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769-10-8 Usage

Description

2-Fluoro-6-nitrotoluene is an organic compound with the molecular formula C7H6FNO2. It is a colorless to light yellow liquid that is characterized by the presence of a fluorine atom at the 2nd position and a nitro group at the 6th position on the toluene ring. 2-Fluoro-6-nitrotoluene is known for its reactivity and is commonly used as an intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
2-Fluoro-6-nitrotoluene is used as a synthetic intermediate for the preparation of 4-fluoroindole via the Leimgruber-Batcho procedure. This is significant in the pharmaceutical industry as 4-fluoroindole and its derivatives have potential applications in the development of new drugs, particularly those targeting the central nervous system.
Used in Chemical Synthesis:
2-Fluoro-6-nitrotoluene is also used as a starting material in the synthesis of various organic compounds. For instance, it can undergo reduction in the presence of stannous chloride, followed by benzoylation to yield N-(3-fluoro-o-tolyl)benzamide. Additionally, it can react with concentrated nitric acid at 100°C to produce 2-fluoro-6-nitrobenzoic acid, which can be further utilized in the synthesis of other compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 769-10-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 9 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 769-10:
(5*7)+(4*6)+(3*9)+(2*1)+(1*0)=88
88 % 10 = 8
So 769-10-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H6FNO2/c1-5-6(8)3-2-4-7(5)9(10)11/h2-4H,1H3

769-10-8 Well-known Company Product Price

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  • Aldrich

  • (247685)  2-Fluoro-6-nitrotoluene  98%

  • 769-10-8

  • 247685-10G

  • 1,042.47CNY

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  • Aldrich

  • (247685)  2-Fluoro-6-nitrotoluene  98%

  • 769-10-8

  • 247685-50G

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769-10-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Fluoro-6-nitrotoluene

1.2 Other means of identification

Product number -
Other names 2-Fluoro-6-nitrotolu

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:769-10-8 SDS

769-10-8Synthetic route

2-Fluorotoluene
95-52-3

2-Fluorotoluene

A

5-nitro-2-fluorotoluene
455-88-9

5-nitro-2-fluorotoluene

B

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
With nitric acid
2-methyl-3-nitrobenzenediazonium tetrafluoroborate

2-methyl-3-nitrobenzenediazonium tetrafluoroborate

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
With sand at 300℃;
at 250℃;
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
Ueberfuehrung in das Diazopiperidid und Erhitzen mit Fluorwasserstoff-Fluorkalium;
(i) NaNO2, HBF4, (ii) (thermolysis); Multistep reaction;
(i) (diazotization), BF4-, (ii) (pyrolysis); Multistep reaction;
Stage #1: 3-nitro-o-tolylamine With sulfuric acid; sodium nitrite at 0 - 20℃; for 2h;
Stage #2: With copper (I) fluoride Sandmeyer reaction; Further stages.;
2-Fluorotoluene
95-52-3

2-Fluorotoluene

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
With nitric acid
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

A

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

B

1-(fluoromethyl)-2-nitrobenzene

1-(fluoromethyl)-2-nitrobenzene

Conditions
ConditionsYield
With pyridine; hydrogen fluoride at 25℃; for 0.81h; electrochemical synthesis: Pt electrodes, applied potential 2.40 V, frequency square wave alternating current of 0.033 Hz, passed charge of 2.00 F mol-1; Yield given. Yields of byproduct given;
2-Fluorotoluene
95-52-3

2-Fluorotoluene

nitric acid
7697-37-2

nitric acid

A

5-nitro-2-fluorotoluene
455-88-9

5-nitro-2-fluorotoluene

B

2-fluoro-4-nitrotoluene
1427-07-2

2-fluoro-4-nitrotoluene

C

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

6-nitro-toluenediazonium-(2)-tetrafluoroborate

6-nitro-toluenediazonium-(2)-tetrafluoroborate

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
at 150 - 250℃;
2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4>2S
2: (i) (diazotization), BF4-, (ii) (pyrolysis)
View Scheme
4-Amino-2,6-dinitrotoluene
19406-51-0

