134-83-8

Basic information

• Product Name: 4-Chlorobenzhydrylchloride
• Synonyms: P-CHLOROBENZHYDRYL CHLORIDE;1-chloro-4-(chlorophenylmethyl)-benzen;Benzene,1-chloro-4-(chlorophenylmethyl)-;Benzene,1-chloro-4-(chlorophenylmethyl)-4-Chlorobenzhydrylchloride;Chloro[4-chlorophenyl]phenylmethone;Methane, chloro(p-chlorophenyl)phenyl-;4-CHLOROBENZHYDRYL CHLORIDE;4-CHLORO DIPHENYL METHANE CHLORIDE
• CAS NO: 134-83-8
• Molecular Formula: C₁₃H₁₀Cl₂
• Molecular Weight: 237.12
• EINECS: 205-158-6
• Mol File: 134-83-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 159-160 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colorless or Off-yellow liquid
• Density: 1.239 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.67E-05mmHg at 25°C
• Refractive Index: n20/D 1.603(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: IMMISCIBLE
• Sensitive: Moisture Sensitive
• BRN: 2050236
• CAS DataBase Reference: 4-Chlorobenzhydrylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorobenzhydrylchloride(134-83-8)
• EPA Substance Registry System: 4-Chlorobenzhydrylchloride(134-83-8)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37-36
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 134-83-8(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

Preparation

Preparation of 4-Chlorobenzhydryl Chloride (4-CBC): The 4-chlorobenzhydrol (4-CB) in 15 mL of toluene, obtained from the previous step, was mixed with 10 mL of conc. HCl at 60oC maintained at the same temperature for 2.5 h. The reaction mixture was cooled to 20oC to separate into organic and aqueous layers. The toluene layer was washed with 10 % aq. sodium carbonate to pH 7, dried over anhydrous sodium sulphate and taken to next step without isolation.

InChI:InChI=1/C13H10Cl2/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9,13H

Synthetic route

(4-chlorophenyl)phenylmethanol (119-56-2) → 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8)

Conditions	Yield
With hydrogenchloride In ethanol Heating;	95%
With hydrogenchloride; diethyl ether
With hydrogenchloride; benzene

4-chlorobenzophenone (134-85-0) → 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / sodium borohydride 2: 95 percent / hydrochloric acid / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / tetrahydrofuran 2: HCl, CaCl2 / benzene View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / propan-2-ol 2: HCl, Drierite / CH2Cl2 View Scheme

4-chlorophenyl(phenyl)methane (831-81-2) → 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8)

Conditions	Yield
With N-chloro-succinimide; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane at 20℃; for 1h; Sealed tube; Inert atmosphere; Irradiation;

4-chlorobenzaldehyde (104-88-1) → 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h / 20 °C 2: SOCl2 / CH2Cl2 / 1 h / 0 °C View Scheme

phenylmagnesium bromide + isopropyl magnesium halide → 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h / 20 °C 2: SOCl2 / CH2Cl2 / 1 h / 0 °C View Scheme

hydrogenchloride (7647-01-0) + (4-chlorophenyl)phenylmethanol (119-56-2) + benzene (71-43-2) → 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + water (7732-18-5)

Conditions	Yield
at 60℃; Equilibrium constant;

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → 4-chlorobenzophenone (134-85-0)

Conditions	Yield
With N-Bromosuccinimide; water In chloroform for 3h; Time; Reflux;	97%

4-ethoxycarbonylpiperazine (120-43-4) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → ethyl {4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}carboxylate (80476-89-7)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 24h;	96%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + (R)-5-Oxo-1-trimethylsilanyl-pyrrolidine-2-carboxylic acid methyl ester → chloro-trimethyl-silane (75-77-4) + (R)-1-[(4-Chloro-phenyl)-phenyl-methyl]-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Conditions	Yield
With trifluorormethanesulfonic acid at 130℃; for 1.5h;	A n/a B 91%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + triphenylphosphine (603-35-0) → <(4-chlorophenyl)phenylmethyl>triphenylphosphonium chloride (25361-60-8)

Conditions	Yield
at 160℃; for 6h;	88%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → bis[p-chlorophenyl(phenyl)methyl] diselenide (795281-42-4)

Conditions	Yield
With sodium hydroxide; selenium; hydrazine hydrate In N,N-dimethyl-formamide at 20℃; for 6h;	86%

carbon monoxide (201230-82-2) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → α-(4-chlorophenyl)phenylacetic acid (21771-88-0)

Conditions	Yield
With sodium hydroxide; sodium tetracarbonyl cobaltate In ethanol at 16℃;	62.8%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + RTI 100 (150583-22-5) → 2β-[(4-chlorophenyl)phenylmethoxymethyl]-3β-(4-fluorophenyl)tropane

Conditions	Yield
at 180℃; for 1h;	60%

piperazine (110-85-0) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → N-(4-chlorobenzhydryl)piperazine (303-26-4)

Conditions	Yield
With K2CO3; Ki In dichloromethane; butanone	57%
With Ki; potassium carbonate In dichloromethane; butanone	57%
With Ki; potassium carbonate In dichloromethane; butanone	57%

benzoimidazole (51-17-2) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → 1-((4-chlorophenyl)(phenyl)methyl)-1H-benzo[d]imidazole (1326231-74-6)

Conditions	Yield
With tetraethylammonium iodide; potassium carbonate; sodium hydroxide In acetonitrile for 36h; Reflux;	56.6%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + 3β-(4-methylphenyl)-2β-hydroxymethyltropane (307519-45-5) → 2β-[(4-chlorophenyl)phenylmethoxymethyl]-3β-tolyltropane

