876-08-4

Basic information

• Product Name: 4-(Chloromethyl)benzoyl chloride
• Synonyms: 4-CHLOROMETHYLBENZOYL CHLORIDE;CMBC;4-CHLOROMETHYLBENZOYL CHLORIDE 98+%;Benzoyl chloride, 4-(chloromethyl)-;4-(Chloromethyl)benzoic acid chloride;4-Chloromethylbenzoic acid chloride;p-(Chloromethyl)benzoic acid chloride;α-Chloro-p-toluoyl chloride
• CAS NO: 876-08-4
• Molecular Formula: C₈H₆Cl₂O
• Molecular Weight: 189.04
• EINECS: 212-881-0
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 876-08-4.mol
• Article Data: 46

Chemical Properties

• Melting Point: 30-32 °C(lit.)
• Boiling Point: 126-128 °C6 mm Hg(lit.)
• Flash Point: 199 °F
• Appearance: White to light beige/Low Melting Crystalline Mass
• Density: 1.2979 (rough estimate)
• Vapor Pressure: 0.00505mmHg at 25°C
• Refractive Index: 1.5605 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 4-(Chloromethyl)benzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Chloromethyl)benzoyl chloride(876-08-4)
• EPA Substance Registry System: 4-(Chloromethyl)benzoyl chloride(876-08-4)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 23-26-27-36/37/39-45-25
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 876-08-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light beige low melting crystalline mass

Uses

Different sources of media describe the Uses of 876-08-4 differently. You can refer to the following data:
1. 4-(Chloromethyl)benzoyl Chloride is used in the synthetic preparation of various compounds and pharmaceuticals. 4-(Chloromethyl)benzoyl Chloride was used in the synthesis of several imidazo[2,1-b]thia zoles.
2. 4-(Chloromethyl)benzoyl chloride was used as an atom transfer radical polymerization (ATRP) initiator in the growth of polyacrylamide (PAAm) brushes from silicon wafers. It was also used as a building block in a microwave-assisted, solid-phase synthesis of imatinib, an anticancer agent.

InChI:InChI=1/C8H6Cl2O/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,5H2

Synthetic route

p-(chloromethyl)benzoic acid (1642-81-5) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	99%
With thionyl chloride for 2h; Substitution; Heating;	96%
With thionyl chloride for 5h; Reflux; Large scale;	96.19%

[4-(trichloromethyl)phenyl]methanol → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
Stage #1: [4-(trichloromethyl)phenyl]methanol With water at 50℃; for 22h; Stage #2: With oxalyl dichloride; N,N-dimethyl-formamide In diethyl ether at 20℃; for 12h;	90.1%

4-methyl-benzoyl chloride (874-60-2) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
With chlorine at 25 - 140℃; for 5h; Temperature; Inert atmosphere;	90%
With chlorine at 75 - 90℃;
durch Chlorieren;

3-hydroxymethyl-benzoic acid (3006-96-0) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; Schlenk technique;	87.2%
With thionyl chloride In DMF (N,N-dimethyl-formamide); chloroform for 3h; Heating / reflux;
With thionyl chloride; N,N-dimethyl-formamide In toluene at 60℃; for 2h;

para-chlorotoluene (106-43-4) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
With chlorine at 120 - 130℃; Irradiation;

4-bromomethylbenzoic Acid (6232-88-8) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 0.5h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
With thionyl chloride at 20 - 50℃; for 17h;	4.4 g

4-methyl-benzoyl chloride (874-60-2) → p-(chloromethyl)benzoyl chloride (876-08-4) + 4-trichloromethylbenzoyl chloride (14815-86-2) + 4-dichloromethylbenzoyl chloride (36747-64-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); chlorine
With 2,2'-azobis(isobutyronitrile); chlorine Title compound not separated from byproducts;

p-Toluic acid (99-94-5) + Nα-Fmoc-Nim-tert-butyloxycarbonyl-L-tryptophan 4-hydroxymethylphenoxy resin → p-(chloromethyl)benzoyl chloride (876-08-4) + MeO-poly(ethylene glycol)

