2-Chloro-6-fluorobenzonitrile supplier

Name
2-Chloro-6-fluorobenzonitrile
EINECS 211-571-2
CAS No. 668-45-1
Article Data18
CAS DataBase
Density 1.33 g/cm³
Solubility Insoluble in water
Melting Point 55-59 °C(lit.)
Formula C₇H₃ClFN
Boiling Point 225.7 °C at 760 mmHg
Molecular Weight 155.559
Flash Point 90.3 °C
Transport Information UN 3439 6.1/PG 3
Appearance colourless to light beige crystals
Safety 26-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn, T, Xi
Synonyms 2-Chloro-6-fluorocyanobenzene;
PSA 23.79000
LogP 2.35078

Synthetic route

: 443-33-4
N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine

: 668-45-1
2-chloro-6-fluorobenzonitrile

Conditions

Conditions	Yield
With trifluoromethylsulfonic anhydride; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 0.166667h;	96%
With 1,1,3,3-tetraphenyl-2-oxa-1,3-phoshpinobenzene bis(trifluoromethanesulfonate); triethylamine In dichloromethane at 20℃; for 0.333333h;	96%
Stage #1: N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine With bis(trichloromethyl) carbonate; N,N-dimethyl-formamide In acetonitrile at 20℃; for 0.166667h; Stage #2: With water; sodium hydrogencarbonate In acetonitrile	94%
With [PdCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}] In acetonitrile at 100℃; for 24h; Inert atmosphere; Sealed tube;	91%
With C24H33ClF3N3Os In acetonitrile at 80℃; for 1h; Sealed tube;	82%

: 6575-07-1
2-chloro-6-nitrobenzonitrile

: 668-45-1
2-chloro-6-fluorobenzonitrile

Conditions

Conditions	Yield
With biphenyl; tetramethylammonium hydrogen difluoride In N,N-dimethyl acetamide at 60℃; for 3h;	84%
With potassium fluoride; tetraphenylphosphonium bromide at 82℃; The ratio of the initial rates of flurine transfer reaction with KF alone and KF-Ph4PBr were measured in CH3CN and sulpholane.;
With potassium fluoride In dimethyl sulfoxide at 82℃; solvent effect of nucleophilie fluorine transfer, var. chloro-nitrobenzene;

: 6575-07-1
2-chloro-6-nitrobenzonitrile

A: 668-45-1
2-chloro-6-fluorobenzonitrile

B: 1897-52-5
2,6 difluorobenzonitrile

Conditions

Conditions	Yield
With biphenyl; tetramethylammonium fluoride In N,N-dimethyl acetamide at 60℃; for 0.666667h;	A 72% B 5%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1.5h; Ambient temperature;	A 75 % Chromat. B 25 % Chromat.

: 6575-07-1
2-chloro-6-nitrobenzonitrile

A: 668-45-1
2-chloro-6-fluorobenzonitrile

B: 1897-52-5
2,6 difluorobenzonitrile

C: 89999-90-6
3-chloro-2-cyanophenol

D: 140675-43-0
2-Fluoro-6-hydroxybenzonitrile

Conditions

Conditions	Yield
With tetramethylammonium fluoride In dimethyl sulfoxide at 100℃; for 1h; Fluorination;

...Expand

: 1194-65-6
2,6-dichloro-benzonitrile

A: 668-45-1
2-chloro-6-fluorobenzonitrile

B: 1897-52-5
2,6 difluorobenzonitrile

Conditions

Conditions	Yield
With potassium fluoride; 1-butyl-3-methylimidazolium tetrafluoroborate In sulfolane at 180℃; for 18h; Product distribution / selectivity;	A 45 %Chromat. B 52 %Chromat.
1-butyl-3-methylimidazolium hexafluorophosphate In sulfolane at 180℃; for 18h; Product distribution / selectivity;	A 79 %Chromat. B 19 %Chromat.

: 6575-07-1
2-chloro-6-nitrobenzonitrile

Ph4 P+ HF: Ph4 P+ HF

: 668-45-1
2-chloro-6-fluorobenzonitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 89999-90-6
3-chloro-2-cyanophenol

Conditions

Conditions	Yield
With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In tetrahydrofuran at 20℃; for 0.5h;	100%
Stage #1: 2-chloro-6-fluorobenzonitrile With 18-crown-6 ether; potassium tert-butylate In acetonitrile Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In water; acetonitrile for 1h; Stage #3: In water pH=4; Acidic conditions;	60%
With 18-crown-6 ether; potassium acetate In acetonitrile for 24h; Heating;	2.20 g

