3970-37-4

Basic information

• Product Name: 1-BROMO-2-CHLORO-3-NITROBENZENE
• Synonyms: 1-BROMO-2-CHLORO-3-NITROBENZENE
• CAS NO: 3970-37-4
• Molecular Formula: C₆H₃BrClNO₂
• Molecular Weight: 236.45
• Mol File: 3970-37-4.mol

Chemical Properties

• Boiling Point: 290.355 °C at 760 mmHg
• Flash Point: 129.403 °C
• Appearance: /
• Density: 1.827 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-BROMO-2-CHLORO-3-NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-CHLORO-3-NITROBENZENE(3970-37-4)
• EPA Substance Registry System: 1-BROMO-2-CHLORO-3-NITROBENZENE(3970-37-4)

Safety Data

• Hazardous Substances Data: 3970-37-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1-Bromo-2-chloro-3-nitrobenzene is used as a reagent in the pharmaceutical industry for the synthesis of various drugs and drug candidates. Its unique structure allows for further functionalization and modification, making it a valuable intermediate in the development of new therapeutic agents.
2. Used in the Synthesis of Benzodiazepinone Bromodomain Inhibitor CPI-?637:
In the field of cancer therapy, 1-bromo-2-chloro-3-nitrobenzene is employed in the synthesis of benzodiazepinone bromodomain inhibitor CPI-?637. Bromodomain inhibitors, such as CPI-?637, are a class of drugs that target specific protein-protein interactions, which play a crucial role in the regulation of gene expression and cellular processes. By inhibiting these interactions, CPI-?637 may have potential applications in the treatment of various types of cancer.
3. Used in the Development of Novel Drug Delivery Systems:
1-BROMO-2-CHLORO-3-NITROBENZENE may also be utilized in the development of innovative drug delivery systems, which aim to improve the bioavailability, targeting, and overall efficacy of therapeutic agents. By incorporating 1-bromo-2-chloro-3-nitrobenzene into the design of these systems, researchers can potentially enhance the delivery of drugs to specific cells or tissues, thereby increasing their therapeutic potential.

InChI:InChI=1/C6H3BrClNO2/c7-4-2-1-3-5(6(4)8)9(10)11/h1-3H

Synthetic route

2-chloro-3-nitrobezoic acid (3970-35-2) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
With bromine; mercury(II) oxide In tetrachloromethane for 3.5h; Heating; Irradiation;	96%
With bromine; mercury(II) oxide In tetrachloromethane light;	96%
With bromine; mercury(II) oxide In tetrachloromethane at 20℃; for 4.5h; Heating / reflux; Irradiation;	95%

2-bromo-6-nitroaniline (59255-95-7) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
With tert.-butylnitrite; copper dichloride In acetonitrile at 60℃; for 1h; Inert atmosphere;	86.2%
With tert.-butylnitrite; copper dichloride In acetonitrile at 60℃; for 1h; Inert atmosphere;	82.7%
Diazotization.Eintropfen der Diazoniumloesung in Kupferchloruerloesung;
Stage #1: 2-bromo-6-nitroaniline With sodium nitrate; sulfuric acid; acetic acid at 25 - 35℃; for 0.5h; Stage #2: With hydrogenchloride; copper(l) chloride In water at 70℃;

2-chloro-3-nitroaniline (3970-41-0) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
Stage #1: 2-chloro-3-nitroaniline With hydrogen bromide; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With hydrogen bromide; copper(I) bromide In water at 70℃; for 1h; Sandmeyer Reaction;	71%
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; for 0.5h;

1,2-dibromo-3-nitrobenzene (26429-41-4) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
With tetrabutylammonium bromchlorocuprate(I) In chlorobenzene at 90℃; Rate constant; halogen exchange reaction of 3-bromo-2-iodonitrobenzene with tetrabutylammonium bromochlorocuprate(I), NMR study;
With tetrabutylammonium dichlorocuprate(I) In dimethyl sulfoxide at 85℃; Rate constant; Thermodynamic data; Kinetics; solvent dependence, ΔH(excit), ΔS(excit);
Multi-step reaction with 2 steps 1: alcohol; ammonia / 180 °C 2: Diazotization.Eintropfen der Diazoniumloesung in Kupferchloruerloesung View Scheme

1-bromo-2-iodo- 3-nitrobenzene (32337-96-5) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
With tetrabutylammonium bromchlorocuprate(I) In chlorobenzene at 90℃; Rate constant; halogen exchange reaction of 3-bromo-2-iodonitrobenzene with tetrabutylammonium bromochlorocuprate(I), NMR study;

