4124-31-6

Basic information

• Product Name: TRICHLOROACETIC ANHYDRIDE
• Synonyms: PERCHLOROACETIC ANHYDRIDE;TCAA;trichloro-aceticacianhydride;TRICHLOROACETIC ACID ANHYDRIDE;TRICHLOROACETIC ANHYDRIDE;Trichloroacetic acid anhydride (TCAA);TRICHLOROACETIC ANHYDRIDE, TECH., 95%;TrichloroaceticAnhydride97%
• CAS NO: 4124-31-6
• Molecular Formula: C₄Cl₆O₃
• Molecular Weight: 308.76
• EINECS: 223-925-3
• Product Categories: Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks;Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Chemical Synthesis;Organic Building Blocks
• Mol File: 4124-31-6.mol

Chemical Properties

• Boiling Point: 139-141 °C60 mm Hg(lit.)
• Flash Point: 98-100°C/11mm
• Appearance: colourless liquid
• Density: 1.69 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.106mmHg at 25°C
• Refractive Index: n20/D 1.484(lit.)
• Solubility: Miscible with ether and acetic acid.
• Sensitive: Moisture Sensitive
• Stability: Stable. Moisture sensitive - store under dry atmosphere. Incompatible with strong bases, strong oxidizing agents.
• BRN: 980355
• CAS DataBase Reference: TRICHLOROACETIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRICHLOROACETIC ANHYDRIDE(4124-31-6)
• EPA Substance Registry System: TRICHLOROACETIC ANHYDRIDE(4124-31-6)

Safety Data

• Hazard Codes: C
• Statements: 22-35
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4124-31-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Trichloroacetic anhydride is used as a reagent in organometallic reactions and for the synthesis of oxadiazole-containing 5-lipoxygenase activating protein inhibitors. Its unique properties make it a valuable component in the development of various chemical compounds and pharmaceuticals.
Used in Derivatization:
Trichloroacetic anhydride is utilized as a derivatization reagent, enhancing the stability, mass fragmentation pattern, and reducing the volatility of the resulting derivatives. This application is particularly useful in the analysis and identification of various compounds in chemical and pharmaceutical research.
Used in Pharmaceutical Research:
In the pharmaceutical industry, trichloroacetic anhydride plays a crucial role in the synthesis of specific protein inhibitors, which can be used for the development of new drugs targeting various diseases and conditions. Its efficiency in producing stable derivatives makes it a preferred choice for researchers in drug discovery and development.

InChI:InChI=1/C4Cl6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10

Synthetic route

trichloroacetic acid (76-03-9) → trichloroacetic acid anhydride (4124-31-6)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 120℃; for 5h;	60%
With phosphorus pentoxide at 210℃;
With 1-ethoxyacetylene

O-acetyl S,S-dipropyl phosphorodithioite (84103-77-5) → mixed anhydride of acetic and trichloroacetic acids (32676-68-9) + dipropyl phosphorochloridodithioite (4104-04-5) + acetic anhydride (108-24-7) + trichloroacetic acid anhydride (4124-31-6)

Conditions	Yield
With trifluoroacetyl chloride for 1h; Ambient temperature;	A n/a B 50% C n/a D n/a

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

Conditions	Yield
zeitlicher Verlauf bei Siedetemperatur;
With potassium chloride

dichloromethane (75-09-2) + ethynyl methyl ether (6443-91-0) + trichloroacetic acid (76-03-9) → trichloroacetic acid anhydride (4124-31-6)

1-Ethoxyvinyl trichloroacetate (90724-35-9) + trichloroacetic acid (76-03-9) → trichloroacetic acid anhydride (4124-31-6)

