76-02-8

Basic information

• Product Name: Trichloroacetyl chloride
• Synonyms: Acetylchloride, trichloro- (6CI,8CI,9CI);2,2,2-Trichloroacetyl chloride;Trichloroacetic acid chloride;Trichloroacetochloride
• CAS NO: 76-02-8
• Molecular Formula: C₂Cl₄O
• Molecular Weight: 181.8328
• EINECS: 200-926-7
• Mol File: 76-02-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: -57℃
• Boiling Point: 118 °C at 760 mmHg
• Flash Point: 31 °C
• Appearance: clear to slightly yellow fuming liquid
• Density: 1.744 g/cm³
• Vapor Pressure: 17mmHg at 25°C
• Refractive Index: 1.5
• Water Solubility: reacts violently
• CAS DataBase Reference: Trichloroacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Trichloroacetyl chloride(76-02-8)
• EPA Substance Registry System: Trichloroacetyl chloride(76-02-8)

Safety Data

• Hazard Codes: T+:Very toxic
• Statements: R14:; R22:; R26:; R29:; R35:
• Safety Statements: S23:; S26:; S28A:; S36/37/39:; S45:; S8:
• Hazardous Substances Data: 76-02-8(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic by inhalationand ingestion. A corrosive irritant to skin, eyes, andmucous membranes. When heated to decomposition itemits toxic fumes of Clí.

InChI:InChI=1/C2Cl4O/c3-1(7)2(4,5)6

Synthetic route

trichloroacetic acid (76-03-9) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With thionyl chloride; pentabutyl propyl guanidinium chloride; silica gel In chlorobenzene at 130℃; for 6h;	95%
With N,N-dimethyl-formamide; trichlorophosphate at 100℃;	92%
With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 2h;	78%

chloroacetic acid (79-11-8) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
Stage #1: chloroacetic acid With chlorine at 90 - 120℃; under 2250.23 Torr; for 18h; Large scale; Stage #2: With disulfur dichloride; chlorine at 100℃; under 750.075 Torr; for 28h; Large scale; Stage #3: With dmap; chlorine; triethylamine at 116℃; Temperature; Pressure; Reagent/catalyst; Large scale;	94.9%

1,1,2,2-tetrachloroethylene (127-18-4) + hypofluorous acid trifluoromethyl ester (373-91-1) → CFC-112a (76-12-0) + dichloro-fluoro-acetyl chloride (354-17-6) + 1,1,2,2-tetrachloro-1-fluoro-2-trifluoromethoxyethane (136649-69-9) + Trichloroacetyl chloride (76-02-8) + Dichloro-trifluoromethoxy-acetyl chloride + COCl2

Conditions	Yield
With oxygen at 40.9℃; under 420.8 Torr; for 1.97833h; Product distribution; Mechanism; Rate constant; var. of partial pressure, temp.;	A n/a B n/a C n/a D 85% E n/a F n/a

chlorotriphenoxy(trichloroacetyl)phosphorane (73569-84-3) → triphenyl phosphite (101-02-0) + Diphenyl phosphorochloridite (5382-00-3) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
at 50℃; under 10 Torr; Mechanism;	A n/a B n/a C 63.6%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + trichloroacetic acid (76-03-9) → 4,6-dichloro-2-hydroxy-1,3,5-triazine (15791-08-9) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
In acetone for 3h; Product distribution; Ambient temperature;	A n/a B 40%

pentachloroethane (76-01-7) → phosgene (75-44-5) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
Irradiation (UV/VIS); with Cl2 sensibilized photochemical oxidn., 80 to 100°C;	A 20% B n/a

trichloro-acetic acid pentachloroethyl ester (65785-42-4) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
bei der Destillation;
at 400℃;

