29091-09-6

Basic information

• Product Name: 2,4-Dichloro-3,5-dinitrobenzotrifluoride
• Synonyms: 2,4-dichloro-1,3-dinitro-5-(trifluoromethyl)-benzen;2,4-DICHLORO-1,3-DINITRO-5-(TRIFLUOROMETHYL)BENZENE;2,4-DICHLORO-3,5-DINITROBENZOTRIFLUORIDE;2,4-Dichloro-3,5-dinitrotrifluoromethylbenzene;2,4-Dichloro-3,5-Dinitrobenzotrifluoride/3,5-Dinitro-2,4-Dichlorobenzotrifluoride;2,4-Dichloro-3,5-dinitrobenzotrifluoride 98%;2,4-Dichloro-3,5-dinitrobenzotrifluoride98%;BENZENE,2,4-DICHLORO-1,3-DINITRO-5-(TRIFLUOROMETHYL)
• CAS NO: 29091-09-6
• Molecular Formula: C₇HCl₂F₃N₂O₄
• Molecular Weight: 305
• EINECS: 249-420-8
• Product Categories: Intermediate for Pesticide, Pharmaceutical and organic synthesis
• Mol File: 29091-09-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 76-78°C
• Boiling Point: 291-294°C
• Flash Point: >110°C
• Appearance: White to light yellow crystal powder
• Density: 1.788 g/cm³
• Vapor Pressure: 0.000849mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 2062037
• CAS DataBase Reference: 2,4-Dichloro-3,5-dinitrobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-3,5-dinitrobenzotrifluoride(29091-09-6)
• EPA Substance Registry System: 2,4-Dichloro-3,5-dinitrobenzotrifluoride(29091-09-6)

Safety Data

• Hazard Codes: Xi,T,Xn
• Statements: 20/21/22-36/37/38-22-50/53
• Safety Statements: 26-36/37/39-57-36/37
• RIDADR: 2811
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 29091-09-6(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powde

Uses

2,4-Dichloro-3,5-dinitrobenzotrifluoride is a reagent used in the synthesis of kinesin spindle protein inhibitors. Potential use as an alternative to neurotoxic MT inhibitors.

InChI:InChI=1/C7HCl2F3N2O4/c8-4-2(7(10,11)12)1-3(13(15)16)5(9)6(4)14(17)18/h1H

Synthetic route

1,3-dichloro-2-nitro-4-(trifluoromethyl)benzene (203915-49-5) → 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6)

Conditions	Yield
With sulfuric acid; nitric acid; disulfuric acid at 55 - 110℃; for 14.58h;	81.4%

2,4-dichloro-benzotrifluoride (320-60-5) → 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6)

Conditions	Yield
With sulfuric acid; nitric acid In water at 80℃; for 96h;	60%
With sulfuric acid; sulfur trioxide; nitric acid; sodium hydrogencarbonate In water; toluene	166.6 grams (79%)
With sulfuric acid; sulfur trioxide; nitric acid

sulfuric acid (7664-93-9) + 4-chlorobenzotrifluoride (98-56-6) → 4-chloro-3,5-dinitrobenzotrifluoride (393-75-9) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6)

Conditions	Yield
With sulfur trioxide; nitric acid In water

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-amino-3-chloro-5-(trifluoromethyl)pyridine (79456-26-1) → fluazinam (79622-59-6)

Conditions	Yield
With potassium hydroxide In 2-methyltetrahydrofuran at 20℃; for 4h; Concentration; Temperature; Solvent;	98%
Stage #1: 2,4-dichloro-3,5-dinitro-benzotrifluoride; 2-amino-3-chloro-5-(trifluoromethyl)pyridine With methoxybenzene; potassium hydroxide at 55℃; for 6h; Stage #2: With hydrogenchloride at 85℃; pH=3.7; Temperature; Reagent/catalyst; pH-value;	98.5%
With edetate disodium; potassium hydroxide In acetonitrile at 0 - 5℃; for 3h; Reagent/catalyst; Temperature;	97.5%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C15H9F3N2O2 → 2-(benzo[d][1,3]dioxol-5-yl)-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	88%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-amino-5-methoxy-thiophenol (6274-29-9) → 2-chloro-3-trifluoromethyl-7-methoxy-1-nitro-10H-phenothiazine (1313243-73-0)

Conditions	Yield
With sodium hydroxide In ethanol for 2h; Smiles rearrangement; Reflux;	82%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → 7-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	82%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-amino-4,6-dimethylbenzenethiol (100601-32-9) → C15H10ClF3N2O2S (1241941-68-3)

Conditions	Yield
With sodium hydroxide In ethanol for 2h; Smiles rearrangement; Reflux;	80%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5) → 7-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)-2-(4-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-5-hydroxy-4H-chromen-4-one

