104-52-9

Basic information

• Product Name: 1-Chloro-3-phenylpropane
• Synonyms: 3-PHENYLPROPYL CHLORIDE;(3-CHLOROPROPYL)BENZENE;1-CHLORO-3-PHENYLPROPANE;3-Chloro-1-phenylpropane;3-Phenyl-1-chloropropane;gamma-Chloropropylbenzene;gamma-Phenylpropyl chloride;3-Penylpropylchloride
• CAS NO: 104-52-9
• Molecular Formula: C₉H₁₁Cl
• Molecular Weight: 154.64
• EINECS: 203-210-2
• Mol File: 104-52-9.mol
• Article Data: 48

Chemical Properties

• Melting Point: -27 °C
• Boiling Point: 219 °C(lit.)
• Flash Point: 189 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.17mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 507635
• CAS DataBase Reference: 1-Chloro-3-phenylpropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-3-phenylpropane(104-52-9)
• EPA Substance Registry System: 1-Chloro-3-phenylpropane(104-52-9)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 23-28-37
• WGK Germany: 2
• Hazardous Substances Data: 104-52-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C9H11Cl/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

Synthetic route

3-Phenyl-1-propanol (122-97-4) → phenylpropyl chloride (104-52-9)

Conditions	Yield
Stage #1: 3-Phenyl-1-propanol With diisopropyl-carbodiimide; copper(l) chloride In tetrahydrofuran at 100℃; for 0.0833333h; microwave irradiation; Stage #2: With acetyl chloride In tetrahydrofuran at 150℃; for 0.0833333h; microwave irradiation; Further stages.;	100%
With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide In dichloromethane at 25℃; for 0.25h;	99%
With thionyl chloride In N,N-dimethyl-formamide at 60℃; Solvent; Reflux; Industrial scale;	99.4%

3-phenylpropanol methanesulfonate (69804-99-5) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With 1-butyl-3-methylimidazolium chloride at 50℃; for 1h; Inert atmosphere; Green chemistry;	99%

3-Phenylpropane-1-thiol (24734-68-7) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With tetrachloromethane; cross-linked polymer (containing 2.50 mmol of phosphine/g) for 2h; Heating;	98%

3-phenylpropyl 2-(methoxyethoxyethylcarboxy)-1-benzosulfonate (866942-18-9) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With lithium chloride In acetone for 0.5h; Product distribution / selectivity; Heating / reflux;	98%

1-iodo-3-phenylpropan (4119-41-9) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With tetrabutyl-ammonium chloride at 20 - 60℃; for 5h;	98%
With 1,10-Phenanthroline; iron(II) chloride In acetonitrile at 60℃; for 0.5h;	83%
With tetrabutyl-ammonium chloride In acetone at 60℃; for 12h; Inert atmosphere;	24 mg

3-phenylpropyl 2-(heptylcarboxy)-1-benzosulfonate → phenylpropyl chloride (104-52-9)

Conditions	Yield
With lithium chloride In acetone for 6h; Product distribution / selectivity; Heating / reflux;	96%

3-chloro-1-phenyl-propan-1-ol (18776-12-0) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With indium(III) chloride; diphenylsilyl chloride In dichloromethane at 20℃; for 3h;	95%

trimethyl(3-phenylpropoxy)silane (14629-60-8) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; N-chloro-succinimide In dichloromethane for 2h; Heating;	95%

3-phenylpropyl 4-methylbenzenesulfonate (3742-75-4) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With 1-butyl-3-methylimidazolium chloride at 50℃; for 1h; Inert atmosphere; Green chemistry;	95%
With lithium chloride In acetone for 18h; Product distribution / selectivity; Heating / reflux;	93%

3-phenylpropyl 2-(methylcarboxy)-1-benzenesulfonate (866942-16-7) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With lithium chloride In acetone for 4h; Product distribution / selectivity; Heating / reflux;	94%

Chloroiodomethane (593-71-5) + phenylacetaldehyde (122-78-1) → phenylpropyl chloride (104-52-9)

Conditions	Yield
Stage #1: Chloroiodomethane; phenylacetaldehyde With methyllithium lithium bromide In tetrahydrofuran at -78℃; for 0.75h; Inert atmosphere; Stage #2: With hexylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;	90%

