2-Amino-5-iodobenzonitrile supplier

Name
2-AMINO-5-IODOBENZONITRILE
EINECS
CAS No. 132131-24-9
Article Data21
CAS DataBase
Density 1.981 g/cm³
Solubility
Melting Point 86℃ (ethanol )
Formula C₇H₅IN₂
Boiling Point 333.622 °C at 760 mmHg
Molecular Weight 244.035
Flash Point 155.569 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-AMINO-5-IODOBENZONITRILE
PSA 49.81000
LogP 2.32628

Synthetic route

: 1885-29-6
anthranilic acid nitrile

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
With K(ICl2) In methanol; water at 20℃; for 2h;	93%
With ammonium iodide; dihydrogen peroxide; acetic acid at 20℃; for 12h;	92.6%
With ammonium iodide; dihydrogen peroxide; acetic acid at 20℃; for 12h;	92.6%

: 516-12-1
N-iodo-succinimide

: 1885-29-6
anthranilic acid nitrile

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	73%

: N-(2-cyano-4-iodo-phenyl)-2,2,2-trifluoro-acetamide

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 12h;

: 878133-06-3
N-(2,4-diiodo-phenyl)-2,2,2-trifluoro-acetamide

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 0.5 h / 100 °C 2: aq. K2CO3 / methanol / 12 h / 20 °C View Scheme

: 533-70-0
2,4-diiodoaniline

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethylformamide / 0.5 h / 20 °C 2: dimethylformamide / 0.5 h / 100 °C 3: aq. K2CO3 / methanol / 12 h / 20 °C View Scheme

: 540-37-4
p-aminoiodobenzene

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ICl / dimethylformamide / 0.5 h / 20 °C 2: dimethylformamide / 0.5 h / 20 °C 3: dimethylformamide / 0.5 h / 100 °C 4: aq. K2CO3 / methanol / 12 h / 20 °C View Scheme

: 1885-29-6
anthranilic acid nitrile

A: 132131-24-9
5-iodoanthranilonitrile

B: 114344-67-1
3-iodo-2-aminobenzonitrile

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid; potassium iodide In water at 20℃; for 24h;

: 7790-99-0
Iodine monochloride

: 1885-29-6
anthranilic acid nitrile

: 132131-24-9
5-iodoanthranilonitrile

Conditions

Conditions	Yield
In acetic acid at 25 - 35℃; for 3h;

: 132131-24-9
5-iodoanthranilonitrile

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

: 903597-10-4
N’-(2-cyano-4-iodophenyl)-N,N-dimethyl formamidine

Conditions

Conditions	Yield
In N,N-dimethyl acetamide at 110℃; for 2h; Product distribution / selectivity; Heating / reflux;	100%
at 70 - 75℃; for 2h;

: 132131-24-9
5-iodoanthranilonitrile

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: (E)-N'-(2-cyano-4-iodophenyl)-N,N-dimethylformamidine

Conditions

Conditions	Yield
at 120℃; for 2h;	100%
at 90℃; for 1h;	98%
at 90℃; for 1h;	1.2 g

: 132131-24-9
5-iodoanthranilonitrile

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 903597-10-4
N’-(2-cyano-4-iodophenyl)-N,N-dimethyl formamidine

Conditions

Conditions	Yield
at 120℃; for 2h;	100%
at 120℃; for 2h;	100%
With acetic acid In toluene at 35℃; for 0.5h;	89.3%
With acetic acid at 35℃; for 0.5h;	89.3%
With acetic acid In toluene at 35℃; for 0.5h;	89.3%

: 18698-97-0
ortho-bromophenylacetic acid

: 132131-24-9
5-iodoanthranilonitrile

: 2-(2-bromophenyl)-N-(2-cyano-4-iodophenyl)acetamide

Conditions

Conditions	Yield
Stage #1: ortho-bromophenylacetic acid With thionyl chloride In dichloromethane for 4h; Reflux; Stage #2: 5-iodoanthranilonitrile In toluene for 16h; Reflux;	99%

: 27329-70-0
5-formylfurane-2-boronic acid

: 132131-24-9
5-iodoanthranilonitrile

: 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile

Conditions

Conditions	Yield
With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 20 - 45℃; for 3h; Suzuki Coupling;	98.6%

: 27329-70-0
5-formylfurane-2-boronic acid

: 104-15-4
toluene-4-sulfonic acid

: 132131-24-9
5-iodoanthranilonitrile

: 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile p-toluenesulfonic acid