Conditions	Yield
With diethyl ether

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

Conditions	Yield
With phosphorus trichloride

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

Conditions	Yield
zeitlicher Verlauf bei Siedetemperatur;

diethyl ether (60-29-7) + 1-ethoxyacetylene (927-80-0) + trichloroacetic acid (76-03-9) → 1-Ethoxyvinyl trichloroacetate (90724-35-9) + ethyl acetate (141-78-6) + trichloroacetic acid anhydride (4124-31-6) + 4-ethoxy-1,1,1-trichloro-4ξ-trichloroacetoxy-but-3-en-2-one

sodium trichloroacetate → trichloroacetic acid anhydride (4124-31-6)

Conditions	Yield
With phosgene; acetic acid ester
With phosgene; oxalic acid ester
With sulfuryl dichloride; acetic acid ester
With sulfuryl dichloride; oxalic acid ester

Dimethylsulfonium-trifluoracetyl-methylid (104917-77-3) + trichloroacetic acid anhydride (4124-31-6) → 1-Trichloracetyl-2-oxo-3-trifluor-1-dimethylsulfonium-1-yl-propanid

Conditions	Yield
In tetrahydrofuran at 24℃; for 4h;	100%

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) + trichloroacetic acid anhydride (4124-31-6) → 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetate (155500-50-8)

Conditions	Yield
With sodium trichloroacetate In dichloromethane for 2h; Heating;	100%

N-hydroxyisobutyramidine (849833-56-3, 35613-84-4, 1202858-97-6) + trichloroacetic acid anhydride (4124-31-6) → 3-isopropyl-5-(trichloromethyl)-1,2,4-oxadiazole (1199-49-1)

Conditions	Yield
In toluene for 1h; Reflux;	100%
In toluene for 1h; Reflux;
In toluene for 1h; Reflux;

di-p-tolyldi(2-pyrrolyl)methane (1343487-95-5) + trichloroacetic acid anhydride (4124-31-6) → C27H20Cl6N2O2

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	100%

benzyl crotyl amine (107733-62-0) + trichloroacetic acid anhydride (4124-31-6) → N-benzyl-N-(but-2-enyl)carbamoyl chloride

Conditions	Yield
With pyridine In benzene for 96h;	99.5%

N-benzyl-N-<1-(2'-benzyloxyethyl)-3-methylbut-2-enyl>amine (132872-29-8) + trichloroacetic acid anhydride (4124-31-6) → N-benzyl-N-<1-(2'-benzyloxyethyl)-3-methylbut-2-enyl>carbamoyl chloride (132872-30-1)

Conditions	Yield
With pyridine In benzene for 96h;	99.5%

methyl 2,3-di-O-benzyl-6-O-acetyl-α-D-glucopyranoside (20771-21-5, 51842-23-0, 51842-24-1, 117561-20-3, 125884-32-4, 51842-22-9) + trichloroacetic acid anhydride (4124-31-6) → Methyl-6-O-acetyl-2,3-di-O-benzyl-4-O-trichloracetyl-α-D-glucopyranosid (79705-88-7)

Conditions	Yield
In pyridine at -20℃; for 0.416667h;	99%

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-galactopyranose (59464-21-0) + trichloroacetic acid anhydride (4124-31-6) → 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-trichloracetyl-β-D-galactopyranose

Conditions	Yield
In pyridine at -20℃; for 0.5h;	99%

Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(2-oxo-propyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester + trichloroacetic acid anhydride (4124-31-6) → 2,3,4-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α/β-D-glucopyranosyl trichloroacetate

Conditions	Yield
With sodium trichloroacetate In dichloromethane for 6h; Heating;	99%

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) + trichloroacetic acid anhydride (4124-31-6) → 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetate (383905-63-3)

Conditions	Yield
With sodium trichloroacetate In dichloromethane for 1.5h; Heating;	99%

2-cyclopentylidene-1,1-diphenylhydrazine (39672-00-9) + trichloroacetic acid anhydride (4124-31-6) → trichloroacetic acid 1-(1-cyclopenten-1-yl)-2,2-diphenylhydrazide

Conditions	Yield
With 2,4,6-trimethyl-pyridine In dichloromethane at 0℃;	99%

N-(2,2-dimethylpent-4-enyl)-N-propylamine (155693-23-5) + trichloroacetic acid anhydride (4124-31-6) → N-(2,2-dimethylpent-4-enyl)-N-propylcarbamoyl chloride (155693-24-6)