1,2-dibromobenzene (583-53-9) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid 2: alcohol; ammonia / 180 °C 3: Diazotization.Eintropfen der Diazoniumloesung in Kupferchloruerloesung View Scheme
Multi-step reaction with 3 steps 1: nitric acid 2: alcohol; ammonia / 180 °C 3: Diazotization.Eintropfen der Diazoniumloesung in Kupferchloruerloesung View Scheme

Ar + mercury(II) oxide (21908-53-2) + 2-chloro-3-nitrobezoic acid (3970-35-2) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
With bromine In tetrachloromethane

2-fluoro-3-bromonitrobenzene (58534-94-4) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / methanol / 16 h / 100 °C / Sealed tube 2: tert.-butylnitrite; copper dichloride / acetonitrile / 1 h / 60 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: ammonia / methanol / 16 h / 100 °C / Sealed tube 2: tert.-butylnitrite; copper dichloride / acetonitrile / 1 h / 60 °C / Inert atmosphere View Scheme

3-nitro-aniline (99-09-2) → 1-bromo-2-chloro-3-nitrobenzene (3970-37-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 20 - 75 °C 2.1: hydrogen bromide; sodium nitrite / water / 0.5 h / 0 - 5 °C 2.2: 1 h / 70 °C View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 3-bromo-2-chlorobenzenamine (56131-46-5)

Conditions	Yield
With iron; acetic acid In ethanol; water at 20℃; for 16h;	100%
With iron; ammonium chloride In ethanol; water at 60℃; for 4h;	93.88%
With iron; ammonium chloride In ethanol; water at 60℃; for 4h;	93.88%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + tert-butylamine (75-64-9) → 2-bromo-N-tert-butyl-6-nitroaniline (183801-89-0)

Conditions	Yield
In ethanol at 150℃; for 96h;	93%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + methylamine (74-89-5) → 2-bromo-N-methyl-6-nitro-aniline (1004618-77-2)

Conditions	Yield
In methanol; ethanol at 85℃; for 2h;	92%

(R)-3-aminobutanoic acid (3775-73-3) + 1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → (R)-3-((2-bromo-6-nitrophenyl)amino)butanoic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃;	90%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + phenylmethanethiol (100-53-8) → benzyl(2-bromo-6-nitrophenyl)sulfane

Conditions	Yield
With sodium In ethanol for 1.08333h; Reflux;	88.5%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 2-fluoro-3-bromonitrobenzene (58534-94-4)

Conditions	Yield
With potassium fluoride; cesium fluoride In N,N-dimethyl-formamide	73%
With potassium fluoride In N,N-dimethyl-formamide at 150℃;
With potassium fluoride; cesium fluoride In DMF (N,N-dimethyl-formamide) for 5h; Heating / reflux;

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (785051-54-9) + 1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → C24H15ClN2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 80℃; for 6h;	70%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + (2-(9H-carbazol-9-yl)phenyl)boronic acid (1189047-28-6) → C24H15ClN2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 3h; Suzuki Coupling;	66%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 3h;	66%

morpholine (110-91-8) + 1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 4-(2-chloro-3-nitrophenyl)morpholine (1146413-10-6)

Conditions	Yield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran at 20 - 85℃; for 16.5h;	58.4%
With palladium diacetate; caesium carbonate In tetrahydrofuran at 85℃; for 16h; Inert atmosphere;	49.5%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + sodium methylate (124-41-4) → 2-bromo-6-nitrophenyl methyl ether (98775-19-0)

Conditions	Yield
With methanol at 100℃; for 3h; Autoclave;	58%
In methanol

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + vinyl magnesium bromide (1826-67-1) → 6-bromo-7-chloro-1H-indole

Conditions	Yield
In tetrahydrofuran at -78℃; for 3h;	49%
In tetrahydrofuran at -40℃; for 1h; Inert atmosphere;	32%
In tetrahydrofuran at -78℃; for 3h;	32%
In tetrahydrofuran at -40℃; for 1h;

pyrrolidine (123-75-1) + 1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → C10H11ClN2O2

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran at 85℃; for 18h;	39.64%

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + (phenylthio)acetonitrile (5219-61-4) → (2-Bromo-3-chloro-4-nitro-phenyl)-acetonitrile (1176315-49-3)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 18.5 - 22℃;	19%

piperidine (110-89-4) + 1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 1-(2-Bromo-6-nitro-phenyl)-piperidine (98775-21-4)

Conditions	Yield
Heating;

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) + 3-pyridylboronic acid (1692-25-7) → 3-(2-chloro-3-nitro-phenyl)-pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 12h; Arylation; Heating;