Conditions	Yield
at 180℃; for 1h;	50%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + 2α-hydroxymethyl-3β-(4-chlorophenyl)tropane (173830-08-5) → 2α-[(4-chlorophenyl)phenylmethoxymethyl]-3β-(4-chlorophenyl)tropane

Conditions	Yield
at 180℃; for 1h;	48%

1,2,3-Benzotriazole (95-14-7) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → 1-[(4-chlorophenyl)(phenyl)methyl]-1H-1,2,3-benzotriazole (182057-17-6)

Conditions	Yield
With tetraethylammonium iodide; potassium carbonate; sodium hydroxide In acetonitrile for 48h; Reflux;	48%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + 2α-hydroxymethyl-3β-p-tolyltropane (409360-24-3) → 2α-[(4-chlorophenyl)phenylmethoxymethyl]-3β-tolyltropane

Conditions	Yield
at 180℃; for 1h;	45%

(+/-)-6β-methoxymethoxy-8-methyl-8-azabicyclo[3.2.1]octan-3α-ol + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → (+/-)-3α-[(4-chlorophenyl)phenylmethoxy]-6β-methoxymethoxy-8-methyl-8-azabicyclo[3.2.1]octan-3α-ol

Conditions	Yield
With tributyl-amine In N,N-dimethyl-formamide at 160℃; for 8h;	44%

1,4-Diazacycloheptane (505-66-8) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → 1-<(4-chlorophenyl)phenylmethyl>homopiperazine (24342-60-7)

Conditions	Yield
In chloroform for 72h; Reflux;	43%

diphenyl diselenide (1666-13-3) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → ((4-chlorophenyl)(phenyl)methyl) phenyl selenide

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol at 20℃; for 36h; Inert atmosphere;	42%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + 1,4-bis(diphenylphosphino)-2,5-dibromo-3,6-difluorobenzene (793684-90-9) → 1,2,4,5-Tetrakis-diphenylphosphanyl-3,6-difluoro-benzene

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 2h;	40%

piperazine-2,2,3,3,5,5,6,6-d8 (134628-42-5) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → 1-[(4-chlorophenyl)phenylmethyl]piperazine-2,2,3,3,5,5,6,6-d8

Conditions	Yield
With potassium carbonate In acetonitrile at 85℃; Sealed tube;	32.1%

1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) + pseudotropine (135-97-7) → 3β-<(4'-chlorophenyl)phenylmethoxy>tropane hydrochloride

Conditions	Yield
at 160℃;	31%

1H-imidazole (288-32-4) + 1-chloro-4-(chloro(phenyl)methyl)benzene (134-83-8) → 1-[(4-chlorophenyl)(phenyl)methyl]-1H-imidazole (102993-83-9)

Conditions	Yield
In acetonitrile for 2h; Heating;	13%
In 1,4-dioxane Reflux;
With tetraethylammonium iodide; potassium carbonate; sodium hydroxide In acetonitrile for 24h; Reflux;

Upstream product

• 7647-01-0 hydrogenchloride 
• 119-56-2 (4-chlorophenyl)phenylmethanol 
• 71-43-2 benzene 
• 831-81-2 4-chlorophenyl(phenyl)methane 
• 104-88-1 4-chlorobenzaldehyde 
• 134-85-0 4-chlorobenzophenone 

Downstream Products

• 101573-69-7 4-((4-chlorophenyl)(phenyl)methyl)morpholine 
• 346451-15-8 1,4-bis-(4-chloro-benzhydryl)-piperazine 
• 82-93-9 chlorcyclizine 
• 102009-34-7 1-ethyl-4-(4-chloro-benzhydryl)-piperazine 
• 848-53-3 Homochlorcyclizine 
• 110145-65-8 4-(4-chloro-benzhydryloxy)-1-methyl-piperidine 
• 10527-65-8 1-butyl-4-(4-chloro-benzhydryl)-piperazine 
• 109806-71-5 2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethan-1-ol 
• 113010-81-4 4-[4-(4-chloro-benzhydryl)-piperazino]-butan-1-ol 
• 95698-58-1 2-{4-[2-(4-chloro-benzhydryloxy)-ethyl]-piperazin-1-yl}-ethanol 
• 97572-82-2 1,4-bis-[2-(4-chloro-benzhydryloxy)-ethyl]-piperazine 
• 303-26-4 N-(4-chlorobenzhydryl)piperazine 
• 54784-27-9 (4-chloro-benzhydryl)-(2-hydroxy-ethyl)-dimethyl-ammonium; chloride 
• 102475-88-7 4-[2-(4-chloro-benzhydryloxy)-ethyl]-piperazine-1-carboxylic acid ethyl ester 

Relevant articles and documents

Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide

By combining "N-chlorosuccinimide (NCS)"as the safe chlorine source with "Acr+-Mes"as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor "N-centered succinimidyl radical,"which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr?-Mes.

Synthesis and cytotoxicity studies of novel benzhydrylpiperazine carboxamide and thioamide derivatives

Synthesis and cytotoxic activities of 32 benzhydrylpiperazine derivatives with carboxamide and thioamide moieties were reported. In vitro cytotoxic activities of compounds were screened against hepatocellular (HUH-7), breast (MCF-7) and colorectal (HCT-116) cancer cell lines by sulphorhodamine B assay. In general, 4-chlorobenzhydrylpiperazine derivatives were more cytotoxic than other compounds. In addition, thioamide derivatives (6a-g) have higher growth inhibition than their carboxamide analogs.

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