2-Amino-5-chlorobenzonitrile supplier

Name
2-Amino-5-chlorobenzonitrile
EINECS 227-651-5
CAS No. 5922-60-1
Article Data23
CAS DataBase
Density 1.33 g/cm³
Solubility
Melting Point 96-99 °C(lit.)
Formula C₇H₅ClN₂
Boiling Point 290.9 °C at 760 mmHg
Molecular Weight 152.583
Flash Point 129.7 °C
Transport Information
Appearance white to light beige crystalline needles
Safety 26-36-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Anthranilonitrile,5-chloro- (6CI,7CI,8CI);1-Cyano-2-amino-5-chlorobenzene;2-Amino-5-chlorobenzenecarbonitrile;2-Amino-5-chlorobenzonitrile;2-Cyano-4-chloroaniline;4-Chloro-2-cyanoaniline;5-Chloro-2-aminobenzonitrile;5-Chloroanthranilonitrile;6-Amino-3-chlorobenzonitrile;
PSA 49.81000
LogP 2.37508

Synthetic route

: 1885-29-6
anthranilic acid nitrile

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With N-chloro-succinimide; isopropyl alcohol for 0.25h; Chlorination; Heating;	89%
With N-chloro-succinimide In acetonitrile for 1.5h; Heating;	71%

: 873-38-1
4-chloro-2-bromoaniline

: copper(l) cyanide

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 140℃; for 5h;	80%

: 5-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)benzonitrile

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In ethanol; water at 120℃; for 0.5h; Microwave irradiation;	76%

: 5202-85-7
2-Amino-5-chlorobenzamide

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With phosphorus pentaoxide for 0.5h;	63%

: 1192690-74-6
5-chloro-2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)benzonitrile

A: 1192691-01-2
3-amino-5-chloroindole-2-carbonitrile

B: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With water; triphenylphosphine In dichloromethane at 20℃;	A 32% B 27%

: 75-16-1
methylmagnesium bromide

: 156149-36-9
2-azido-5-chlorobenzonitrile

A: 1262111-20-5
6-chloro-3,4-dihydro-4-imino-3-methyl-1,2,3-benzotriazine

B: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h;	A 31% B 29%

...Expand

: 85124-16-9
5-Chloroisatin 3-oxime

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
at 250℃;

: 34662-31-2
3-chloro-6-nitrobenzonitrile

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With tin(ll) chloride Yield given;
With titanium(III) chloride In water; acetone for 0.5h;
With hydrogen In neat (no solvent) at 110℃; under 15001.5 Torr; for 15h; chemoselective reaction;

: 106-47-8
4-chloro-aniline

: 545-06-2
trichloroacetonitrile

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With boron trichloride; tin(IV) chloride; potassium carbonate 1.) C6H6, reflux, 6 h, 2.) CH3OH, reflux, 2.5 h,; Yield given. Multistep reaction;

: 63069-48-7
p-chloro-o-iodoaniline

CuCN: CuCN

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With pyridine

: 618889-14-8
N-(4-Chloro-2-cyanophenyl)-2,2,2-trifluoroacetamide

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

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

: 63069-48-7
p-chloro-o-iodoaniline

: 5922-60-1
2-amino-5-chlorobenzonitrile

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

: 784183-51-3
2,2,2-trifluoro-N-(2-iodo-4-chlorophenyl)acetamide

: 5922-60-1
2-amino-5-chlorobenzonitrile

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

: 118-92-3
anthranilic acid

1-chloro-4-methyl-thioxanthone: 1-chloro-4-methyl-thioxanthone

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 35 percent / sulfuryl chloride; hydrochloric acid / diethyl ether / 1.5 h / 60 - 70 °C 2: 37 percent / thionyl chloride / 0.5 h / Heating 3: 68 percent / liq. ammonia / 0.5 h / 0 °C 4: 63 percent / phosphorus pentoxide / 0.5 h View Scheme

: 635-21-2
5-chloroanthranilic acid

4-halogen-1-amino-anthraquinone: 4-halogen-1-amino-anthraquinone

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 37 percent / thionyl chloride / 0.5 h / Heating 2: 68 percent / liq. ammonia / 0.5 h / 0 °C 3: 63 percent / phosphorus pentoxide / 0.5 h View Scheme