3-Phenyl-1-propanol (122-97-4) + Benzotrichlorid (98-07-7) → benzylidene dichloride (98-87-3) + phenylpropyl chloride (104-52-9)

Conditions	Yield
With TOP; phenylsilane In neat (no solvent) at 100℃; for 24h; Appel Halogenation; Inert atmosphere;	A n/a B 85%

3-chloropropiophenone (936-59-4) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With polymethylhydrosiloxane; tris(pentafluorophenyl)borate In dichloromethane at 20℃;	84%

diphenylmethanone O-(4-phenylbutanoyl) oxime (115975-11-6) → benzophenone (119-61-9) + hexachloroethane (67-72-1) + phenylpropyl chloride (104-52-9) + benzophenone azine (983-79-9)

Conditions	Yield
With tetrachloromethane Ambient temperature; Irradiation; Yields of byproduct given;	A n/a B n/a C 82% D n/a

bis(trichloromethyl) carbonate (32315-10-9) + 3-Phenyl-1-propanol (122-97-4) + triethylamine (121-44-8) → γ-Phenylpropyl-N,N-diethylcarbamat (92322-64-0) + phenylpropyl chloride (104-52-9)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	A n/a B 82%

3-Phenylpropionic acid (501-52-0) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With gallium(III) trichloride; Hexamethyldisiloxane; copper dichloride In 1,2-dichloro-ethane at 80℃; for 8h; Sealed tube; Inert atmosphere;	81%
Multi-step reaction with 2 steps 1: indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; iodine / chloroform / 1.08 h / 20 - 60 °C / Sealed tube; Inert atmosphere 2: tetrabutyl-ammonium chloride / 5 h / 20 - 60 °C View Scheme
Multi-step reaction with 4 steps 1: indium(III) bromide / chloroform / 1 h / 20 °C / Sealed tube; Inert atmosphere 2: indium(III) bromide; triethylsilane / chloroform / 1 h / 60 °C / Sealed tube; Inert atmosphere 3: indium(III) bromide; trimethylsilyl iodide / chloroform / 5 h / 60 °C / Sealed tube; Inert atmosphere 4: tetrabutyl-ammonium chloride / 5 h / 20 - 60 °C View Scheme

3-Phenyl-1-propanol (122-97-4) → 1-Bromo-3-phenylpropane (637-59-2) + phenylpropyl chloride (104-52-9)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide; sodium bromide In dichloromethane at 25℃; for 0.25h;	A 80% B n/a

2-(3-phenylpropoxy)tetrahydro-2H-pyran (112471-51-9) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; N-chloro-succinimide In dichloromethane for 4h; Heating;	80%

1,3-diisopropyl-2-(3-phenyl-propyl)-isourea → phenylpropyl chloride (104-52-9)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran at 160℃; for 0.0833333h; microwave irradiation;	77%

1-(3-phenylpropyl)-5-aza-1-stanna-bicyclo[3.3.3]undecane → phenylpropyl chloride (104-52-9)

Conditions	Yield
With trichloroisocyanuric acid In acetonitrile at 20℃; Inert atmosphere; Sealed tube;	65%

1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (59457-26-0) + 3-Phenyl-1-propanol (122-97-4) → 3-phenylpropyl-2-iodobenzoate + phenylpropyl chloride (104-52-9)

Conditions	Yield
With triphenylphosphine In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	A n/a B 58%

2-(1-chloro-3-phenyl-propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → phenylpropyl chloride (104-52-9)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4-tert-Butylcatechol; 2-methoxybenzo[d][1,3,2]dioxaborole; trans-di-O-tert-butyl hyponitrite In methanol; dichloromethane; benzene at 70℃; for 16h; Inert atmosphere;	56%

phenylmagnesium bromide + 1,3-chlorobromopropane (109-70-6) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; cobalt(II) chloride In tetrahydrofuran at -15℃; for 0.5h;	47%

1-Bromo-3-phenylpropane (637-59-2) → allylbenzene (300-57-2) + Propylbenzene (103-65-1) + INDANE (496-11-7) + 1,6-diphenylhexane (1087-49-6) + phenylpropyl chloride (104-52-9)

