(-)-4-Chlorobenzhydrylamine supplier

Name
(-)-ALPHA-(4-CHLOROPHENYL)BENZYLAMINE (+)-TARTRATE SALT
EINECS
CAS No. 163837-57-8
Article Data19
CAS DataBase
Density 1.175g/cm³
Solubility
Melting Point
Formula C₁₃H₁₂ClN
Boiling Point 336.8 °C at 760 mmHg
Molecular Weight 217.698
Flash Point 194.3 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (-)-4-Chlorobenzhydrylamine;(-)-[(4-Chlorophenyl)phenylmethyl]amine;(R)-a-(4-Chlorophenyl)benzylamine;
PSA 141.08000
LogP 1.96580

Synthetic route

: (-)-(R)-Phenyl N-(4-chlorobenzhydryl)carbamate

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With lithium hydroxide; water In acetonitrile at 50℃; for 3h; Hydrolysis;	100%

: 898231-59-9
(R)-N-((4-chlorophenyl)(phenyl)methyl)-N’,N’-dimethylsulfamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With Trimethylenediamine for 0.5h; Microwave irradiation; enantioselective reaction;	99%
With Trimethylenediamine for 2h; microwave irradiation;	96%

: 1000693-79-7
(R)-N-tert-butyloxycarbonyl-α-(4-chlorophenyl)benzylamine

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	95%
With hydrogenchloride In dichloromethane; ethyl acetate at 0℃; Schlenk technique;	88%

: 1174154-53-0
(R)-N-((4-chlorophenyl)(phenyl)methyl)benzamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Stage #1: (R)-N-((4-chlorophenyl)(phenyl)methyl)benzamide With triphenyl phosphite; chlorine; triethylamine In chloroform at -30℃; for 3h; Inert atmosphere; Stage #2: With propan-1-ol In chloroform at -30 - 20℃; for 3h; Inert atmosphere; Stage #3: With water In methanol at 20℃; for 12h; optical yield given as %ee;	80%

: 28022-43-7
p-chlorobenzhydrylamine

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With L-Tartaric acid at 30 - 90℃; Inert atmosphere;	70%
With sodium tetrahydroborate; porcine kidney D-amino acid oxidase variant I230A/R283G In aq. buffer at 30℃; for 1h; pH=9; Enzymatic reaction; stereoselective reaction;	46.2%

: 960-71-4
triphenylborane

: (1S,3S,4R)-2-(4-chlorophenylmethyl)-3-[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-2-thioniabicyclo[2.2.1]heptane tetrafluoroborate

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Stage #1: triphenylborane; (1S,3S,4R)-2-(4-chlorophenylmethyl)-3-[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-2-thioniabicyclo[2.2.1]heptane tetrafluoroborate With lithium hexamethyldisilazane In tetrahydrofuran; 1,4-dioxane at 5℃; for 5h; Stage #2: With hydroxylamine-O-sulfonic acid	68%

: 28022-43-7
p-chlorobenzhydrylamine

A: 119-56-2
(4-chlorophenyl)phenylmethanol

B: 134-85-0
4-chlorobenzophenone

C: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With hydrogenchloride; borane-ammonia complex In aq. phosphate buffer at 37℃; pH=7.8;	A n/a B n/a C 45%

...Expand

: phenylmagnesium bromide

: 336105-23-8
(R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide; (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide In diethyl ether at -20℃; Stage #2: With hydrogenchloride In methanol at 22℃;
Stage #1: phenylmagnesium bromide; (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide In toluene Stage #2: With hydrogenchloride In methanol

...Expand

: 474654-18-7
(R)-(+)-N-[(4-chlorophenyl)(phenyl)methyl]formamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 50℃; for 4h;

: phenylmagnesium bromide

: 2-Methyl-butane-2-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide; 2-Methyl-butane-2-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide In toluene Stage #2: With hydrogenchloride In methanol

...Expand

: phenylmagnesium bromide

: 3-Ethyl-pentane-3-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide; 3-Ethyl-pentane-3-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide In toluene Stage #2: With hydrogenchloride In methanol

...Expand

: phenylmagnesium bromide

: Adamantane-1-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide; Adamantane-1-sulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide In toluene Stage #2: With hydrogenchloride In methanol

...Expand

: phenylmagnesium bromide

: 2,4,6-Triisopropyl-benzenesulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide; 2,4,6-Triisopropyl-benzenesulfinic acid 1-(4-chloro-phenyl)-meth-(E)-ylideneamide In toluene at -20 - 0℃; Stage #2: With hydrogenchloride In methanol	A n/a B 80 % Chromat.