4-Amino-2,6-dinitrotoluene

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) (diazotization), (ii) (reduction)
2: 4>2S
3: (i) (diazotization), BF4-, (ii) (pyrolysis)
View Scheme
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

1-fluoro-2-methyl-3,4-dinitro-benzene

1-fluoro-2-methyl-3,4-dinitro-benzene

Conditions
ConditionsYield
With sulfuric acid; uronium nitrate at 0 - 20℃; Nitration;94%
formaldehyd
50-00-0

formaldehyd

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

2-(2-fluoro-6-nitrophenyl)ethanol
118665-03-5

2-(2-fluoro-6-nitrophenyl)ethanol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; dimethyl sulfoxide for 72h; Ambient temperature;89%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

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

N,N-dimethyl-formamide dimethyl acetal

3-fluoro-trans-2-[β-(dimethylamino)vinyl]nitrobenzene

3-fluoro-trans-2-[β-(dimethylamino)vinyl]nitrobenzene

Conditions
ConditionsYield
With copper(l) iodide; N,N-dimethyl-formamide at 180℃; under 6000.6 - 7500.75 Torr; for 0.333333h; microwave irradiation;85%
With triethylamine In N,N-dimethyl-formamide at 110℃; for 20h;
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

dimethyl 2-(4-methoxybenzylidene)malonate
7443-25-6

dimethyl 2-(4-methoxybenzylidene)malonate

2-[2-(2-Fluoro-6-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

2-[2-(2-Fluoro-6-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester

Conditions
ConditionsYield
With 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium carbonate In tetrahydrofuran for 0.5h; Ambient temperature;82%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

phenylboronic acid
98-80-6

phenylboronic acid

3-fluoro-2-methyl-N-phenylaniline

3-fluoro-2-methyl-N-phenylaniline

Conditions
ConditionsYield
With triethylphosphine In m-xylene at 120℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;82%
Dimethyl oxalate
553-90-2

Dimethyl oxalate

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

methyl 3-(2-fluoro-6-nitrophenyl)-2-oxopropanoate
912819-08-0

methyl 3-(2-fluoro-6-nitrophenyl)-2-oxopropanoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 19h;80%
Stage #1: 1-fluoro-2-methyl-3-nitrobenzene With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: Dimethyl oxalate In N,N-dimethyl-formamide at 0 - 25℃; for 13h; Further stages.;
80%
pyrrolidine
123-75-1

pyrrolidine

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

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

N,N-dimethyl-formamide dimethyl acetal

1-(2-(2-fluoro-6-nitrophenyl)vinyl)pyrrolidine
344790-94-9

1-(2-(2-fluoro-6-nitrophenyl)vinyl)pyrrolidine

Conditions
ConditionsYield
for 48h; Reflux;80%
In N,N-dimethyl-formamide at 40 - 100℃; for 1h; Inert atmosphere;
pyrrolidine
123-75-1

pyrrolidine

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

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

N,N-dimethyl-formamide dimethyl acetal

1-[(E)-2-(2-Fluoro-6-nitro-phenyl)-vinyl]-pyrrolidine

1-[(E)-2-(2-Fluoro-6-nitro-phenyl)-vinyl]-pyrrolidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Heating;77%
PE

PE

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

2-(2-fluoro-6-nitrophenyl)ethanol
118665-03-5

2-(2-fluoro-6-nitrophenyl)ethanol

Conditions
ConditionsYield
With paraformaldehyde In dimethyl sulfoxide; ethyl acetate; SiO2; tert-butyl alcohol71%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

polyoxymethylene

polyoxymethylene

2-(2-fluoro-6-nitrophenyl)ethanol
118665-03-5

2-(2-fluoro-6-nitrophenyl)ethanol

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 70℃; for 1h; Inert atmosphere;69%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