: 910230-30-7
2-amino-5-chlorobenzoic chloride

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / liq. ammonia / 0.5 h / 0 °C 2: 63 percent / phosphorus pentoxide / 0.5 h View Scheme

: 2516-95-2
5-chloro-2-nitrobenzoic acid

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) SOCl2; 2.) NH4OH / 1.) PhMe, reflux 2: SOCl2 / Heating 3: 15 percent TiCl3 / acetone; H2O / 0.5 h View Scheme

: 40763-96-0
2-nitro-5-chlorobenzamide

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: 15 percent TiCl3 / acetone; H2O / 0.5 h View Scheme

: 93033-30-8
5-chloro-2-nitrobenzaldehyde oxime

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / PCl5 2: SnCl2 View Scheme

: 109-69-3
n-Butyl chloride

: 1885-29-6
anthranilic acid nitrile

: 5922-60-1
2-amino-5-chlorobenzonitrile

Conditions

Conditions	Yield
With N-chloro-succinimide In acetonitrile

: 124-38-9
carbon dioxide

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 1640-60-4
6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione

Conditions

Conditions	Yield
With bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 750.075 Torr; for 4h; Inert atmosphere;	100%
With potassium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In dimethyl sulfoxide at 120℃; under 750.075 Torr; for 8h; High pressure; Autoclave;	99%
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 110℃; under 15001.5 Torr; for 24h; Autoclave;	99%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 105-13-5
4-Methoxybenzyl alcohol

: 685540-87-8
5-chloro-2-(4-methoxy-benzylamino)-benzonitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 70℃; for 12h;	99%

: chloro-formamidine hydrochloride

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 18671-95-9
2,4-diamino-6-chloroquinazoline

Conditions

Conditions	Yield
Stage #1: chloro-formamidine hydrochloride; 2-amino-5-chlorobenzonitrile In sulfolane; dimethylsulfone at 165℃; for 0.5h; Stage #2: With ammonia; water In sulfolane; dimethylsulfone pH=7 - 8;	99%
Stage #1: chloro-formamidine hydrochloride; 2-amino-5-chlorobenzonitrile In sulfolane; dimethylsulfone at 165℃; for 0.5h; Stage #2: With ammonia; water In sulfolane; dimethylsulfone pH=7 - 8;	99%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 156149-36-9
2-azido-5-chlorobenzonitrile

Conditions

Conditions	Yield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 20℃; for 2h;	97%
Stage #1: 2-amino-5-chlorobenzonitrile With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With sodium azide; sodium acetate In water at 0 - 5℃; for 0.5h;	72%
With hydrogenchloride; sodium azide; sodium acetate; sodium nitrite 1.) water, 0-5 deg C, 10 min; 2.) water, 0-5 deg C, 0.5 h; Multistep reaction;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 79-22-1
methyl chloroformate

: 104615-85-2
5-chloro-2-<(methoxycarbonyl)amino>benzonitrile

Conditions

Conditions	Yield
With sodium hydrogencarbonate Reflux;	97%
With sodium hydrogencarbonate In butanone Reflux;	97%
With sodium hydrogencarbonate In butanone Reflux;	97%
With sodium hydrogencarbonate In butanone at 80℃; for 18h;	76%
With dmap In N,N-dimethyl acetamide at 10 - 90℃;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 5202-85-7
2-Amino-5-chlorobenzamide

Conditions

Conditions	Yield
With silica-gel-supported sulfuric acid In toluene for 2.5h; Inert atmosphere; Reflux;	97%
With water; potassium carbonate In water at 150℃; for 0.5h; Microwave irradiation;	89%
With potassium hydroxide; ethanol Heating / reflux;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 115-80-0
Triethyl orthopropionate

: 1088610-86-9
ethyl N-(4-chloro-2-cyanophenyl)propanimidate

Conditions

Conditions	Yield
With trifluoroacetic acid	97%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 108047-39-8
2-(aminomethyl)-4-chloroaniline

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃; for 24.17h; Inert atmosphere;	96%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 24.1667h; Inert atmosphere;	50%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18h;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 98-80-6
phenylboronic acid