...Expand

: 16635-23-7
phenyltriisopropoxytitanium(IV)

: N-(4-chlorophenyl)methylidene-2,4,6-triisopropylbenzenesulfonamide

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
Stage #1: phenyltriisopropoxytitanium(IV); N-(4-chlorophenyl)methylidene-2,4,6-triisopropylbenzenesulfonamide With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); bis(ethylene)rhodium(I) chloride dimer In tetrahydrofuran at 20℃; for 1h; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 1h; Heating; Title compound not separated from byproducts;

Yield

Stage #1: phenyltriisopropoxytitanium(IV); N-(4-chlorophenyl)methylidene-2,4,6-triisopropylbenzenesulfonamide With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); bis(ethylene)rhodium(I) chloride dimer In tetrahydrofuran at 20℃; for 1h;
Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 1h; Heating; Title compound not separated from byproducts;

...Expand

: 940939-32-2
(E)-N-(4-chlorobenzylidene)-N’,N’-dimethylsulfamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (R)-1,1'-binaphthyl-2,2'-diyl 4-methoxyphenylamidophosphite / Rh(acac)(C2H4)2 / acetone / 4 h / 40 °C 2: 96 percent / 1,3-diaminopropane / 2 h / microwave irradiation View Scheme

: 104-88-1
4-chlorobenzaldehyde

substututed benzylbromide phosphonium salt: substututed benzylbromide phosphonium salt

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / toluene / 16 h / Heating 2: (R)-1,1'-binaphthyl-2,2'-diyl 4-methoxyphenylamidophosphite / Rh(acac)(C2H4)2 / acetone / 4 h / 40 °C 3: 96 percent / 1,3-diaminopropane / 2 h / microwave irradiation View Scheme

: 98-80-6
phenylboronic acid

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (R)-1,1'-binaphthyl-2,2'-diyl 4-methoxyphenylamidophosphite / Rh(acac)(C2H4)2 / acetone / 4 h / 40 °C 2: 96 percent / 1,3-diaminopropane / 2 h / microwave irradiation View Scheme

: 622-95-7
4-chlorobenzyl bromide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: AgBF4 / CH2Cl2 / 48 h / 20 °C 2.1: LiHMDS / tetrahydrofuran; dioxane / 5 h / 5 °C 2.2: 68 percent / H2NOSO3H View Scheme

: 104-88-1
4-chlorobenzaldehyde

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 95 percent / Ti(OEt)4 / tetrahydrofuran / 20 °C 2.1: toluene 2.2: HCl / methanol View Scheme
Multi-step reaction with 2 steps 1.1: 95 percent / Ti(OEt)4 / tetrahydrofuran / 20 °C 2.1: toluene 2.2: HCl / methanol View Scheme
Multi-step reaction with 2 steps 1.1: 95 percent / Ti(OEt)4 / tetrahydrofuran / 20 °C 2.1: toluene 2.2: HCl / methanol View Scheme
Multi-step reaction with 2 steps 1.1: 95 percent / Ti(OEt)4 / tetrahydrofuran / 20 °C 2.1: toluene 2.2: HCl / methanol View Scheme
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux 2: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique 3: pyridine; water / 16 h / Reflux View Scheme

: 1078-58-6
diphenylzinc

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (Rp,S)-C31H29NO; Et2Zn / toluene / 12 h / -20 °C 2: HCl / methanol / 4 h / 50 °C View Scheme

: N-{(4-chlorophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (Rp,S)-C31H29NO; Et2Zn / toluene / 12 h / -20 °C 2: HCl / methanol / 4 h / 50 °C View Scheme

: 104-88-1
4-chlorobenzaldehyde

resin-bound p-methylphenylboronic acid: resin-bound p-methylphenylboronic acid

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 90 percent / Ti(OEt)4 / tetrahydrofuran / 22 °C 2.1: diethyl ether / -20 °C 2.2: HCl / methanol / 22 °C View Scheme

: 1309582-68-0
N,N'-sulfonyl bis-[(4-chlorophenyl)(phenyl)methanamine]

