88-95-9

Basic information

• Product Name: Phthaloyl dichloride
• Synonyms: 1,2-Bis(chlorocarbonyl)benzene;benzenedioylchloride;Phthalic chloride;Phthalic dichloride;Phthalyl dichloride;1,2-BENZENEDICARBONYL CHLORIDE;1,2-BENZENEDICARBONYL DICHLORIDE;PHTHALIC ACID DICHLORIDE
• CAS NO: 88-95-9
• Molecular Formula: C₈H₄Cl₂O₂
• Molecular Weight: 203.02
• EINECS: 201-869-0
• Product Categories: o-Phthaloyl Dichloride, o-Diacetyl Chloride;ACID CHLORIDES
• Mol File: 88-95-9.mol
• Article Data: 24

Chemical Properties

• Melting Point: 6-12 °C(lit.)
• Boiling Point: 269-271 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.409 g/mL at 25 °C(lit.)
• Vapor Pressure: 30 mm Hg ( 47 °C)
• Refractive Index: n20/D 1.568(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Miscible with ether.
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• Merck: 14,7375
• BRN: 608200
• CAS DataBase Reference: Phthaloyl dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: Phthaloyl dichloride(88-95-9)
• EPA Substance Registry System: Phthaloyl dichloride(88-95-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 88-95-9(Hazardous Substances Data)

Usage

Chemical Properties

colorless or clear yellow oily liquid. decompose with water and alcohol, soluble in ether, chloroform and benzene.

Uses

Different sources of media describe the Uses of 88-95-9 differently. You can refer to the following data:
1. Phthaloyl chloride is used for the preparation of volatile acid chlorides from the acids. It acts as a trapping agent for the nitrite ion in the fluorodenitration of aromatic substrates with potassium fluoride. It serves as an additive in polymers and fibers to improve the color stability. It is used as an ingredient in ceramic mold binders, as a stabilizer for polymers and in reverse osmosis membranes.
2. o-Phthaloyl Dichloride is used in the phthaloylation of hemicelluloses as an efficient way to improve their lipophilicity and hydrophilicity. Phthaloylation of hemicelluloses is also a key precursor to preparing polysaccharide derivatives.

Preparation

Synthesis of phthaloyl dichloride: Mix 148g of phthalic anhydride with 220g of phosphorus pentachloride, heat, gradually increase the temperature to 250°C, escape the phosphorus oxychloride, distill the reaction product under reduced pressure, collect the 131-133°C (1.2-1.33kPa) fraction to obtain 187g of phthaloyl dichloride.

General Description

equilibrium mixture (phthaloyl chloride ~80% and pseudochloride ~10%) both components show equal chemical behaviour

InChI:InChI=1/C8H4Cl2O2/c9-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H

Synthetic route

phthalic anhydride (85-44-9) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With phosgene; N,N-dibutylformamide In toluene at 70℃; for 7.5h; Product distribution / selectivity;	97.8%
With phosgene; N-methyl-N-stearylformamide In toluene at 75℃; for 7.5h; Product distribution / selectivity;	95%
With phosgene; N,N-dibutylformamide In toluene at 70℃; for 8h; Product distribution / selectivity;	91%

phthalic anhydride (85-44-9) + 4-chlorotrichloromethylbenzene (5216-25-1) → 4-chloro-benzoyl chloride (122-01-0) + Phthaloyl dichloride (88-95-9)

Conditions	Yield
zirconium(IV) chloride at 160℃; for 6h;	A 93% B 70%

phthalic anhydride (85-44-9) → N,N-dibutylcarbamoyl chloride (13358-73-1) + Phthaloyl dichloride (88-95-9)

Conditions	Yield
With phosgene; N,N-dibutylformamide In toluene at 70℃; for 7.5h; Product distribution / selectivity;	A 0.9 %Chromat. B 89.3%

o-xylene (95-47-6) → ortho-toluoyl chloride (933-88-0) + Phthaloyl dichloride (88-95-9)

