59767-24-7

Basic information

• Product Name: 1 -(4-CHLOROPHENYL)-1 -PHENYLETHANOL
• Synonyms: 1 -(4-CHLOROPHENYL)-1 -PHENYLETHANOL;1-(p-Chlorophenyl)-1-phenylethanol;4-Chloro-α-methyl-α-phenylbenzenemethanol;α-Methyl-α-phenyl-4-chlorobenzenemethanol;CleMastine FuMarate IMpurity C
• CAS NO: 59767-24-7
• Molecular Formula: C₁₄H₁₃ClO
• Molecular Weight: 232.70542
• Mol File: 59767-24-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 358℃
• Flash Point: 170℃
• Appearance: /
• Density: 1.189
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.41±0.29(Predicted)
• CAS DataBase Reference: 1 -(4-CHLOROPHENYL)-1 -PHENYLETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1 -(4-CHLOROPHENYL)-1 -PHENYLETHANOL(59767-24-7)
• EPA Substance Registry System: 1 -(4-CHLOROPHENYL)-1 -PHENYLETHANOL(59767-24-7)

Safety Data

• Hazardous Substances Data: 59767-24-7(Hazardous Substances Data)

Usage

Uses

1-(4-Chlorophenyl)-1-phenylethanol (Clemastine EP Impurity C) is used in the synthetic preparation of rhodium-catalyzed arylation of nitriles, ketones and imines with tetrafluoroborate or arylboronic acids

Synthetic route

sodium tetraphenyl borate (143-66-8) + para-chloroacetophenone (99-91-2) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
With chloro(η4-1,5-cyclooctadiene){1,3-bis(4-methylbenzyl)perhydrobenzimidazolin-2-ylidene}rhodium(I); ammonium chloride In o-xylene at 120℃; for 25h; Reagent/catalyst; Schlenk technique;	98%
With ammonium chloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer In o-xylene at 120℃; for 25h;

para-chloroacetophenone (99-91-2) + phenyltriisopropoxytitanium(IV) (16635-23-7) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
In diethyl ether for 5h; -20 deg C to r.t.;	95%

(4-chlorphenyl)magnesium bromide (873-77-8) + acetophenone (98-86-2) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.55h; Grignard reaction; Inert atmosphere;	95%

para-chloroacetophenone (99-91-2) + phenylmagnesium bromide (100-58-3) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
Stage #1: phenylmagnesium bromide With Et2AlBr In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol In toluene at 0℃; for 0.5h; Inert atmosphere; Stage #3: para-chloroacetophenone Further stages;	90%
In tetrahydrofuran; diethyl ether at 20℃; Grignard Reaction; Inert atmosphere;	51%
With ammonium chloride In tetrahydrofuran
In tetrahydrofuran at 0℃; Grignard Reaction; Inert atmosphere;

methyl carbamic acid 1-(4-chlorophenyl)-1-phenylethyl ester (1118917-34-2) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
With sodium ethanolate In ethanol at 78℃;	77%

methyltriisopropoxytitanium(IV) (18006-13-8) + 4-chlorobenzophenone (134-85-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
In diethyl ether for 20h; -20 deg C to r.t.;	50%

bromobenzene (108-86-1) + para-chloroacetophenone (99-91-2) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
Stage #1: bromobenzene With magnesium; iodine In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: para-chloroacetophenone In tetrahydrofuran at 0 - 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran at 0℃;	25%

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) + phenylmagnesium chloride → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) + phenylmagnesium bromide → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

methylmagnesium chloride (676-58-4) + 4-chlorobenzophenone (134-85-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
With diethyl ether

methanol (67-56-1) + Clemastine (7723-51-5, 15686-51-8, 61826-27-5, 61826-28-6, 61826-31-1, 63813-90-1, 63813-91-2) → 2-(1-methyl-2-pyrrolidine)ethanol (67004-64-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 1-Chloro-4-(1-methoxy-1-phenyl-ethyl)-benzene

Conditions	Yield
Ambient temperature; 6 weeks;

propan-1-ol (71-23-8) + Clemastine (7723-51-5, 15686-51-8, 61826-27-5, 61826-28-6, 61826-31-1, 63813-90-1, 63813-91-2) → 2-(1-methyl-2-pyrrolidine)ethanol (67004-64-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 1-Phenyl-1-(4-chlorphenyl)-ethylenglycol (28523-14-0) + 1-methyl-2-vinylpyrrolidine (85151-07-1) + 4-chlorobenzophenone (134-85-0) + 1-Phenyl-1-(4-chlorphenyl)-1-n-propoxyethan (117932-40-8)