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 108-95-2
phenol

: 91692-70-5
2-chloro-6-phenyloxybenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 190℃; for 0.1h; Microwave irradiation; Sealed tube;	97%
With potassium carbonate In dimethyl sulfoxide at 190℃; for 0.1h; Microwave irradiation; Sealed tube;	97%
With potassium fluoride on basic alumina; 18-crown-6 ether In dimethyl sulfoxide at 140℃; for 20h;	90%

: 766-85-8
3-methoxy-1-iodobenzene

: 668-45-1
2-chloro-6-fluorobenzonitrile

: C14H9ClFNO

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluorobenzonitrile With lithium chlorozincate; lithium dicyclohexylamide In tetrahydrofuran at 0℃; for 0.0111111h; Flow reactor; Stage #2: 3-methoxy-1-iodobenzene With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 2h; Negishi Coupling; Flow reactor;	97%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 434-75-3
2-chloro-6-fluorobenzoic acid

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.5h; Green chemistry;	95%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 60-34-4
methylhydrazine

: 959240-93-8
4-chloro-1-methyl-1H-indazol-3-amine

Conditions

Conditions	Yield
In ethanol Reflux; regioselective reaction;	94%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 124-46-9, 20734-13-8, 100224-74-6, 593-85-1
guanidine hydrogen carbonate

: 17511-21-6
5-chloro-2,4-diaminoquinazoline

Conditions

Conditions	Yield
In N,N-dimethyl acetamide at 140 - 142℃; for 7h;	92%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 2-chloro-6-hydrazinobenzonitrile

Conditions

Conditions	Yield
With hydrazine In tetrahydrofuran at 20 - 30℃; for 0.75h;	90%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 146374-27-8
S-tert-butylsulfinimide

: 1338209-85-0
N-(2-cyano-3-fluorophenyl)-2-methylpropane-2-sulfinamide

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 15h; Inert atmosphere;	90%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 124-41-4
sodium methylate

: 6575-10-6
2-Chlor-6-methoxybenzoesaeurenitril

Conditions

Conditions	Yield
In methanol at 85℃;	89.8%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 15205-15-9
2-chloro-6-fluorobenzyl amine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0℃; for 24h; Inert atmosphere;	89%
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4h; Inert atmosphere;	75%
With lithium borohydride In tetrahydrofuran at 25℃; for 3h;	70%
With lithium borohydride; diisopropopylaminoborane In tetrahydrofuran for 2h; Reflux;	70%
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	16%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 2-chloro-6-ethoxybenzonitrile

Conditions

Conditions	Yield
In tetrahydrofuran; ethanol	87%
In tetrahydrofuran; ethanol	87%

: 64-17-5
ethanol

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 2-chloro-6-ethoxybenzonitrile

Conditions

Conditions	Yield
Stage #1: ethanol With sodium t-butanolate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-fluorobenzonitrile In tetrahydrofuran at 20℃; for 0.5h;	87%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 72371-52-9
2-chloro-6-mercapto-benzonitrile

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluorobenzonitrile With sodium sulfide In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride; zinc In water Cooling with ice; Inert atmosphere;	86%
Stage #1: 2-chloro-6-fluorobenzonitrile In dimethyl sulfoxide at 75℃; for 0.333333h; Stage #2: With sodiumsulfide nonahydrate In dimethyl sulfoxide at 75℃; for 2h;

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 4294-57-9
para-methylphenylmagnesium bromide

: 1239886-78-2
3-fluoro-4'-methylbiphenyl-2-carbonitrile

Conditions

Conditions	Yield
With manganese(ll) chloride In tetrahydrofuran at 0℃; for 0.5h;	83%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 105-34-0
methyl 2-cyanoacetate

: 1184843-24-0
2-chloro-6-(cyanomethyl)benzonitrile

Conditions

Conditions	Yield
Stage #1: methyl 2-cyanoacetate With sodium hydride In dimethyl sulfoxide at 0 - 20℃; for 0.5h; Stage #2: 2-chloro-6-fluorobenzonitrile In dimethyl sulfoxide at 90℃;	83%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 66073-54-9
2-chloro-6-fluoro-benzamide

Conditions

Conditions	Yield
With sulfuric acid at 75℃; for 3.5h;	80%
With sulfuric acid at 70℃; for 4h;	80%
With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide at 0 - 25℃;
With sulfuric acid at 60 - 70℃;	5.5 g

: 668-45-1
2-chloro-6-fluorobenzonitrile

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

: 6-chloro-2-fluoro-3-formylbenzonitrile

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -40℃; Flow reactor;	80%
Stage #1: 2-chloro-6-fluorobenzonitrile With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -70℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; n-heptane at -70℃; for 0.5h;	17%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 95-55-6
2-amino-phenol

: 1-chlorodibenzo[b,f][1,4]oxazepin-11-amine

Conditions

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 6h;	80%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 346656-39-1
2-(2-fluorophenyl)-5,5-dimethyl-[1,3,2]dioxaborinane

