6285-05-8

Basic information

• Product Name: 4'-Chloropropiophenone
• Synonyms: 1-(4-chlorophenyl)-1-propanon;4’-chloro-propiophenon;chloropropiophenone;Ethyl p-chlorophenyl ketone;p-chloro-propiophenon;Propiophenone, 4'-chloro-;Propiophenone, p-chloro-;USAF ek-5296
• CAS NO: 6285-05-8
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• EINECS: 228-511-6
• Product Categories: Acetophenone Series;Aromatic Propiophenones (substituted);Ketones;Adehydes, Acetals & Ketones;Chlorine Compounds;C9;Carbonyl Compounds
• Mol File: 6285-05-8.mol
• Article Data: 65

Chemical Properties

• Melting Point: 35-37 °C(lit.)
• Boiling Point: 95-97 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: crystalline mass
• Density: 1.151
• Refractive Index: 1.5325-1.5345
• Storage Temp.: 0-10°C
• Water Solubility: Insoluble
• BRN: 1100638
• CAS DataBase Reference: 4'-Chloropropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Chloropropiophenone(6285-05-8)
• EPA Substance Registry System: 4'-Chloropropiophenone(6285-05-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• RTECS: UG9275000
• TSCA: Yes
• PackingGroup: II
• Hazardous Substances Data: 6285-05-8(Hazardous Substances Data)

Usage

Chemical Properties

CRYSTALLINE MASS

Uses

4-Chlorophenylacetone is a chemical raw material and pharmaceutical intermediate with important application value. It has very important applications in modern pharmaceutical, chemical and biological fields.

Safety Profile

Poison by intraperitoneal and intravenous routes. When heated to decomposition it emits toxic fumes of Cl-.

Synthetic route

1-allyl-4-chlorobenzene (1745-18-2) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; Wacker Oxidation; chemoselective reaction;	98%

propionyl chloride (79-03-8) + chlorobenzene (108-90-7) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 10 - 25℃; for 2h; Solvent; Temperature; Reagent/catalyst;	96.5%
With aluminum (III) chloride at 0 - 60℃; Inert atmosphere;	87%
With aluminium trichloride for 3h; Friedel-Crafts acylation; cooling;	74%

1-(4-chlorophenyl)-N-hydroxypropan-1-imine (56962-09-5) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.366667h; Reflux;	94%

p-chlorophenylvinylcarbinol (58824-54-7) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With 2C25H28N2OP(1-)*2Cl(1-)*2Ru(2+) In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	93%
With tetrapropylammonium perruthennate; undecan-2-ol In fluorobenzene Isomerization; Heating;	87%
With C13H21Cl2N3PRu(1+)*Cl(1-); potassium carbonate In tetrahydrofuran at 75℃; for 20h; Catalytic behavior; Inert atmosphere; Sealed tube;	80%

C10H12ClN3O (99360-14-2) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.466667h; Reflux;	90%

methanol (67-56-1) + 1-(p-chlorophenyl)ethyl alcohol (3391-10-4) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; potassium hydroxide In water at 80℃; Schlenk technique; Inert atmosphere;	90%
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; potassium hydroxide In water at 80℃; for 14h; Schlenk technique; Inert atmosphere; chemoselective reaction;	90%

C10H13ClO → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 24h;	89%

1-(4-chlorophenyl)-1-propanol (13856-85-4) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With peracetic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 20℃; for 10h;	88%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; (S)-3-phenyl-2-(phenylamino)propionic acid; copper(ll) bromide In water for 24h; Reflux; Schlenk technique;	87%
With diisopropoxyaluminium trifluoroacetate; 4-nitrobenzaldehdye In benzene for 0.75h; Ambient temperature;	85%

4-chloro-benzoyl chloride (122-01-0) + EtMgX → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With iron(III)-acetylacetonate In tetrahydrofuran at -78℃;	87%

C9H10BrClO (1021934-07-5) → 4'-chloropropiophenone (6285-05-8) + 1-(4-chlorophenyl)propan-2-one (5586-88-9)