Benzotrichlorid (98-07-7) + trichloroacetic acid (76-03-9) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With zinc(II) chloride at 100℃;

acetyl chloride (75-36-5) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With phosphorus pentachloride

chloroacetyl chloride (79-04-9) → dichloroacethyl chloride (79-36-7) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With pyridine; chlorine at 75 - 80℃;

phosgene (75-44-5) + trichloroacetic acid (76-03-9) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With anionexchanger at 130℃;

trichloroacetic acid (76-03-9) → Trichloroacetyl chloride (76-02-8) + trichloroacetic acid anhydride (4124-31-6)

Conditions	Yield
With phosphorus trichloride

tetrachloromethane (56-23-5) + carbon monoxide (201230-82-2) → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With aluminium trichloride; copper(l) chloride; iron(II) chloride at 120℃; under 75005.9 Torr; for 5h; Mechanism; other polychloroalkanes; other metallic salt mixtures; var. pressure, temp. and time of reaction;

1,1,2,2-tetrachloroethylene (127-18-4) → perchloroethylene oxide (16650-10-5) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With oxid. agent

pentachloroethane (76-01-7) → phosgene (75-44-5) + trichloromethyl radical (3170-80-7) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With chlorine In gas at 22.9℃; Rate constant; Product distribution; Irradiation; FTIR techniques; var. reag.: F2;

1,2,2,2-Tetrachloro-1-fluoroethyl methyl ether (37021-34-4) → methylene chloride (74-87-3) + Methyl fluoride (593-53-3) + trichloroacetyl fluoride (354-13-2) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With antimonypentachloride at 55 - 60℃; for 1h; Decomposition;

perchloroethylene oxide (16650-10-5) + sulfuric acid (7664-93-9) → Trichloroacetyl chloride (76-02-8)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 2-chloro-2,5-bis-trichloromethyl-[1,3]dioxolan-4-one → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
at 180℃; im Rohr;

1,4-dioxane (123-91-1) + chlorine (7782-50-5) → hexachloroethane (67-72-1) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
at 190℃;

tetrachloromethane (56-23-5) + CO → Trichloroacetyl chloride (76-02-8)

Conditions	Yield
With aluminium trichloride at 200℃; under 183877 Torr;

N-Methylpyrrole (96-54-8) + Trichloroacetyl chloride (76-02-8) → 1-methyl-2-trichloroacetyl-1H-pyrrole (21898-65-7)

Conditions	Yield
In dichloromethane for 3h;	100%
In dichloromethane at 20℃; for 3h; Inert atmosphere;	100%
Stage #1: N-Methylpyrrole; trifluoroacetyl chloride In diethyl ether at 0 - 20℃; for 1h; Stage #2: With potassium carbonate In diethyl ether; water	96%

Isopropylphenyl(trimethylsilyl)phosphan (29574-16-1) + Trichloroacetyl chloride (76-02-8) → Isopropylphenyl(trichloracetyl)phosphan (104192-62-3)

Conditions	Yield
In diethyl ether at -80℃; for 5h;	100%

methyl(phenyl)(trimethylsilyl)phosphine (59877-21-3) + Trichloroacetyl chloride (76-02-8) → (trichloroacetyl)methylphenylphosphane

Conditions	Yield
In diethyl ether at -80℃; for 5h;	100%

Ethylphenyl(trimethylsilyl)phosphan (59877-22-4) + Trichloroacetyl chloride (76-02-8) → Ethylphenyl(trichloracetyl)phosphan

Conditions	Yield
In diethyl ether at -80℃; for 5h;	100%

Phenyl-n-propyl(trimethylsilyl)phosphan (59877-23-5) + Trichloroacetyl chloride (76-02-8) → Phenyl-n-propyl(trichloracetyl)phosphan

Conditions	Yield
In diethyl ether at -80℃; for 5h;	100%

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) + Trichloroacetyl chloride (76-02-8) → 4-benzyloxy-1-trichloroacetoxybut-2-ene (93553-68-5)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1h;	100%

1-(benzyloxy)but-3-en-2-ol (93553-66-3) + Trichloroacetyl chloride (76-02-8) → 1-benzyloxy-2-trichloroacetoxybut-3-ene (93553-67-4)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1h;	100%