Conditions	Yield
With pyridine In benzene for 72h;	98%

6--4-chloro-2-(methylthio)pyrimidine (155670-17-0) + trichloroacetic acid anhydride (4124-31-6) → C16H11Cl4N3O2S

Conditions	Yield
With triethylamine In dichloromethane	98%

7-isopropyl-1,4-dimethyl-azulene (489-84-9) + trichloroacetic acid anhydride (4124-31-6) → 3-trichloroacetylguaiazulene (846-33-3)

Conditions	Yield
In dichloromethane	98%
In dichloromethane	76%
In dichloromethane
In dichloromethane at 20℃; for 2h;

O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-D-glucopyranose (81243-75-6, 81243-76-7, 91852-38-9) + trichloroacetic acid anhydride (4124-31-6) → 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl trichloroacetate

Conditions	Yield
With sodium trichloroacetic In dichloromethane Heating;	98%
With sodium trichloroacetate In dichloromethane Heating;	98%

Acetic acid (3S,4S,5R,6R)-6-acetoxymethyl-4,5-bis-benzyloxy-2-hydroxy-tetrahydro-pyran-3-yl ester + trichloroacetic acid anhydride (4124-31-6) → 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetate (183885-17-8)

Conditions	Yield
With sodium trichloroacetate In dichloromethane for 1h; Heating;	98%
With sodium trichloroacetate In dichloromethane for 1h; Heating; Yield given;

(Z)-(oxiran-2-yl)methyl octadec-9-enoate (5431-33-4) + trichloroacetic acid anhydride (4124-31-6) → 2-O-oleoyl-1,3-bis-O-(trichloroacetyl)glycerol

Conditions	Yield
In dichloromethane at -20 - 20℃;	98%

6,7-dimethylinden-1-ol + trichloroacetic acid anhydride (4124-31-6) → 1-(3',3',3'-trichloroacetoxy-6,7-dimethyl)indene (1263309-94-9)

Conditions	Yield
With pyridine In tetrahydrofuran for 0.25h; Inert atmosphere;	98%

benzylamine (100-46-9) + trichloroacetic acid anhydride (4124-31-6) → benzyl 2,2,2-trichloroacetamide (4257-83-4)

Conditions	Yield
	98%

N-(3-butenyl)n-butylamine (18903-55-4) + trichloroacetic acid anhydride (4124-31-6) → N-but-3-enyl-N-butylcarbamoyl chloride (155693-21-3)

Conditions	Yield
With pyridine In benzene for 96h;	97%

N-benzyl-N-(1,3-dimethylbut-2-enyl)amine (60519-98-4) + trichloroacetic acid anhydride (4124-31-6) → N-benzyl-N-(1,3-dimethylbut-2-enyl)carbamoyl chloride (156627-40-6)

Conditions	Yield
With pyridine In benzene for 72h;	97%

6-fluoro-3-methylisoquinolin-5-amine (608515-64-6) + trichloroacetic acid anhydride (4124-31-6) → 2,2,2-trichloro-N-(6-fluoro-3-methylisoquinolin-5-yl)acetamide (1221445-04-0)

Conditions	Yield
With pyridine In acetonitrile at -10℃; for 0.166667h;	97%
With pyridine In acetonitrile at -10 - -5℃; for 0.25h;	87%
With pyridine at -10 - -5℃;	86%
With pyridine at -10 - -5℃;	86%

4-methoxyphenyl 2-amino-4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-glucopyranoside + trichloroacetic acid anhydride (4124-31-6) → 4-methoxyphenyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2,6-dideoxy-2-trichloroacetamido-β-D-glucopyranoside

Conditions	Yield
In pyridine at 0℃;	97%

morphine (57-27-2, 143-70-4, 6912-73-8, 16206-77-2, 27067-73-8, 65165-99-3, 70982-47-7) + trichloroacetic acid anhydride (4124-31-6) → C19H18Cl3NO4

