2338-76-3

Basic information

• Product Name: 3-Trifluoromethylbenzylcyanide
• Synonyms: M-(TRIFLUOROMETHYL)PHENYLACETONITRILE;M-TRIFLUOROMETHYLBENZYL CYANIDE;3-(Trifluoromethyl)ohenylacetonitrile;3-(TRIFLUOROMETHYL)PHENYLACETONITRILE, 9 7%;3-(Trifluoromethyl)phenylacetonitrile 97%;BENZENEACETONITRILE,3-(TRIFLUOROMETHYL)-;META-TRIFLUOROMETHYLPHENYLACETONITRILE;(a,a,a-Trifluoro-m-tolyl)acetonitrile
• CAS NO: 2338-76-3
• Molecular Formula: C₉H₆F₃N
• Molecular Weight: 185.15
• EINECS: 219-053-8
• Product Categories: Fluorobenzene;Aromatic Nitriles;Nitrile;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C8 to C9;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2338-76-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 92-93 °C4 mm Hg(lit.)
• Flash Point: 120 °F
• Appearance: clear yellow-brown liquid
• Density: 1.187 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0413mmHg at 25°C
• Refractive Index: n20/D 1.4565(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 909640
• CAS DataBase Reference: 3-Trifluoromethylbenzylcyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Trifluoromethylbenzylcyanide(2338-76-3)
• EPA Substance Registry System: 3-Trifluoromethylbenzylcyanide(2338-76-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-27-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: CY1820000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2338-76-3(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW-BROWN LIQUID

Uses

3-(Trifluoromethyl)phenylacetonitrile may be used in chemical synthesis studies.

InChI:InChI=1/C9H6F3N/c10-9(11,12)8-3-1-2-7(6-8)4-5-13/h1-3,6H,4H2

Synthetic route

potassium cyanide (151-50-8) + 1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
In ethanol; water for 1.5h; Heating / reflux;	100%
In dimethyl sulfoxide

sodium cyanide (773837-37-9) + 3-Trifluoromethylbenzyl chloride (705-29-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 55 - 65℃; for 10h; Temperature;	91%

3-chlorotrifluoromethylbenzene (98-15-7) + ethyl 2-cyanoacetate (105-56-6) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
Stage #1: 3-chlorotrifluoromethylbenzene; ethyl 2-cyanoacetate With N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(I) bromide; sodium t-butanolate In isopropyl alcohol at 105℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In isopropyl alcohol at 105℃; for 12h; Schlenk technique; Inert atmosphere; Cooling;	71%

potassium cyanide (151-50-8) + 3-Trifluoromethylbenzyl chloride (705-29-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
With potassium iodide In methanol

(+/-)-ethyl cyano[3-(trifluoromethyl)phenyl]acetate (91322-61-1) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
With sulfuric acid In water; acetic acid at 80 - 90℃; for 3h; Yield given;

sodium cyanide (143-33-9) + 3-Trifluoromethylbenzyl chloride (705-29-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

C9H5F3NNa → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
With methanol In dimethyl sulfoxide at 25℃; Equilibrium constant;

sodium cyanide (143-33-9) + 1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

1-methyl-3-trifluoromethyl-benzene (401-79-6) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NBS View Scheme

3-bromo-1-trifluoromethylbenzene (401-78-5) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH, CuI / hexamethylphosphoric acid triamide / 5 h / 150 - 160 °C 2: H2SO4 / H2O; acetic acid / 3 h / 80 - 90 °C View Scheme

3-(trifluoromethyl)benzyl alcohol (349-75-7) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (bromination) 2: dimethylsulfoxide View Scheme

3-(trifluoromethyl)phenylmagnesium bromide (402-26-6) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
Multi-step reaction with 3 steps 2: (bromination) 3: dimethylsulfoxide View Scheme

3-Trifluoromethylbenzyl chloride (705-29-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
In dimethyl sulfoxide
In dimethyl sulfoxide
In dimethyl sulfoxide

(α,α,α-trifluoro-m-tolyl)acetamide (22902-93-8) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
In acetonitrile
In acetonitrile

1-Bromo-2-chloroethane (107-04-0) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 1-(3-(trifluoromethyl)phenyl)cyclopropane-1-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃;	100%
With benzyltriethylammonium bromide; sodium hydroxide In water; toluene at 0 - 20℃; for 96h; Inert atmosphere;	72%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃;

ethylene dibromide (106-93-4) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 1-(3-(trifluoromethyl)phenyl)cyclopropane-1-carbonitrile