Conditions	Yield
With tetrachloromethane for 96h; Product distribution; Mechanism; Ambient temperature; Irradiation; further phenylalkyl halides;	A 26% B 21% C 8% D 6% E n/a

1-benzyloxy-3-phenylpropane (70770-06-8) → phenylpropyl chloride (104-52-9)

Conditions	Yield
With pyridine hydrochloride at 200℃; for 1h; Microwave irradiation; Ionic liquid;	24%

3-Phenyl-1-propanol (122-97-4) + 1,1'-carbonyldiimidazole (530-62-1) → bis(3-phenylpropyl) carbonate (102162-49-2) + phenylpropyl chloride (104-52-9) + 1-(3-phenylpropoxycarbonyl)-1H-imidazole (170895-01-9)

Conditions	Yield
Stage #1: 3-Phenyl-1-propanol; 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Molecular sieve; Stage #2: With dibenzo-18-crown-6; potassium chloride; toluene-4-sulfonic acid In acetonitrile for 24h; Reflux; Molecular sieve;	A n/a B 11% C n/a

3-chloropropyl p-toluenesulfonate (632-02-0) + diethyl ether (60-29-7) + phenylmagnesium bromide → phenylpropyl chloride (104-52-9)

3-chloropropyl p-toluenesulfonate (632-02-0) + phenylmagnesium bromide → phenylpropyl chloride (104-52-9)

Conditions	Yield
With diethyl ether

diethyl ether (60-29-7) + sulfuric acid bis-(2-chloroethyl) ester (5411-48-3) + benzylmagnesium chloride → phenylpropyl chloride (104-52-9)

phenylpropyl chloride (104-52-9) + acetyl chloride (75-36-5) → 1-[4-(3-chloropropyl)phenyl]ethanone (91427-06-4)

Conditions	Yield
Stage #1: acetyl chloride With aluminum (III) chloride In dichloromethane at -7 - 20℃; for 0.5h; Stage #2: phenylpropyl chloride In dichloromethane at 0℃; Stage #3: With hydrogenchloride In dichloromethane; water at 10℃; for 1.5h;	100%
aluminium chloride In dichloromethane	98%

potassium phtalimide (1074-82-4) + phenylpropyl chloride (104-52-9) → 2-(3-phenylpropyl)-1H-isoindole-1,3(2H)-dione (54981-86-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Temperature; Industrial scale;	99.9%
In N,N-dimethyl-formamide at 80℃; for 2h;

Bis(trimethylsilyl)methyl-methylether (120703-53-9) + phenylpropyl chloride (104-52-9) → (4-Methoxy-4,4-bis-trimethylsilanyl-butyl)-benzene (120703-47-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane	98%
With n-butyllithium 1) hexane, THF, 0 deg C, 20 min, 2a) -78 deg C, 5 min, 2b) 0 deg C, 1 h; Yield given. Multistep reaction;

phenylpropyl chloride (104-52-9) → 1-bromo-3-chloro-1-phenylpropane (21763-00-8)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane	98%
With N-Bromosuccinimide; dibenzoyl peroxide In chlorobenzene at 85℃; for 4h;	68%
With Oxone; potassium bromide In nitromethane at 50℃; for 24h;	47%

phenylpropyl chloride (104-52-9) → 3-chloropropiophenone (936-59-4)

Conditions	Yield
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation;	97%

phenylpropyl chloride (104-52-9) + S-pent-4-yn-1-yl ethanethioate (524689-75-6) → (pent-4-ynyl)(3-phenylpropyl)sulfane (1010447-25-2)

Conditions	Yield
Stage #1: S-pent-4-yn-1-yl ethanethioate With potassium hydroxide In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: phenylpropyl chloride In methanol at 50℃; for 2h;	96%

N-(2-pyridyl)indole (3419-91-8) + phenylpropyl chloride (104-52-9) → 2-(3-phenyl-n-propyl)-1-(pyridin-2-yl)-1H-indole

Conditions	Yield
With [2,2]bipyridinyl; (thf)2NiBr2; lithium hexamethyldisilazane In toluene at 60℃; for 16h;	96%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; C27H37N2(1+)*Cl(1-); cyclohexylmagnesiumchloride; cobalt(II) aceylacetonate at 23℃; for 16h; Inert atmosphere;	89%

tert-butyl 4-(((4-oxo-3,4-dihydroquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylate + phenylpropyl chloride (104-52-9) → tert-butyl 4-({[4-oxo-3-(3-phenylpropyl)-3,4-dihydroquinazolin-7-yl]oxy}methyl)piperidine-1-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃;	95%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 12h;	95%