Conditions	Yield
Multi-step reaction with 2 steps 1: NCS; benzoylperoxide / chlorobenzene / 8 h / 95 °C 2: SOCl2 / toluene / 15 h / 85 - 90 °C View Scheme

oxalyl dichloride (79-37-8) + p-(chloromethyl)benzoic acid (1642-81-5) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
In dichloromethane
In dichloromethane; chloroform; N,N-dimethyl-formamide
In dichloromethane; chloroform; N,N-dimethyl-formamide

oxalyl dichloride (79-37-8) + 4-bromomethylbenzoic Acid (6232-88-8) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
In dichloromethane

methyl 4-formylbenzoate (1571-08-0) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol 2: potassium hydroxide / water; methanol 3: thionyl chloride / chloroform / Reflux View Scheme

4-(methoxycarbonyl)benzyl alcohol (6908-41-4) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / water; methanol 2: thionyl chloride / chloroform / Reflux View Scheme

p-Toluic acid (99-94-5) → p-(chloromethyl)benzoyl chloride (876-08-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / 40 - 90 °C / Large scale 2: chlorine / 5 h / 25 - 140 °C / Inert atmosphere View Scheme

N,N'-diethyl-1,3-propanediamine (10061-68-4) + 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) + p-(chloromethyl)benzoyl chloride (876-08-4) + benzyl bromide (100-39-0) + benzylamine (100-46-9) → 3-(4-{[3-(benzyl-ethyl-amino)-propyl]-ethyl-carbamoyl}-benzyl)-3H-[1,2,3]triazole-4-carboxylic acid benzylamide

Conditions	Yield
Multistep reaction;	100%

N,N'-diethyl-1,3-propanediamine (10061-68-4) + 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) + p-(chloromethyl)benzoyl chloride (876-08-4) + benzylamine (100-46-9) + methyl iodide (74-88-4) → 3-(4-{ethyl-[3-(ethyl-methyl-amino)-propyl]-carbamoyl}-benzyl)-3H-[1,2,3]triazole-4-carboxylic acid benzylamide

Conditions	Yield
Multistep reaction;	100%

N-n-butyl-N-methylamine (110-68-9) + N,N'-diethyl-1,3-propanediamine (10061-68-4) + 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) + p-(chloromethyl)benzoyl chloride (876-08-4) + methyl iodide (74-88-4) → 3-(4-{ethyl-[3-(ethyl-methyl-amino)-propyl]-carbamoyl}-benzyl)-3H-[1,2,3]triazole-4-carboxylic acid butyl-methyl-amide

Conditions	Yield
Multistep reaction;	100%

p-(chloromethyl)benzoyl chloride (876-08-4) → N-hydroxysuccinimidyl 4-(chloromethyl)benzoate (713123-22-9)

Conditions	Yield
Stage #1: 1-hydroxy-pyrrolidine-2,5-dione With triethylamine In dichloromethane Stage #2: p-(chloromethyl)benzoyl chloride In dichloromethane at 0℃; Stage #3: at 20℃; for 12h;	100%

p-(chloromethyl)benzoyl chloride (876-08-4) + methylamine hydrochloride (593-51-1) → 4-(chloromethyl)-N-methylbenzamide (220875-88-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;	100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;

p-(chloromethyl)benzoyl chloride (876-08-4) + 5-((2-aminopyridin-4-yl)oxy)-6-(2-ethoxyethoxy)-N-methyl-1H-indole-1-carboxamide (1622205-71-3) → 5-((2-(4-(chloromethyl)-N-(4-(chloromethyl)benzoyl)benzamide)pyridin-4-yl)oxy)-6-(2-ethoxyethoxy)-N-methyl-1H-indole-1-carboxamide (1622205-80-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	100%

(2-hydroxyethyl)(methyl)amine (109-83-1) + p-(chloromethyl)benzoyl chloride (876-08-4) → 4-(chloromethyl)-N-(2-hydroxyethyl)-N-methylbenzamide (1182906-72-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 10℃; for 0.166667h; Solvent; Reagent/catalyst;	100%

p-(chloromethyl)benzoyl chloride (876-08-4) → 4-(chloromethyl)benzohydrazide

Conditions	Yield
With hydrazine In dichloromethane at 20℃; for 18h;	99.5%

p-(chloromethyl)benzoyl chloride (876-08-4) → tert-butyl 4-(chloromethyl)benzamide (84545-14-2)

