700-37-8

Basic information

• Product Name: 4-Chloro-2-fluoronitrobenzene
• Synonyms: 4-CHLORO-2-FLUORONITROBENZENE;4-CHLORO-2-FLUORO-1-NITROBENZENE;2-FLUORO-4-CHLORONITROBENZENE;1-CHLORO-3-FLUORO-4-NITROBENZENE;Chlorofluoronitrobenzene;4-Chlor-2-fluor-1-nitrobenzol;2-fluoro-4-chloroitrobenzene;4-Chloro-5-fluoronitrobenzene
• CAS NO: 700-37-8
• Molecular Formula: C₆H₃ClFNO₂
• Molecular Weight: 175.54
• EINECS: 211-842-5
• Product Categories: Fluorine series
• Mol File: 700-37-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 48°C
• Boiling Point: 241.8 °C at 760 mmHg
• Flash Point: ＞110℃
• Appearance: light brown solid
• Density: 1.494 g/cm³
• Refractive Index: 1.531
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-Chloro-2-fluoronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-fluoronitrobenzene(700-37-8)
• EPA Substance Registry System: 4-Chloro-2-fluoronitrobenzene(700-37-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39-37
• HazardClass: IRRITANT
• Hazardous Substances Data: 700-37-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow solid

InChI:InChI=1/C8H8BrFO/c1-11-8-3-2-7(10)4-6(8)5-9/h2-4H,5H2,1H3

Synthetic route

2,4-dichloronitrobenzene (611-06-3) → 2-chloro-4-fluoro-1-nitrobenzene (2106-50-5) + 2,4-Difluoronitrobenzene (446-35-5) + 4-chloro-2-fluoro-nitrobenzene (700-37-8)

Conditions	Yield
With potassium fluoride; water; tetramethlyammonium chloride In acetic acid at 120℃; for 3.5h;	A n/a B 70% C n/a

3,4-dinitro-chlorobenzene (610-40-2) → 2-fluoro-5-chloronitrobenzene (345-18-6) + 4-chloro-2-fluoro-nitrobenzene (700-37-8)

Conditions	Yield
With N-methylhexamethylenetetrammonium fluoride In dimethyl sulfoxide at 65℃; for 0.1h; Title compound not separated from byproducts;

2,4-dichloronitrobenzene (611-06-3) → 4-chloro-2-fluoro-nitrobenzene (700-37-8)

Conditions	Yield
With potassium fluoride; tetramethlyammonium chloride In malononitrile at 170℃; for 4h; Product distribution / selectivity;	7 %Chromat.

2,4-dichloronitrobenzene (611-06-3) → 2,4-Difluoronitrobenzene (446-35-5) + 4-chloro-2-fluoro-nitrobenzene (700-37-8)

Conditions	Yield
With potassium fluoride; tetramethlyammonium chloride In sulfolane at 170℃; for 4h; Product distribution / selectivity;	A 57 %Chromat. B 13 %Chromat.
With cesium fluoride In hexanedinitrile at 180 - 220℃; for 0.166667h; Microwave irradiation;	A 8 - 54 %Chromat. B 32 - 50 %Chromat.
With potassium fluoride; tetramethlyammonium chloride In pimelonitrile at 170℃; for 4h; Product distribution / selectivity;	A 48 %Chromat. B 20 %Chromat.

3-chlorofluorobenzene (625-98-9) → 4-chloro-2-fluoro-nitrobenzene (700-37-8)

Conditions	Yield
With sulfuric acid; potassium nitrate at 0 - 20℃;

4-chloro-2-fluoro-nitrobenzene (700-37-8) + sodium thiomethoxide (5188-07-8) → 4-chloro-2-(methylthio)-1-nitrobenzene (70019-41-9)

Conditions	Yield
In methanol at 15 - 25℃;	100%

4-carbethoxypiperidine (1126-09-6) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → 1-(5-chloro-2-nitrophenyl)-piperidine-4-carboxylic acid ethyl ester (847408-05-3)