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	78%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on (485-72-3) → 7-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)-3-(4-methoxyphenyl)-4H-chromen-4-one

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	78%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + daidzein (486-66-8) → 7-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)-3-(4-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-4H-chromen-4-one

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	77%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (10444-89-0) → (3-Chloro-2,6-dinitro-4-trifluoromethyl-phenyl)-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 20h; Ambient temperature;	75%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → 7-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)-3-(4-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-5-hydroxy-4H-chromen-4-one

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	73%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → 7-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)-2-(4-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-5-hydroxychroman-4-one

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	72%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-(benzi[1,3]dioxol-5-yl)-6-bromo-1H-benzimidazole → 2-(benzo[d][1,3]dioxol-5-yl)-5-bromo-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	60%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-methyl-1H-benzo[d]imidazole → 1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methyl-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	58%

2-(2,3-dihydro-1,4-benzodioxin-6-yl)-1H-benzimidazole + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) → 1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	48%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C15H11BrN2O2 → 5-bromo-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)-phenyl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	46%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C14H9FN2O2 → 2-(benzo[d][1,3]dioxol-5-yl)-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-fluoro-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	43%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C14H9ClN2O2 → 2-(benzo[d][1,3]dioxol-5-yl)-5-chloro-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	38%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-benzo[1,3]dioxol-5-yl-1H-benzoimidazole (2562-69-8) → 2-(benzo[d][1,3]dioxol-5-yl)-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	33%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C16H11F3N2O2 → 1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(trifluoromethyl)-1Hbenzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	32%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C15H12N2O2 → 2-(benzo[d][1,3]dioxol-5-yl)-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-methyl-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	31%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C15H12N2O3 → 2-(benzo[d][1,3]dioxol-5-yl)-1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-methoxy-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	31%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + C16H14N2O3 → 1-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methoxy-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 12h;	30%

morpholine (110-91-8) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + sodium dimethyldithiocarbamate (128-04-1) → 4-morpholin-4-yl-5-nitro-7-trifluoromethyl-benzo[1,3]dithiol-2-one (63417-98-1)

Conditions	Yield
(i) CHCl3, (ii) /BRN= 3569024/, DMSO; Multistep reaction;

2-bromoethylamine (107-09-5) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) → N3-(2-Bromo-ethyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine (29090-93-5)

Conditions	Yield
(i), (ii) NH3; Multistep reaction;

3-aziridin-1-yl-propionic acid ethyl ester (4078-22-2) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) → 3-[(3-Chloro-2,6-dinitro-4-trifluoromethyl-phenyl)-(2-chloro-ethyl)-amino]-propionic acid ethyl ester (41104-21-6)

SEC-BUTYLAMINE (33966-50-6) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) → N3-sec-Butyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine (29091-04-1)

Conditions	Yield
(i), (ii) NH3; Multistep reaction;

SEC-BUTYLAMINE (33966-50-6) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) → N1-sec-Butyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine (29091-08-5)

Conditions	Yield
(i) NH3, (ii) /BRN= 1361345/; Multistep reaction;

N-methylcyclopentylamine (2439-56-7) + 2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) → N3-Cyclopentyl-N3-methyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine (29091-37-0)

Conditions	Yield
(i), (ii) NH3; Multistep reaction;

Upstream product

• 203915-49-5 1,3-dichloro-2-nitro-4-(trifluoromethyl)benzene 
• 7664-93-9 sulfuric acid 
• 98-56-6 4-chlorobenzotrifluoride 
• 320-60-5 2,4-dichloro-benzotrifluoride 

Downstream Products

• 29090-93-5 N³-(2-Bromo-ethyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 41104-21-6 3-[(3-Chloro-2,6-dinitro-4-trifluoromethyl-phenyl)-(2-chloro-ethyl)-amino]-propionic acid ethyl ester 
• 29091-04-1 N³-sec-Butyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 29091-08-5 N¹-sec-Butyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 29091-37-0 N³-Cyclopentyl-N³-methyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 63418-02-0 2-Chlor-3,5-dinitro-4-(n-propylthio)benzotrifluorid 
• 29090-98-0 N³-Ethyl-N³-methyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 29090-92-4 N³-(3-Chloro-propyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 29090-94-6 N³,N³-Bis-(2-methoxy-ethyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 29091-03-0 N³-(2-Chloro-allyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 29104-51-6 N¹,N³-Bis-(2-chloro-allyl)-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 
• 53064-03-2 N-Allyl-3-chlor-N-(2-chlorethyl)-2,6-dinitro-4-(trifluormethyl)anilin 
• 53064-02-1 N-Propyl-3-chlor-N-(2-chlorethyl)-2,6-dinitro-4-(trifluormethyl)anilin 
• 29091-24-5 N³-sec-Butyl-N¹-ethyl-2,4-dinitro-6-trifluoromethyl-benzene-1,3-diamine 

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