride in pyridine

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 5933, 1974 DOI: 10.1021/ja00825a039The Journal of Organic Chemistry, 43, p. 944, 1978 DOI: 10.1021/jo00399a030Tetrahedron Letters, 32, p. 1007, 1991 DOI: 10.1016/S0040-4039(00)74473-X

Safety Profile

Poison by intravenous route. Seealso NITRILES. When heated to decomposition it emitstoxic fumes of NOx and CN- .

Check Digit Verification of cas no

The CAS Registry Mumber 1885-29-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,8 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1885-29:
(6*1)+(5*8)+(4*8)+(3*5)+(2*2)+(1*9)=106
106 % 10 = 6
So 1885-29-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2/c8-5-6-3-1-2-4-7(6)9/h1-4H,9H2

1885-29-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A12286)  2-Aminobenzonitrile, 98%   

  • 1885-29-6

  • 50g

  • 471.0CNY

  • Detail
  • Alfa Aesar

  • (A12286)  2-Aminobenzonitrile, 98%   

  • 1885-29-6

  • 250g

  • 2111.0CNY

  • Detail

1885-29-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-aminobenzonitrile

1.2 Other means of identification

Product number -
Other names 2-amino-benzonitrile

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:1885-29-6 SDS

1885-29-6Synthetic route

o-nitrobenzonitrile
612-24-8

o-nitrobenzonitrile

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water at 20℃; for 0.0666667h; Sealed tube; Green chemistry; chemoselective reaction;99%
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;98%
With borane-ammonia complex In methanol; water at 20℃; for 0.166667h;98%
anthranilic acid amide
28144-70-9

anthranilic acid amide

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With 3 Angstroem melecular sieves at 180 - 500℃; under 0.005 Torr; for 0.666667h; Pyrolysis;99%
With thionyl chloride In toluene at 90 - 100℃;91.6%
With oxalyl dichloride; 2,3-bis(4-methoxyphenyl)cyclopropenone; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 5h; Reflux;89%
With vanadium oxide on hydrotalcite (V/HT) In 1,3,5-trimethyl-benzene for 24h; Reflux;79%
With sieve-supported lead catalyst at 200℃; under 2250.23 Torr; for 0.3h;
sodium cyanide
773837-37-9

sodium cyanide

2-bromoaniline
615-36-1

2-bromoaniline

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;99%
2-amino-1-benzylamine
4403-69-4

2-amino-1-benzylamine

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;96.2%
potassium cyanide

potassium cyanide

2-bromoaniline
615-36-1

2-bromoaniline

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 20℃; Sealed tube;
Stage #2: 2-bromoaniline With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube;
95%
2-aminobenzaldehyde oxime
3398-07-0

2-aminobenzaldehyde oxime

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With eosin; carbon tetrabromide; N,N-dimethyl-formamide In acetonitrile at 25℃; for 14h; Irradiation; Inert atmosphere;93%
Stage #1: 2-aminobenzaldehyde oxime With triethylamine In dichloromethane at 0 - 23℃; Inert atmosphere;
Stage #2: With methanesulfonyl chloride In dichloromethane at 0 - 23℃; for 5h; Inert atmosphere;
69%
With formamide at 140 - 150℃;
2-azidobenzonitrile
31656-77-6

2-azidobenzonitrile

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With Decaborane; palladium on activated charcoal In methanol at 20℃; for 2.5h;91%
With hexamethyldisilathiane In methanol for 1.5h; Ambient temperature;90%
With dicobalt octacarbonyl In water at 20℃; for 5h;87%
In decalin at 144℃; for 5h; Product distribution;
With 2,6-di-tert-butyl-4-methyl-phenol In decalin at 161.3℃; Rate constant; Kinetics; Thermodynamic data; ΔEact, ΔSact, other temperatures, other solvent;
triphenylphosphine
603-35-0

triphenylphosphine

N-(2-cyanophenyl)cyanothioformamide
174969-51-8

N-(2-cyanophenyl)cyanothioformamide

A

3-amino-1H-indole-2-carbonitrile
1192690-93-9

3-amino-1H-indole-2-carbonitrile

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
Stage #1: N-(2-cyanophenyl)cyanothioformamide With toluene-4-sulfonic acid In methanol at 20℃; for 0.0833333h;
Stage #2: triphenylphosphine In methanol at 20℃; for 0.833333h;
A 90%
B 8%
4-chloroquinazoline
5190-68-1

4-chloroquinazoline

phenylmagnesium bromide

phenylmagnesium bromide

A

benzaldehyde
100-52-7

benzaldehyde

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With hydrogenchloride multistep reaction; other arylmagnesium bromides; product yields;A 89%
B n/a
2-iodophenylamine
615-43-0

