50-43-1

Basic information

• Product Name: 2,4,6-Trichlorobenzoic acid
• Synonyms: TIMTEC-BB SBB003323;2,4,6-trichloro-benzoicaci;RARECHEM AL BO 0563;2,4,6-TRICHLOROBENZOIC ACID 99+%;2,4,6-TRICHLOROBENZOIC ACID 98% (HPLC);2,4,6-trichlorobbenzoicacid;2,4,6-TRICHLOROBENZOIC ACID (2,4,6-TB);2,4,6-Trichlorobenzoic acid,97%
• CAS NO: 50-43-1
• Molecular Formula: C7H3Cl3O2
• Molecular Weight: 225.46
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;C7;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 50-43-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 160-164 °C(lit.)
• Boiling Point: 329.7 °C at 760 mmHg
• Flash Point: 153.2 °C
• Appearance: beige to brown crystalline powder
• Density: 1.5599 (estimate)
• Vapor Pressure: 7.02E-05mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 1.40±0.25(Predicted)
• BRN: 1874127
• CAS DataBase Reference: 2,4,6-Trichlorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trichlorobenzoic acid(50-43-1)
• EPA Substance Registry System: 2,4,6-Trichlorobenzoic acid(50-43-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DH8050000
• Hazardous Substances Data: 50-43-1(Hazardous Substances Data)

Usage

Chemical Properties

beige to light brown crystalline powder

Uses

Different sources of media describe the Uses of 50-43-1 differently. You can refer to the following data:
1. 2,4,6-Trichlorobenzoic acid can be used as reactant involved in Active-sodium-promoted reductive cleavage of halogenated benzoic acids; Synthesis of aryl aminopyrazole benzamides for use as non-steroidal selective glucocorticoid receptor agonists ; Flame retardant monomer synthesis; Synthesis of 3,4,7-trisubstituted coumarins for use as antifungals and Solid-phase synthesis of saphenamycin analogs with antimicrobial activity.
2. 2,4,6-Trichlorobenzoic Acid is a possible degradation intermediate of Polychlorinated Biphenyls (PCBs) in contaminated soil, suggesting the occurrence of microbial transformation processes over time.
3. Reactant involved in:Active-sodium-promoted reductive cleavage of halogenated benzoic acidsSynthesis of aryl aminopyrazole benzamides for use as non-steroidal selective glucocorticoid receptor agonistsFlame retardant monomer synthesisSynthesis of 3,4,7-trisubstituted coumarins for use as antifungalsSolid-phase synthesis of saphenamycin analogs with antimicrobial activityCocatalyst for cis-dihydroxylation and epoxidation of alkenes

General Description

Structure and hydrogen bonding pattern in 2,4,6-trichlorobenzoic acid is reported.

InChI:InChI=1/C7H3Cl3O2/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H,(H,11,12)/p-1

Synthetic route

2,4,6-trichlorobenzoyl chloride (4136-95-2) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With water; triethylamine In acetone at 20℃; for 18h;	99%
With water In acetone at 55℃; Kinetics; Mechanism; Concentration;

1,3,5-trichloro-2-iodobenzene (6324-50-1) + carbon dioxide (124-38-9) → 2,4,6-trichlorobenzoic acid (50-43-1) + 2,4,6-trichloro-3-iodobenzoic acid

Conditions	Yield
Stage #1: 1,3,5-trichloro-2-iodobenzene With n-butyllithium; (tert-butyldimethylsilyl)-tert-butylamine In tetrahydrofuran at -75℃; Stage #2: carbon dioxide In tetrahydrofuran at -75℃;	A 3.2% B 31%

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With hydrogenchloride at 200℃; im Druckrohr;
With sulfuric acid; water; acetic acid

2,4,6-trichlorotoluene (23749-65-7) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With nitric acid

1,3,5-trichlorobenzene (108-70-3) + carbon dioxide (124-38-9) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With n-butyllithium 1.) THF, hexane, -50 deg C, 1.5 h, 2.) Et2O, from -50 deg C to RT; Yield given. Multistep reaction;
With methyllithium 1) THF, -30 deg C to -78 deg C; 2) 3 h; Yield given. Multistep reaction;