Conditions	Yield
Stage #1: o-xylene With ruthenium(II) chloride; C88H48Cl8Fe2N8O; oxygen at 185℃; under 10501.1 Torr; Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;	A 63.1% B 10.1%
Stage #1: o-xylene With ruthenium(II) chloride; C88H48Cl8Fe2N8O; oxygen at 185℃; under 10501.1 Torr; Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;	A 24.1% B 38.7%

tetrachloromethane (56-23-5) + phthalic anhydride (85-44-9) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With zinc(II) chloride at 220 - 300℃;

phthalic anhydride (85-44-9) + chloroform (67-66-3) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With zinc(II) chloride at 220 - 300℃;

phthalic anhydride (85-44-9) + hexachloroethane (67-72-1) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With zinc(II) chloride at 220 - 300℃;

phthalic anhydride (85-44-9) + Benzotrichlorid (98-07-7) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With zinc(II) chloride at 110 - 200℃;

3,3-dichlorophthalide (601-70-7) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
at 130℃; Kinetik der Umwandlung;
durch Destillation;
at 100℃;
With hydrogenchloride
at 130℃;

3-thioxo-3H-isobenzofuran-1-one (13699-68-8) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With chlorine at 245℃;

2-trichloromethyl-benzoic acid ethyl ester → phthalic anhydride (85-44-9) + chloroethane (75-00-3) + Phthaloyl dichloride (88-95-9)

benzene-1,2-dicarboxylic acid (88-99-3) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With phosphorus pentachloride
With thionyl chloride
With thionyl chloride at 60 - 65℃;

2,5-dioxo-2,5-dihydrobenzotellurophene (69246-89-5) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With chlorine In tetrachloromethane Yield given;

2-phenyl-isophosphindole-1,3-dione (54552-89-5) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With chlorine In diethyl ether

phthalic anhydride (85-44-9) + phosphorus pentachloride (10026-13-8, 874483-75-7) → Phthaloyl dichloride (88-95-9)

benzo[c]thiophene-1,3-dione (5698-59-9) + chlorine (7782-50-5) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
at 245℃;

phthalic anhydride (85-44-9) + phosphorus pentachloride (10026-13-8, 874483-75-7) → 1,1,3,3-tetrachloro-1,3-dihydroisobenzofuran (3199-08-4) + Phthaloyl dichloride (88-95-9)

Conditions	Yield
at 245℃;

phthalic anhydride (85-44-9) + phosphoric acid-dichloride → 1,1,3,3-tetrachloro-1,3-dihydroisobenzofuran (3199-08-4) + α,α,α-trichloro-o-toluic chloride (76716-56-8) + Phthaloyl dichloride (88-95-9)

Conditions	Yield
at 245℃;

21.21.21-trichloro-o-toluic acid ethyl ester → Phthaloyl dichloride (88-95-9)

phosphorus pentachloride (10026-13-8, 874483-75-7) + benzene-1,2-dicarboxylic acid (88-99-3) → Phthaloyl dichloride (88-95-9)

phosphorus pentachloride (10026-13-8, 874483-75-7) + benzene-1,2-dicarboxylic acid (88-99-3) → phthalic anhydride (85-44-9) + Phthaloyl dichloride (88-95-9)

N-cyclohexyl-cyclohexanamine (101-83-7) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
In benzene

N,N,N',N'-tetracyclohexyl-phthalamide + N-cyclohexyl-cyclohexanamine (101-83-7) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
In benzene

oxalyl dichloride (79-37-8) + benzene-1,2-dicarboxylic acid (88-99-3) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
With N,N-dimethyl-formamide

N-<(3-chloro)-propanoxy>phtalimide (92635-22-8) → Phthaloyl dichloride (88-95-9)

Conditions	Yield
Stage #1: N-<(3-chloro)-propanoxy>phtalimide With hydrogenchloride In water at 100 - 105℃; for 3h; Stage #2: With thionyl chloride In toluene for 4h; Reflux;

Tris(trimethylsilyl)phosphane (15573-38-3) + Phthaloyl dichloride (88-95-9) → 3-(trimethysiloxy)-1H-2-benzophosphol-1-one