Conditions	Yield
With diethylzinc In dichloromethane at 20℃; for 2h;	A 5% B 86%

4-Chlorophenylboronic acid (1679-18-1) + propiononitrile (107-12-0) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave;	81%

1-(4-chlorophenyl)-2-nitro-1-propanone (74261-45-3) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In benzene at 80℃; for 1.5h;	78%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 2h;	78%
With 1-Benzyl-1,4-dihydronicotinamide In N,N,N,N,N,N-hexamethylphosphoric triamide for 48h; Ambient temperature; Irradiation;	62%
With 1-Benzyl-1,4-dihydronicotinamide In N,N,N,N,N,N-hexamethylphosphoric triamide for 48h; Ambient temperature; Irradiation;	45%

N-<1-(4-chlorophenyl)propylidene>-2,6-xylylamine (157894-17-2) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 15h; Ambient temperature;	78%

1-(4-chlorophenyl)-2-tosylethanone (61820-94-8) + methylmagnesium bromide (75-16-1) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With bis(triphenylphosphine)nickel(II) diiodide; tricyclohexylphosphine In tetrahydrofuran at 80℃; Kumada Cross-Coupling; Inert atmosphere;	77%

ethylmagnesium bromide (925-90-6) + 4-chloro-N-methoxy-N-methylbenzamide (122334-37-6) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
In diethyl ether at 0℃; for 3h;	77%

Zn(2+)*Li(1+)*2C3H7(1-)*C5H11(1-) + para-chlorobenzoic acid (74-11-3) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
Stage #1: para-chlorobenzoic acid With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: Zn(2+)*Li(1+)*2C3H7(1-)*C5H11(1-) In 1,4-dioxane at 50℃; for 18h; Schlenk technique; Inert atmosphere; chemoselective reaction;	76%

para-chloroacetophenone (99-91-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With ammonium peroxydisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 110℃; for 3h; Inert atmosphere; Sealed tube;	73%

sodium p-chlorobenzenesulphinate (14752-66-0) + propiononitrile (107-12-0) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With palladium(II) trifluoroacetate; trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 100℃; for 1h; Microwave irradiation;	73%

propionic acid (802294-64-0) + chlorobenzene (108-90-7) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With polyphosphoric acid for 0.025h; Microwave irradiation;	70%

2-chloro-1-(4-chlorophenyl)propan-1-one (126918-29-4, 877-38-3) → 4'-chloropropiophenone (6285-05-8) + 1-(4-chlorophenyl)-2-hydroxypropan-1-one (49656-24-8) + 2-(4-Chloro-phenyl)-propionic acid (938-95-4)

Conditions	Yield
With methyloxirane In water; acetone Irradiation; pH neutral;	A 25% B 20% C 45%

bromochlorobenzene (106-39-8) + propionaldehyde (123-38-6) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: With iodine; potassium carbonate In tert-butyl alcohol for 4h; Reflux;	45%

2-chloro-1-(4-chlorophenyl)propan-1-one (126918-29-4, 877-38-3) → 4'-chloropropiophenone (6285-05-8) + methyl 2-(p-chlorophenyl)propionate (50415-70-8) + α-methoxy-p-chloropropiophenone (90919-32-7)

Conditions	Yield
With methyloxirane In methanol Irradiation; pH neutral;	A 24% B n/a C 30%

methylidene di(4-chlorobenzoate) (56741-11-8) + ethylmagnesium bromide (925-90-6) → 4'-chloropropiophenone (6285-05-8) + propyl 4-chloro benzoate (25800-30-0) + 3-(4'-chlorophenyl)pentan-3-ol (76481-35-1) + para-chlorobenzoic acid (74-11-3)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 3h; Substitution; addition;	A 21% B 26% C 16% D 17%

propionaldehyde oxime (627-39-4) + 4-chlorophenyldiazonium salt (17333-85-6) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With sodium acetate; copper(II) sulfate; sodium sulfite in wss. Loesung und anschl. mit wss. HCl;

4-chlorophenyldiazonium salt (17333-85-6) + N,N-dipropyl-hydroxylamine; hydrochloride → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With sodium hydroxide; water Behandeln des Reaktionsgemisches mit Luft und anschl. Erhitzen mit ws. HCl;

