4136-95-2

Basic information

• Product Name: 2,4,6-Trichlorobenzoyl chloride
• Synonyms: 2,4,6-TRICHLOROBENZOYL CHLORIDE;2,4,6-TRICHLORBENZOYLCHLORID;2,4,6-TrichlorobenzoyChloride;2,4,6-TRICHLOROBENZOYL CHLORIDE 98%;2,4,6-Trichlorobenzoic acid chloride;2,4,6-Trichlorobenzoyl chloride,98%;2,4,6-Ttrichlorobenzoyl chloride;2,4,6-Trichlorobenzoyl chloride, 98% 5GR
• CAS NO: 4136-95-2
• Molecular Formula: C₇H₂Cl₄O
• Molecular Weight: 243.9
• Product Categories: Condensation & Active Esterification;Synthetic Organic Chemistry;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 4136-95-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 165-166 °C
• Boiling Point: 107-108 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.561 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00302mmHg at 25°C
• Refractive Index: n20/D 1.5754(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 2050280
• CAS DataBase Reference: 2,4,6-Trichlorobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trichlorobenzoyl chloride(4136-95-2)
• EPA Substance Registry System: 2,4,6-Trichlorobenzoyl chloride(4136-95-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45-25
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4136-95-2(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

2,4,6-Trichlorobenzoyl chloride may be used in the preparation of:γ-lactone and δ-lactonealiphatic aromatic anhydrides, required for the synthesis of amphiphilic hyaluronanmixed anhydride, required for the synthesis of angelate esterssynthesis of both spongistatin 1 and spongistatin 2large-ring lactones in high yields.

InChI:InChI=1/C7H2Cl4O/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H

Synthetic route

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

2-Bromo-6-chloro-4-methyl-benzoyl chloride (135365-02-5) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 3h; Heating;

2-bromo-6-chloro-4-methylaniline (135340-78-2) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) concd. H2SO4, NaNO2 / 1.) HOAc, 15 deg C, 3 h, 2.) H2O, 35-40 deg C, 1 h 2: 40.8 percent / concd. H2SO4 / 3 h / Heating 3: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h 4: SOCl2, DMF / 3 h / Heating 5: SOCl2, DMF / 3 h / Heating View Scheme

2-bromo-6-chloro-4-methylbenzonitrile (135340-79-3) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 40.8 percent / concd. H2SO4 / 3 h / Heating 2: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h 3: SOCl2, DMF / 3 h / Heating 4: SOCl2, DMF / 3 h / Heating View Scheme

2-chloro-6-bromo-4-methylbenzoic acid (135340-36-2) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, DMF / 3 h / Heating 2: SOCl2, DMF / 3 h / Heating View Scheme

2-bromo-6-chloro-4-methylbenzamide (135340-80-6) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h 2: SOCl2, DMF / 3 h / Heating 3: SOCl2, DMF / 3 h / Heating View Scheme

2-chloro-4-methyl-benzenamine (615-65-6) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) Br2, HOAc, 2.) 50percent aq. NaOH / 0.5 h / Ambient temperature 2: 1.) concd. H2SO4, NaNO2 / 1.) HOAc, 15 deg C, 3 h, 2.) H2O, 35-40 deg C, 1 h 3: 40.8 percent / concd. H2SO4 / 3 h / Heating 4: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h 5: SOCl2, DMF / 3 h / Heating 6: SOCl2, DMF / 3 h / Heating View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid; water 2: phosphorus (V)-chloride View Scheme

2,4,6-trichlorobenzoyl chloride (4136-95-2) + <3-14C>-cinnamic acid (4469-06-1) → C15(14)CH9Cl3O3

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;	100%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + Fmoc-Pro-OH (71989-31-6) → C27H20Cl3NO5 (1160053-32-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;	100%
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 0.166667h; Inert atmosphere;

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid → 2,4,6-trichlorobenzoic 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic anhydride

Conditions	Yield
With potassium carbonate In acetone at 25 - 30℃; for 3h; Product distribution / selectivity; Inert atmosphere;	100%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid + C53H81NO14 → C68H103NO17

Conditions	Yield
Stage #1: 2,4,6-trichlorobenzoyl chloride; 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid With triethylamine In dichloromethane at 0 - 5℃; for 2h; Inert atmosphere; Stage #2: C53H81NO14 With dmap In toluene at 20℃; Product distribution / selectivity;	100%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid + C54H87NO13Si → C69H109NO16Si

Conditions	Yield
Stage #1: 2,4,6-trichlorobenzoyl chloride; 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid With triethylamine In dichloromethane at 0 - 5℃; for 2h; Inert atmosphere; Stage #2: C54H87NO13Si With dmap In toluene at 20℃; Product distribution / selectivity;	100%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 4-iodo-9H-carbazole → 9-(2,4,6-trichlorobenzoyl)-4-iodo-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	100%

3-(1,1-dimethylethyl)-9H-carbazole (22401-74-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-3-(1,1-dimethylethyl)-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	100%

4-chloro-9H-carbazole (3652-88-8) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-4-chloro-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	100%

4-Nitro-9H-carbazole (57905-76-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-4-nitro-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	100%

4-bromo-9H-carbazole (3652-89-9) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-4-bromo-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	100%

N-ethyl-N-hydroxy-ethanamine (3710-84-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → N,N-diethyl-O-(2,4,6-trichlorobenzoyl)hydroxylamine

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.333333h;	100%

10-Nitrooleic Acid (875685-46-4) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 2,4,6-Trichlorobenzoyl 10-nitrooleate

Conditions	Yield
Stage #1: 10-Nitrooleic Acid With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 23℃; for 0.25h; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 23℃; for 3h; Inert atmosphere;	100%