: 537036-82-1
2′-fluoro-3-fluorobiphenyl-2-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 63h; Suzuki-Miyaura coupling;	78%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 769-05-1
2-chloro-6-fluorobenzenecarbothioamide

Conditions

Conditions	Yield
With pyridine; diammonium sulfide; triethylamine at 50℃; for 4h;	78%
With diammonium sulfide; triethylamine In pyridine at 50℃;	75%
With pyridine; triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	72%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene

: C31H18ClN3

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluorobenzonitrile; 5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene With sodium t-butanolate In toluene for 0.5h; Reflux; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux;	78%

: 75-89-8
2,2,2-trifluoroethanol

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 93624-59-0
3-chloro-6-2',2',2'-trifluoroethoxybenzonitrile

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 150℃; for 15h;	77%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 420-87-1
sodium 2,2,2-trifluoroethanolate

: 93624-59-0
3-chloro-6-2',2',2'-trifluoroethoxybenzonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃;	77%

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 1247053-55-9
5,12-dihydro-5-phenyl indolo[3,2-a]carbazole

: C31H18ClN3

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluorobenzonitrile; 5,12-dihydro-5-phenyl indolo[3,2-a]carbazole With sodium t-butanolate In toluene for 0.5h; Reflux; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux;	77%

: 121-43-7
Trimethyl borate

: 668-45-1
2-chloro-6-fluorobenzonitrile

: (4-chloro-3-cyano-2-fluorophenyl)boronic acid

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -40℃; Flow reactor;	76%

: 124-38-9
carbon dioxide

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 4-chloro-3-cyano-2-fluorobenzoic acid

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -50℃; Flow reactor;	76%
Stage #1: 2-chloro-6-fluorobenzonitrile With lithium diisopropyl amide In tetrahydrofuran at -65℃; for 0.25h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at -50 - 20℃; for 1.75h;	42%

: 1060735-14-9
9-phenyl-3,3'-bicarbazole

: 668-45-1
2-chloro-6-fluorobenzonitrile

: C37H22ClN3

Conditions

Conditions	Yield
Stage #1: 9-phenyl-3,3'-bicarbazole; 2-chloro-6-fluorobenzonitrile With sodium t-butanolate In toluene for 0.5h; Reflux; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux;	75%

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 668-45-1
2-chloro-6-fluorobenzonitrile

: 6-chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -40℃; Flow reactor;	73%

2-Chloro-6-fluorobenzonitrile Specification

The Benzonitrile,2-chloro-6-fluoro- with the CAS number 668-45-1 is also called 2-Chloro-6-fluorocyanobenzene. Both the systematic name and IUPAC name are 2-chloro-6-fluorobenzonitrile. Its molecular formula is C₇H₃ClFN. The EINECS registry number is 211-571-2. This chemical belongs to the following product categories: (1)Aromatic Nitriles; (2)Benzene nitrile; (3)Chlorine Compounds; (4)Fluorine Compounds; (5)Nitriles; (6)C6 to C7; (7)Cyanides/Nitriles; (8)Nitrogen Compounds.

The properties of the Benzonitrile,2-chloro-6-fluoro- are: (1)ACD/LogP: 1.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.63; (4)ACD/LogD (pH 7.4): 1.63; (5)ACD/BCF (pH 5.5): 10.14; (6)ACD/BCF (pH 7.4): 10.14; (7)ACD/KOC (pH 5.5): 182.74; (8)ACD/KOC (pH 7.4): 182.74; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 23.79 Å²; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 36.26 cm³; (15)Molar Volume: 116.1 cm³; (16)Polarizability: 14.37×10^-24cm³; (17)Surface Tension: 43 dyne/cm; (18)Enthalpy of Vaporization: 46.22 kJ/mol; (19)Vapour Pressure: 0.0852 mmHg at 25°C.

Preparation: This chemical can be prepared by 2-chloro-6-nitrobenzonitrile. This reaction needs reagent potassium fluoride and solvent dimethylsulfoxide at temperature of 82 °C.

Uses: This chemical can react with 2,2,2-trifluoro-ethanol to prepare 2-chloro-6-(2,2,2-trifluoroethoxy)benzonitrile. This reaction needs reagent sodium hydride and solvent dimethylformamide at temperature of 150 °C. The reaction time is 15 hours. The yield is 77%.

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: N#Cc1c(F)cccc1Cl
(2)InChI: InChI=1/C7H3ClFN/c8-6-2-1-3-7(9)5(6)4-10/h1-3H
(3)InChIKey: XPTAYRHLHAFUOS-UHFFFAOYAZ

Product Name

2-Chloro-6-fluorobenzonitrile

Synthetic route

2-Chloro-6-fluorobenzonitrile Specification

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