1-(p-chlorophenyl)-1-methoxyethene (67471-39-0) → 4'-chloropropiophenone (6285-05-8) + 1,4-bis-(4-chloro-phenyl)-2-methyl-butane-1,4-dione (74103-64-3)

Conditions	Yield
at 300℃;

propionic acid anhydride (123-62-6) + chlorobenzene (108-90-7) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With carbon disulfide; aluminium trichloride

4-Cyanochlorobenzene (623-03-0) + ethyltriphenylphosphonium iodide (4736-60-1) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 1072122/, (iii) aq. HCl; Multistep reaction;

1-(4-chlorophenyl)-2,2-dichloro-1-propanone (57169-53-6) → 4'-chloropropiophenone (6285-05-8)

Conditions	Yield
With hydrogen; methylamine; palladium on barium sulfate In methanol

1-(4-Chlorophenyl)-2-(4-methoxyphenyl)-3-methylcyclopropane (127257-92-5) → 4'-chloropropiophenone (6285-05-8) + r-3-(4-Chlorophenyl)-c-4-methyl-t-5-(4-methoxyphenyl)-1,2-dioxolane (127257-97-0, 127308-73-0) + r-3-(4-Chlorophenyl)-t-4-methyl-c-5-(4-methoxyphenyl)-1,2-dioxolane (127257-97-0, 127308-73-0) + 4-chlorobenzaldehyde (104-88-1) + 4-methoxy-benzaldehyde (123-11-5) + E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8)

Conditions	Yield
With magnesium(II) perchlorate; oxygen; 9,10-Dicyanoanthracene In acetonitrile for 0.0333333h; Rate constant; Thermodynamic data; Mechanism; Ambient temperature; Irradiation; ΔG;

4'-chloropropiophenone (6285-05-8) → 2-bromo-1-(4-chlorophenyl)-1-propanone (877-37-2)

Conditions	Yield
With bromine at 20℃; for 0.333333h;	100%
Stage #1: 4'-chloropropiophenone With bromine In methanol at 20℃; for 0.166667h; Stage #2: With hydrogen bromide In methanol; water for 110h; Inert atmosphere;	98%
With bromine; hydrogen bromide In methanol at 20℃; for 110h; Inert atmosphere;	98%

4'-chloropropiophenone (6285-05-8) → 1-phenyl-propan-1-one (93-55-0)

Conditions	Yield
With potassium hydroxide; hydrogen; Aliquat 336; tetrakis(triphenylphosphine) palladium(0); 1-Decanol In 2,2,4-trimethylpentane at 25℃; for 2h; atmospheric pressure;	100%
With palladium on activated charcoal; formic acid; N,N-dimethyl-formamide for 6h; Heating;	85%

4'-chloropropiophenone (6285-05-8) + oxalic acid diethyl ester (95-92-1) → 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester (169544-41-6)

Conditions	Yield
With sodium In ethanol at 20℃; for 18h; Claisen Condensation;	100%
With lithium tert-butoxide In tetrahydrofuran at 0 - 20℃; for 4h; Claisen Condensation; Inert atmosphere;	82%
Stage #1: oxalic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4'-chloropropiophenone In ethanol at 20℃; for 24h;	76.9%

4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-1-propanol (13856-85-4)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 4h;	99%
With sodium tetrahydroborate In tetrahydrofuran; water for 0.25h; Heating;	98%
With sodium tetrahydroborate; sodium hydrogen sulfate In acetonitrile at 20℃; for 0.333333h;	97%

4'-chloropropiophenone (6285-05-8) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → 3-(4-chlorophenyl)hex-5-en-3-ol

Conditions	Yield
With indium iodide In tetrahydrofuran at 40℃; for 24h;	99%
With methanol; indium (III) tris(hexamethyldisilyl) amide In toluene at 20℃; for 6h; Inert atmosphere;	98%

4'-chloropropiophenone (6285-05-8) + benzoic acid (65-85-0) → 1-(4-chlorophenyl)-1-oxopropan-2-yl benzoate (55705-16-3)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane; ethyl acetate at 75℃; for 24h; Product distribution / selectivity;	99%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In ethyl acetate at 20 - 75℃; for 23h;	91%
With potassium carbonate; ethylene dibromide; potassium iodide In N,N-dimethyl-formamide at 60℃; Sealed tube;	33%