2-iodophenylamine

K4[Fe(CN)6]

K4[Fe(CN)6]

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium fluoride; palladium diacetate In water at 150℃; for 0.333333h;88%
potassium hexacyanoferrate(III) trihydrate

potassium hexacyanoferrate(III) trihydrate

2-iodophenylamine
615-43-0

2-iodophenylamine

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 2h;88%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

2-iodophenylamine
615-43-0

2-iodophenylamine

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 8h;87%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

2-bromoaniline
615-36-1

2-bromoaniline

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 12h; Schlenk technique; Inert atmosphere;84%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 15h;84%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With ammonium hydroxide; copper(I) iodide; 1-ethylacetoacetate-3-methyl imidazolium hydroxide In acetonitrile at 120℃; for 12h; Inert atmosphere;81%
With ((+/-)-binap)Ni[P(OPh)3]2; ammonia; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 120℃; for 18h; Sealed tube;< 10 %Chromat.
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With sodium azide; copper; L-proline In water; dimethyl sulfoxide at 150℃; under 37503.8 Torr; for 0.583333h; Flow reactor; chemoselective reaction;79%
2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

A

3-amino-3,4-dihydroquinazolin-4-one
14663-46-8

3-amino-3,4-dihydroquinazolin-4-one

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With hydrazine dihydrochloride; triethylamine In methanol; N,N-dimethyl-formamide at 80℃; for 36h;A 77%
B n/a
2-iodophenylamine
615-43-0

2-iodophenylamine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; copper(II) bis(trifluoromethanesulfonate); potassium carbonate at 130℃; for 24h;75%
nitromethane
75-52-5

nitromethane

o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With 1,10-Phenanthroline; copper(II) nitrate trihydrate; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h;73%
2-bromoaniline
615-36-1

2-bromoaniline

malononitrile
109-77-3

malononitrile

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium t-butanolate In N,N-dimethyl-formamide at 130℃; for 24h;72%
benzo[c]isothiazol-3-ylamine
2400-12-6

benzo[c]isothiazol-3-ylamine

A

2-(2'-aminophenyl)-4(3H)-quinazolinone
27259-73-0

2-(2'-aminophenyl)-4(3H)-quinazolinone

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With sodium hydrogensulfite In water for 60h; Heating;A 66%
B 15%
2-iodobenzonitrile
4387-36-4

2-iodobenzonitrile

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate; copper(II) ferrite at 100℃; for 12h; Sealed tube; chemoselective reaction;64%
2-bromoaniline
615-36-1

2-bromoaniline

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; palladium on activated charcoal; potassium carbonate; triphenylphosphine at 25 - 130℃; for 12.1667h;64%
propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

A

3-(3-hydroxypropyl)quinazolin-4(3H)-one

3-(3-hydroxypropyl)quinazolin-4(3H)-one

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 48h;A 63%
B n/a
2-iodophenylamine
615-43-0

2-iodophenylamine

malononitrile
109-77-3

malononitrile

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With potassium fluoride; 1,10-Phenanthroline; copper diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 120℃; for 18h;60%
2-ethyl-N-hydroxy-2-methyl-2,3-dihydro-1H-indol-3-imine

2-ethyl-N-hydroxy-2-methyl-2,3-dihydro-1H-indol-3-imine

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With thionyl chloride In dichloromethane60%
o-nitrobenzonitrile
612-24-8

o-nitrobenzonitrile

A

anthranilic acid amide
28144-70-9

anthranilic acid amide

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With baker's yeast In ethanol; water at 32℃;A 56%
B 10%
methylamine
74-89-5

methylamine

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

A

3-methylquinazolin-4(3H)-one
2436-66-0

3-methylquinazolin-4(3H)-one

B

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at 20℃; for 10h;A 56%
B n/a
potassium ferrocyanide

potassium ferrocyanide

2-Chloroaniline
95-51-2

2-Chloroaniline

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With 2-(dicyclohexylphosphino)-1-(2,6-diisopropylphenyl)-1H-imidazole; sodium carbonate; palladium dichloride In N,N-dimethyl acetamide at 140℃; for 16h; Inert atmosphere;55%
N-acetyl isatin-β-oxime-O-acetate

N-acetyl isatin-β-oxime-O-acetate

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Conditions
ConditionsYield
With sodium azide In acetonitrile for 20h; Heating;53%
allylisocyanate
1476-23-9

allylisocyanate

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-(3-allylureido)benzonitrile
122372-27-4