A: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

B: 163837-32-9
(S)-4-chloro-α-phenyl-benzenemethanamine

Conditions

Conditions	Yield
With pyridine; water Reflux; optical yield given as %ee;

: C14H11ClF3NO3S

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
With formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 50℃; for 2h;	145 mg

: 1334334-91-6
2-((4-chlorophenyl)(imino)methyl)phenol

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate / benzene / 72 h / 50 °C / Inert atmosphere; Sealed tube 2: triethylamine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 3: formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C View Scheme

Yield

Multi-step reaction with 3 steps
1: (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate / benzene / 72 h / 50 °C / Inert atmosphere; Sealed tube
2: triethylamine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere
3: formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C
View Scheme

: 1334247-23-2
(S)-2-(amino(4-chlorophenyl)methyl)phenol

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 2: formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1.1: dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 1.2: 12 h / 0 - 20 °C / Inert atmosphere 2.1: palladium diacetate; triethylamine; formic acid; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 20 h / 50 °C / Inert atmosphere; Sealed tube 3.1: hydrogenchloride / dichloromethane; methanol / 4 h / 0 - 20 °C / Inert atmosphere View Scheme

: 2985-79-7
4'-chloro-2-hydroxybenzophenone

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonia / methanol / 16 h / 20 °C / Cooling with ice 2: (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate / benzene / 72 h / 50 °C / Inert atmosphere; Sealed tube 3: triethylamine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 4: formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: ammonium acetate; hydrogen; titanium(IV) isopropylate; Ru[(S)-SegPhos](OAc)2 / methanol / 24 h / 80 °C / 38002.6 Torr / Autoclave 2.1: dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 2.2: 12 h / 0 - 20 °C / Inert atmosphere 3.1: palladium diacetate; triethylamine; formic acid; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 20 h / 50 °C / Inert atmosphere; Sealed tube 4.1: hydrogenchloride / dichloromethane; methanol / 4 h / 0 - 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1: ammonia / methanol / 16 h / 20 °C / Cooling with ice
2: (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate / benzene / 72 h / 50 °C / Inert atmosphere; Sealed tube
3: triethylamine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere
4: formic acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C
View Scheme

Multi-step reaction with 4 steps
1.1: ammonium acetate; hydrogen; titanium(IV) isopropylate; Ru[(S)-SegPhos](OAc)2 / methanol / 24 h / 80 °C / 38002.6 Torr / Autoclave
2.1: dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere
2.2: 12 h / 0 - 20 °C / Inert atmosphere
3.1: palladium diacetate; triethylamine; formic acid; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 20 h / 50 °C / Inert atmosphere; Sealed tube
4.1: hydrogenchloride / dichloromethane; methanol / 4 h / 0 - 20 °C / Inert atmosphere
View Scheme

: 1438244-01-9
N-methyl-N'-[4-chlorophenylmethylidene]sulfamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: water; potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; phenylboronic acid; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene / dichloromethane / 16 h / 35 °C / Inert atmosphere; Schlenk technique 2: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux 3: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique 4: pyridine; water / 16 h / Reflux View Scheme

Yield

Multi-step reaction with 4 steps
1: water; potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; phenylboronic acid; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene / dichloromethane / 16 h / 35 °C / Inert atmosphere; Schlenk technique
2: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux
3: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique
4: pyridine; water / 16 h / Reflux
View Scheme

: 100-52-7
benzaldehyde

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux 2: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique 3: pyridine; water / 16 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux 2: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique 3: pyridine; water / 16 h / Reflux View Scheme
Multi-step reaction with 5 steps 1: formic acid / methanol; water / 24 h / 20 °C 2: potassium carbonate; sodium sulfate / tetrahydrofuran / 18 h / Inert atmosphere; Reflux 3: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; sodium t-butanolate; copper(l) chloride; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diisopropylphosphine / toluene / 12 h / 20 °C 4: potassium carbonate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; XPhos; water / toluene / 14 h / 80 °C / Schlenk technique 5: hydrogenchloride / dichloromethane; ethyl acetate / 0 °C / Schlenk technique View Scheme

: 1438244-02-0
N-methyl-N'-[phenylmethylidene]sulfamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: water; potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / dichloromethane / 16 h / 35 °C / Inert atmosphere; Schlenk technique 2: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux 3: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique 4: pyridine; water / 16 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: water; potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / dichloromethane / 16 h / 35 °C / Inert atmosphere; Schlenk technique 2: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux 3: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique 4: pyridine; water / 16 h / Reflux View Scheme