Conditions	Yield
In diethyl ether at -50℃; for 2h;	100%

sodium amalgam + cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + Phthaloyl dichloride (88-95-9) → 1,2-C6H4(COFp)2

Conditions	Yield
With mercury In tetrahydrofuran soln. of Na#Hg, Hg, Fp2, THF was stirred for 1h, excess amalgam was drained, filtration through celite (medium porosity frit), cooling to -78°C (dry ice/aceton), addn. of 1,2-C6H4(COCl)2, warming to room temp.(1h), drying in vac., Et2O, stirring;	0%

chromeno[4,3,2-gh]phenanthridin-2-amine (1416857-67-4) + Phthaloyl dichloride (88-95-9) → 2-(chromeno[4,3,2-gh]phenanthridin-2-yl)isoindoline-1,3-dione (1416857-68-5)

Conditions	Yield
With pyridine; dmap In dichloromethane at 17 - 25℃; for 0.166667h; Inert atmosphere;	100%

4-bromo-benzaldehyde (1122-91-4) + Phthaloyl dichloride (88-95-9) → phthalic anhydride (85-44-9) + p-bromo-α,α-dichlorotoluene (67627-98-9)

Conditions	Yield
With 1-pyrrolidinecarboxaldehyde In toluene at 60℃; for 17h;	A 100% B 89%

4-ethylpyridin-2-amine (33252-32-3) + Phthaloyl dichloride (88-95-9) → 2-(4-ethylpyridin-2-yl)-1H-isoindole-1,3(2H)-dione (416852-12-5)

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	99.8%
With triethylamine In dichloromethane at 20℃; for 1h; Cooling;	90%
With triethylamine In dichloromethane at 20℃; for 1h;	90%
With triethylamine In dichloromethane at 20℃; for 1h;	90%

Phthaloyl dichloride (88-95-9) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With triethylsilane; iron(III)-acetylacetonate at 60℃; for 0.666667h;	99%
With triethylsilane; iron(III)-acetylacetonate at 60℃; for 0.666667h; other catalysts: Co(acac)2, Ni(acac)2; same reaction of iso- and terephthaloyl chloride;	99%
With tricyclohexylborane at 300℃; for 2h;	11.5%

Phthaloyl dichloride (88-95-9) → benzo[c]thiophene-1,3-dione (5698-59-9)

Conditions	Yield
With N,N-dimethylthioformamide; hydrogen sulfide In dichloromethane at 25℃;	99%
With sodium sulfide; cetyltributylphosphonium bromide In dichloromethane at 0℃; for 1.33333h;	95%
With sodium disulfide; cetyltributylphosphonium bromide In water; benzene for 0.5h; Ambient temperature; also Na2S as reagent;	87%

Phthaloyl dichloride (88-95-9) + 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane (175854-39-4) → 1,1'-phthaloylbis<4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane> (175854-41-8)

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;	99%

thiourea (17356-08-0) + Phthaloyl dichloride (88-95-9) → 2,2'-Thiocarbonyl-bis(2H-isoindol-1,3-dion) (101883-39-0)

Conditions	Yield
With sodium carbonate In dichloromethane for 4h; Heating;	98%
With N,N-dimethyl-aniline; acetone

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + Phthaloyl dichloride (88-95-9) → α,ω-bis(methacryloylethyleneglycol)phthalate (10552-43-9)

Conditions	Yield
With pyridine In benzene for 5h; Heating;	98%

Phthaloyl dichloride (88-95-9) + bis(1,1-dimethylethyl) 1,5,9-triazacyclododecane-1,5-dicarboxylate (174192-40-6) → 1,1'-phthaloylbis<5,9-bis(tert-butyloxycarbonyl)-1,5,9-triazacyclododecane> (175854-44-1)

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;	98%

(phthalocyanine-2,3:9,10:16,17:23,24-tetrakis(dicarboxanhydride))cobalt(II) (148448-11-7) + Phthaloyl dichloride (88-95-9) → cobalt octa-4,5-(chlorocarbonyl)phthalocyanine