2-(3-allylureido)benzonitrile

Conditions
ConditionsYield
for 48h; Ambient temperature;100%
for 48h; Ambient temperature;100%
In dichloromethane for 3h; Ambient temperature;88%
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

Glycine ethyl ester isocyanate
2949-22-6

Glycine ethyl ester isocyanate

2-(3-ethoxycarbonylmethylureido)benzonitrile
78754-91-3

2-(3-ethoxycarbonylmethylureido)benzonitrile

Conditions
ConditionsYield
for 48h; Ambient temperature;100%
rac-7-isopropylbicyclo[3.3.1]non-6-en-3-one
247591-83-9

rac-7-isopropylbicyclo[3.3.1]non-6-en-3-one

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

C19H22N2

C19H22N2

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane for 12h; Condensation; Heating;100%
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile
1020252-22-5

2-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;100%
In N,N-dimethyl-formamide for 2h; Heating;
In acetonitrile for 0.0333333h;
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

ethyl (2-cyanophenyl)imidoformate
104326-76-3

ethyl (2-cyanophenyl)imidoformate

Conditions
ConditionsYield
for 0.75h; Reflux;100%
m-anisoyl chloride
1711-05-3

m-anisoyl chloride

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

C15H12N2O2

C15H12N2O2

Conditions
ConditionsYield
In pyridine at 0℃; for 4h;100%
1,1,1-trifluoro-4,4-dimethoxy-but-3-en-2-one
1071146-39-8

1,1,1-trifluoro-4,4-dimethoxy-but-3-en-2-one

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

(E)-1,1,1-trifluoro-4-methoxy-4-(2-cyanophenyl)aminobut-3-en-2-one

(E)-1,1,1-trifluoro-4-methoxy-4-(2-cyanophenyl)aminobut-3-en-2-one

Conditions
ConditionsYield
In acetonitrile for 18h; Reflux;100%
In acetonitrile for 18h; Reflux;100%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

1,2,3,4-tetrahydro-quinazoline-2,4-dione
86-96-4

1,2,3,4-tetrahydro-quinazoline-2,4-dione

Conditions
ConditionsYield
With carbon dioxide In water at 150℃; under 37503.8 Torr; for 5h;99.2%
With zinc(II) chloride at 200℃; for 5h; sealed tube;90%
benzaldehyde
100-52-7

benzaldehyde

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

(E)-2-<(Phenylmethylene)amino>benzonitrile
125743-39-7

(E)-2-<(Phenylmethylene)amino>benzonitrile

Conditions
ConditionsYield
With 4 A molecular sieve In toluene at 23℃; for 10h;99%
In toluene Schlenk technique; Inert atmosphere; Molecular sieve; Reflux;89%
With toluene-4-sulfonic acid In toluene Reflux; Molecular sieve; Inert atmosphere; Schlenk technique;89%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

N-ethoxymethylene-2-aminobenzonitrile
58314-88-8

N-ethoxymethylene-2-aminobenzonitrile

Conditions
ConditionsYield
In acetic acid; toluene at 100 - 110℃; for 3h;99%
Heating;
3-Chloropropyl isocyanate
13010-19-0

3-Chloropropyl isocyanate

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-<3-(3-Chloropropyl)ureido>benzonitrile
94507-24-1

2-<3-(3-Chloropropyl)ureido>benzonitrile

Conditions
ConditionsYield
Heating;99%
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2,2'-(iminodimethylene)bisaniline
69084-37-3

2,2'-(iminodimethylene)bisaniline

Conditions
ConditionsYield
With hydrogen In toluene at 90℃; under 750.075 Torr; for 20h; chemoselective reaction;99%
With hydrogen; Rh/Al2O3
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

anthranilic acid amide
28144-70-9

anthranilic acid amide

Conditions
ConditionsYield
With water; potassium carbonate at 150℃; for 0.5h; Microwave irradiation;99%
With phosphate buffer at 30℃; for 1h; rhodococcus rhodocrous AJ270, pH 7.0;98%
With potassium phosphate buffer at 30℃; for 1h; Rhodococcus sp. AJ270 cells;97.7%
(S)-tert-leucinol
112245-13-3

(S)-tert-leucinol

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-[(4S)-4-(tert-butyl)-4,5-dihydro-1,3-oxazol-2-yl]aniline
194350-71-5

2-[(4S)-4-(tert-butyl)-4,5-dihydro-1,3-oxazol-2-yl]aniline

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene for 24h; Inert atmosphere; Reflux;99%
With zinc(II) chloride In dichloromethane at 140℃; for 24h;85%
With zinc(II) chloride In chlorobenzene at 130℃; for 36h;82%
Triethyl orthopropionate
115-80-0