Conditions	Yield
With cesium fluoride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 5h;	100%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + (R)-1,2,2-trimethylpropylamine (3850-30-4, 22526-47-2, 59367-75-8, 66228-31-7) → (5-chloro-2-nitrophenyl)-(1-(R)-methyl-2,2-dimethylpropyl)amine (863605-26-9)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 75℃; for 3h;	100%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → tert-butyl 4-((5-chloro-2-nitrophenyl)amino)piperidine-1-carboxylate (932700-82-8)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;	100%
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;	100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 18h;	93.2%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 80℃; for 1h;
With potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;

4-fluoropiperidine hydrochloride + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → 1-(5-chloro-2-nitro-phenyl)-4-fluoro-piperidine (885705-11-3)

Conditions	Yield
With sodium carbonate In toluene at 40℃; for 6h;	99%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + (2R)-methylpiperazine (75336-86-6) → (R)-1-(5-chloro-2-nitrophenyl)-3-methylpiperazine (907991-13-3)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 3h;	98%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 16h;

4-chloro-2-fluoro-nitrobenzene (700-37-8) + 1-amino-3-(dimethylamino)propane (109-55-7) → N1-(5-chloro-2-nitrophenyl)-N3,N3-dimethylpropane-1,3-diamine (92547-10-9)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	98%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 60℃; for 18h;

4-chloro-2-fluoro-nitrobenzene (700-37-8) + 3-fluoropiperidine (104223-69-0, 116574-75-5) → 1-(5-chloro-2-nitro-phenyl)-3-fluoro-piperidine (885705-14-6)

Conditions	Yield
With sodium carbonate In toluene at 40℃; for 6h;	98%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + 4-methoxy-phenol (150-76-5) → 4-chloro-2-(4-methoxy-phenoxy)nitrobenzene (1299465-90-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 3h;	98%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
In dimethyl sulfoxide at 110℃; for 4h;	98%
With triethylamine In dimethyl sulfoxide at 20℃; for 43h;
With potassium carbonate In dimethyl sulfoxide at 50℃;
With potassium carbonate In dimethyl sulfoxide at 50℃;

4-chloro-2-fluoro-nitrobenzene (700-37-8) + (S)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (169447-70-5) → (S)-tert-butyl 4-(5-chloro-2-nitrophenyl)-2-methylpiperazine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane Reflux;	98%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + 2-tert-butyloxycarbonyl-5-hydroxy-1,2,3,4-tetrahydroisoquinoline (216064-48-1) → 2-tert-butoxycarbonyl-5-(5-chloro-2-nitrophenoxy)-1,2,3,4-tetrahydroisoquinoline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	97.7%

piperidine (110-89-4) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → 1-(5-chloro-2-nitrophenyl)piperidine (53013-43-7)

Conditions	Yield
In ethanol at 0 - 23℃; for 0.75h;	97%
In ethanol at 0 - 23℃; for 0.666667h;	96%
In ethanol	2.33 g (97%)

4-chloro-2-fluoro-nitrobenzene (700-37-8) + N-(t-butoxycarbonyl)-2-(3-hydroxyphenyl)-ethylamine (129150-68-1) → tert-butyl 2-[3-(5-chloro-2-nitrophenoxy)phenyl]ethylcarbamate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	96.6%

4-methylpiperidin (626-58-4) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → 1-(5-chloro-2-nitrophenyl)-4-methylpiperidine (885704-47-2)

Conditions	Yield
In ethanol at 0 - 23℃; for 0.666667h;	96%

4-chloro-2-fluoro-nitrobenzene (700-37-8) → 1-bromo-2-chloro-4-fluoro-5-nitrobenzene (111010-08-3)

Conditions	Yield
With sulfuric acid; bromine; silver sulfate	95%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + benzylamine (100-46-9) → N-benzyl-N-(2-nitro-5-chlorophenyl)-amine (10066-19-0)

Conditions	Yield
In water at 100℃; for 1h;	95%
With potassium carbonate In ethanol at 20℃;

morpholine (110-91-8) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → 4-(5-chloro-2-nitrophenyl)morpholine (65976-63-8)

Conditions	Yield
With potassium carbonate at 30℃; for 16h;	94%
With potassium carbonate In toluene at 0 - 20℃;	67%

N'-ethyl-N,N-dimethyl-hydrazine (29559-82-8) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → N-(5-Chloro-2-nitrophenyl)-N',N'-dimethylethylenediamine (5010-24-2)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide	94%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + methylamine (74-89-5) → 4-chloro-2-methylaminonitrobenzene (35966-84-8)