2-(bromomethyl)-1-fluoro-3-nitrobenzene
1958-93-6

2-(bromomethyl)-1-fluoro-3-nitrobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 90℃; for 14h;66%
44%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Heating;22%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

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

N,N-dimethyl-formamide dimethyl acetal

2-fluoro-6-nitrobenzaldehyde
1644-82-2

2-fluoro-6-nitrobenzaldehyde

Conditions
ConditionsYield
Stage #1: 1-fluoro-2-methyl-3-nitrobenzene; N,N-dimethyl-formamide dimethyl acetal at 135℃; for 12h;
Stage #2: With sodium periodate In water; N,N-dimethyl-formamide at 20℃; for 3h;
23%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

3-(2-fluoro-6-nitrophenyl)-2-oxopropanoic acid
7593-91-1

3-(2-fluoro-6-nitrophenyl)-2-oxopropanoic acid

Conditions
ConditionsYield
Stage #1: 1-fluoro-2-methyl-3-nitrobenzene; oxalic acid diethyl ester With ethanol; sodium for 0.75h; Reflux;
Stage #2: With water In ethanol
21%
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

3-fluoro-2-methylaniline
443-86-7

3-fluoro-2-methylaniline

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride
With hydrogenchloride; tin(ll) chloride
With hydrogenchloride; tin(ll) chloride at 0 - 50℃; for 2h;
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

6-fluoro-2-nitrobenzoic acid
385-02-4

6-fluoro-2-nitrobenzoic acid

Conditions
ConditionsYield
With nitric acid
With potassium permanganate
Multi-step reaction with 3 steps
1: NBS, (PhCO)2O2 / CCl4
2: aq. Na2CO3
3: aq. H2SO4, K2Cr2O7
View Scheme
With potassium permanganate In water11.81 g (40%)
With potassium permanganate; potassium carbonate In water
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

4-fluoro-1H-indole-2-carboxylic acid
399-68-8

4-fluoro-1H-indole-2-carboxylic acid

Conditions
ConditionsYield
With diethyl ether; potassium ethoxide Behandeln des Reaktionsprodukts mit wss. NH3 unf FeSO4;
Stage #1: 1-fluoro-2-methyl-3-nitrobenzene; oxalic acid diethyl ester With sodium ethanolate In diethyl ether at 35 - 38℃; for 18h;
Stage #2: With ferrous(II) sulfate heptahydrate In aq. ammonia; water
tris(piperidino)-methane
22630-08-6

tris(piperidino)-methane

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

4-fluoroindole
387-43-9

4-fluoroindole

Conditions
ConditionsYield
With iron; silica gel 1) 120 deg C, 3 h, under vacuum 2) 1 h reflux in toluene-acetic acid; Yield given. Multistep reaction;
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

ethyl (6-fluoro-2-nitrophenyl)pyruvate

ethyl (6-fluoro-2-nitrophenyl)pyruvate

Conditions
ConditionsYield
With potassium ethoxide In ethanol for 6h; Heating;
Stage #1: oxalic acid diethyl ester With potassium tert-butylate In diethyl ether for 0.166667h;
Stage #2: 1-fluoro-2-methyl-3-nitrobenzene In diethyl ether at 20℃;
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

nitric acid
7697-37-2

nitric acid

6-fluoro-2-nitrobenzoic acid
385-02-4

6-fluoro-2-nitrobenzoic acid

1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

methyl 3-(2-fluoro-6-nitrophenyl)-2-oxobut-3-enoate
912819-11-5

methyl 3-(2-fluoro-6-nitrophenyl)-2-oxobut-3-enoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaH / dimethylformamide; various solvent(s) / 0.17 h / 0 °C
1.2: 80 percent / dimethylformamide; various solvent(s) / 13 h / 0 - 25 °C
2.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 °C
2.2: 74 percent / tetrahydrofuran; various solvent(s) / 12 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 80 percent / sodium hydride / dimethylformamide / 19 h / 0 - 25 °C
2: 74 percent / sodium hydride / tetrahydrofuran / 13 h / 0 - 25 °C
View Scheme
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