Triethyl orthopropionate

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

ethyl N-(2-cyanophenyl)propanimidate
132121-43-8

ethyl N-(2-cyanophenyl)propanimidate

Conditions
ConditionsYield
With trifluoroacetic acid99%
2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-(4,5-dihydrothiazol-2-yl)aniline
1370477-92-1

2-(4,5-dihydrothiazol-2-yl)aniline

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) at 80℃; for 2h;99%
With sodium hydroxide at 80℃;96%
With tetrakis(μ2-α-methacrylate-O,O')-bis(H2O)-dicopper(II); sodium acetate at 80℃; for 3.5h; Neat (no solvent);92%
C14H14ClN2(1+)*CF3O3S(1-)

C14H14ClN2(1+)*CF3O3S(1-)

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)benzonitrile

2-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)benzonitrile

Conditions
ConditionsYield
In dichloromethane at 20℃; Inert atmosphere;99%
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

N-ethyl-N-(2-cyanoethyl)aniline
148-87-8

N-ethyl-N-(2-cyanoethyl)aniline

2-{4-[(2-Cyano-ethyl)-ethyl-amino]-phenylazo}-benzonitrile
52547-43-0

2-{4-[(2-Cyano-ethyl)-ethyl-amino]-phenylazo}-benzonitrile

Conditions
ConditionsYield
Stage #1: anthranilic acid nitrile With sulfuric acid; nitrosyl sulphuric acid In water at 0 - 20℃; for 2h;
Stage #2: N-ethyl-N-(2-cyanoethyl)aniline With sulfuric acid In water at 0℃; for 1h;
99%
3,4-dichloro-isothiazole-5-carbonyl chloride
56914-82-0

3,4-dichloro-isothiazole-5-carbonyl chloride

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

isotianil
224049-04-1

isotianil

Conditions
ConditionsYield
In toluene at 80℃; for 2h; Solvent; Temperature;98.8%
With pyridine In tetrahydrofuran at 5 - 20℃; for 1.25h; Product distribution / selectivity;89%
With pyridine In tetrahydrofuran at 5 - 20℃; for 1.25h; Product distribution / selectivity;89%
With pyridine In tetrahydrofuran; water; ethyl acetate; Petroleum ether
carbon dioxide
124-38-9

carbon dioxide

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

4-thioxo-1H,3H-quinazolin-2-one
17796-47-3

4-thioxo-1H,3H-quinazolin-2-one

Conditions
ConditionsYield
Stage #1: anthranilic acid nitrile With sodium hydrogen sulfide In N,N-dimethyl-formamide for 0.5h; Autoclave; Heating;
Stage #2: carbon dioxide In N,N-dimethyl-formamide at 100℃; under 30003 Torr; for 24h; Reagent/catalyst; Temperature; Pressure; Solvent; Autoclave;
98.4%
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

3,5-dibromoanthranilonitrile
68385-95-5

3,5-dibromoanthranilonitrile

Conditions
ConditionsYield
With bromine In acetic acid at 20℃;98%
With bromine In acetic acid at 15 - 20℃; for 5h;98%
With bromine; acetic acid at 15 - 20℃; for 5h; Cooling with ice;98%
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-amino-1-benzylamine
4403-69-4

2-amino-1-benzylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran98%
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 50℃; for 3h; Inert atmosphere; Autoclave;98%
With C28H29Cl2CoNP2; hydrogen; sodium triethylborohydride In 1,4-dioxane at 80℃; under 37503.8 Torr; for 6h;78%
cyclohexanone
108-94-1

cyclohexanone

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

tacrin
321-64-2

tacrin

Conditions
ConditionsYield
With zinc(II) chloride at 120℃; for 16h;98%
With silica gel; toluene-4-sulfonic acid for 0.133333h; microwave irradiation;95%
With sulfuric acid-modified polyethylene glycol 6000 at 130℃; for 0.133333h; Friedlaender synthesis; Microwave irradiation; Neat (no solvent);93%
diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

8-cyano-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinolone
127285-75-0

8-cyano-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinolone

Conditions
ConditionsYield
1.) 130 degC, 1-2 h, 2.) C6H5OC6H5, 250 degC, 1h;98%
In diphenylether at 250℃; Gould-Jacobs condensation;60%
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

5-(2-aminophenyl)tetrazole
18216-38-1

5-(2-aminophenyl)tetrazole

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 120℃; for 4h;98%
Stage #1: anthranilic acid nitrile With sodium azide In N,N-dimethyl-formamide at 120℃; for 36h;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.0833333h;
95%
With iron(III) oxide; sodium azide In N,N-dimethyl-formamide at 120℃; for 36h;92%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

