790-41-0

Basic information

• Product Name: P-CHLOROBENZOIC ANHYDRIDE
• Synonyms: 4-CHLOROBENZOIC ANHYDRIDE;P-CHLOROBENZOIC ANHYDRIDE;bis(4-chlorobenzoic) anhydride;(4-chlorobenzoyl) 4-chlorobenzoate;(4-chlorophenyl)carbonyl 4-chlorobenzoate;4-chlorobenzoic acid (4-chlorobenzoyl) ester
• CAS NO: 790-41-0
• Molecular Formula: C₁₄H₈Cl₂O₃
• Molecular Weight: 295.12
• EINECS: 212-335-1
• Mol File: 790-41-0.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 439°C at 760 mmHg
• Flash Point: 182.5°C
• Appearance: /
• Density: 1.401g/cm³
• Vapor Pressure: 6.63E-08mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Acetone (Slightly), Chloroform (Slightly)
• Stability: Moisture Sensitive
• CAS DataBase Reference: P-CHLOROBENZOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-CHLOROBENZOIC ANHYDRIDE(790-41-0)
• EPA Substance Registry System: P-CHLOROBENZOIC ANHYDRIDE(790-41-0)

Safety Data

• Hazard Codes: T
• Hazardous Substances Data: 790-41-0(Hazardous Substances Data)

Usage

Preparation

To a flask containing 17.5 gm (0.1 mole) of p-chlorobenzoyl chloride is added 50 ml (0.6 mole) of pyridine and the mixture heated for 5 min on the steam bath. The mixture is poured upon 100 gm of cracked ice and 50 ml of concentrated hydrochloric acid, allowed to warm to room temperature, filtered, the solid washed successively with 15 ml of methanol and 15 ml of dry benzene, and dried to afford 14.2-14.6 gm (96-98%), m.p. 192- 193°C (recrystallized from 250 ml of dry benzene).

InChI:InChI=1/C14H8Cl2O3/c15-11-5-1-9(2-6-11)13(17)19-14(18)10-3-7-12(16)8-4-10/h1-8H

Synthetic route

para-chlorobenzoic acid (74-11-3) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃;	99%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; tributyl-amine In acetonitrile at 20℃; for 0.5h;	97%
With thionyl chloride In dichloromethane at 22 - 25℃; for 1h;	96.9%

p-chlorobenzoic acid potassium salt (15163-60-7) + 4-chloro-benzoyl chloride (122-01-0) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 0.116667h;	98%
With N-benzyl-N,N,N-triethylammonium chloride In chloroform at 20℃; for 2h; Acylation;	97%

4-chloro-benzoyl chloride (122-01-0) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 45℃; for 5h; ultrasound;	97%
With bis(triphenylphosphine)dichlorocobalt(II); tetrabutylammomium bromide; sodium hydrogencarbonate In acetonitrile at 120℃; for 12h;	95%
With N,N-dimethyl-formamide; zinc In pentane at 20℃; for 2h;	95%

4,5-dichloro-2-(4-chloro-benzoyl)-2H-pyridazin-3-one (450408-66-9) → 4,5-dichloro-2H-pyridazin-3-one (932-22-9) + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With zinc(II) chloride In acetonitrile for 7h; Heating;	A n/a B 95%

p-chlorobenzoic acid potassium salt (15163-60-7) + para-chlorobenzoic acid (74-11-3) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
Stage #1: para-chlorobenzoic acid With trichloroisocyanuric acid; triphenylphosphine In dichloromethane at 0 - 20℃; Stage #2: p-chlorobenzoic acid potassium salt In dichloromethane at 20℃; for 1.5h;	94%

1-(4-Aminophenyl)-5-phenyl-1,2,3-triazole (15966-68-4) + 4-chloro-benzoyl chloride (122-01-0) → 5-phenyl-1-<4-(4-chlorobenzoylamino)phenyl>-1H-1,2,3-triazole (89779-05-5) + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
In pyridine at 70℃; for 3h;	A 80% B n/a

1-(4-Aminophenyl)-5-methyl-1,2,3-triazole (84292-45-5) + 4-chloro-benzoyl chloride (122-01-0) → 5-methyl-1-<4-(4-chlorobenzoylamino)phenyl>-1H-1,2,3-triazole (89779-17-9) + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
In pyridine at 70℃; for 3h;	A 55% B n/a