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 20℃; for 3h;	100%

2-Aminonicotinaldehyde (7521-41-7) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-[3-(trifluoromethyl)phenyl][1,8]naphthyridin-2-amine (1082325-94-7)

Conditions	Yield
With potassium hydroxide for 0.0416667h; Microwave irradiation;	98%

phenylacetyl chloride (103-80-0) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → (3-trifluoromethylphenyl)benzylcarbonylacetonitrile (68084-26-4)

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at 10℃; for 24h; Reagent/catalyst; Solvent; Temperature; Autoclave;	94.1%

methyl 2-bromo-3-methylbutanoic ester (69367-52-8, 70332-52-4, 114528-93-7, 26330-51-8) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → methyl 2-isopropyl-3-oxo-4-(3-trifluoromethylphenyl)butyrate (1015701-13-9)

Conditions	Yield
With zinc In tetrahydrofuran for 0.5h; Heating;	94%

3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-trifluoromethylbenzamide (1801-10-1)

Conditions	Yield
With ammonium hydroxide; ruthenium-carbon composite In tetrahydrofuran at 30℃; for 25h; Time;	94%
With ammonium hydroxide; 5 wt% ruthenium/carbon; oxygen In tetrahydrofuran at 30℃; for 25h;	94%

naphthalen-2-yl tosylate (7385-85-5) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 2-(naphthalen-2-yl)-2-(3-(trifluoromethyl)phenyl)acetonitrile

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	93%

3-trifluoromethylphenylacetonitrile (2338-76-3) → 2-(3-(trifluoromethyl)phenyl)ethanethioamide (952182-78-4)

Conditions	Yield
With hydrogenchloride; O,O-Diethyl hydrogen phosphorodithioate In ethyl acetate at 20℃; Product distribution / selectivity;	92%
With hydrogenchloride; O,O-Diethyl hydrogen phosphorodithioate In ethyl acetate at 0 - 20℃;	65%

cyclohexylamine (108-91-8) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → N-cyclohexyl-3-(trifluoromethyl)benzamide (418795-69-4)

Conditions	Yield
With 5 wt% ruthenium/carbon; oxygen In tetrahydrofuran at 30℃; for 23h;	92%

3-trifluoromethylphenylacetonitrile (2338-76-3) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-ethyl-3-oxo-4-(3-trifluoromethylphenyl)butyrate (1015701-12-8)

Conditions	Yield
With zinc In tetrahydrofuran for 0.5h; Heating;	91%

methyllithium (917-54-4) + 1,2-Epoxy-3-bromopropane (3132-64-7) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-hydroxy-1-[3-(trifluoromethyl)phenyl]cyclobutanecarbonitrile (1432050-72-0)

Conditions	Yield
Stage #1: methyllithium; 3-trifluoromethylphenylacetonitrile In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With hydrogenchloride; methylmagnesium bromide In tetrahydrofuran; diethyl ether; water at -75 - 20℃;	91%

1,2-Epoxy-3-bromopropane (3132-64-7) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-hydroxy-1-[3-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile (1432050-56-0)

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With hydrogenchloride; methylmagnesium bromide In tetrahydrofuran; diethyl ether; water at -75 - 20℃;	91%

1,2-Epoxy-3-bromopropane (3132-64-7) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-hydroxy-1-[3-(trifluoromethyl)phenyl]cyclobutanecarbonitrile (1432050-72-0)

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile With methyllithium In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With methylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃;	91%
Stage #1: 3-trifluoromethylphenylacetonitrile With methyllithium In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane With methylmagnesium bromide In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With methylmagnesium bromide In tetrahydrofuran; diethyl ether at -75 - 20℃; for 16h;	91%

3-trifluoromethylphenylacetonitrile (2338-76-3) + 1,2,3,4-tetrahydroquinoline-8-carboxylic acid methyl ester → 3-amino-2-(3-trifluoromethylphenyl)-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinolin-1-one

Conditions	Yield
With pyridine; sodium t-butanolate for 6h; Reflux;	90%

piperidine (110-89-4) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → (piperidin-1-yl)(3-(trifluoromethyl)phenyl)methanone (69001-08-7)

Conditions	Yield
With 5 wt% ruthenium/carbon; oxygen In tetrahydrofuran at 30℃; for 21h;	88%

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 2-(3-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrothieno[2,3-d]pyrimidin-4(3H)-one

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	88%

3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-(trifluoromethyl)phenylacetic acid (351-35-9)