4-Iodoacetophenone (13329-40-3) + phenylpropyl chloride (104-52-9) → 1-(4-(3-phenylpropyl)phenyl)ethan-1-one (113138-08-2)

Conditions	Yield
Stage #1: phenylpropyl chloride With indium; lithium iodide In tetrahydrofuran at 60℃; for 24h; Stage #2: 4-Iodoacetophenone With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide at 100℃; for 24h; Reagent/catalyst;	95%

phenylpropyl chloride (104-52-9) + phenylacetyl chloride (103-80-0) → 1-<4-(3-chloropropyl)phenyl>-2-phenyl-1-ethanone (115372-90-2)

Conditions	Yield
With aluminium trichloride In tetrachloromethane at 8 - 20℃;	94%
With aluminum (III) chloride In tetrachloromethane	94%
With aluminium trichloride In dichloromethane for 0.5h; Ambient temperature;	69%

4-iodobenzonitrile (3058-39-7) + phenylpropyl chloride (104-52-9) → 4-(3-phenyl-propyl)-benzonitrile (139597-68-5)

Conditions	Yield
Stage #1: phenylpropyl chloride With indium; lithium iodide In tetrahydrofuran at 60℃; for 24h; Stage #2: 4-iodobenzonitrile With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide at 100℃; for 24h;	94%

carbon disulfide (75-15-0) + hexan-1-amine (111-26-2) + phenylpropyl chloride (104-52-9) → S-(3-phenylpropyl) n-hexyldithiocarbamate

Conditions	Yield
Stage #1: carbon disulfide With N-benzyl-trimethylammonium hydroxide In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: hexan-1-amine In dimethyl sulfoxide at 20℃; for 1h; Stage #3: phenylpropyl chloride In dimethyl sulfoxide at 20℃; for 3h;	92%

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) + phenylpropyl chloride (104-52-9) → C18H20O4 (1354549-23-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Inert atmosphere; Reflux;	91%

phenylpropyl chloride (104-52-9) → 1-iodo-3-phenylpropan (4119-41-9)

Conditions	Yield
With sodium iodide In acetone at 60℃; for 12h; Sealed tube;	90%
With sodium iodide In acetone Reflux;	86%
With ethanol; sodium iodide
With sodium iodide In acetone for 60h; Heating;

phenylpropyl chloride (104-52-9) → (3-azidopropyl)benzene (27126-20-1)

Conditions	Yield
With sodium azide; tetraethylammonium bromide In dimethyl sulfoxide for 48h;	90%
With sodium azide In 1-methyl-pyrrolidin-2-one; water at 80℃; for 2h;
With sodium azide In 2,4-dichlorophenoxyacetic acid dimethylamine at 100℃; for 0.166667h; Microwave irradiation;
With sodium azide In N,N-dimethyl-formamide

phenylpropyl chloride (104-52-9) + n-octanoic acid chloride (111-64-8) → p-octanoyl chloropropylbenzene

Conditions	Yield
With aluminum (III) chloride at -5℃;	90%

hexan-1-amine (111-26-2) + carbon dioxide (124-38-9) + phenylpropyl chloride (104-52-9) → 3-phenylpropyl n-hexyl-carbamate

Conditions	Yield
Stage #1: hexan-1-amine; carbon dioxide; N-benzyl-trimethylammonium hydroxide In dimethyl sulfoxide at 90℃; for 1h; Stage #2: phenylpropyl chloride In dimethyl sulfoxide at 90℃; for 3.5h;	88%

ethanamine hydrochloride (557-66-4) + phenylpropyl chloride (104-52-9) → alverine (150-59-4)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide at 85 - 90℃; Reagent/catalyst;	88%

o-nitroiodobenzene (609-73-4) + phenylpropyl chloride (104-52-9) → 1-nitro-2-(3-phenylpropyl)benzene

Conditions	Yield
Stage #1: phenylpropyl chloride With indium; lithium iodide In tetrahydrofuran at 60℃; for 24h; Stage #2: o-nitroiodobenzene With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide at 100℃; for 24h;	87%