4-chlorobenzaldehyde (104-88-1) → 4-chlorobenzoic anhydride (790-41-0) + para-chlorobenzoic acid (74-11-3)

Conditions	Yield
With bromine; oxygen In acetonitrile at 20℃; for 5h; UV-irradiation;	A 28% B 45%

4-chloro-N-hydroxybenzamide (1613-88-3) → 4-chlorobenzoic anhydride (790-41-0) + para-chlorobenzoic acid (74-11-3)

Conditions	Yield
With dinitrogen tetraoxide In acetonitrile at -20℃; for 2h;	A 25% B 41%

ethanol (64-17-5) + para-chlorobenzoic acid (74-11-3) → ethyl 4-chlorobenzoate (7335-27-5) + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With magnesium chloride at 40℃; for 24h;	A 20% B n/a

4-methyleneoxetan-2-one (674-82-8) + para-chlorobenzoic acid (74-11-3) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With diethyl ether; sulfuric acid

S-(4-chloro-benzoyl)-dithiocarbonic acid O-ethyl ester (93507-05-2) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
under 19 Torr; Destillation;

acetic anhydride (108-24-7) + para-chlorobenzoic acid (74-11-3) → 4-chlorobenzoic anhydride (790-41-0)

bis(4-chlorobenzoyl)peroxide (94-17-7) + triethylphosphine (554-70-1) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With diethyl ether

Conditions	Yield
(heating);

→ 4-chlorobenzoic anhydride

Conditions	Yield
(heating);

trimethylsilyl benzoate (2078-12-8) + trimethylsilyl 4-chlorobenzoate (25436-27-5) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With phosphorus pentaoxide; sodium iodide 1) 50 deg C, 1 h, 2) 35 deg C, 12 h; Yield given. Multistep reaction;

trimethylsilyl benzoate (2078-12-8) + p-chlorobenzoic acid potassium salt (15163-60-7) → 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With phosphorus pentaoxide 1) 50 deg C, 1 h, 2) 90 deg C, 8 h; Yield given. Multistep reaction;

chloroformic acid ethyl ester (541-41-3) + para-chlorobenzoic acid (74-11-3) → ethyl 4-chlorobenzoate (7335-27-5) + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With dmap; triethylamine 1.) CH2Cl2, 0 deg C, 5 min, 2.) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

+ meta-chlorobenzoic anhydride + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With palladium diacetate; ethylene dibromide at 100℃; under 11400 Torr; for 20h; Yield given. Further byproducts given. Yields of byproduct given;

carbon monoxide (201230-82-2) + chlorobenzene (108-90-7) → 2-chlorobenzoic anhydride (49619-43-4) + meta-chlorobenzoic anhydride (30070-63-4) + C14H8Cl2O3 + 4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With palladium diacetate; ethylene dibromide at 100℃; under 11400 Torr; for 20h; Yield given. Further byproducts given. Yields of byproduct given;

Conditions	Yield
With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Ambient temperature;	A 94% B 100%

sipholenol A (78518-73-7) + 4-chlorobenzoic anhydride (790-41-0) → C37H55ClO5 (1455460-32-8)

Conditions	Yield
With dmap In dichloromethane Reflux;	98.5%

cyanoacetic acid tert-butyl ester (1116-98-9) + 4-chlorobenzoic anhydride (790-41-0) → tert-butyl 2-(4-chlorophenyl)-2-cyanoacetate (724767-52-6)

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -45℃; for 0.75h; Inert atmosphere; Stage #2: 4-chlorobenzoic anhydride In tetrahydrofuran; hexane at -45℃; for 1h; Inert atmosphere;	98%
Stage #1: cyanoacetic acid tert-butyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -45℃; for 0.75h; Stage #2: 4-chlorobenzoic anhydride In tetrahydrofuran; hexane at -45 - 20℃; Further stages.;

N-methyl-N-phenylmethacrylamide (15796-89-1) + 4-chlorobenzoic anhydride (790-41-0) → 3-(2-(4-chlorophenyl)-2-oxoethyl)-1,3-dimethylindolin-2-one (75116-28-8)

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III) In N,N-dimethyl acetamide at 20℃; for 14h; Sealed tube; Inert atmosphere; Irradiation;	98%

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium carbonate In o-xylene at 145℃; for 24h; Inert atmosphere; Molecular sieve; regioselective reaction;	97%