9-hydroxyphenalenone sodium salt (129087-30-5) + Trichloroacetyl chloride (76-02-8) → 9-trichloroacetoxyphenalenone (129087-28-1)

Conditions	Yield
In tetrahydrofuran for 24h; Ambient temperature;	100%

trimethylsilyldicyclohexylphosphane (104202-80-4) + Trichloroacetyl chloride (76-02-8) → (trichloroacetyl)dicyclohexylphosphane

Conditions	Yield
In diethyl ether at -25℃;	100%

thiophenol (108-98-5) + Trichloroacetyl chloride (76-02-8) → trichlorothioacetic acid S-phenyl ester (24197-68-0)

Conditions	Yield
for 2h;	100%
at 60℃; for 4h;	94%

oct-1-ene (111-66-0) + Trichloroacetyl chloride (76-02-8) → 2,2-Dichloro-3-hexyl-cyclobutanone (217805-08-8)

Conditions	Yield
With zinc In diethyl ether at 15 - 20℃; for 1.5h; sonication;	100%
With zinc/copper couple; trichlorophosphate In diethyl ether Reflux;
With zinc-copper couple; trichlorophosphate In diethyl ether Reflux; Inert atmosphere;
With zinc/copper couple; trichlorophosphate In diethyl ether at 0℃; Inert atmosphere; Reflux;

6-benzyloxy-1H-indole (15903-94-3) + Trichloroacetyl chloride (76-02-8) → 6-benzyloxy-3-trichloroacetylindole (371971-12-9)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 16h;	100%

1-(2-(ethylamino)phenyl)ethanone (1859-97-8) + Trichloroacetyl chloride (76-02-8) → N-(2-acetylphenyl)-2,2,2-trichloro-N-ethylacetamide (528856-11-3)

Conditions	Yield
In toluene Heating;	100%

o-(methylamino)acetophenone (1859-75-2) + Trichloroacetyl chloride (76-02-8) → N-(2-acetylphenyl)-2,2,2-trichloro-N-methylacetamide (528856-10-2)

Conditions	Yield
In toluene Heating;	100%

Trichloroacetyl chloride (76-02-8) + 2-(methylamino)benzophenone (1859-76-3) → N-(2-benzoylphenyl)-2,2,2-trichloro-N-methylacetamide (342598-46-3)

Conditions	Yield
In toluene Heating;	100%

Trichloroacetyl chloride (76-02-8) + 1-(2-(isopropylamino)phenyl)ethan-1-one (78350-37-5) → N-(2-acetylphenyl)-2,2,2-trichloro-N-isopropylacetamide (528856-12-4)

Conditions	Yield
In toluene Heating;	100%

(E)-1-ethoxyprop-1-ene (4696-26-8) + Trichloroacetyl chloride (76-02-8) → (E)-1,1,1-trichloro-4-ethoxy-3-methylbut-3-en-2-one (121781-57-5)

Conditions	Yield
With pyridine In dichloromethane at -10 - 25℃; for 16h;	100%
With pyridine In dichloromethane at 20℃; for 3h;	74%
With pyridine In dichloromethane at -10 - 20℃;	18.64%

[4-amino-3-(3-chlorobenzoyl)phenyl](5-chloro-2-thienyl)methanone (406196-65-4) + Trichloroacetyl chloride (76-02-8) → 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-[(5-chloro-2-thienyl)carbonyl]phenyl]acetamide (406196-67-6)

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

Trichloroacetyl chloride (76-02-8) + 5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → 1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2,2-trichloroethanone

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃; for 0.166667h; Stage #2: trifluoroacetyl chloride In dichloromethane at 20℃;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 0℃; for 3h; Stage #2: trifluoroacetyl chloride In dichloromethane at 25℃; for 16h;	72%
With aluminum (III) chloride In dichloromethane at 20℃;
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoroacetyl chloride for 14h;	16.36 g
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 0℃; for 3h; Stage #2: trifluoroacetyl chloride In dichloromethane at 25℃; for 16h;