4'-chloropropiophenone (6285-05-8) + 2,2,6,6-tetramethyl-piperidine-N-oxyl (2564-83-2) → 1-(4-chlorophenyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-1-one (1394206-51-9)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

4'-chloropropiophenone (6285-05-8) + 2,2,6,6-tetramethylheptane-3,5-dione (1118-71-4) → 1-(4-chlorophenyl)-6,6-dimethyl-4-pivaloylheptane-1,5-dione

Conditions	Yield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique;	99%

4'-chloropropiophenone (6285-05-8) + phenylboronic acid (98-80-6) → 1-biphenyl-4-yl-propan-1-one (37940-57-1)

Conditions	Yield
With potassium phosphate; Pd(OAc)2*3H2O In 1,4-dioxane for 12h; Suzuki-Miyaura cross-coupling; Heating;	98%
With 4,4'-(phenylphosphinediyl)bis(2,6-dimethylmorpholine); caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 16h; Suzuki-Miyaura coupling; Heating;	96%

4'-chloropropiophenone (6285-05-8) + propylene glycol (57-55-6) → 2-(4-chlorophenyl)-2-ethyl-4-methyl-1,3-dioxolane

Conditions	Yield
toluene-4-sulfonic acid In toluene Heating / reflux; Dean-Stark apparatus;	98%

morpholine (110-91-8) + 4'-chloropropiophenone (6285-05-8) → 2-morpholino-1-(4-(chloro)phenyl)propan-1-one (1152853-28-5)

Conditions	Yield
With 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide In dimethyl sulfoxide at 10℃; for 15h;	98%
Stage #1: 4'-chloropropiophenone With 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide In dimethyl sulfoxide at 20℃; for 0.166667h; Green chemistry; Stage #2: morpholine In dimethyl sulfoxide at 10℃; for 10h; Green chemistry;	97%
With sodium percarbonate; ammonium iodide In acetonitrile at 50℃; for 18h;	78%
With ammonium iodide In acetonitrile at 20℃; Electrolysis;	48%

4'-chloropropiophenone (6285-05-8) + potassium cyanide → 4-propionylbenzonitrile (52129-98-3)

Conditions	Yield
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine In acetonitrile at 200℃; for 1h; Microwave irradiation; Inert atmosphere;	97%

piperidine (110-89-4) + 4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-2-(piperidin-1-yl)propan-1-one

Conditions	Yield
Stage #1: 4'-chloropropiophenone With 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide In dimethyl sulfoxide at 20℃; for 0.166667h; Green chemistry; Stage #2: piperidine In dimethyl sulfoxide at 10℃; for 10h; Green chemistry;	97%
With ammonium iodide In acetonitrile at 20℃; Electrolysis;	70%

4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-2-(hydroxyimino)propan-1-one (56472-72-1)

Conditions	Yield
With chloro-trimethyl-silane; isopentyl nitrite In dichloromethane at -20℃;	96%
With n-Butyl nitrite In Petroleum ether for 5h;	96.9%
With chloro-trimethyl-silane; tert.-butylnitrite In tetrahydrofuran; dichloromethane at -20 - 20℃; Inert atmosphere;	81%

4'-chloropropiophenone (6285-05-8) + ethyl bromoacetate (105-36-2) → 3-(4-Chloro-phenyl)-3-hydroxy-pentanoic acid ethyl ester (21134-02-1)

Conditions	Yield
With zinc In diethyl ether; benzene for 5h; Heating;	96.9%
With zinc In diethyl ether; benzene for 3h; Heating;	88%
With zinc In toluene; benzene Heating;

4'-chloropropiophenone (6285-05-8) + trimethyl orthoformate (149-73-5) → methyl 2-(p-chlorophenyl)propionate (50415-70-8)

Conditions	Yield
With sulfuric acid; 3-[4-(diacetoxyiodo)phenoxy]-1-propyl-N,N,N-trimethylammonium 4-methylbenzenesulfonate at 60℃; for 5h; Inert atmosphere;	96%
With iodine; lithium perchlorate Ambient temperature; anodic oxidation at constant current;	88%