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 2-chloro-3-(3-pyridyl)aniline (264617-06-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine)palladium(0); Na2CO3 / 1,2-dimethoxy-ethane; H2O / 12 h / Heating 2: stannous chloride; aq. HCl View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → (2-chloro-3-pyridin-3-yl-phenyl)-carbamic acid phenyl ester (264617-22-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine)palladium(0); Na2CO3 / 1,2-dimethoxy-ethane; H2O / 12 h / Heating 2: stannous chloride; aq. HCl 3: 100 percent / Et3N / CH2Cl2 / 18 h / 20 °C View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 5-methoxy-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid (2-chloro-3-pyridin-3-yl-phenyl)-amide

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine)palladium(0); Na2CO3 / 1,2-dimethoxy-ethane; H2O / 12 h / Heating 2: stannous chloride; aq. HCl 3: 100 percent / Et3N / CH2Cl2 / 18 h / 20 °C 4: 45 percent / Et3N / dimethylformamide / 1 h / 95 - 105 °C View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 3-Bromo-N2-tert-butyl-benzene-1,2-diamine (183802-24-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 5-bromo-1,2,3,4-tetrahydroquinoxalin-2-one (183801-94-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature 3: 77 percent / diisopropylethylamine / tetrahydrofuran / a) -60 deg C, 3 h, b) RT, 16 h 4: 79 percent / diisopropylethylamine, NaI / acetonitrile / 22 h / Heating 5: 1.) TFA, 2.) NaBH4 / 1.) RT, 20 h, 2.) MeOH, EtOH, RT, 6 h View Scheme
Multi-step reaction with 5 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature 3: 77 percent / diisopropylethylamine / tetrahydrofuran / a) -60 deg C, 3 h, b) RT, 16 h 4: 79 percent / diisopropylethylamine, NaI / acetonitrile / 22 h / Heating 5: TFA / 20 h / Ambient temperature View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 5-Bromo-1H-quinoxalin-2-one

Conditions	Yield
Multi-step reaction with 5 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature 3: 77 percent / diisopropylethylamine / tetrahydrofuran / a) -60 deg C, 3 h, b) RT, 16 h 4: 79 percent / diisopropylethylamine, NaI / acetonitrile / 22 h / Heating 5: TFA / 20 h / Ambient temperature View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 5-bromo-4-tert-butyl-1,2,3,4-tetrahydroquinoxalin-2-one (183801-92-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature 3: 77 percent / diisopropylethylamine / tetrahydrofuran / a) -60 deg C, 3 h, b) RT, 16 h 4: 79 percent / diisopropylethylamine, NaI / acetonitrile / 22 h / Heating View Scheme

1-bromo-2-chloro-3-nitrobenzene (3970-37-4) → 6,7-Dihydro-1H-pyrido[1,2,3-de]quinoxaline-2,5-dione (180990-30-1)

Conditions	Yield
Multi-step reaction with 7 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature 3: 77 percent / diisopropylethylamine / tetrahydrofuran / a) -60 deg C, 3 h, b) RT, 16 h 4: 79 percent / diisopropylethylamine, NaI / acetonitrile / 22 h / Heating 5: 1.) TFA, 2.) NaBH4 / 1.) RT, 20 h, 2.) MeOH, EtOH, RT, 6 h 6: 63 percent / Et3N, Pd(PPh3)4 / dimethylformamide / 6 h / 120 °C 7: 79 percent / H2, p-TsOH*H2O / 5percent Pd/C / ethanol; methanol / 40 h / 2068.6 Torr / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: 93 percent / ethanol / 96 h / 150 °C 2: 97 percent / aq. TiCl3, aq. AcONa / methanol / 2 h / Ambient temperature 3: 77 percent / diisopropylethylamine / tetrahydrofuran / a) -60 deg C, 3 h, b) RT, 16 h 4: 79 percent / diisopropylethylamine, NaI / acetonitrile / 22 h / Heating 5: TFA / 20 h / Ambient temperature 6: 63 percent / Et3N, Pd(PPh3)4 / dimethylformamide / 6 h / 120 °C 7: 79 percent / H2, p-TsOH*H2O / 5percent Pd/C / ethanol; methanol / 40 h / 2068.6 Torr / Ambient temperature View Scheme

Upstream product

• 59255-95-7 2-bromo-6-nitroaniline 
• 26429-41-4 1,2-dibromo-3-nitrobenzene 
• 32337-96-5 1-bromo-2-iodo-3-nitro-benzene 
• 3970-35-2 2-chloro-3-nitrobezoic acid 
• 3970-41-0 2-chloro-3-nitroaniline 
• 583-53-9 2,3-dibromobenzene 
• 21908-53-2 mercury(II) oxide 
• 58534-94-4 2-fluoro-3-bromonitrobenzene 
• 99-09-2 3-nitro-aniline 
• 121-18-6 3-nitro-4-chlorobenzenesulfonic acid 