[2-amino-5(4-methoxybenzoyl)phenyl](3-chlorophenyl)-methanone (615277-26-4) + Trichloroacetyl chloride (76-02-8) → 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide (615277-28-6)

Conditions	Yield
Stage #1: [2-amino-5(4-methoxybenzoyl)phenyl](3-chlorophenyl)-methanone; trifluoroacetyl chloride In dichloromethane at 5℃; for 0.5h; Stage #2: With triethylamine In dichloromethane at 5 - 20℃; for 3h;	100%

[2-amino-5(4-methylbenzoyl)phenyl](3-chlorophenyl)-methanone (615277-44-6) + Trichloroacetyl chloride (76-02-8) → 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methylbenzoyl)phenyl]-acetamide (615277-46-8)

Conditions	Yield
With triethylamine In dichloromethane at 5 - 20℃; for 3h;	100%

Trichloroacetyl chloride (76-02-8) + 2-[5-(2-furyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzamide (228259-31-2) → 2-[5-(2-furyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (228259-32-3)

Conditions	Yield
With triethylamine In dichloromethane	100%

10-deacetylbaccatin III (32981-86-5) + Acetyl bromide (506-96-7) + Trichloroacetyl chloride (76-02-8) → 7-trichloroacetylbaccatin III (204124-97-0)

Conditions	Yield
Stage #1: 10-deacetylbaccatin III; trifluoroacetyl chloride With pyridine In chloroform at 35℃; for 4h; Stage #2: Acetyl bromide In chloroform at 20℃; for 5h;	100%
Stage #1: 10-deacetylbaccatin III; trifluoroacetyl chloride With pyridine In chloroform at 35℃; for 4h; Stage #2: Acetyl bromide In chloroform at 20℃; for 5h;	100%

vinyl pivalate (3377-92-2) + Trichloroacetyl chloride (76-02-8) → 2,2-dichloro-3-oxocyclobutyl 2,2-dimethyipropanoate (1089709-01-2)

Conditions	Yield
With zinc In diethyl ether at 20℃;	100%
With zinc In diethyl ether at 15 - 30℃; for 2.5h;	97%
With zinc In diethyl ether at 15 - 30℃; for 2.5h;	97%

ethyl α-amino-α-(phenylhydrazono)glyoxylate (36999-43-6) + Trichloroacetyl chloride (76-02-8) → ethyl 1-phenyl-5-(trichloromethyl)-1H-1,2,4-triazole-3-carboxylate (1105634-65-8)

Conditions	Yield
In toluene for 28.25h; Heating / reflux;	100%

methanol (67-56-1) + 7-methoxy-1H-indole (3189-22-8) + Trichloroacetyl chloride (76-02-8) → methyl 7-methoxy-1H-indole-3-carboxylate (582319-20-8)

Conditions	Yield
Stage #1: 7-methoxy-1H-indole; trifluoroacetyl chloride With pyridine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: methanol With potassium hydroxide; water Reflux; Inert atmosphere;	100%

methyl but-3-enoate (3724-55-8) + Trichloroacetyl chloride (76-02-8) → methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate (1148130-29-3)

Conditions	Yield
With zinc copper In 1,2-dimethoxyethane; diethyl ether at 20℃; for 72h;	100%
In 1,2-dimethoxyethane; diethyl ether at 20℃; for 60h; Inert atmosphere;	1.0 g
In 1,2-dimethoxyethane; diethyl ether at 20℃; for 60h; Inert atmosphere;	1 g

Upstream product

• 16650-10-5 perchloroethylene oxide 
• 60-29-7 diethyl ether 
• 597-38-6 bis-pentachloroethyl ether 
• 76-03-9 trichloroacetic acid 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 52764-60-0 trichloro-acetic acid ; sodium-compound 
• 79-36-7 dichloroacethyl chloride 
• 56-23-5 tetrachloromethane 
• 201230-82-2 carbon monoxide 
• 37021-34-4 1,2,2,2-Tetrachloro-1-fluoroethyl methyl ether 
• 76-01-7 pentachloroethane 
• 73569-84-3 chlorotriphenoxy(trichloroacetyl)phosphorane 