α,α,α,2,4,6-hexachlorotoluene (14379-95-4) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With sulfuric acid; Methamphetamin 1) 24 h, r.t.; Yield given. Multistep reaction;

3,3-Dimethyl-1-(2,4,6-trichloro-phenoxy)-butan-2-one (24473-01-6) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
at 285 - 305℃;

2.2.2-trichloro-1-<2.4.6-trichloro-phenyl>-ethanone-(1) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With sodium hydroxide

hydrogenchloride (7647-01-0) + 2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
at 200℃;

2,4,6-trichlorotoluene (23749-65-7) + nitric acid (7697-37-2) → 2,4,6-trichlorobenzoic acid (50-43-1)

sulfuric acid (7664-93-9) + 2,4,6-trichloro-benzoic acid amide (23400-04-6) + sodium nitrite → 2,4,6-trichlorobenzoic acid (50-43-1)

2,2-dibromo-1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione (854651-12-0) + concentrated aq. NaOH solution → 2,4,6-trichlorobenzoic acid (50-43-1)

1,3,5-trichlorobenzene (108-70-3) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 91 percent / I2 / tetrahydrofuran; hexane / -75 °C 2.1: BuLi; N-tert-butyl-N-(tert-butyldimethylsilyl)amine / tetrahydrofuran / -75 °C 2.2: 3.2 percent / tetrahydrofuran / -75 °C View Scheme
Multi-step reaction with 3 steps 1: 98 percent / 1a) AlCl3, 1b) AlCl3 / 1a) 4 h, r.t., 1b) 4 h, -10 deg C 2: 76.5 percent / AlCl3 / CS2 / 6 h / Ambient temperature 3: 1) 30percent Oleum, 2) ice / 1) 24 h, r.t. View Scheme

1,3,5-trichloro-2-(trifluoromethyl)benzene (567-59-9) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76.5 percent / AlCl3 / CS2 / 6 h / Ambient temperature 2: 1) 30percent Oleum, 2) ice / 1) 24 h, r.t. View Scheme

aniline (62-53-3) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: CHCl3; chlorine 2: hydrochloric acid / Behandlung der Diazoniumchloridloesung mit Kaliumkupfercyanuerloesung 3: concentrated hydrochloric acid / 200 °C / im Druckrohr View Scheme

2,4,6-trichloroaniline (634-93-5) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrochloric acid / Behandlung der Diazoniumchloridloesung mit Kaliumkupfercyanuerloesung 2: concentrated hydrochloric acid / 200 °C / im Druckrohr View Scheme

3-Methylacetanilide (537-92-8) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrochloric acid; glacial acetic acid 2: sulfuric acid 4: HNO3 View Scheme

3-Methyl-2,4,6-trichloroaniline (5400-76-0) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: HNO3 View Scheme

acetic acid-(2,4,6-trichloro-3-methyl-anilide) (60093-98-3) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid 3: HNO3 View Scheme

2,4,6-Trichlorophenol (88-06-2) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: 285 - 305 °C View Scheme

C22H17Cl3O4 → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
In ethanol; dichloromethane at 25℃; Kinetics;

2,4,6-trichlorobenzoic acid (50-43-1) → (2,4,6-trichlorophenyl)methanol (217479-60-2)

Conditions	Yield
Stage #1: 2,4,6-trichlorobenzoic acid With borane-dimethyl sulfide complex In tetrahydrofuran at 22℃; Inert atmosphere; Cooling with ice; Reflux; Stage #2: With methanol In tetrahydrofuran	100%
With aluminium(III) triflate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In methanol; water; toluene at 160℃; under 45004.5 Torr; for 24h; Autoclave;	67 %Chromat.

diazomethane (186581-53-3, 908094-01-9) + 2,4,6-trichlorobenzoic acid (50-43-1) → methyl 2,4,6-trichlorobenzoate (86569-78-0)

Conditions	Yield
In diethyl ether	94%

2,4,6-trichlorobenzoic acid (50-43-1) + methyl iodide (74-88-4) → methyl 2,4,6-trichlorobenzoate (86569-78-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h;	86%