4'-chloropropiophenone (6285-05-8) + di-p-tolylcarbodiimide (726-42-1) → 4-chloro-N-(4-tolyl)benzamide (2447-95-2)

Conditions	Yield
With [{HMn(CO)4}3] In 1,4-dioxane at 135℃; for 24h; Sealed tube; Inert atmosphere;	96%

methanol (67-56-1) + 4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-2-methylidenepropan-1-one (6230-73-5)

Conditions	Yield
With potassium carbonate; triphenylphosphine at 20℃; for 4h; Irradiation; Green chemistry;	96%

methanol (67-56-1) + 4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-2-methylpropan-1-one (18713-58-1)

Conditions	Yield
With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Inert atmosphere;	95%
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; potassium carbonate at 80℃; for 24h;	91%
With C21H17ClN5ORu(1+)*Cl(1-); potassium tert-butylate at 85℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;	90%

NH-pyrazole (288-13-1) + 4'-chloropropiophenone (6285-05-8) + dimethyl sulfoxide (67-68-5) → 1-(4-chlorophenyl)-2-methyl-3-(1H-pyrazol-1-yl)propan-1-one

Conditions	Yield
With Selectfluor at 120℃; Mannich Aminomethylation; Sealed tube;	95%

4'-chloropropiophenone (6285-05-8) + N-methyl-3-formylindole (19012-03-4) + acetophenone (98-86-2) → (3-benzoyl-9-methyl-9H-carbazol-1-yl)(4-chlorophenyl)methanone

Conditions	Yield
Stage #1: N-methyl-3-formylindole; acetophenone With sodium hydroxide In ethanol at 25℃; Stage #2: 4'-chloropropiophenone With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) choride dihydrate; acetic acid In chlorobenzene at 120℃; for 16h;	95%

4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-2-(hydroxyamino)propan-1-one

Conditions

Yield

Stage #1: 4'-chloropropiophenone With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; under 3750.38 Torr; for 0.0166667h; Flow reactor; Inert atmosphere; Green chemistry; Stage #2: With 1-chloro-1-nitrosocyclopentane In tetrahydrofuran; tert-butyl methyl ether at 0℃; under 3750.38 Torr; for 0.0166667h; Flow reactor; Inert atmosphere; Green chemistry; Stage #3: With hydrogenchloride In tetrahydrofuran; tert-butyl methyl ether; water at 60℃; under 3750.38 Torr; for 0.0166667h; Flow reactor; Inert atmosphere; Green chemistry;

95%

4'-chloropropiophenone (6285-05-8) → 1-(4-chlorophenyl)-2-iodopropan-1-one

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene; iodine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃; Ionic liquid;	94%
With N-iodo-succinimide; toluene-4-sulfonic acid Microwave irradiation;	83%

4'-chloropropiophenone (6285-05-8) → 2-chloro-1-(4-chlorophenyl)propan-1-one (126918-29-4, 877-38-3)

Conditions	Yield
With N-chloro-succinimide; urea-hydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃;	94%
With Aluminum(III) chloride hexahydrate; urea-hydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃; for 9h;	80%

2-Butylfuran (4466-24-4) + 4'-chloropropiophenone (6285-05-8) → 2-n-butyl-5-(4-propionylphenyl)furan (1253967-16-6)

Conditions	Yield
With 1,1'-bis(dicyclohexylphosphanyl)-3,3'-di(triphenylmethyl)ferrocene; tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	94%
With 1,1',2-tris(diphenylphosphino)-3',4-di-tert-butyl ferrocene; tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	84%

4'-chloropropiophenone (6285-05-8) + 2-(2-fluorophenoxy)-5-methylpyridine (1357293-57-2) → 1-{3'-fluoro-2'-[(5-methylpyridin-2-yl)oxy]-[1,1'-biphenyl]-4-yl}propan-1-one (1357293-26-5)