Conditions	Yield
With zinc(II) chloride In neat (no solvent) a mixt. of complex, phthaloyl chloride and anhydrous zinc chloride was stirred for 24 h at 210-215°C;	98%

2-(4-aminophenoxy)-2-methyl propionic acid (117011-70-8) + Phthaloyl dichloride (88-95-9) → phthaloyl dichloride

Conditions	Yield
With sodium hydroxide at 20℃;	98%

3,6-diamino-9H-carbazole (86-71-5) + Phthaloyl dichloride (88-95-9) → 3,6-diphthalimidocarbazole (166272-33-9)

Conditions	Yield
With pyridine for 6h; Heating;	97%
With pyridine Yield given;

(μ-dithio)bis(tricarbonyliron) (14243-23-3) + Phthaloyl dichloride (88-95-9) + para-methylphenylmagnesium bromide (4294-57-9) → {Fe(CO)3(SC6H4CH3S)Fe(CO)3}2C(O)C6H4C(O)

Conditions	Yield
In tetrahydrofuran p-TolMgBr in THF was added under N2 with stirring to a THF soln. of Fe2-complex at -78°C, o-C6H4(COCl)2 was added to the resulting anionsoln. at -78°C, mixt. was allowed to warm to room temp.; volatiles were removed, residue purified by column chromy.; elem. anal.;	97%

4-amino-2-hydroxybutyric acid (13477-53-7) + Phthaloyl dichloride (88-95-9) → γ-phthalimidoimino-α-hydroxybutyric acid (40732-91-0)

Conditions	Yield
With dmap; sodium methylate at 60 - 100℃; for 1.36667h; Reagent/catalyst; Temperature;	96.3%

1,2-diamino-benzene (95-54-5) + Phthaloyl dichloride (88-95-9) → 1,4,9,12-tetraazacyclo-2,3,6,7,10,11,14,15-tetrabenzo-cetanan-5,8,13,16-tetraone

Conditions	Yield
With PEG-400; sodium hydroxide In dichloromethane for 1h; Product distribution; Heating; other reagent, solvent;	96%

Phthaloyl dichloride (88-95-9) + N-allyl (L)-leucine methyl ester (73270-65-2) → (S)-2-(Allyl-{2-[allyl-((S)-1-methoxycarbonyl-3-methyl-butyl)-carbamoyl]-benzoyl}-amino)-4-methyl-pentanoic acid methyl ester (313969-96-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Acylation;	96%

2-amino-3-nitropyridine (4214-75-9) + Phthaloyl dichloride (88-95-9) → 3-nitro-2-phthalimidopyridine (928163-49-9)

Conditions	Yield
With pyridine In toluene for 42h; Heating;	96%

Phthaloyl dichloride (88-95-9) → cyclic phthalic selenoanhydride (69246-88-4)

Conditions	Yield
Stage #1: Phthaloyl dichloride With selenium; lithium aluminium tetrahydride In tetrahydrofuran; dichloromethane at 50℃; for 1h; Stage #2: With sulfuric acid In tetrahydrofuran; dichloromethane for 0.0833333h;	95%
Stage #1: Phthaloyl dichloride With lithium hydrogen selenide In tetrahydrofuran; dichloromethane at 50℃; for 1h; Stage #2: With sulfuric acid In tetrahydrofuran; dichloromethane for 0.0833333h; Reagent/catalyst; Solvent;	80%
With triethylamine; p-methylselenobenzamide In dichloromethane at 0℃; for 2h; Acylation; cyclization;	59.6%
With LiAlHSeH In tetrahydrofuran at 20℃; for 2h;	57%
With aluminium trichloride; selen(o) hydrogen

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + succinoyl dichloride (543-20-4) + Phthaloyl dichloride (88-95-9) → 2-(4-{2-[4-(3-{4-[3-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-propionylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-propionylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid (78491-83-5)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	95%

2-methyl-2-butylamine (594-39-8) + Phthaloyl dichloride (88-95-9) → N-tert-amylisophthalimide (93272-72-1)

Conditions	Yield
With triethylamine In benzene at 6 - 7℃; for 0.05h;	95%

2,2-dimethylpropylamine (5813-64-9) + Phthaloyl dichloride (88-95-9) → tert-amylisophtalimide