2,4,6-trichlorobenzoic acid (50-43-1) → 1,3,5-trichloro[2-2H]benzene (16463-22-2)

Conditions	Yield
With water-d2; silver(I) acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Inert atmosphere; regioselective reaction;	71%

2,4,6-trichlorobenzoic acid (50-43-1) + triphenylantimony dichloride (594-31-0, 34716-91-1, 20265-29-6) → Ph3SbCl(2,4,6-trichlorobenzoate)

Conditions	Yield
With CH3ONa In toluene 2,4,6-trichlorobenzoic acid and CH3ONa added to soln. of Ph3SbCl2 in toluene under stirring (molar ratio=1:1), mixt. refluxed for 8 h; soln. filtered, filtrate gradually evapd. under vac., recrystn. from petroleum ether/CH2Cl2 (1/1); elem. anal.;	68%

2,4,6-trichlorobenzoic acid (50-43-1) + triphenylantimony dichloride (594-31-0, 34716-91-1, 20265-29-6) → Ph3Sb(2,4,6-trichlorobenzoate)2

Conditions	Yield
With CH3ONa In toluene 2,4,6-trichlorobenzoic acid and CH3ONa added to soln. of Ph3SbCl2 in toluene under stirring (molar ratio=2:1), mixt. refluxed for 8 h; soln. filtered, filtrate gradually evapd. under vac., recrystn. from petroleum ether/CH2Cl2 (1/1); elem. anal.;	65%

2,4,6-trichlorobenzoic acid (50-43-1) + tetraphenylantimony(V) bromide (16894-69-2) → Ph4Sb(2,4,6-trichlorobenzoate)

Conditions	Yield
With CH3ONa In toluene 2,4,6-trichlorobenzoic acid and CH3ONa added to soln. of Ph4SbBr in toluene under stirring (molar ratio=1:1), mixt. refluxed for 8 h; soln. filtered, filtrate gradually evapd. under vac., recrystn. from petroleum ether/CH2Cl2 (1/1); elem. anal.;	61%

2,4,6-trichlorobenzoic acid (50-43-1) + benzylamine (100-46-9) → C7H3Cl3O2*C7H9N

Conditions	Yield
In methanol at 20℃; for 288h;	60.13%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 2,4,6-trichlorobenzoic acid (50-43-1) → (Z)-methyl 2-fluoro-3-(2,4,6-trichlorophenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Sealed tube; diastereoselective reaction;	40%

4-aminopyridine (504-24-5) + 2,4,6-trichlorobenzoic acid (50-43-1) → 2,4,6-trichloro-N-(pyridin-4-yl)benzamide (1258291-82-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	24%

2-methoxyacrylic acid ethyl ester (36997-05-4) + 2,4,6-trichlorobenzoic acid (50-43-1) → 1,3,5-trichlorobenzene (108-70-3) + (Z)-ethyl 2-methoxy-3-(2,4,6-trichlorophenyl)acrylate + (E)-ethyl 2-methoxy-3-(2,4,6-trichlorophenyl)acrylate + diethyl 2,5-dimethoxyhexa-2,4-dienedioate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 130℃; for 24h; Solvent; Sealed tube; Inert atmosphere; stereoselective reaction;	A n/a B 24% C 16% D n/a

2-methoxyacrylic acid ethyl ester (36997-05-4) + 2,4,6-trichlorobenzoic acid (50-43-1) → (Z)-ethyl 2-methoxy-3-(2,4,6-trichlorophenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Sealed tube; Inert atmosphere; stereoselective reaction;	20%

2,4,6-trichlorobenzoic acid (50-43-1) + 2,4-dichloro-4'-aminodiphenyl ether (14861-17-7) → 2,4,6-trichloro-N-(4-(2,4-dichlorophenoxy)phenyl)benzamide

Conditions	Yield
Stage #1: 2,4,6-trichlorobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2,4-dichloro-4'-aminodiphenyl ether In N,N-dimethyl-formamide	13%

2,4,6-trichlorobenzoic acid (50-43-1) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
With phosphorus pentachloride
With phosphorus pentachloride
With thionyl chloride