Conditions	Yield
With ammonia; water In toluene at 0 - 20℃; for 2h;	99.3%
With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.166667h;

p-(chloromethyl)benzoyl chloride (876-08-4) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide (404844-11-7)

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 4h;	99%
With triethylamine In tetrahydrofuran at 0℃; for 1h; Large scale;	98.1%
With triethylamine In tetrahydrofuran at 0℃; for 4h;	97.4%

p-(chloromethyl)benzoyl chloride (876-08-4) + N-methyl-N-nitrosotoluene-p-sulfonamide (80-11-5) → p-(diazoacetyl)benzyl chloride (1137172-09-8)

Conditions	Yield
With triethylamine; sodium hydroxide In water; Petroleum ether for 2h;	99%

p-(chloromethyl)benzoyl chloride (876-08-4) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → 4-(сhloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide hydrochloride (404844-10-6)

Conditions	Yield
In 1,4-dioxane at 22 - 34℃; for 2.75h;	99%

2,2,3,3,3-pentafluoropropyl alcohol (422-05-9) + p-(chloromethyl)benzoyl chloride (876-08-4) → C11H8ClF5O2 (1293408-10-2)

Conditions	Yield
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	99%

p-(chloromethyl)benzoyl chloride (876-08-4) + (bpy)CuSCF3 → S-(trifluoromethyl) 4-(chloromethyl)benzothioate

Conditions	Yield
In 1,4-dioxane at 25℃; for 1.5h; Inert atmosphere;	99%

aminopropane diethyl acetal (41365-75-7) + p-(chloromethyl)benzoyl chloride (876-08-4) → 4-(chloromethyl)-N-(3,3-diethoxypropyl)benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	99%

p-(chloromethyl)benzoyl chloride (876-08-4) + bis(2-methyl-2-propanyl) (1-piperazinylmethylylidene)biscarbamate (203258-20-2) → 1-[4-(chloromethyl)benzoyl]-4-[N,N'-bis(tert-butoxycarbonyl)]guanylpiperazine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2h; Acylation;	98%

p-(chloromethyl)benzoyl chloride (876-08-4) + 1-(4-tetradecyloxyphenyl)piperazine hydrochloride → 1-(4-chloromethylbenzoyl)-4-(4-tetradecyloxyphenyl)piperazine (1229612-63-8)

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

p-(chloromethyl)benzoyl chloride (876-08-4) + 2-(Ethylamino)ethanol (110-73-6) → N-ethyl-N-(2-hydroxyethyl)-4-(chloromethyl)benzamide (948877-06-3)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 4h;	98%

p-(chloromethyl)benzoyl chloride (876-08-4) + benzyl-methyl-amine (103-67-3) → N-benzyl-4-(chloromethyl)benzamide

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 1h; Inert atmosphere;	98%

prednisolon (50-24-8) + p-(chloromethyl)benzoyl chloride (876-08-4) → prednisolone 21-[4'-(chloromethyl)benzoate]

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h;	97%

N-n-butyl-N-methylamine (110-68-9) + N,N'-diethyl-1,3-propanediamine (10061-68-4) + 3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) + p-(chloromethyl)benzoyl chloride (876-08-4) + allyl bromide (106-95-6) → 3-(4-{[3-(allyl-ethyl-amino)-propyl]-ethyl-carbamoyl}-benzyl)-3H-[1,2,3]triazole-4-carboxylic acid butyl-methyl-amide

Conditions	Yield
Multistep reaction;	97%

2-Amino-6-methylpyridine (1824-81-3) + p-(chloromethyl)benzoyl chloride (876-08-4) → 4-chloromethyl-N-(6-methyl-pyridin-6-yl)benzamide (915701-45-0)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 16h;	97%