Conditions

Conditions	Yield
Stage #1: 5-formylfurane-2-boronic acid; 5-iodoanthranilonitrile With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 20 - 45℃; for 3h; Stage #2: toluene-4-sulfonic acid In water at 60℃;	96%

...Expand

: (E)-N'-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)formamidine

: 132131-24-9
5-iodoanthranilonitrile

: 231278-20-9
N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 5h;	92.2%

: 108-94-1
cyclohexanone

: 132131-24-9
5-iodoanthranilonitrile

: 252357-65-6
9-amino-7-iodo-1,2,3,4-tetrahydroacridine

Conditions

Conditions	Yield
Stage #1: cyclohexanone; 5-iodoanthranilonitrile With zinc(II) chloride at 145 - 150℃; for 0.5h; Condensation; Stage #2: With sodium hydroxide In water at 60℃; for 1h; Hydrolysis;	91%
With sodium hydroxide; zinc(II) chloride Multistep reaction;
Stage #1: cyclohexanone; 5-iodoanthranilonitrile With zinc(II) chloride at 140℃; Condensation; Stage #2: With sodium hydroxide Addition;

: 50-01-1
guanidine hydrochloride

: 132131-24-9
5-iodoanthranilonitrile

: 132131-20-5
2,4-diamino-6-iodoquinazoline

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 80 - 150℃; for 26h;	90%

: 21511-55-7, 34643-89-5
(methoxymethylidene)dimethylammonium methyl sulfate

: 132131-24-9
5-iodoanthranilonitrile

: 903597-10-4
N’-(2-cyano-4-iodophenyl)-N,N-dimethyl formamidine

Conditions

Conditions	Yield
With sodium methylate In toluene at 20℃; for 9h;	86.9%

: 132131-24-9
5-iodoanthranilonitrile

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

: 16353-27-8
6-Iodo-1H-quinazoline-2,4-dione

Conditions

Conditions	Yield
With zinc(II) chloride at 200℃; for 5h; sealed tube;	80%

: 108-24-7
acetic anhydride

: 132131-24-9
5-iodoanthranilonitrile

: 2-cyano-4-iodoacetanilide

Conditions

Conditions	Yield
In acetic acid Heating;	79%

: 132131-24-9
5-iodoanthranilonitrile

: 2-cyano-4-iodobenzenediazonium tetrafluoroborate

Conditions

Conditions	Yield
With tert.-butylnitrite; boron trifluoride diethyl etherate In tetrahydrofuran at -20 - 5℃; for 0.5h;	77%

: 132131-24-9
5-iodoanthranilonitrile

: 1122-91-4
4-bromo-benzaldehyde

: 98-80-6
phenylboronic acid

: 2-(4-bromophenyl)-6-iodo-4-phenylquinazoline

Conditions

Conditions	Yield
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	76%

...Expand

: (E)-N'-(1-(3-fluorobenzyl)-1H-indol-5-yl)-N,N-dimethylformamide

: 132131-24-9
5-iodoanthranilonitrile

: 231278-79-8
N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)-6-iodoquinazolin-4-amine

Conditions

Conditions	Yield
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Reflux;	75.63%

: 1765-93-1
4-fluoroboronic acid

: 100-52-7
benzaldehyde

: 132131-24-9
5-iodoanthranilonitrile

: 4-(4-fluorophenyl)-6-iodo-2-phenylquinazoline

Conditions

Conditions	Yield
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	72%

...Expand

: 132131-24-9
5-iodoanthranilonitrile

: 73183-34-3
bis(pinacol)diborane

: 934426-22-9
2‐amino‐5‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)benzonitrile

Conditions

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 80℃; for 4h;	69%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In N,N-dimethyl-formamide at 80℃; for 4h;	69%