[(2-cyanophenyl)aminocarbonylmethyl]chloride
71993-21-0

[(2-cyanophenyl)aminocarbonylmethyl]chloride

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 0 - 40℃; Microwave irradiation;98%
With triethylamine In dichloromethane at 0 - 20℃; for 48h;55%
With pyridine In N,N-dimethyl-formamide at 20℃; Acylation;54%

1885-29-6Relevant articles and documents

Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as multi-targeted compounds against Alzheimer's disease

Zhang, Chao,Du, Qiao-Yi,Chen, Lang-Di,Wu, Wen-Hao,Liao, Si-Yan,Yu, Li-Hong,Liang, Xin-Tong

, p. 200 - 209 (2016)

A series of benzoates (or phenylacetates or cinnamates) - tacrine hybrids (7a-o) were designed, synthesized and evaluated as multi-potent anti-Alzheimer drug candidates. The screening results showed that most of them exhibited a significant ability to inhibit ChEs, certain selectivity for AChE over BuChE and strong potency inhibitory of self-induced β-amyloid (Aβ) aggregation. All IC50 values of biological activity were at the nanomolar range. Especially, compound 7c displayed the greatest ability to inhibit AChE with an IC50 value of 5.63 nM and the highest selectivity with ratio of BuChE/AChE value of 64.6. Moreover, it also exhibited a potent inhibitory of Aβ aggregation with an IC50 value of 51.81 nM. A Lineweaver-Burk plot and molecular modeling study showed that compound 7c targeted both the CAS and PAS of ChEs. A structure-activity relationship analysis suggested that the electron density of aromatic ring which was linked with tacrine through acetyl group played a significant role in determining the inhibitory activity.

Biehl et al.

, p. 3674,3675-3677 (1979)

Ring-expansion reaction of cyano-substituted singlet phenyl nitrenes: Theoretical predictions and kinetic results from laser flash photolysis and chemical trapping experiments

Gritsan,Likhotvorik,Tsao,Celebi,Platz,Karney,Kemnitz,Borden

, p. 1425 - 1433 (2001)

On the basis of the open-shell electronic structure of the lowest-singlet state of phenylnitrene, it is predicted that substitution of a radical-stabilizing cyano group at an ortho carbon should facilitate cyclization at that carbon, whereas cyano substitution at the para carbon should retard the rate of cyclization. These qualitative predictions have been tested computationally by performing (8/8)CASSCF and CASPT2/6-31G* ab initio calculations and experimentally by carrying out laser flash photolysis and chemical trapping studies. The calculations and experiments both find that, unlike the case with ortho fluoro and ortho methyl substituents, the rate of cyclization at a substituted carbon is not retarded by an ortho cyano group. In contrast, a para cyano group is found, both computationally and experimentally, to raise the barrier to cyclization of singlet phenylnitrene by > 1 kcal/mol.

Transformations of 2-Ethyl-2-methyl-2,3-dihydro-1H-indole at the 3-Position

Abdrakhmanov, I. B.,Latypova, L. R.,Mustafin, A. G.,Salikhov, Sh. M.

, (2020)

The oxidation of N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indole with pyridinium chlorochromate, CrO3 · 2 Py, or CrO3 gave N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one which was hydrolyzed to 2-ethyl-2-methyl-2,3-dihydro-1H-i

Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines

Guan, Xinyu,Zhu, Haoran,Driver, Tom G.

, p. 12417 - 12422 (2021/10/12)

The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C-NAr bond formation of the nitrosoarene with the aryl boronic acid.

The benzonitrile derivative

-

Paragraph 0048; 0050-0065, (2021/10/08)

[A] suppressing the generation of impurities caused by side reactions and reaction, and benzonitrile derivative can be obtained in high purity of the benzonitrile derivative method. The compound represented by general formula [a] I, III and IV compound represented by general formula compound represented by a general formula selected from the group consisting of tertiary amines in the presence of at least 1 species is reacted, the benzonitrile derivative represented by general formula II comprises obtaining the benzonitrile derivative. In the general formula I, R1 - R4 Each independently, a hydrogen atom, an alkyl group of carbon number 1 - 5 represent the like, in the general formula II, R21 - R24 Each independently, a hydrogen atom, an alkyl group of carbon number 1 - 5 represent the like, in the general formula III, R31 - R33 Is, each independently represents an alkyl group or a phenyl group, having the general formula IV in, R41 - R44 Is, each independently represents an alkyl group. The details of the code as described herein. [Drawing] no

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