Downstream Products

• 58534-94-4 2-fluoro-3-bromonitrobenzene 
• 98775-21-4 1-(2-Bromo-6-nitro-phenyl)-piperidine 
• 98775-19-0 2-bromo-6-nitrophenyl methyl ether 
• 183801-89-0 2-bromo-N-tert-butyl-6-nitroaniline 
• 56131-46-5 3-bromo-2-chlorobenzenamine 
• 1004618-77-2 2-bromo-N-methyl-6-nitro-aniline 
• 264617-06-3 2-chloro-3-(3-pyridyl)aniline 
• 264617-22-3 (2-chloro-3-pyridin-3-yl-phenyl)-carbamic acid phenyl ester 
• 183802-24-6 3-Bromo-N²-tert-butyl-benzene-1,2-diamine 
• 183801-91-4 3'-bromo-2'-(tert-butylamino)-2-chloroacetanilide 
• 313544-90-0 (2-bromo-6-nitrophenyl)(3-chloropropyl)sulfane 
• 1146413-10-6 4-(2-chloro-3-nitrophenyl)morpholine 
• 1196131-17-5 C₁₀H₁₃BrN₂O₂ 
• 1269233-02-4 N-(3-bromo-2-chlorophenyl)propane-1-sulfonamide 

Relevant articles and documents

Preparation method 2 - chloro -3 - bromoaniline

The invention discloses a preparation method of 2 - chloro -3 - bromoaniline, and the specific steps of the preparation method are as follows: (1) the compound II and the bromosuccinimide are subjected to electrophilic substitution reaction to generate the compound III. (2) The sulfonic acid group of the compound III was removed to give compound IV. (3) Compound IV is reduced to compound I with a safety powder, i.e. said 2 - chloro -3 - bromoaniline. To the invention, 4 - chlorine -3 - nitrobenzene sulfonic acid is used as a starting raw material in a full synthetic route process, reagents with large toxicity and large pollution are avoided, and meanwhile, the raw materials are low in price and higher in yield.

SUBSTITUTED QUINAZOLINE COMPOUNDS AND THEIR USE AS INHIBITORS OF G12C MUTANT KRAS, HRAS AND/OR NRAS PROTEINS

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INHIBITORS OF KRAS G12C

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Compounds and Compositions as Protein Kinase Inhibitors

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DIKETOPIPERAZINE DERIVATIVES AS P2X7 MODULATORS

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein: A represents an aryl, heteroaryl or heterocyclyl group; and any ring or ring system of said aryl or heteroaryl is optionally substituted with 1 to 3 substituents, which may be the same or different, selected from the group consisting of halogen, C1-6 alkyl, -CF3, - OCF3, cyano, C1-6 alkoxy, -NR10R11, -X-aryl, -X-heteroaryl and -X-heterocyclyl; R1, R2, R3, R4 and R5 independently represent hydrogen, fluorine, chlorine, -CF3, cyano or C1-6 alkyl, such that at least one of R1, R2, R3, R4 and R5 is other than hydrogen; R6, R7, R8, R9, R10 and R11 independently represent hydrogen or C1-6 alkyl; X represents a linker selected from a bond, -(CH2)n- and -O-(CH2)n-; and n represents an integer from 1 to 3. The compounds or salts modulate P2X7 receptor function and are capable of antagonizing the effects of ATP at the P2X7 receptor ("P2X7 receptor antagonists").

IMIDAZOLINYLMETHYL ARYL SULFONAMIDE

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FUSED PYRIMIDINE DERIVATIVE AND USES THEREOF

A compound represented by the formula (I) wherein ring A is a 5-membered aromatic heterocycle optionally having substituent(s), R1 is a hydrogen atom or a hydrocarbon group optionally having substituent(s), W is an oxygen atom or a sulfur atom, X1 and X2 may be the same or different and each is a hydrogen atom, a hydrocarbon group optionally having substituent(s) or a heterocyclic group, or, X1 and X2 in combination optionally form an oxygen atom, a sulfur atom or =NR2, ring B is an aromatic ring optionally further having substituent(s), Y is a bond, C1-6 alkylene C2-6 alkenylene or C2-6 alkynylene, optionally having substituent(s), and Z is a group represented by formula: -SOnR3, or a group represented by formula: -COR4, or a salt thereof, is useful as a pharmaceutical agent having GnRH antagonistic action.