Conditions	Yield
With (p-cymene)ruthenium(II) chloride; mesitylenecarboxylic acid; potassium carbonate In toluene at 120℃; for 20h; Inert atmosphere;	94%

methanol (67-56-1) + 4'-chloropropiophenone (6285-05-8) → α-methoxy-p-chloropropiophenone (90919-32-7)

Conditions	Yield
With p-nitrobenzenesulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide In acetonitrile at 80℃; for 24h; Inert atmosphere; Schlenk technique;	94%

Upstream product

• 126918-29-4 2-chloro-1-(4-chlorophenyl)propan-1-one 
• 1073-67-2 4-vinylbenzyl chloride 
• 201230-82-2 carbon monoxide 
• 56741-11-8 methylidene di(4-chlorobenzoate) 
• 925-90-6 ethylmagnesium bromide 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 1021934-07-5 C₉H₁₀BrClO 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 99-91-2 para-chloroacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 104-88-1 4-chlorobenzaldehyde 
• 127257-92-5 1-(4-Chlorophenyl)-2-(4-methoxyphenyl)-3-methylcyclopropane 
• 57169-53-6 1-(4-chlorophenyl)-2,2-dichloro-1-propanone 
• 623-03-0 4-Cyanochlorobenzene 

Downstream Products

• 438531-53-4 6-bromo-2-(4-chloro-phenyl)-3-methyl-quinoline-4-carboxylic acid 
• 6317-15-3 2-ethyl-2-(4-chloro-phenyl)-[1,3]dithiolane 
• 18713-58-1 1-(4-chlorophenyl)-2-methylpropan-1-one 
• 79341-98-3 1-Chloro-4-((E)-1-methoxy-propenyl)-benzene 
• 111315-87-8 C₁₅H₁₅ClN₂O₂S 
• 16621-14-0 1-(2-Chlor-phenyl)-1-(4-chlor-phenyl)-propanol-⁽¹⁾ 
• 2809-65-6 4-chloro-1-propynylbenzene 
• 57169-53-6 1-(4-chlorophenyl)-2,2-dichloro-1-propanone 
• 66498-50-8 2,2-dibromo-1-(4-chlorophenyl)propan-1-one 
• 26089-02-1 2-[1-(4-Chloro-phenyl)-propylidene]-malononitrile 
• 1678-92-8 propylcyclohexane 
• 103-65-1 phenylpropane 
• 93-54-9 1-Phenyl-1-propanol 
• 1123-86-0 cyclohexyl ethyl ketone 

Relevant articles and documents

V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls

The versatile application of different functional groups such as alcohols (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, we report a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions. The method was successfully applied for the alcohol oxidation, oxidative scission of styrenes, and benzylic C?H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30 % aq.), TBHP (70 % aq.), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol.

Rhizopus arrhizus mediated SAR studies in chemoselective biotransformation of haloketones at ambient temperature

We have demonstrated a green chemistry approach using the fungus Rhizopus arrhizus for the reductive dehalogenation and synthesis of chiral secondary carbinols and halohydrins of pharmaceutical importance in mild, inexpensive, and environmental friendly process at ambient temperature. In the present study, we have succeeded in unravelling the relationship between the position of the substituent group in the structure of substrate and bioreduction activity of the fungus Rhizopus arrhizus. The asymmetric reduction of the carbonyl group to corresponding chiral halohydrin takes place with good yield and excellent enantiomeric excess (≥92%) when the substituent halogen is on the aromatic nucleus. However, novel results concerning reductive dehalogenation are obtained when halogen is incorporated in the alkyl side chain. Thus, the fungus Rhizopus arrhizus has great potential to bring chemoenzymatic biotransformation of halo ketones. Various influential processing parameters such as microbe selection, temperature, pH, etc. were also investigated to optimize the growth of biocatalyst.

Combination of organocatalytic oxidation of alcohols and organolithium chemistry (RLi) in aqueous media, at room temperature and under aerobic conditions

A tandem protocol to access tertiary alcohols has been developed which combines the organocatalytic oxidation of secondary alcohols to ketones followed by their chemoselective addition by several RLi reagents. Reactions take place at room temperature, under air and in aqueous solutions, a trio of conditions that are typically forbidden in polar organometallic chemistry.