: 719-59-5
2-Amino-5-chlorobenzophenone

Conditions

Conditions	Yield
With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate; water In 2-methyltetrahydrofuran at 80℃; for 36h; Schlenk technique;	96%
With [2,2]bipyridinyl; methanesulfonic acid; palladium(II) trifluoroacetate In tetrahydrofuran; water at 80℃; for 36h;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 25465-36-5
2-amino-5-chlorobenzothioamide

Conditions

Conditions	Yield
With sodium hydrogen sulfide monohydrate; magnesium chloride In N,N-dimethyl-formamide at 20℃; for 72h; Sealed tube;	96%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: d5-phenylboronic acid

: C14H8(2)H4ClNO3

Conditions

Conditions	Yield
With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate In 2-methyltetrahydrofuran; water at 80℃; for 12h; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere; Cooling with ice;	96%

: 5922-60-1
2-amino-5-chlorobenzonitrile

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

: 1640-60-4
6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione

Conditions

Conditions	Yield
With carbon dioxide In water at 150℃; under 37503.8 Torr; for 5h;	95.6%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 19808-35-6
4-amino-6-chloroquinazoline

Conditions

Conditions	Yield
Stage #1: 2-amino-5-chlorobenzonitrile; formamide at 180℃; for 6h; Stage #2: With water	95%
at 180℃; for 6h;	95%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 98-88-4
benzoyl chloride

: 84197-47-7
N-(4-chloro-2-cyanophenyl)benzonitrile

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	94%

: 75-15-0
carbon disulfide

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 6-chloroquinazoline-2,4(1H,3H)-dithione

Conditions

Conditions	Yield
With C7H14OS2*C9H16N2 In neat (no solvent) at 40℃; for 18h; Green chemistry;	94%

: 18698-97-0
ortho-bromophenylacetic acid

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 2-(2-bromophenyl)-N-(4-chloro-2-cyanophenyl)acetamide

Conditions

Conditions	Yield
Stage #1: ortho-bromophenylacetic acid With thionyl chloride In dichloromethane for 4h; Reflux; Stage #2: 2-amino-5-chlorobenzonitrile In toluene for 16h; Reflux;	94%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 502-42-1
cycloheptanone

: 2-chloro-6H,7H,8H,9H,10H-cyclohepta[b]quinolin-11-amine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-amino-5-chlorobenzonitrile; cycloheptanone With aluminum (III) chloride at 150℃; for 0.166667h; Microwave irradiation; Stage #2: With hydrogenchloride In methanol; water at 20℃;	94%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 541-41-3
chloroformic acid ethyl ester

: 104615-49-8
(2-cyano-4-chloro-phenyl)-carbamic acid ethyl ester

Conditions

Conditions	Yield
for 6h; Reflux;	93%
at 93℃; for 18h;	85%
for 6h; Reflux;	68%
for 6h; Heating;
Reflux;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 15239-25-5
Benzyldithiophosphonsaeureanhydrid

: 2-Benzyl-6-chloro-2-thioxo-1,2-dihydro-2λ5-benzo[d][1,3,2]thiazaphosphinin-4-ylideneamine

Conditions

Conditions	Yield
In toluene at 90℃; for 3h;	92%

: 5922-60-1
2-amino-5-chlorobenzonitrile

A: 5606-39-3
(2-amino-5-chlorophenyl)-phenyl-methane-imine

B: 100-58-3
phenylmagnesium bromide

Conditions

Conditions	Yield
	A 92% B n/a

: 43083-12-1
1,1,1-trimethoxybutane

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 1088610-88-1
methyl N-(4-chloro-2-cyanophenyl)butanimidate

Conditions

Conditions	Yield
With trifluoroacetic acid	92%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 914636-84-3
2-amino-3-bromo-5-chlorobenzonitrile

Conditions

Conditions	Yield
With bromine; sodium bromide In water at 25℃; for 0.5h;	92%
With bromine In acetic acid at 50℃;

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 873-55-2
sodium benzenesulfonate

: 719-59-5
2-Amino-5-chlorobenzophenone

Conditions

Conditions	Yield
With p-nitrobenzenesulfonic acid; palladium diacetate In tetrahydrofuran; water at 80℃; for 48h; Inert atmosphere; Schlenk technique;	92%

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 5720-05-8
4-methylphenylboronic acid