: 100-52-7
benzaldehyde

: 132131-24-9
5-iodoanthranilonitrile

: 98-80-6
phenylboronic acid

: 6-iodo-2,4-diphenylquinazoline

Conditions

Conditions	Yield
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	68%

...Expand

: 104-87-0
4-methyl-benzaldehyde

: 132131-24-9
5-iodoanthranilonitrile

: 98-80-6
phenylboronic acid

: 6-iodo-4-phenyl-2-(p-tolyl)quinazoline

Conditions

Conditions	Yield
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	67%

...Expand

: 342-54-1
2-(methoxycarbonyl)benzenediazonium tetrafluoroborate

: 132131-24-9
5-iodoanthranilonitrile

: 75-05-8
acetonitrile

: 10-iodo-6-methyl-13H-quinazolino[3,4-a]quinazolin-13-one

Conditions

Conditions	Yield
at 80℃; for 5h; Sealed tube;	66%

...Expand

: 666859-79-6
7-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLIC acid

: 132131-24-9
5-iodoanthranilonitrile

: N-(2-CYANO-4-IODOPHENYL)-7-(PHENYLSULFONYL)-1H-INDOLE-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 7-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLIC acid With oxalyl dichloride In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 3h; Stage #2: 5-iodoanthranilonitrile In pyridine; dichloromethane at 20℃;	65%

: 1679-18-1
4-Chlorophenylboronic acid

: 100-52-7
benzaldehyde

: 132131-24-9
5-iodoanthranilonitrile

: 4-(4-chlorophenyl)-6-iodo-2-phenylquinazoline

Conditions

Conditions	Yield
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	65%

...Expand

: 132131-24-9
5-iodoanthranilonitrile

: 2-naphthylmethylzinc chloride

: 378791-67-4
2-amino-5-(2'-naphthylmethyl)benzonitrile

Conditions

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran for 0.5h; Heating;	63%

: 132131-24-9
5-iodoanthranilonitrile

: 312624-11-6
(2-chlorobenzyl)zinc(II) chloride

: 378791-55-0
2-amino-5-(2'-chlorobenzyl)benzonitrile

Conditions

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran for 0.5h; Heating;	62%

: 132131-24-9
5-iodoanthranilonitrile

: 312693-15-5
(2-methoxybenzyl)zinc(II) chloride

: 378791-60-7
2-amino-5-(2'-methoxybenzyl)benzonitrile

Conditions

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran for 0.5h; Heating;	61%

: 5720-05-8
4-methylphenylboronic acid

: 100-52-7
benzaldehyde

: 132131-24-9
5-iodoanthranilonitrile

: 6-iodo-2-phenyl-4-(p-tolyl)quinazoline

Conditions

Conditions	Yield
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	61%

...Expand

: 132131-24-9
5-iodoanthranilonitrile

: (4-chlorobenzyl)zinc(II) chloride

: 2-amino-5-(4'-chlorobenzyl)benzonitrile

Conditions

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran for 0.5h; Heating;	59%

: 132131-24-9
5-iodoanthranilonitrile

: 3,5-dimethoxybenzylzinc chloride

: 2-amino-5-(3',5'-dimethoxybenzyl)benzonitrile

Conditions

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran for 0.5h; Heating;	59%

2-Amino-5-iodobenzonitrile Specification

The 2-Amino-5-iodobenzonitrile, with the CAS registry number 132131-24-9, is also known as Benzonitrile, 2-amino-5-iodo-. This chemical's molecular formula is C₇H₅IN₂ and molecular weight is 244.03. What's more, its systematic name is 2-Amino-5-iodobenzonitrile.

Physical properties of 2-Amino-5-iodobenzonitrile are: (1)ACD/LogP: 2.867; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.87; (4)ACD/LogD (pH 7.4): 2.87; (5)ACD/BCF (pH 5.5): 88.92; (6)ACD/BCF (pH 7.4): 88.92; (7)ACD/KOC (pH 5.5): 864.38; (8)ACD/KOC (pH 7.4): 864.41; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 49.81 Å²; (13)Index of Refraction: 1.705; (14)Molar Refractivity: 47.86 cm³; (15)Molar Volume: 123.198 cm³; (16)Polarizability: 18.973×10^-24cm³; (17)Surface Tension: 68.9 dyne/cm; (18)Density: 1.981 g/cm³; (19)Flash Point: 155.569 °C; (20)Enthalpy of Vaporization: 57.65 kJ/mol; (21)Boiling Point: 333.622 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1cc(I)ccc1N
(2)Std. InChI: InChI=1S/C7H5IN2/c8-6-1-2-7(10)5(3-6)4-9/h1-3H,10H2
(3)Std. InChIKey: PRIOKVMBFXTMRV-UHFFFAOYSA-N

Product Name

2-AMINO-5-IODOBENZONITRILE

Synthetic route

2-Amino-5-iodobenzonitrile Specification

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