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydroxide; water Heating / reflux; Stage #2: With hydrogenchloride In water pH=2;	87%
With sodium hydroxide In ethanol
With sulfuric acid; acetic acid

salicylaldehyde (90-02-8) + p-toluenesulfonyl chloride (98-59-9) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 4-methyl-N-(3-(3-(trifluoromethyl)phenyl)-2H-chromen-2-ylidene)benzenesulfonamide

Conditions	Yield
Stage #1: salicylaldehyde; 3-trifluoromethylphenylacetonitrile With 1,4-diaza-bicyclo[2.2.2]octane In 2-methyltetrahydrofuran at 80℃; for 8h; Reflux; Stage #2: p-toluenesulfonyl chloride With 1,4-diaza-bicyclo[2.2.2]octane In 2-methyltetrahydrofuran at 0℃;	87%

3-trifluoromethylphenylacetonitrile (2338-76-3) → C18H8F6N2

Conditions	Yield
With 5% active carbon-supported ruthenium; potassium carbonate In 1,2-dichloro-benzene at 160℃; for 35h;	87%
With methanol; iodine; sodium In diethyl ether at -78 - 0℃; for 2.25h; Inert atmosphere;	65%

2-hydroxy-4,6-dimethoxybenzaldehyde (708-76-9) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 5,7-dimethoxy-3-(3'-trifluoromethylphenyl)iminocoumarin

Conditions	Yield
With Amberlite IRA 900 (OH-) In cyclohexane for 15h; Condensation; Heating;	85%

3-oxa-1,5-dichloropentane (111-44-4) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 4-(3-(trifluoromethyl)phenyl)-tetrahydro-2H-pyran-4-carbonitrile (1035261-83-6)

Conditions	Yield
In N,N-dimethyl-formamide; mineral oil at 20 - 55℃; for 21.5h; Inert atmosphere;	85%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 55℃; for 21.5h;	85%
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Cooling with ice; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 0℃; for 0.5h;	84%
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Cooling with ice; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: With lithium chloride In N,N-dimethyl-formamide	84%
Stage #1: 3-trifluoromethylphenylacetonitrile With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 0 - 20℃; for 6h;

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → N,N-dimethyl 3-(trifluoromethyl)benzamide (90238-10-1)

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; oxygen; toluene-4-sulfonic acid at 140℃; under 760.051 Torr; for 24h; Sealed tube;	84%

benzyl alcohol (100-51-6) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-phenyl-2-(3-(trifluoromethyl)phenyl)propanamide

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide In tert-Amyl alcohol at 130℃; for 2h; Microwave irradiation;	84%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide at 130℃; for 2h; Microwave irradiation; Green chemistry;	84%

carbonic acid dimethyl ester (616-38-6) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → methyl (3-trifluoromethylphenyl)cyanoacetate

Conditions	Yield
With sodium methylate In methanol; toluene at 75 - 80℃; for 12h;	83%

salicylaldehyde (90-02-8) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 3-(3-(trifluoromethyl)phenyl)-2H-chromen-2-imine

Conditions	Yield
Stage #1: salicylaldehyde With amberlite IRA-900 form OH In toluene at 85℃; for 3h; Inert atmosphere; Stage #2: 3-trifluoromethylphenylacetonitrile In toluene for 12h; Reflux; Inert atmosphere;	83%

4-[(E)-2-{4-[(E)-2-(4-formylphenyl)ethenyl]-2,5-bis(octyloxy)phenyl}ethenyl]benzaldehyde (370563-61-4) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → (2Z)-3-[4-{(E)-2-[4-{(E)-2-[4-{(Z)-2-cyano-2-[3-(trifluoromethyl)phenyl]ethenyl}phenyl]ethenyl}-2,5-bis(octyloxy)phenyl]ethenyl}phenyl]-2-[3-(trifluoromethyl)phenyl]-2-propenenitrile

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol	79%
Knoevenagel condensation;

triethylbenzylammonium chloride (TEBA) + ethylene dibromide (106-93-4) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 1-(3-(trifluoromethyl)phenyl)cyclopropane-1-carbonitrile

Conditions	Yield
With sodium hydroxide	79%

naphthalen-2-yl methanesulfonate (10290-91-2) + 3-trifluoromethylphenylacetonitrile (2338-76-3) → 2-(naphthalen-2-yl)-2-(3-(trifluoromethyl)phenyl)acetonitrile

