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65896-11-9 Usage

Chemical Properties

Clear yellow to brown liquid

Uses

2-BroMo-6-fluoroaniline is used for preparation of cycloalkylated benzothiadiazine derivatives and their use as AMPA receptor modulators.

Check Digit Verification of cas no

The CAS Registry Mumber 65896-11-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,8,9 and 6 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 65896-11:
(7*6)+(6*5)+(5*8)+(4*9)+(3*6)+(2*1)+(1*1)=169
169 % 10 = 9
So 65896-11-9 is a valid CAS Registry Number.

65896-11-9 Well-known Company Product Price

  • Brand
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  • Detail
  • Alfa Aesar

  • (H25774)  2-Bromo-6-fluoroaniline, 98+%   

  • 65896-11-9

  • 5g

  • 646.0CNY

  • Detail
  • Alfa Aesar

  • (H25774)  2-Bromo-6-fluoroaniline, 98+%   

  • 65896-11-9

  • 25g

  • 3226.0CNY

  • Detail

65896-11-9SDS

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-BROMO-6-FLUOROANILINE

1.2 Other means of identification

Product number -
Other names 2-bromo-6-fluoro-aniline

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:65896-11-9 SDS

65896-11-9Synthetic route

2-bromo-6-fluorobenzoic acid
2252-37-1

2-bromo-6-fluorobenzoic acid

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

Conditions
ConditionsYield
Stage #1: 2-bromo-6-fluorobenzoic acid With sulfuric acid at 60℃; for 1.5h;
Stage #2: With sodium azide at 20℃; for 42h; Schmidt rearrangement;
Stage #3: With ammonium hydroxide at 0℃;
86%
2-Fluoroaniline
348-54-9

2-Fluoroaniline

A

4-bromo-2-fluoroaniline
367-24-8

4-bromo-2-fluoroaniline

B

2,4-dibromo-6-fluorophenylamine
141474-37-5

2,4-dibromo-6-fluorophenylamine

C

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

Conditions
ConditionsYield
Stage #1: 2-Fluoroaniline With n-butyllithium In diethyl ether; hexane at -78℃; for 1h;
Stage #2: With poly[4-(dibutyliodostannyl)butyl]styrene In diethyl ether; hexane at 20℃; for 18h;
Stage #3: With bromine In diethyl ether; hexane; dichloromethane at -78 - 20℃; for 2h;
A 70%
B n/a
C n/a
2-Fluoroaniline
348-54-9

2-Fluoroaniline

A

4-bromo-2-fluoroaniline
367-24-8

4-bromo-2-fluoroaniline

B

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

Conditions
ConditionsYield
With sodium perborate; ammonium heptamolybdate; potassium bromide In acetic acid at 20℃; for 1h; Bromination;
2-Fluoroaniline
348-54-9

2-Fluoroaniline

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

Conditions
ConditionsYield
With hydrogen bromide; dimethyl sulfoxide In ethyl acetate at 60℃; for 12h;
acetic anhydride
108-24-7

acetic anhydride

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

N-(2-bromo-6-fluorophenyl)acetamide

N-(2-bromo-6-fluorophenyl)acetamide

Conditions
ConditionsYield
In dichloromethane Inert atmosphere; Reflux;100%
2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

3-fluoro-2'-methoxy-[1,1'-biphenyl]-2-amine
1338379-58-0

3-fluoro-2'-methoxy-[1,1'-biphenyl]-2-amine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 108h; Inert atmosphere;98%
With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl In toluene at 100℃; for 3h;62%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

C10H10FNO2

C10H10FNO2

Conditions
ConditionsYield
With N-Methyldicyclohexylamine; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II) In Isopropyl acetate at 80℃; for 5h; Inert atmosphere;97%
2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

2‑bromo‑6‑fluoronitrobenzene
886762-70-5

2‑bromo‑6‑fluoronitrobenzene

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 70℃; for 2h;88%
Stage #1: 2-bromo-6-fluoroaniline With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.5h; Reflux;
Stage #2: With dihydrogen peroxide; nitric acid; acetic acid at 20 - 90℃; for 0.5h;
Stage #1: 2-bromo-6-fluoroaniline With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.5h; Reflux;
Stage #2: With dihydrogen peroxide; nitric acid In acetic acid at 20 - 90℃; for 0.5h;
2-methoxy-5-trifluoromethylphenyl isocyanate
16588-75-3

2-methoxy-5-trifluoromethylphenyl isocyanate

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

3-(2-bromo-6-fluorophenyl)-1-[2-methoxy-5-(trifluoromethyl)phenyl]urea
917389-23-2

3-(2-bromo-6-fluorophenyl)-1-[2-methoxy-5-(trifluoromethyl)phenyl]urea

Conditions
ConditionsYield
In acetonitrile at 35 - 88℃; for 38 - 45h; Product distribution / selectivity;87.5%
Glutaraldehyde
111-30-8