Upstream product

• 6575-05-9 2,4,6-Trichlorobenzonitrile 
• 23749-65-7 2,4,6-trichlorotoluene 
• 108-70-3 1,3,5-trichlorobenzene 
• 124-38-9 carbon dioxide 
• 14379-95-4 α,α,α,2,4,6-hexachlorotoluene 
• 24473-01-6 3,3-Dimethyl-1-(2,4,6-trichloro-phenoxy)-butan-2-one 
• 7647-01-0 hydrogenchloride 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 23400-04-6 2,4,6-trichloro-benzoic acid amide 
• 854651-12-0 2,2-dibromo-1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione 
• 6324-50-1 1,3,5-trichloro-2-iodobenzene 
• 4136-95-2 2,4,6-trichlorobenzoyl chloride 
• 567-59-9 2,4,6-trichloro-1-(trifluoromethyl)benzene 

Downstream Products

• 4136-95-2 2,4,6-trichlorobenzoyl chloride 
• 71372-03-7 2,4,6-trichloro-3-nitrobenzoic acid 
• 86569-78-0 methyl 2,4,6-trichlorobenzoate 
• 23400-04-6 2,4,6-trichloro-benzoic acid amide 
• 160647-00-7 2,4,6-Trichloro-3-nitrobenzyl alcohol 
• 160647-04-1 2,4,6-Trichloro-3-nitrobenzyl methanesulfonate 
• 160641-93-0 8-(3-Amino-2,4,6-trichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine 
• 160647-14-3 8-(2,4,6-Trichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine 
• 160641-61-2 3-Bromo-8-(2,4,6-trichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridin 
• 65305-79-5 1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione 
• 217479-60-2 (2,4,6-trichlorophenyl)methanol 

Relevant articles and documents

Method for estimating SN1 rate constants: Solvolytic reactivity of benzoates

Nucleofugalities of pentafluorobenzoate (PFB) and 2,4,6-trifluorobenzoate (TFB) leaving groups have been derived from the solvolysis rate constants of X,Y-substituted benzhydryl PFBs and TFBs measured in a series of aqueous solvents, by applying the LFER equation: log k = sf(Ef + Nf). The heterolysis rate constants of dianisylmethyl PFB and TFB, and those determined for 10 more dianisylmethyl benzoates in aqueous ethanol, constitute a set of reference benzoates whose experimental ΔG ? have been correlated with the ΔH? (calculated by PCM quantum-chemical method) of the model epoxy ring formation. Because of the excellent correlation (r = 0.997), the method for calculating the nucleofugalities of substituted benzoate LGs have been established, ultimately providing a method for determination of the SN1 reactivity for any benzoate in a given solvent. Using the ΔG? vs ΔH? correlation, and taking sf based on similarity, the nucleofugality parameters for about 70 benzoates have been determined in 90%, 80%, and 70% aqueous ethanol. The calculated intrinsic barriers for substituted benzoate leaving groups show that substrates producing more stabilized LGs proceed over lower intrinsic barriers. Substituents on the phenyl ring affect the solvolysis rate of benzhydryl benzoates by both field and inductive effects.

INHIBITORS OF STEAROYL-COA DESATURASE

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.

Extensive halogen scrambling and buttressing effects encountered upon treatment of oligobromoarenes with bases

As a rule, tri-, tetra- and pentahaloarenes readily undergo ortho-lithiation when treated with amide-type bases. However, halogen migration occurs whenever the substrate contains three or more contiguous halogen atoms, provided that at least one of them is bromine or iodine. Dismutation and reduction processes often take place concomitantly. In this manner, a variety of organometallic intermediates may be formed, the driving force always being a decrease in basicity. When no such energy gain can be achieved, a sterically crowded substrate may just turn out to be inert; this was found to be the case with 1,5-dibromo-3-fluoro-2-(trimethylsilyl)benzene, 1,5-dibromo-3-fluoro-2,4-bis(trimethylsilyl)benzene, and 1,5-dibromo-3-fluoro-2,4-diiodobenzene. Buttressing effects are apparently strong enough to prevent expedient deprotonation of those substrates.