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;

2,4,6-trichlorobenzoyl chloride (4136-95-2) + (E)-((hex-3-en-1-yloxy)methyl)benzene (121441-39-2) → C13H13Cl3O2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	99%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 1-butyn-4-ol (927-74-2) → C11H7Cl3O2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	99%

3-Nitro-carbazol (3077-85-8) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-3-nitro-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 23℃; for 2h; Inert atmosphere;	99%

dibenzoazepine (256-96-2) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: dibenzoazepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	98%

3-hexen-1-ol (544-12-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → C13H13Cl3O2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	98%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 4-(trimethylsilyl)-9H-carbazole → 9-(2,4,6-trichlorobenzoyl)-4-trimethylsilyl-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	98%

3-(trifluoromethyl)-9H-carbazole (2467-83-6) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-3-trifluoromethyl-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	98%

2-hexen-1-ol (2305-21-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → C13H13Cl3O2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	97%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + (S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol (1280222-59-4) + (R)-4-((tert-butyldimethylsilyl)oxy)hex-5-ynoic acid → (R)-(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octyl 4-((tert-butyldimethylsilyl)oxy)hex-5-ynoate

Conditions	Yield
Stage #1: 2,4,6-trichlorobenzoyl chloride; (R)-4-((tert-butyldimethylsilyl)oxy)hex-5-ynoic acid With triethylamine In toluene for 1h; Inert atmosphere; Stage #2: (S)-1-[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]octan-1-ol With dmap In toluene for 5h; Inert atmosphere;	96%

10-methoxy-5H-dibenzo[b,f]azepine (4698-11-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 10-methoxy-5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	96%

3-iodocarbazole (16807-13-9) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-3-iodo-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	96%

3-methoxycarbazole (18992-85-3) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-3-methoxy-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	96%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate (7588-36-5) → methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate (1267907-58-3)

Conditions	Yield
Stage #1: methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate With potassium hexamethylsilazane In tetrahydrofuran; toluene at 20℃; for 0.0833333h; Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran; toluene at 20℃; for 2h;	95%

(E) and (Z)-4-cyclohexyl-3-buten-1-ol (865444-41-3) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → C17H19Cl3O2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	95%

4-methyl-9H-carbazole (3770-48-7) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 9-(2,4,6-trichlorobenzoyl)-4-methyl-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	95%

2,4,6-trichlorobenzoyl chloride (4136-95-2) + 3-trimethylsilyl-9H-carbazole → 9-(2,4,6-trichlorobenzoyl)-3-trimethylsilyl-9H-carbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;	94%

tert.-butylhydroperoxide (75-91-2) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 2,4,6-trichloro-benzenecarboperoxoic acid tert-butyl ester

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Oxidation;	93%

Upstream product

• 4136-91-8 TETRAISOPROPYLTHIURAM DISULFIDE 
• 4136-86-1 2-Butylsuccinic acid dimethyl ester 
• 41368-47-2 (2Z,5E)-2,5-Heptadien-1-ol 
• 41366-99-8 Histamine, N-acetyl-5-fluoro- 
• 41366-77-2 1-benzyl-3,5-dibromopyridin-4(1H)-one 
• 41366-64-7 2-oxo-2a,3,8,8a-tetrahydro-3,8-methanonaphtho[2,3-b]azete-1(2H)-sulfonyl chloride 
• 4136-64-5 2-(2-{[3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}hydrazino)-N-naphthalen-1-yl-2-oxoacetamide 
• 41366-03-4 2-nonoxyethanol 
• 41366-02-3 2-(nonyloxy)ethanol 
• 41366-01-2 2-(nonyloxy)ethanol 
• 41365-75-7 1-AMINO-3,3-DIETHOXYPROPANE 
• 41365-37-1 2-(3,4-Dimethoxyphenyl)-7-methoxy-3-methyl-5-[(E)-1-propenyl]benzofuran 
• 41365-35-9 2-(4-Hydroxy-3-methoxyphenyl)-3-methyl-5-benzofurancarbaldehyde 
• 41365-34-8 rac-2-Methoxy-4-[3-methyl-5-[(1R*,2S*)-1,2-dihydroxypropyl]benzofuran-2-yl]phenol 

Downstream Products

• 4136-97-4 METHYL 4-AMINOSALICYLATE 
• 4137-02-4 3-(4-bromophenyl)-2-thioxo-1,3-thiazinan-4-one 
• 41370-29-0 2-(3,3-dimethylcyclohexylidene)ethanol 
• 41370-56-3 Tricyclo[4.4.0.02,7]dec-8-ene-3-methanol, alpha.,alpha.,6,8-tetrmethyl-, stereoisomer 
• 41370-57-4 (1S)-2β-Acetyloxy-4β-ethenyl-5α-(1-methylethenyl)-α,α,4-trimethylcyclohexanemethanol 
• 4137-10-4 DIMCARB 
• 41371-14-6 CHOLESTEROL N-BUTYL CARBONATE 
• 4137-11-5 p,p',p''-(1-propanyl-3-ylidene)triphenol 
• 4137-12-6 1-(3-Nitrophenyl)-3-methylenepyrrolidine-2,5-dione 
• 41371-53-3 2-IMIDAZOLIDONE-4-CARBOXYLIC ACID 
• 41372-02-5 BENZATHINE PENICILLINE G TETRAHYDRATE 
• 41372-08-1 alpha-Methyldopa sesquihydrate 
• 41372-10-5 PIPERAZINE CITRATE HYDRATE 
• 41372-20-7 R-(-)-Apomorphine 

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