Glutaraldehyde

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

C11H13BrFN

C11H13BrFN

Conditions
ConditionsYield
Stage #1: Glutaraldehyde; 2-bromo-6-fluoroaniline With sodium tris(acetoxy)borohydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: With sodium triacetoxy borohydride In tetrahydrofuran at 0 - 20℃; for 3h;
85%
carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

trimethyl orthoformate
149-73-5

trimethyl orthoformate

8-Ffuoro-3-phenylquinazolin-4(3H)-one
1593583-16-4

8-Ffuoro-3-phenylquinazolin-4(3H)-one

Conditions
ConditionsYield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; catacxium A In 1,4-dioxane at 100℃; under 7500.75 Torr; for 16h; Inert atmosphere; Autoclave;84%
carbon monoxide
201230-82-2

carbon monoxide

acetic anhydride
108-24-7

acetic anhydride

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

8-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one
1044749-59-8

8-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
With potassium tetrachloropalladate(II); N-ethyl-N,N-diisopropylamine; catacxium A In toluene at 100℃; under 1500.15 Torr; for 16h; Autoclave;83%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

C13H12FNO

C13H12FNO

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere;81%
2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

methyl iodide
74-88-4

methyl iodide

C8H9BrFN

C8H9BrFN

Conditions
ConditionsYield
Stage #1: 2-bromo-6-fluoroaniline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
80%
2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

isopropyl zinc bromide
77047-87-1

isopropyl zinc bromide

2-fluoro-6-isopropylaniline
126476-48-0

2-fluoro-6-isopropylaniline

Conditions
ConditionsYield
With palladium diacetate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Sealed tube;77%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

N-(2-bromo-6-fluorophenyl)pivalamide
865626-99-9

N-(2-bromo-6-fluorophenyl)pivalamide

Conditions
ConditionsYield
With pyridine at 20℃; for 3h;76%
With pyridine In methanol at 20℃; for 3h;76%
With triethylamine In dichloromethane at 0 - 20℃;
N-methylaniline
100-61-8

N-methylaniline

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

C13H11BrFN3

C13H11BrFN3

Conditions
ConditionsYield
Stage #1: 2-bromo-6-fluoroaniline With hydrogenchloride In acetonitrile at 20℃;
Stage #2: With sodium nitrite In water; acetonitrile at 0℃;
Stage #3: N-methylaniline at 0 - 20℃; pH=< 6 - < 8;
76%
Stage #1: 2-bromo-6-fluoroaniline With hydrogenchloride In acetonitrile at 0℃; for 0.25h;
Stage #2: With sodium nitrite In water; acetonitrile at 0 - 5℃; for 0.5h;
Stage #3: N-methylaniline With sodium hydrogencarbonate In acetonitrile pH=6 - 8;
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

carbon dioxide
124-38-9

carbon dioxide

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

3-(tert-butyl)-8-fluoroquinazoline-2,4(1H,3H)-dione

3-(tert-butyl)-8-fluoroquinazoline-2,4(1H,3H)-dione

Conditions
ConditionsYield
With palladium diacetate; triphenylphosphine; cesium fluoride In dimethyl sulfoxide at 90℃; under 15001.5 Torr; for 12h; Reagent/catalyst; Schlenk technique; Autoclave;74%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

methyl (2E)-3-(2-amino-3-fluorophenyl)acrylate
690664-20-1

methyl (2E)-3-(2-amino-3-fluorophenyl)acrylate

Conditions
ConditionsYield
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile for 48h; Heck Reaction; Heating / reflux;68%
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile for 48h;68%
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine for 48h; Heck Reaction;68%
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile for 48h; Heck coupling; Heating / reflux;68%
With N-Methyldicyclohexylamine; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) In Isopropyl acetate at 80℃; for 5h; Heck Reaction; Inert atmosphere; Large scale;16.2 kg
trifluoroacetic acid
76-05-1

trifluoroacetic acid

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

N-(2-bromo-6-hydroxyphenyl)-2,2,2-trifluoroacetamide

N-(2-bromo-6-hydroxyphenyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With Oxone In 1,4-dioxane at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction;68%
ethyl N-(2-cyano-4-nitrophenyl)formimidate
22363-16-2

ethyl N-(2-cyano-4-nitrophenyl)formimidate

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

N-(2-bromo-6-fluorophenyl)-6-nitroquinazolin-4-amine
1474030-52-8

N-(2-bromo-6-fluorophenyl)-6-nitroquinazolin-4-amine

Conditions
ConditionsYield
With acetic acid for 1h; Dimroth Rearrangement; Reflux;67%
C18H17NO3
884048-29-7