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	79%

Upstream product

• 91322-61-1 (+/-)-ethyl cyano[3-(trifluoromethyl)phenyl]acetate 
• 143-33-9 sodium cyanide 
• 705-29-3 3-Trifluoromethylbenzyl chloride 
• 402-23-3 1-bromomethyl-3-trifluoromethylbenzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 98-15-7 3-chlorotrifluoromethylbenzene 
• 105-56-6 ethyl 2-cyanoacetate 
• 773837-37-9 sodium cyanide 
• 22902-93-8 (α,α,α-trifluoro-m-tolyl)acetamide 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 
• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 401-79-6 1-methyl-3-trifluoromethyl-benzene 
• 151-50-8 potassium cyanide 

Downstream Products

• 19051-33-3 α-Cyan-3-trifluormethyl-stilben 
• 29786-43-4 1-(3-(trifluoromethyl)phenyl)cyclobutane-1-carbonitrile 
• 51715-83-4 α-Isopropyl-3-trifluorphenylacetonitril 
• 122376-69-6 Pyridin-2-yl-(3-trifluoromethyl-phenyl)-acetonitrile 
• 94559-32-7 2-(Benzoylimino)-3-<3-(trifluormethyl)phenyl>pyrrolidin 
• 94559-34-9 4-(Benzoylamino)-2-<3-(trifluormethyl)phenyl>butyronitril 
• 94559-33-8 3-<2-(Benzoylamino)ethyl>-2-(benzoylimino)-3-<3-(trifluormethyl)phenyl>pyrrolidin 
• 19051-33-3 (E)-3-Phenyl-2-(3-trifluoromethyl-phenyl)-acrylonitrile 
• 99726-60-0 2-(3-(trifluoromethyl)phenyl)malononitrile 
• 135561-75-0 1-[(3′-trifluoromethyl)phenyl]-2-propanol 
• 161809-65-0 3-trifluoromethylbenzyl trifluoromethyl ketone 
• 174812-92-1 6-chloro-3-pyridazinyl(3-trifluoromethylphenyl)acetonitrile 
• 77186-51-7 3-oxo-2-(3-(trifluoromethyl)phenyl)butanenitrile 
• 77186-59-5 3-oxo-2-(3-(trifluoromethyl)phenyl)pentanenitrile 

Relevant articles and documents

Synthesis method of 1-phenyl-3-(3-trifluoromethylphenyl)-2-acetone

The invention belongs to the technical field of chemical intermediates, and particularly relates to a synthesis method of 1-phenyl-3-(3-trifluoromethylphenyl)-2-acetone. A compound A is used as a basic raw material, and 1-phenyl-3-(3-trifluoromethylphenyl)-2-acetone is obtained through Blanc chloromethylation, substitution reaction, Claisen ester condensation and hydrolysis reaction in sequence. The synthesis method of 1-phenyl-3-(3-trifluoromethylphenyl)-2-acetone is high in purity, high in yield and simple to operate.

Preparation method of 3-trifluoromethylphenylacetonitrile

The invention discloses a preparation method of 3-trifluoromethylphenylacetonitrile; 3-trifluoromethylbenzyl chloride is synthesized from trifluoromethyl benzene, tripolyformaldehyde, sulfuric acid and thionyl chloride under the action of the catalyst and is cyanided with sodium cyanide under the action of a phase transfer catalyst to obtain 3-trifluoromethylphenylacetonitrile; the preparation method is simple and is high in yield, produced wastewater is recyclable, environmental pollution is greatly reduced, reaction with the catalysts is faster, reaction temperature is lower, equipment corrosion due to side reaction where products are decomposed into HF is reduced, and the method is easy to industrialize.

Synthesis and electronic spectra of substituted oligo(phenylenevinylene)s

A series of substituted oligo(p-phenylenevinylene)s (OPVs) with five benzene rings was prepared via PO-activated olefinations and Knoevenagel condensations. The central ring is substituted with two octyloxy groups to ensure good solubility of the OPVs and the lateral styrene units carry further substituents, with either electron-accepting or donating character and also combinations thereof. The spectral features of these OPVs are dominated by the basic chromophore; further auxochrome groups on the lateral rings (meta and para positions) shift the absorption and emission spectra only slightly to longer wavelengths. Significant bathochromic shifts (absorption ca 20 nm, emission ca 40 nm) are observed for OPVs with cyano groups on the terminal vinylene segments. The absorption spectra are independent from the concentration and solvatochromism is very small. The OPVs are photochemically stable to near-UV irradiation (366 nm) in neutral solution, whereas mid-UV irradiation (254 nm) causes decomposition of the chromophore. The presence of traces of acids or amines leads to different photochemical pathways. Copyright