Conditions	Yield
In ethanol at 0℃; for 2.25h;	92.7%
In ethanol; water for 1h;	33%
In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 24h; Product distribution / selectivity;
In tetrahydrofuran at 20℃;
In tetrahydrofuran at 20℃; for 1h; Microwave irradiation; Sealed tube;

4-chloro-2-fluoro-nitrobenzene (700-37-8) + Methyl thiosalicylate (4892-02-8) → methyl 2-((4-chloro-2-nitrophenyl)thio)benzoate (92161-65-4)

Conditions	Yield
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;	92%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	92%

trans-4-(tert-butoxycarbonylamino)cyclohexylamine + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → tert-butyl ((1r,4r)-4-((5-chloro-2-nitrophenyl)amino)cyclohexyl)carbamate

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 5h;	90%

pyrrolidine (123-75-1) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → 4-chloro-2-(1-pyrrolidinyl)nitrobenzene (133387-30-1)

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 1h;	89%
With potassium carbonate In dimethyl sulfoxide at 120℃;

4-chloro-2-fluoro-nitrobenzene (700-37-8) + tert-butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate (158985-25-2) → tert-butyl 4-[4-(5-chloro-2-nitrophenoxy)phenyl]piperazine-1-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	89%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + (RS)-2-methylpiperazine (109-07-9) → 1-(5-chloro-2-nitro-phenyl)-3-methyl-piperazine (709023-21-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 16h;	88%

4-chloro-2-fluoro-nitrobenzene (700-37-8) → cis-4-(5-chloro-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 16h;	87%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + (S)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (169447-70-5) → (S)-1-(5-chloro-2-nitrophenyl)-3-methylpiperazine

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	86.3%

methyl 3-hydroxy-2-thiophenecarboxylate (5118-06-9) + 4-chloro-2-fluoro-nitrobenzene (700-37-8) → methyl 3-(5-chloro-2-nitrophenoxy)thiophene-2-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	85%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + Cyclopropylamine (765-30-0) → 5-chloro-N-cyclopropyl-2-nitroaniline (147245-29-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere;	83%
With triethylamine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere;	83%

4-chloro-2-fluoro-nitrobenzene (700-37-8) + methyl salicylate (119-36-8) → methyl 2-(4-chloro-2-nitrophenoxy)benzoate (858670-83-4)

Conditions	Yield
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;	82%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	82%

Upstream product

• 611-06-3 2,4-dichloronitrobenzene 
• 625-98-9 3-chlorofluorobenzene 
• 610-40-2 3,4-dinitro-chlorobenzene 

Downstream Products

• 925211-88-7 5-chloro-2-nitro-N-propylaniline 
• 1026490-44-7 (1-Benzyl-pyrrolidin-3-yl)-(5-chloro-2-nitro-phenyl)-amine 
• 28096-58-4 N-cyclohexyl-2-nitro-5-chloro-aniline 
• 5010-24-2 N-(5-Chloro-2-nitrophenyl)-N',N'-dimethylethylenediamine 
• 907991-13-3 (R)-1-(5-chloro-2-nitrophenyl)-3-methylpiperazine 
• 85076-03-5 4-(5-chloro-2-nitro-phenylamino)-piperidine-1-carboxylic acid ethyl ester 
• 859307-61-2 ethyl 2-(4-chloro-2-nitrophenylamino)acetate 
• 907991-14-4 (R)-4-(5-Chloro-2-nitro-phenyl)-2-methyl-piperazine-1-carboxylic acid benzyl ester 
• 907991-15-5 (R)-4-(2-Amino-5-chloro-phenyl)-2-methyl-piperazine-1-carboxylic acid benzyl ester 
• 907991-16-6 (R)-4-(5-Chloro-2-iodo-phenyl)-2-methyl-piperazine-1-carboxylic acid benzyl ester 
• 907991-20-2 {4-[5-chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-2-methyl-piperazin-1-yl}-acetic acid tert-butyl ester 
• 907991-18-8 (R)-4-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-2-methyl-piperazine-1-carboxylic acid benzyl ester 
• 907991-19-9 (R)-1-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-3-methyl-piperazine 

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