Upstream product

• 60-29-7 diethyl ether 
• 5411-48-3 sulfuric acid bis-(2-chloroethyl) ester 
• 122-97-4 3-Phenyl-1-propanol 
• 63014-04-0 3-Phenyl-propane-1-sulfonyl chloride 
• 142-28-9 1,3-Dichloropropane 
• 71-43-2 benzene 
• 936-59-4 3-chloropropiophenone 
• 866942-16-7 3-phenylpropyl 2-(methylcarboxy)-1-benzenesulfonate 
• 866942-18-9 3-phenylpropyl 2-(methoxyethoxyethylcarboxy)-1-benzosulfonate 
• 122-60-1 Phenyl glycidyl ether 
• 530-62-1 1,1'-carbonyldiimidazole 
• 632-02-0 3-chloropropyl p-toluenesulfonate 
• 1821-12-1 4-Phenylbutyric acid 
• 1841512-58-0 1,3-dioxoisoindolin-2-yl 4-phenylbutanoate 

Downstream Products

• 119967-39-4 2-(3-phenylpropoxy)ethanol 
• 75391-40-1 2-(3-Phenyl-propyl)-isothiourea 
• 71271-17-5 C₁₄H₂₆N₃OP 
• 300-57-2 allylbenzene 
• 99839-83-5 3-(2-nitrophenyl)propyl chloride 
• 2038-62-2 1-fluoro-3-phenylpropane 
• 3381-02-0 3-phenylpropylhydrazine 
• 21327-50-4 ethyl 1-(3-phenylpropyl)piperidine-4-carboxylate 
• 110045-73-3 9-(3-phenylpropyl)-9H-carbazole 
• 55455-92-0 1-(3-phenylpropyl)piperazine 
• 33254-43-2 Methyl-[9-(3-phenyl-propyl)-9H-purin-6-yl]-amine; hydrochloride 
• 908351-89-3 (5-benzyloxycarbonylamino-6-hydroxy-6-{5-[4-(3-phenyl-propyl)-piperazin-1-ylmethyl]-[1,2,4]oxadiazol-3-yl}-hexyl)-carbamic acid tert-butyl ester 
• 21763-00-8 1-bromo-3-chloro-1-phenylpropane 
• 59698-38-3 4-(3-phenyl-propyl)-piperazine-1-carboxylic acid ethyl ester 

Relevant articles and documents

An efficient method for chlorination of alcohols using PPh3/Cl3CCONH2

A new and convenient method for the chlorination of alcohols utilizing PPh3/Cl3CCONH2 is addressed. Various alcohols could smoothly be converted into their corresponding alkyl chlorides in high yield under mild conditions with short reaction times. A mechanism is disclosed with the evidence of inversion of configuration of the analogous alkyl chloride derived from R-(-)-2-octanol.

Remarkable interaction effects of molecular packing on site- and stereoselectivity in photocycloaddition of 2-pyrones with maleimide in the solid state

Solid-state photoirradiation of 1:1 complex crystals of 4-[ω-(2-furyl)alkyloxy]-6-methyl-2-pyrones 1b, 1c or 4-(ω-arylalkyloxy)-6-methyl-2-pyrones 1d-j with maleimide 2 gave [2+2]cycloadducts 3b-f, 3i, 3j with exclusive stereoselectivity. The high reaction selectivity was confirmed by X-ray structure analyses and MO method of the complex crystals, which were composed of two sets of a 1:1 complex between 1 and 2, arising from an CH-π interaction between 2 and the aromatic rings of 1, and/or π-π stacking between the aromatic rings in addition to four kinds of hydrogen bonding between the ground state 2-pyrone moieties and 2.

Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene

While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

Ionic-Liquid-Supported 1,3-Dimethylimidazolidin-2-one: Application as a Reusable Halogenation Reagent

We describe the synthesis of ionic-liquid-supported 1,3-dimethylimidazolidin-2-one, together with the halogenation of alcohols in a reaction system in which this reagent is combined with oxalyl chloride. A new method was established that does not require additives such as bases, and which permits the ready isolation and purification of the product. Good conversions were obtained, and good reusability of the reagent was observed.