Downstream Products

• 53456-47-6 2-pyridinamine trichloroacetate 
• 33560-54-2 N-(2,4-dichlorophenyl)-2,2,2,-trichloroacetamide 
• 90273-66-8 N-benzoyl-N'-trichloroacetyl-hydrazine 
• 2514-53-6 1,2-bis-trichloroacetoxy-ethane 
• 95038-13-4 N_α-trichloroacetyl-α-aminoisobutyric acid 
• 61161-13-5 4'-methoxy-2,2-bis(p-methoxyphenyl)acetophenone 
• 99071-23-5 trichloro-acetic acid-(4-dimethylamino-anilide) 
• 23326-83-2 N-(2-nitrophenyl)-2,2,2,-trichloroacetamide 
• 16112-66-6 2,2,2-trichloro-N-(4-phenylazo-phenyl)-acetamide 
• 29205-54-7 trichloro-acetic acid-(4-nitro-phenacylamide) 
• 27704-37-6 2,2,2-trichloro-1-(4-chlorophenyl)ethanone 
• 6943-66-4 trichloroacetylurea 
• 5825-81-0 trichloro-acetic acid-(2-chloro-ethylamide) 
• 3702-98-5 ethyl 4,4,4-trichloroacetoacetate 

Relevant articles and documents

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Direct Carbonylation of Polychloroalkanes into Acid Chlorides Using Metallic Salts Ternary Systems: an Example of Multistep Catalysis

A catalytic cycle for the direct carbonylation of CCl4 into CCl3COCl, catalysed by metallic salts mixtures. e.g.AlCl3/MCln/CuCl, under unexpectedly mild conditions, is proposed on the basis of FTIR, 17O and 27Al NMR spectroscopic studies.

A high-purity 3, 5, 6 - trichloro-pyridine -2 - sodium alcoholate production process (by machine translation)

The present invention relates to the technical field of chemical material production, and in particular relates to a high-purity 3, 5, 6 - trichloro-pyridine - 2 - sodium alcoholate production process, comprises the following steps: chlorine acetyl chloride; preparing trichlor; addition cyclization: the protection of inert gas atmosphere by adding solvent, the pure product of the chloroacetyl chloride, acrylonitrile and catalyst, the temperature of the stirred to back flow, so that the reflux to return to below the liquid level, reduced pressure distillation, heat filter, the catalyst can be recycled for use, get filtrate for use; preparing 3, 5, 6 - trichloro-pyridine - 2 - sodium alcoholate crude; for preparing high-purity 3, 5, 6 - trichloro-pyridine - 2 - sodium alcoholate. The invention solves the problems in the prior art 3, 5, 6 - trichloro-pyridine - 2 - sodium alcoholate preparation technical difficulty is high, the yield is low and low purity of, the prepared 3, 5, 6 - trichloro-pyridine - 2 - sodium alcoholate has high purity, high yield and relatively shallow the advantages of luster, reasonable production process and is favorable for industrial production. (by machine translation)

A synthetic method of trichloroacetyl chloride

A synthetic method of trichloroacetyl chloride is provided and belongs to the field of organic synthesis. The method includes steps of subjecting chlorine and chloroacetic acid in a melt state to a contact reaction to prepare a primary chlorination material, heating and reacting the primary chlorination material with sulfur monochloride and chlorine to prepare a secondary chlorination material, and heating and reacting the secondary chlorination material with chlorine under actions of a catalyst to obtain the trichloroacetyl chloride. The method synthesizes the trichloroacetyl chloride in a non-water system by utilizing the chloroacetic acid. The non-water system is adopted, thus avoiding generation of toxic and harmful compounds in a preparation process, avoiding a dewatering step, improving environment protection performance of the preparation process, simplifying the synthetic process and facilitating reduction of a synthesis cost.