4-Hydroxy-2-quinolone (70254-43-2, 70254-44-3) + p-(chloromethyl)benzoyl chloride (876-08-4) → 4-(4-chloromethylbenzoyl)oxyquinol-2(1H)-one (1472655-54-1)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	97%

p-(chloromethyl)benzoyl chloride (876-08-4) + hydroquinone (123-31-9) → C22H16Cl2O4

Conditions	Yield
With triethylamine In dichloromethane for 1h; Reflux; Inert atmosphere;	97%

bis(2-hydroxyethyl) disulfide (1892-29-1) + p-(chloromethyl)benzoyl chloride (876-08-4) → disulfanediyldiethane-2,1-diyl bis[4-(chloromethyl)benzoate]

Conditions	Yield
Stage #1: bis(2-hydroxyethyl) disulfide With triethylamine In chloroform at 0℃; Inert atmosphere; Sealed tube; Stage #2: p-(chloromethyl)benzoyl chloride In chloroform at 20℃; Inert atmosphere;	97%

p-(chloromethyl)benzoyl chloride (876-08-4) + C15H14N4S → C23H19ClN4OS

Conditions	Yield
Stage #1: C15H14N4S With triethylamine In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: p-(chloromethyl)benzoyl chloride In tetrahydrofuran at 0℃; for 3.16667h; Inert atmosphere; Schlenk technique;	96.6%

ethanol (64-17-5) + p-(chloromethyl)benzoyl chloride (876-08-4) → ethyl 4-chloromethylbenzoate (1201-90-7)

Conditions	Yield
With pyridine; dmap In diethyl ether at 0℃; Inert atmosphere;	96%
With pyridine
at 45℃; for 4h;
for 0.5h; Heating;

4-piperidinopiperidin (4897-50-1) + p-(chloromethyl)benzoyl chloride (876-08-4) → 1-(4-chloromethylbenzoyl)-4-piperidinopiperidine hydrochloride

Conditions	Yield
In acetonitrile at 20℃; for 2h;	96%

p-(chloromethyl)benzoyl chloride (876-08-4) + cyclohexylmagnesiumchloride (931-51-1) → (4-(chloromethyl)phenyl)(cyclohexyl)methanone

Conditions	Yield
Stage #1: cyclohexylmagnesiumchloride With zinc(II) chloride In tetrahydrofuran; diethyl ether at -10℃; for 0.666667h; Stage #2: With copper(I) cyanide di(lithium chloride) In tetrahydrofuran; diethyl ether for 0.5h; Stage #3: p-(chloromethyl)benzoyl chloride In tetrahydrofuran; diethyl ether for 2h;	96%

Upstream product

• 1642-81-5 p-(chloromethyl)benzoic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 3006-96-0 3-hydroxymethyl-benzoic acid 
• 79-37-8 oxalyl dichloride 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 99-94-5 p-Toluic acid 
• 106-43-4 para-chlorotoluene 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 135654-21-6 4-carboxybenzylthioacetic acid 
• 64965-85-1 n-butyl (4-chloromethyl)benzoate 
• 58810-96-1 2-[4-(5,5-dimethyl-4,5-dihydro-oxazol-2-yl)-benzyl]-[1,3]dithiane-2-carboxylic acid ethyl ester 
• 34040-64-7 p-methyloxycarbonylbenzyl chloride 
• 99598-00-2 para-chloromethylbenzoyloxy-3α cholanate de methyle 
• 133446-60-3 diethyl N-[(4-chloromethyl)benzoyl]-L-glutamate 
• 74433-29-7 4-Chloromethyl-2',6'-dimethylbenzanilide 
• 1027841-55-9 3-(4-Chloromethyl-benzoyl)-4-methyl-indole-1-carboxylic acid dimethylamide 
• 170499-26-0 6-(4-fluorophenyl)-3-(4-chloromethylbenzoyl)indole-1-carboxylic acid dimethylamide 
• 150191-54-1 α-chloro-N-hydroxy-p-toluamide 
• 206554-92-9 tert-butylpiperazine-4-[[(4′-chloromethyl)benzoyl]-1′-carbonyl]-1-carboxylate 
• 222833-19-4 1-amino-2-<4-(chloromethyl)benzoylamino>anthraquinone 

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