Yield

Multi-step reaction with 4 steps
1: water; potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / dichloromethane / 16 h / 35 °C / Inert atmosphere; Schlenk technique
2: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux
3: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique
4: pyridine; water / 16 h / Reflux
View Scheme

Multi-step reaction with 4 steps
1: water; potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / dichloromethane / 16 h / 35 °C / Inert atmosphere; Schlenk technique
2: titanium(IV) tetraethanolate / tetrahydrofuran / 7 h / Reflux
3: potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate / toluene; water / 16 h / 35 °C / Inert atmosphere; Schlenk technique
4: pyridine; water / 16 h / Reflux
View Scheme

: 108-24-7
acetic anhydride

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: N-[(R)-(4-chlorophenyl)(phenyl)methyl]acetamide

Conditions

Conditions	Yield
With triethylamine In toluene at 20℃;	96%
In diethyl ether Inert atmosphere;
In water at 20℃; for 7h;

: 86357-59-7
4-methoxy-benzenesulfonic acid-[bis-(2-chloro-ethyl)-amide]

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: 943987-59-5
(-)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methoxyphenyl)sulfonyl]piperazine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 125 - 130℃; for 10h; Heating / reflux; Industry scale;	90.83%
With tributyl-amine for 4h; Reflux;

: 42137-88-2
N,N-bis(2-chloroethyl)-p-toluenesulfonamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: 942283-97-8
(-)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 127℃; for 4h; Heating / reflux;	87.2%

: 24424-99-5
di-tert-butyl dicarbonate

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: 1000693-79-7
(R)-N-tert-butyloxycarbonyl-α-(4-chlorophenyl)benzylamine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; enantioselective reaction;	86%

: 1150310-73-8
N-benzyl-2-(2-(bis(2-chloroethyl)amino)ethoxy)acetamide

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: 1150310-68-1
levocetirizine N-benzyl amide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 130℃; for 4h; Inert atmosphere;	75%
With N-ethyl-N,N-diisopropylamine at 120 - 125℃; for 6h;	n/a

: 7252-83-7
1-bromo-2,2-dimethoxyethane

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: 292066-74-1
(R)-(+)-α-(4-chlorophenyl)-N-(2,2-dimethoxyethyl)benzylamine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Alkylation;	70%

: 555-77-1
tris-(2-chloro-ethyl)-amine

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

: C19H22Cl2N2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 120℃; for 3h;	70%

: 10429-82-0
N-benzyl-2-chloro-N-(2-chloroethyl)ethanamine hydrochloride

: 163837-57-8
(R)-(4-chlorophenyl)(phenyl)methylamine

A: 80476-91-1
1-benzyl-4-(4-chloro-benzhydryl)-piperazine

B: 7647-14-5
sodium chloride

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In butan-1-ol at 0 - 110℃; for 4h;

...Expand

(-)-4-Chlorobenzhydrylamine Specification

The (-)-4-Chlorobenzhydrylamine, with CAS registry number 163837-57-8, has the systematic name of 1-(4-chlorophenyl)-1-phenylmethanamine. Besides this, it is also called benzenemethanamine, 4-chloro-α-phenyl. And the chemical formula od this chemical is C₁₃H₁₂ClN.

Physical properties of (-)-4-Chlorobenzhydrylamine: (1)ACD/LogP: 3.39; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 1; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 3.24 Å²; (7)Index of Refraction: 1.607; (8)Molar Refractivity: 64 cm³; (9)Molar Volume: 185.2 cm³; (10)Polarizability: 25.37×10^-24cm³; (11)Surface Tension: 45.8 dyne/cm; (12)Enthalpy of Vaporization: 58 kJ/mol; (13)Vapour Pressure: 0.000109 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc(cc1)C(N)c2ccccc2
(2)InChI: InChI=1/C13H12ClN/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9,13H,15H2
(3)InChIKey: XAFODXGEQUOEKN-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C13H12ClN/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9,13H,15H2
(5)Std. InChIKey: XAFODXGEQUOEKN-UHFFFAOYSA-N

Product Name

(-)-ALPHA-(4-CHLOROPHENYL)BENZYLAMINE (+)-TARTRATE SALT

Synthetic route

(-)-4-Chlorobenzhydrylamine Specification

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