2-Benzoxazolinone (59-49-4) + 4-chlorobenzoic anhydride (790-41-0) → 3-(4-chlorobenzoyl)-3H-1,3-benzoxazol-2-one (13787-58-1)

Conditions	Yield
for 3h; Heating;	94%

potassium phenyltrifluoborate + 4-chlorobenzoic anhydride (790-41-0) → 4-chlorobenzophenone (134-85-0)

Conditions	Yield
With copper(l) iodide; tris(triphenylphosphine)rhodium(l) chloride; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 2h;	93%

4-chlorobenzoic anhydride (790-41-0) + phenylboronic acid (98-80-6) → 4-chlorobenzophenone (134-85-0)

Conditions	Yield
With PEG200; sodium carbonate; palladium diacetate at 60℃; for 2h; Suzuki reaction;	91%
With sodium carbonate; palladium dichloride In water; acetone at 20℃; for 1.5h; Suzuki type reaction; Inert atmosphere;	87%
With [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; potassium carbonate In 1,4-dioxane at 110℃; for 12h; Inert atmosphere;	87%
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h;	81%
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 5h;	87 % Chromat.

diphenyl diselenide (1666-13-3) + 4-chlorobenzoic anhydride (790-41-0) → 4-chlorobenzenecarboselenoic acid Se-phenyl ester (38447-69-7)

Conditions	Yield
With rongalite; cesium fluoride In water; N,N-dimethyl-formamide at 20℃; for 0.416667h;	91%

ethyl 2-cyanoacetate (105-56-6) + 4-chlorobenzoic anhydride (790-41-0) → ethyl 2-(4-chlorophenyl)-2-cyanoacetate (147795-56-0, 15032-43-6)

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -45℃; for 0.75h; Inert atmosphere; Stage #2: 4-chlorobenzoic anhydride In tetrahydrofuran; hexane at -45℃; for 1h; Inert atmosphere;	89%

4-chlorobenzoic anhydride (790-41-0)

Conditions	Yield
With potassium fluoride; oxygen; palladium dichloride In acetonitrile at 60℃; for 5h;	89%

+ 4-chlorobenzoic anhydride

Conditions	Yield
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h;	87%
With sodium carbonate; palladium dichloride In water; acetone at 20℃; for 1.5h; Suzuki type reaction; Inert atmosphere;	81%

diphenyldisulfane + 4-chlorobenzoic anhydride (790-41-0) → S-phenyl 4-chlorobenzothioate (28122-82-9)

Conditions	Yield
With rongalite; cesium fluoride In water; N,N-dimethyl-formamide at 20℃; for 0.5h;	87%

1,2-diamino-benzene (95-54-5) + 4-chlorobenzoic anhydride (790-41-0) → 2-(4-chlorophenyl)benzimidazole (1019-85-8)

Conditions	Yield
With o-benzenedisulfonimide In tetrahydrofuran for 6.5h; Reflux; Green chemistry;	86%

4-chlorobenzoic anhydride (790-41-0) + Isosorbide (652-67-5) → 4-Chloro-benzoic acid (3R,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (111878-16-1)

Conditions	Yield
With lead(II) oxide In dichloromethane	84%

urethane (51-79-6) + 4-chlorobenzoic anhydride (790-41-0) → ethyl 4-chlorobenzoylcarbamate (13733-20-5)

Conditions	Yield
With silica sulfuric acid at 20℃; for 15h; Neat (no solvent);	84%
With perchloric acid on silica at 20℃; for 15h;	82%

naphthalene-2-boronic acid (32316-92-0) + 4-chlorobenzoic anhydride (790-41-0) → (4-chlorophenyl)(naphthalen-2-yl)methanone (7495-98-9)

Conditions	Yield
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h;	83%

2-(3,5-dimethoxyphenyl)benzoxazol-5-amine + 4-chlorobenzoic anhydride (790-41-0) → 4-chloro-N-(2-(3,5-dimethoxyphenyl)benzoxazol-5-yl)benzamide

Conditions	Yield
With acetic acid; zinc In dichloromethane at 20℃;	82%

3-phenyl-1,2-nonadiene (201735-42-4) + 4-chlorobenzoic anhydride (790-41-0) → C22H25ClO

Conditions	Yield
With (dimethoxy)methylsilane; copper diacetate; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In tetrahydrofuran at 20℃; for 6h; enantioselective reaction;	81%