: 78-39-7
Triethyl orthoacetate

: 6-chloro-2-methyl-4-(p-tolyl)quinazoline

Conditions

Conditions	Yield
With [2,2]bipyridinyl; palladium diacetate; acetic acid In N,N-dimethyl-formamide at 100℃; for 12h;	91%

...Expand

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 55579-69-6
5-<4-(trifluoromethyl)phenyl>-1,3-cyclohexanedione

: 144155-89-5
5-chloro-2-<<5-<4-(trifluoromethyl)phenyl>-3-oxo-1-cyclohexenyl>amino>benzonitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Heating;	90.58%

: 32315-10-9
bis(trichloromethyl) carbonate

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 20028-68-6
2,4,6-trichloroquinazoline

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate With triethylamine; Triphenylphosphine oxide In chlorobenzene at 20℃; for 0.5h; Cooling with ice; Stage #2: 2-amino-5-chlorobenzonitrile In chlorobenzene at 120℃; for 8h;	90.3%

: 5922-60-1
2-amino-5-chlorobenzonitrile

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

: (E)-N′-(4-chloro-2-cyanophenyl)-N,N-dimethylformimidamide

Conditions

Conditions	Yield
at 70 - 75℃; for 2h;	90%
In methanol for 6h; Reflux;

: 1005500-77-5
N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide

: 5922-60-1
2-amino-5-chlorobenzonitrile

: N-(4-amino-6-chloro-3-phenylquinolin-2-yl)-N,4-dimethylbenzenesulfonamide

Conditions

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,4-dioxane at 80℃; for 7h; Schlenk technique; regioselective reaction;	90%

: 41391-49-5
Ethyldithioxo-λ5-phosphoran

: 5922-60-1
2-amino-5-chlorobenzonitrile

: 6-Chloro-2-ethyl-2-thioxo-1,2-dihydro-2λ5-benzo[d][1,3,2]thiazaphosphinin-4-ylideneamine

Conditions

Conditions	Yield
In toluene at 90℃; for 3h;	89%

2-Amino-5-chlorobenzonitrile Specification

The Benzonitrile,2-amino-5-chloro- with the CAS number 5922-60-1 is also called 2-Cyano-4-chloroaniline. Both the systematic name and IUPAC name are 2-amino-5-chlorobenzonitrile. Its molecular formula is C₇H₅ClN₂. The EINECS registry number is 227-651-5. This chemical belongs to the following product categories: (1)Fine Chemical & Intermediates; (2)Anilines, Aromatic Amines and Nitro Compounds; (3)Pharmacetical; (4)Nitriles.

The properties of the Benzonitrile,2-amino-5-chloro- are: (1)ACD/LogP: 2.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.32; (4)ACD/LogD (pH 7.4): 2.32; (5)ACD/BCF (pH 5.5): 34.27; (6)ACD/BCF (pH 7.4): 34.27; (7)ACD/KOC (pH 5.5): 436.82; (8)ACD/KOC (pH 7.4): 436.84; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 27.03 Å²; (13)Index of Refraction: 1.609; (14)Molar Refractivity: 39.76 cm³; (15)Molar Volume: 114.7 cm³; (16)Polarizability: 15.76×10^-24cm³; (17)Surface Tension: 59.1 dyne/cm; (18)Enthalpy of Vaporization: 53.03 kJ/mol; (19)Vapour Pressure: 0.00201 mmHg at 25°C.

Uses: This chemical can react with (1,1-dimethoxy-ethyl)-dimethyl-amine to prepare N'-(4-chloro-2-cyano-phenyl)-N,N-dimethyl-acetamidine. This reaction needs solvent cyclohexane at heating condition. The reaction time is 4.5 hours. The yield is 79%.

While using this chemical, you should be very cautious. This chemical is harmful by inhalation, in contact with skin and if swallowed. It is not only irritating to skin, but also irritating to eyes and respiratory system. Therefore, you should take the following instructions. Firstly, you should wear suitable protective clothing, gloves and eye/face protection. Then in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(C#N)c(N)cc1
(2)InChI: InChI=1/C7H5ClN2/c8-6-1-2-7(10)5(3-6)4-9/h1-3H,10H2
(3)InChIKey: QYRDWARBHMCOAG-UHFFFAOYAW

Product Name

2-Amino-5-chlorobenzonitrile

Synthetic route

2-Amino-5-chlorobenzonitrile Specification

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