Conditions	Yield
With pyridine In tetrahydrofuran; water at 0 - 10℃; for 1.5h; Reagent/catalyst; Solvent; Temperature; Industrial scale;	97%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2, 10034-19-2, 10034-20-5, 34948-62-4, 110253-00-4) + trichloroacetic acid anhydride (4124-31-6) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose (56644-75-8, 10353-00-1)

Conditions	Yield
With pyridine In dichloromethane at 0℃;	97%

N-allyl-N-butylamine (4538-09-4) + trichloroacetic acid anhydride (4124-31-6) → N-allyl-N-butylcarbamoyl chloride (125012-90-0)

Conditions	Yield
With pyridine In benzene for 96h;	96%

(Z)-4-amino-N'-hydroxy-1,2,5-oxadiazole-3-carbimidoyl chloride (13490-32-9) + trichloroacetic acid anhydride (4124-31-6) → 2,2,2-trichloro-N-[4-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-furazan-3-yl]-acetamide

Conditions	Yield
at 120℃; for 5h;	96%

6-chloro-3-methylisoquinolin-5-amine (919994-53-9) + trichloroacetic acid anhydride (4124-31-6) → 2,2,2-trichloro-N-(6-chloro-3-methylisoquinolin-5-yl)acetamide

Conditions	Yield
With pyridine In acetonitrile at -10 - -5℃; for 0.333333h;	96%

3,3,3-trifluoro-N'-hydroxypropanimidamide (1016726-53-6) + trichloroacetic acid anhydride (4124-31-6) → 5-(trichloromethyl)-3-(2,2,2-trifluoroethyl)-1,2,4-oxadiazole

Conditions	Yield
With trichloroacetic acid at 110℃; for 1h; Inert atmosphere;	96%

ethyl trimethylsilyl ether (1825-62-3) + trichloroacetic acid anhydride (4124-31-6) → trimethylsilyl trichloroacetate (25436-07-1)

Conditions	Yield
With iron perchlorate hexahydrate at 25℃; for 0.5h;	96%

Upstream product

• 76-02-8 trifluoroacetyl chloride 
• 76-03-9 trichloroacetic acid 
• 75-09-2 dichloromethane 
• 6443-91-0 ethynyl methyl ether 
• 90724-35-9 1-Ethoxyvinyl trichloroacetate 
• 84103-77-5 O-acetyl S,S-dipropyl phosphorodithioite 
• 60-29-7 diethyl ether 
• 927-80-0 1-ethoxyacetylene 

Downstream Products

• 15166-50-4 N-(Trichloroacetyl)glycine 
• 30362-65-3 bis-(4-chloro-phenyl)-trichloromethyl-[1,3,5]triazine 
• 15167-27-8 N-trichloroacetyl-DL-phenylalanine 
• 6340-88-1 N-Trichloracetyl-p-aminosalicylsaeure 
• 67467-20-3 2-trichloroacetylcyclohexanone 
• 22780-11-6 1-(2,2,2-trichloroacetoxy)cyclohexene 
• 22780-08-1 1,1-bis(trichloroacetoxy)cyclohexane 
• 27389-43-1 2-(4-chloro-phenyl)-5-trichloromethyl-[1,3,4]oxadiazole 
• 59938-07-7 (3E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one 
• 1195-25-1 3-methyl-5-trichloromethyl-1,2,4-oxadiazole 
• 1208-05-5 3-phenyl-5-(trichloromethyl)-1,2,4-oxadiazole 
• 27389-46-4 2-p-tolyl-5-trichloromethyl-[1,3,4]oxadiazole 
• 24693-07-0 3,4-dimethyl-1-oxo-1-phenyl-4-trichloroacetoxy-1λ⁵-phospholan-3-ol 
• 1822-97-5 3-(4-chlorophenyl)-5-(trichloromethyl)-1,2,4-oxadiazole 

Relevant articles and documents

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