methyl 4-fluoro-1-hydroxy-3-(2-methyl-3-oxopentyl)-1H-indole-2-carboxylate

methyl 4-fluoro-1-hydroxy-3-(2-methyl-3-oxopentyl)-1H-indole-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / dimethylformamide; various solvent(s) / 0.17 h / 0 °C
1.2: 80 percent / dimethylformamide; various solvent(s) / 13 h / 0 - 25 °C
2.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 °C
2.2: 74 percent / tetrahydrofuran; various solvent(s) / 12 h / 25 °C
3.1: 61 percent / SnCl2*2H2O; molecular sieves 4 Angstroem / 1,2-dimethoxy-ethane / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: 80 percent / sodium hydride / dimethylformamide / 19 h / 0 - 25 °C
2: 74 percent / sodium hydride / tetrahydrofuran / 13 h / 0 - 25 °C
3: 61 percent / tin(II) chloride dihydrate; molecular sieves 4 Angstroem / 1,2-dimethoxy-ethane / 1.5 h / 40 °C
View Scheme
1-fluoro-2-methyl-3-nitrobenzene
769-10-8

1-fluoro-2-methyl-3-nitrobenzene

methyl 4-fluoro-1-hydroxy-3-[(2-oxocyclohexyl)methyl]-1H-indole-2-carboxylate

methyl 4-fluoro-1-hydroxy-3-[(2-oxocyclohexyl)methyl]-1H-indole-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / dimethylformamide; various solvent(s) / 0.17 h / 0 °C
1.2: 80 percent / dimethylformamide; various solvent(s) / 13 h / 0 - 25 °C
2.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 °C
2.2: 74 percent / tetrahydrofuran; various solvent(s) / 12 h / 25 °C
3.1: 44 percent / SnCl2*2H2O; molecular sieves 4 Angstroem / 1,2-dimethoxy-ethane / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: 80 percent / sodium hydride / dimethylformamide / 19 h / 0 - 25 °C
2: 74 percent / sodium hydride / tetrahydrofuran / 13 h / 0 - 25 °C
3: 44 percent / tin(II) chloride dihydrate; molecular sieves 4 Angstroem / 1,2-dimethoxy-ethane / 1.5 h / 40 °C
View Scheme

769-10-8Relevant articles and documents

4-Substituted indazoles as new inhibitors of neuronal nitric oxide synthase

Boulouard, Michel,Schumann-Bard, Pascale,Butt-Gueulle, Sabrina,Lohou, Elodie,Stiebing, Silvia,Collot, Valerie,Rault, Sylvain

, p. 3177 - 3180 (2008/02/04)

A series of halo-1-H-indazoles has been synthesized and evaluated for its inhibitory activity on neuronal nitric oxide synthase. Introduction of bromine at the C4 position of the indazole ring system provided a compound almost as potent as the reference compound, that is, 7-nitroindazole (7-NI). The importance of position 4 is further demonstrated by the synthesis and pharmacological evaluation of the 4-nitroindazole which was also a potent inhibitor of NOS activity. These compounds also exhibited in vivo NOS inhibitory activity, as attested by potent antinociceptive effects following systemic administration.

Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones

-

, (2008/06/13)

Optionally substituted 1,2,3,5-tetrahydroimidazol[2,1-b]-quinazolin-2-ones and 6-[H]-1,2,3,4-tetrahydropyrimidol[2,1-b]quinazolin-2-ones or the pharmaceutically acceptable salts thereof are compounds useful as blood platelet anti-aggregative and/or antihypertensive and/or bronchodilator agents in mammals, including humans.

The synthesis of ortho-substituted 2-diethylaminoethyl benzoates as potential local anaesthetics.

THOMAS,CANTY

, p. 587 - 596 (2007/10/05)

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