Conditions	Yield
With sodium hydroxide for 53h; Heating; further time and temp.; also without n-propanol, with H2O or HCl addition;

ethanol (64-17-5) + Clemastine (7723-51-5, 15686-51-8, 61826-27-5, 61826-28-6, 61826-31-1, 63813-90-1, 63813-91-2) → 2-(1-methyl-2-pyrrolidine)ethanol (67004-64-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 1-Chloro-4-(1-ethoxy-1-phenyl-ethyl)-benzene (87273-95-8)

Conditions	Yield
Ambient temperature; 6 weeks;

methyllithium (917-54-4) → 1,1-diphenylethanol (599-67-7) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
In diethyl ether at 0℃; competition reaction with bezophenone and 4-chlorobenzophenone, relative velocity constant;

methyllithium (917-54-4) + C6H5BrMn (109603-92-1) + 4-chloro-benzoyl chloride (122-01-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
1.) 0 to 20 deg C, 1.5 h; 2.) 0 to 20 deg C, 2.5 h; Yield given. Multistep reaction;

methylmagnesium bromide (75-16-1) + 4-chlorobenzophenone (134-85-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
0 deg C then 20 deg C, 4h; Yield given;

(+)-2-<2-<1-(4-Chlorphenyl)-1-phenylethoxy>ethyl>-1-methylpyrroliden-hydrogenfumarat (14976-57-9, 20271-71-0, 61826-29-7, 61826-30-0, 61826-32-2, 61826-33-3, 61826-34-4, 61826-35-5, 61826-36-6, 63537-12-2, 66727-90-0) → 2-(1-methyl-2-pyrrolidine)ethanol (67004-64-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 1-Phenyl-1-(4-chlorphenyl)-ethylenglycol (28523-14-0) + 4-chlorobenzophenone (134-85-0)

Conditions	Yield
With water Heating;

Clemastin-hydrogenfumarat (63537-12-2) → 2-(1-methyl-2-pyrrolidine)ethanol (67004-64-2) + 1-(4-chlorophenyl)-1-phenylethene (18218-20-7) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 1-(4-Chlorphenyl)-1-(4'-hydroxyphenyl)ethen (110203-93-5) + 1-(4-Chlorphenyl)-1-(4'-hydroxyphenyl)ethanol + 4-{1-(4-Chloro-phenyl)-1-[2-(1-methyl-pyrrolidin-2-yl)-ethoxy]-ethyl}-phenol

Conditions	Yield
With 1H-imidazole; water; dihydrogen peroxide; MnTPFPS4PCl In methanol; dichloromethane at 20℃; for 24h; Product distribution; also without water, var. catalyst;

Clemastin-hydrogenfumarat (63537-12-2) → 2-(1-methyl-2-pyrrolidine)ethanol (67004-64-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 2-{2-[1-(4-Chloro-phenyl)-1-phenyl-ethoxy]-ethyl}-pyrrolidine + Clemastin-N-oxid

Conditions	Yield
With 1H-imidazole; dihydrogen peroxide; manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride In methanol; dichloromethane at 20℃; for 24h; Further byproducts given;

Clemastin-hydrogenfumarat (63537-12-2) → 1-(4-chlorophenyl)-1-phenylethene (18218-20-7) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 2-{2-[1-(4-Chloro-phenyl)-1-phenyl-ethoxy]-ethyl}-pyrrolidine + Clemastin-N-oxid

Conditions	Yield
With 1H-imidazole; dihydrogen peroxide; manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride In methanol; dichloromethane at 20℃; for 24h; Further byproducts given;

methyllithium (917-54-4) + 4-chlorobenzophenone (134-85-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
In diethyl ether at 0℃;

4-chloro-benzoyl chloride (122-01-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) anhydr. manganese bromide / 1.) 0 deg C then 20 deg C, 45 min; 2.) 0 deg C then 20 deg C, 1.5 h 2: 0 deg C then 20 deg C, 4h View Scheme

phenyllithium (591-51-5) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) anhydr. manganese bromide / 1.) 0 deg C then 20 deg C, 45 min; 2.) 0 deg C then 20 deg C, 1.5 h 2: 0 deg C then 20 deg C, 4h View Scheme

bromochlorobenzene (106-39-8) + acetophenone (98-86-2) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
Stage #1: bromochlorobenzene With magnesium In tetrahydrofuran Stage #2: acetophenone In tetrahydrofuran at 0℃; for 2h;

methyl magnesium iodide (917-64-6) + 4-chlorobenzophenone (134-85-0) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0 - 20℃; Schlenk technique; Inert atmosphere;

1-(4-chlorophenyl)-1-phenylethene (18218-20-7) → 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7)

Conditions	Yield
With oxygen; potassium carbonate; isopropyl alcohol at 150℃; under 3000.3 Torr; for 12h; regioselective reaction;	> 99 %Chromat.