4-p-methylphenyl-1,2-oxaborol-2(5H)-ol (1379820-13-9) + 4-chlorobenzoic anhydride (790-41-0) → C17H13ClO (344339-78-2)

Conditions	Yield
With palladium diacetate; sodium carbonate; tricyclohexylphosphine In water; toluene at 80℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	80%

2-Naphthalenethiol (91-60-1) + 4-chlorobenzoic anhydride (790-41-0) → (4-chlorophenyl)(naphthalen-2-yl)sulfane (127567-54-8)

Conditions	Yield
With manganese; 1,3-bis-(diphenylphosphino)propane; sodium carbonate; nickel dichloride In toluene at 150℃; for 24h; Sealed tube; Inert atmosphere;	80%

C27H26Si + 4-chlorobenzoic anhydride (790-41-0) → C34H31ClO2Si

Conditions	Yield
With methanol; di(rhodium)tetracarbonyl dichloride; C76H62NO5P; potassium carbonate In 1,4-dioxane at 70℃; for 48h; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction;	80%

4-trifluoromethylphenylboronic acid (128796-39-4) + 4-chlorobenzoic anhydride (790-41-0) → (4-chloro-phenyl)-(4-trifluoromethyl-phenyl)-methanone (34328-31-9)

Conditions	Yield
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h;	78%
With sodium carbonate; palladium dichloride In water; acetone at 20℃; for 1.5h; Suzuki type reaction; Inert atmosphere;	74%

4-chlorobenzoic anhydride (790-41-0) + 1-(di-tert-butylphosphino)-1H-indole → 1-(di-tert-butylphosphino)-7-(4-chlorophenyl)-1H-indole

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium hydrogencarbonate In toluene at 150℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	78%

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 74-11-3 para-chlorobenzoic acid 
• 93507-05-2 S-(4-chloro-benzoyl)-dithiocarbonic acid O-ethyl ester 
• 108-24-7 acetic anhydride 
• 122-01-0 4-chloro-benzoyl chloride 
• 94-17-7 bis(4-chlorobenzoyl)peroxide 
• 554-70-1 triethylphosphine 
• 59318-22-8 C₁₀H₉ClO₃S₄ 
• 59318-20-6 C₁₃H₈Cl₂O₂S₃ 
• 2078-12-8 trimethylsilyl benzoate 
• 25436-27-5 trimethylsilyl p-chlorobenzoate 
• 15163-60-7 p-chlorobenzoic acid potassium salt 
• 1613-88-3 4-chloro-N-hydroxybenzamide 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 52669-45-1 N-(4-chloro-benzoyl)-glycine hexadecyl ester 
• 13787-58-1 3-(4-chlorobenzoyl)-3H-1,3-benzoxazol-2-one 
• 133044-33-4 6-(4-chlorobenzoyl)-2(3H)-benzothiazolone 
• 133044-34-5 3-Methyl-6-(4-Chlorobenzoyl)Benzothiazolinone 
• 145702-36-9 2-(4-Chloro-benzoylsulfanyl)-benzoic acid 
• 58948-38-2 2-(4-Chlorophenyl)-1,3-benzoxathiolium tetrafluoroborate 
• 77507-54-1 (1-phenylsulfonyl-3-methyl-1H-indol-2-yl)(4-chlorophenyl)methanone 
• 60045-27-4 3-phenylpropionic acid 3-phenylpropyl ester 
• 115583-65-8 4-Chloro-benzoic acid (3S,5R)-3-(4-chloro-phenyl)-3-imidazol-1-ylmethyl-2-methyl-isoxazolidin-5-ylmethyl ester 
• 115583-65-8 4-Chloro-benzoic acid (3S,5S)-3-(4-chloro-phenyl)-3-imidazol-1-ylmethyl-2-methyl-isoxazolidin-5-ylmethyl ester 
• 77507-56-3 (1-Benzenesulfonyl-3-ethyl-1H-indol-2-yl)-(4-chloro-phenyl)-methanone 
• 93181-94-3 3-{4-[(4-chlorobenzoyl)oxy]piperidino}-6-(2-chlorophenyl)pyridazine 
• 93241-12-4 4-Chloro-benzenecarboperoxoic acid 1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl ester 
• 113857-91-3 N^α-(4-amino-4-deoxy-N¹⁰-formylpteroyl)-N^δ-(4-chlorobenzoyl)-L-ornithine 

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