C18H17NO3

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

C24H21FN2O3
884034-53-1

C24H21FN2O3

Conditions
ConditionsYield
With isopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 90℃; for 0.5h;62%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

N-(2-bromo-6-fluorophenyl)-4-methylbenzenesulfonamide

N-(2-bromo-6-fluorophenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 40℃;61%
2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

1-bromo-2-iodo-3-methoxybenzene
450412-22-3

1-bromo-2-iodo-3-methoxybenzene

2-bromo-N-(2-bromo-6-methoxyphenyl)-6-fluoroaniline

2-bromo-N-(2-bromo-6-methoxyphenyl)-6-fluoroaniline

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis(diphenylphosphino)biphenyl; sodium t-butanolate In toluene for 94h; Inert atmosphere; Reflux;61%
4-methyl-3-cyclohexen-1-one
5259-65-4

4-methyl-3-cyclohexen-1-one

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

8-fluoro-4a-methyl-4,4a,9,9a-tetrahydro-1H-carbazol-2(3H)-one

8-fluoro-4a-methyl-4,4a,9,9a-tetrahydro-1H-carbazol-2(3H)-one

Conditions
ConditionsYield
With potassium carbonate; tris(dibenzylideneacetone)dipalladium (0); 1,1'-bis(diisopropylphosphino)ferrocene In toluene at 110℃; for 8h;60%
(2,3-difluorophenyl)boronic acid
121219-16-7

(2,3-difluorophenyl)boronic acid

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

2',3,3'-trifluoro-[1,1'-biphenyl]-2-amine

2',3,3'-trifluoro-[1,1'-biphenyl]-2-amine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 15h; Inert atmosphere; Reflux;60%
4,4-dimethylpent-1-en-3-ol
60041-31-8, 61348-36-5, 24580-44-7

4,4-dimethylpent-1-en-3-ol

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

2-(tert-butyl)-8-fluoroquinoline
1286756-88-4

2-(tert-butyl)-8-fluoroquinoline

Conditions
ConditionsYield
Stage #1: 4,4-dimethylpent-1-en-3-ol; 2-bromo-6-fluoroaniline With bis(η3-allyl-μ-chloropalladium(II)); N-Methyldicyclohexylamine; di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine In acetonitrile at 90℃; for 1h; Improved Larock synthesis; Inert atmosphere;
Stage #2: With di-isopropyl azodicarboxylate; acetic acid In acetonitrile at 90℃; for 0.25h; Improved Larock synthesis; Inert atmosphere;
59%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;58%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(S)-(-)-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride
64982-62-3

(S)-(-)-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

(1S)-N-(2-bromo-6-fluorophenyl)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxamide

(1S)-N-(2-bromo-6-fluorophenyl)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxamide

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 2-bromo-6-fluoroaniline In tetrahydrofuran at 0 - 20℃; for 1.5h;
Stage #2: (S)-(-)-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride With triethylamine In tetrahydrofuran at 20 - 60℃;
52%
ethyl N-phenylformimidate
6780-49-0

ethyl N-phenylformimidate

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

N-(6-fluoro-2-bromophenyl)-N’-phenylformamidine

N-(6-fluoro-2-bromophenyl)-N’-phenylformamidine

Conditions
ConditionsYield
In neat (no solvent) at 50℃;49%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 12h;49%
2-bromo-6-fluoroaniline
65896-11-9

2-bromo-6-fluoroaniline

4-Bromophenyl isothiocyanate
1985-12-2

4-Bromophenyl isothiocyanate

N-(4-bromophenyl)-4-fluorobenzothiazol-2-ylamine
1431300-97-8

N-(4-bromophenyl)-4-fluorobenzothiazol-2-ylamine

Conditions
ConditionsYield
Stage #1: 2-bromo-6-fluoroaniline; 4-Bromophenyl isothiocyanate In dimethyl sulfoxide at 18 - 25℃; for 0.5h; Inert atmosphere;
Stage #2: With copper(l) iodide In dimethyl sulfoxide at 120℃; Inert atmosphere;
45.2%

65896-11-9Relevant articles and documents

Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals

Shen, Tao,Zhu, Bencong,Lin, Fengguirong,Pan, Jun,Wei, Jialiang,Luo, Xiao,Liu, Jianzhong,Jiao, Ning

supporting information, p. 815 - 818 (2018/07/31)

A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.

Polymer-supported organotin reagents for regioselective halogenation of aromatic amines

Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul

, p. 2870 - 2873 (2007/10/03)

(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.

Sedative having analgesic and bradycardiac properties

-

, (2008/06/13)

The invention relates to the use of a substance as a sedative with an analgesic and bradycardiac effect in warm-blooded animals. The possible applications are, for example, in the field of veterinary medicine for general tranquilizing and for producing analgesia.

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