1-(2-Chloroethyl)-4-ethoxycarbonylpiperazine (64822-11-3) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) → 4-{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-(ethoxycarbonyl)piperazine (101620-46-6)

Conditions	Yield
	89%
	89%

2-(2-chloro-ethyl)-1-methyl-pyrrolidine (54777-54-7, 61771-17-3, 63527-58-2, 67529-19-5) + succinic acid (110-15-6) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) → clemastine succinate

Conditions	Yield
Stage #1: 2-(2-chloro-ethyl)-1-methyl-pyrrolidine; 1-(4-chloro-phenyl)-1-phenyl-ethanol With sodium amide In toluene at 80℃; Large scale; Stage #2: succinic acid In ethyl acetate at 60 - 65℃; for 0.5h; Large scale;	55%

dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate (3709-20-4) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) → (Z)-dimethyl 2-(4-(4-chlorophenyl)-2,4-diphenylbut-3-en-1-yl)malonate

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 80℃; Sealed tube; diastereoselective reaction;	42%

(+)-(R)-2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (67499-71-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) → (R)-2-[2-[1-(4-Chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine (1174565-35-5)

Conditions	Yield
With sodium amide In toluene for 8h; Reflux;	36%

1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + (-)-(S)-2-(2-chloroethyl)-1-methylpyrrolidine → 4-[1-(4-Chloro-phenyl)-1-phenyl-ethoxy]-1-methyl-azepane (61771-18-4) + (S)-2-(2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl)-1-methylpyrrolidine (61826-31-1) + (S)-2-(2-[(1S)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl)-1-methylpyrrolidine

Conditions	Yield
Stage #1: 1-(4-chloro-phenyl)-1-phenyl-ethanol With sodium hydride In toluene; mineral oil for 3h; Reflux; Stage #2: (-)-(S)-2-(2-chloroethyl)-1-methylpyrrolidine In toluene; mineral oil at 20℃; Reflux; Inert atmosphere;	A 15% B n/a C n/a

2-(piperidin-4-yl)ethyl chloride (1932-03-2) + 1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) → 1-{2-[1-(4-chloro-phenyl)-1-phenyl-ethoxy]-ethyl}-piperidine (102071-02-3)

Conditions	Yield
With sodium amide; toluene
With sodium amide; toluene

1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + p-Tolylisocyanate (622-58-2) → p-Tolyl-carbamic acid 1-(4-chloro-phenyl)-1-phenyl-ethyl ester (90862-22-9)

Conditions	Yield
With stannous octoate In toluene at 60℃;

1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 2-(dimethylamino)ethyl chloride (107-99-3) → chlorphenoxamine (77-38-3)

Conditions	Yield
With sodium amide In toluene for 4h; Heating; Yield given;

1-(4-chloro-phenyl)-1-phenyl-ethanol (59767-24-7) + 4-nitro-benzoyl chloride (122-04-3) → 4-nitro-benzoic acid 1-(4-chloro-phenyl)-1-phenyl-ethyl ester (460742-55-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -30 - 20℃;

Upstream product

• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 676-58-4 methylmagnesium chloride 
• 134-85-0 4-chlorobenzophenone 
• 67-56-1 methanol 
• 7723-51-5 Clemastine 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 917-54-4 methyllithium 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 75-16-1 methylmagnesium bromide 
• 143-66-8 sodium tetraphenyl borate 
• 99-91-2 para-chloroacetophenone 
• 100-58-3 phenylmagnesium bromide 
• 1118917-34-2 methyl carbamic acid 1-(4-chlorophenyl)-1-phenylethyl ester 

Downstream Products

• 101620-46-6 4-{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-(ethoxycarbonyl)piperazine 
• 1174565-35-5 (R)-2-[2-[1-(4-Chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine 
• 61771-18-4 4-[1-(4-Chloro-phenyl)-1-phenyl-ethoxy]-1-methyl-azepane 
• 61826-31-1 (S)-2-(2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl)-1-methylpyrrolidine 
• 18218-20-7 1-(4-chlorophenyl)-1-phenylethene 
• 92252-92-1 N-phenyl-1-(p-chlorophenyl)ethylamine 
• 881846-79-3 4-chloro-N-(1-phenylethyl)benzenamine 
• 1158041-52-1 1-(4-chlorophenyl)-1-phenylethan-1-amine 
• 17508-50-8 N-(1-(4-chlorophenyl)ethylidene)aniline 
• 25287-19-8 N-(1-phenylethylidene)-4-chloroaniline 
• 101620-47-7 1-{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}piperazine 
• 150556-95-9 1-[2-(1,1-diphenylethoxy)ethyl]-piperazine 
• 460742-55-6 4-nitro-benzoic acid 1-(4-chloro-phenyl)-1-phenyl-ethyl ester 
• 77-38-3 chlorphenoxamine 

Relevant articles and documents

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