Conditions	Yield
With triethylamine In benzene at 20℃; for 0.05h;	95%
With triethylamine In benzene at 20℃; for 0.0833333h;	92%

1-amino-2,6-dicyanopiperidine (13195-81-8, 110814-87-4, 110814-88-5) + Phthaloyl dichloride (88-95-9) → 1-phthalimido-2,6-dicyanopiperidine (110814-92-1, 110814-93-2)

Conditions	Yield
With dmap; triethylamine In dichloromethane for 16h; Ambient temperature;	95%

Phthaloyl dichloride (88-95-9) + 3,3-(α-hydroxypentamethylene)diaziridine (4469-71-0) → 2-Hydroxyspiro-diazirino<1,2-b>phthalazine>-3',8'-dione (72866-28-5)

Conditions	Yield
With triethylamine In diethyl ether at 5 - 10℃; for 5h;	95%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) + Phthaloyl dichloride (88-95-9) → phthalic acid 5-hydroxymethylfurfural di-ester

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 10h; Product distribution / selectivity;	95%

(phthalocyanine-2,3:9,10:16,17:23,24-tetrakis(dicarboxanhydride))zinc(II) (873430-63-8) + Phthaloyl dichloride (88-95-9) → zinc octa-4,5-(chlorocarbonyl)phthalocyanine

Conditions	Yield
With zinc(II) chloride In neat (no solvent) a mixt. of complex, phthaloyl chloride and anhydrous zinc chloride was stirred for 24 h at 210-215°C;	95%

ethanol (64-17-5) + C14H15N3O + Phthaloyl dichloride (88-95-9) → 3-(2-ethoxycarbonylphenyl)-4-(4'-methoxyphenyl)-5-phenyl-4H-1,2,4-triazole dihydrochloride

Conditions	Yield
With triethylamine Reflux;	95%

thiophenol (108-98-5) + Phthaloyl dichloride (88-95-9) → 1,2-bis(phenyl thioester)benzene (42797-33-1)

Conditions	Yield
With sodium methylate In methanol at 0℃;	94%
With triethylamine In chloroform at 25℃; for 12h;	77%
With sodium methylate

Upstream product

• 56-23-5 tetrachloromethane 
• 85-44-9 phthalic anhydride 
• 98-07-7 Benzotrichlorid 
• 69246-89-5 2,5-dioxo-2,5-dihydrobenzotellurophene 
• 10026-13-8 phosphorus pentachloride 
• 5698-59-9 benzo[c]thiophene-1,3-dione 
• 7782-50-5 chlorine 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 13699-68-8 3-thioxo-3H-isobenzofuran-1-one 
• 601-70-7 3,3-dichlorophthalide 
• 67-72-1 hexachloroethane 
• 67-66-3 chloroform 
• 92635-22-8 N-<(3-chloro)-propanoxy>phtalimide 
• 95-47-6 o-xylene 

Downstream Products

• 84-61-7 dicyclohexyl phthalate 
• 63542-24-5 2-(1H-pyridin-2-ylidene)-indan-1,3-dione 
• 73815-24-4 1,2-bis-(3,5-dimethyl-pyrazole-1-carbonyl)-benzene 
• 36469-01-9 2-methyl-2-[2]pyridyl-indan-1,3-dione 
• 627-63-4 fumaryl dichloride 
• 83-08-9 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione 
• 101439-77-4 2-(8-hydroxy-quinoline-7-carbonyl)-benzoic acid 
• 85-44-9 phthalic anhydride 
• 42908-86-1 2-Chloromethylbenzoyl chloride 
• 71107-30-7 2-phenyl-2-[2]pyridyl-indan-1,3-dione 
• 103162-91-0 N,N'-bis-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-phthalamide 
• 20171-91-9 N,N‘-di(4-chlorophenyl)phthaldiamide 
• 41513-78-4 2-phthalimidobenzoic acid 
• 46492-29-9 phthalic acid divinyl ester 

Relevant articles and documents

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