7325-46-4

Basic information

• Product Name: 1,4-Phenylenediacetic acid
• Synonyms: 1,4-Benzenediacetic acid;4-Phenylenediacetic acid;1,4-Phenylenebis(acetic acid);1,4-Phenylenebisacetic acid;2,2'-(1,4-Phenylene)bisacetic acid;Benzene-1,4-bisacetic acid;1.4-Phenylenediacetic acid,97%;1,4-Phenylenediaceti
• CAS NO: 7325-46-4
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 230-801-2
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;C10;Carbonyl Compounds;Carboxylic Acids;Pyridines ,Halogenated Heterocycles
• Mol File: 7325-46-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 248-252 °C(lit.)
• Boiling Point: 290.62°C (rough estimate)
• Flash Point: 216.4 °C
• Appearance: Light yellow to beige/Powder
• Density: 1.2534 (rough estimate)
• Vapor Pressure: 1.75E-07mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.03±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 1960342
• CAS DataBase Reference: 1,4-Phenylenediacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Phenylenediacetic acid(7325-46-4)
• EPA Substance Registry System: 1,4-Phenylenediacetic acid(7325-46-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 7325-46-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 7325-46-4 differently. You can refer to the following data:
1. 1,4-Phenylenediacetic Acid is an arenediacetic acid used in the preparation of flurorescent whitening agents. 1,4-Phenylenediacetic Acid has fluorescent properties that allow for use in fluorescent pr obes.
2. 1,4-Phenylenediacetic Acid is an arenediacetic acid used in the preparation of flurorescent whitening agents. 1,4-Phenylenediacetic Acid has fluorescent properties that allow for use in fluorescent probes.

InChI:InChI=1/C10H10O4/c11-9(12)5-7-1-2-8(4-3-7)6-10(13)14/h1-4H,5-6H2,(H,11,12)(H,13,14)/p-2

Synthetic route

1,4-phenylenediacetonitrile (622-75-3) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With hydrogenchloride; acetic acid at 100℃; for 2h;	90%
With hydrogenchloride; water at 100℃; for 12h;	88%
With hydrogenchloride

carbon monoxide (201230-82-2) + p-Xylylene dichloride (623-25-6) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
Stage #1: carbon monoxide With C28H16N2O6Se In butan-1-ol under 750.075 Torr; for 2h; Reflux; Stage #2: p-Xylylene dichloride With tetrabutylammomium bromide; sodium hydroxide In butan-1-ol at 50℃; under 750.075 Torr; for 24h;	90%
Stage #1: carbon monoxide With C28H22CoN4O6 In butan-1-ol at 60℃; under 760.051 Torr; for 2h; Glovebox; High pressure; Green chemistry; Stage #2: p-Xylylene dichloride With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; under 760.051 Torr; for 22h; Glovebox; High pressure; Green chemistry; regioselective reaction;	80%

1,4-bis(bromomethyl)benzene (623-24-5) + carbon monoxide (201230-82-2) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide In formic acid at 90℃; under 760 Torr; for 18h; Carbonylation;	89%

1,4-bis(2,2-dibromoethenyl)benzene (77295-67-1) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
Stage #1: 1,4-bis(2,2-dibromoethenyl)benzene With n-butyllithium In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h;	60%

diethyl 2,2'-(1,4-phenylene)diacetate (36076-26-3) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With sodium hydroxide In ethanol; water for 9h; Heating;	57%

carbon monoxide (201230-82-2) + p-xylylene glycol (589-29-7) → 1,4-phenylenediacetic acid (7325-46-4) + 4-tolylacetic acid (622-47-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;	A 48% B 16 % Spectr.

carbon monoxide (201230-82-2) + p-xylylene glycol (589-29-7) → para-xylene (106-42-3) + 1,4-phenylenediacetic acid (7325-46-4) + 4-tolylacetic acid (622-47-9)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A n/a B 48% C 16%

octane (111-65-9) + para-xylene (106-42-3) + n-pentylsodium (1822-71-5) → 1,4-phenylenediacetic acid (7325-46-4) + 4-tolylacetic acid (622-47-9) + hexanoic acid (142-62-1)

Conditions	Yield
Behandlung des Reaktionsprodukts mit festem CO2;

4-acetyl-phenylacetic acid (7398-52-9) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With morpholine; sulfur Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

ethyl 4-acetylphenylacetate (1528-42-3) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With morpholine; sulfur Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge;

para-xylene (106-42-3) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With octane; n-pentylsodium anschliessendes Behandeln mit festem Kohlendioxid;

p-phenylene-bis-thioacetic acid diamide + alcoholic potash → 1,4-phenylenediacetic acid (7325-46-4) + hydrogen sulfide (7783-06-4) + ammonia (7664-41-7)

p-Xylylene dichloride (623-25-6) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / triethylene glycol / 1 h / 90 °C 2: 90 percent / conc. HCl; acetic acid / 2 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: aq. ethanol / Heating 2: aq. H2SO4 / Heating View Scheme

Ethyl 2-phenylethanoate (101-97-3) + butylamine salts → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / SnCl4 / CH2Cl2 / 24 h / Ambient temperature 2: 86 percent / Raney nickel / ethanol / 4 h / Heating 3: 57 percent / sodium hydroxide / ethanol; H2O / 9 h / Heating View Scheme

diethyl α-methylthio-1,4-benzenediacetate (105077-01-8) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / Raney nickel / ethanol / 4 h / Heating 2: 57 percent / sodium hydroxide / ethanol; H2O / 9 h / Heating View Scheme

diethyl 2,2'-(1,4-phenylene)diacetate (36076-26-3) → 2-(4-(2-ethoxy-2-oxoethyl)phenyl)acetic acid (113520-36-8) + 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran; ethanol

C10H8O4(2-)*Zn(2+)*C10H8N2*CH4O → 4,4'-bipyridine (553-26-4) + 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With sulfuric acid-d2 In dimethylsulfoxide-d6

1,4-diethynylbenzene (935-14-8) → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
Stage #1: 1,4-diethynylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h; Stage #3: With oxone In acetone at 50℃; for 12h;
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: oxone||potassium monopersulfate triple salt; water / acetone / 12 h / 50 °C / Inert atmosphere View Scheme

1,4-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)benzene → 1,4-phenylenediacetic acid (7325-46-4)

Conditions	Yield
With oxone||potassium monopersulfate triple salt; water In acetone at 50℃; for 12h; Inert atmosphere;	689 mg

methanol (67-56-1) + 1,4-phenylenediacetic acid (7325-46-4) → (4-methoxycarbonylmethylphenyl)acetic acid methyl ester (36076-25-2)

Conditions	Yield
With sulfuric acid Reflux;	100%
With sulfuric acid at 80℃; for 94h; Inert atmosphere;	90%
With thionyl chloride for 4h; Reflux;	85%

ethanol (64-17-5) + 1,4-phenylenediacetic acid (7325-46-4) → (4-methoxycarbonylmethylphenyl)acetic acid methyl ester (36076-25-2)

Conditions	Yield
With sulfuric acid In water at 80℃; for 12h; Inert atmosphere;	99%

N(1),N(2)-bis(t-butyloxycarbonyl)-1,2,4-butanetriamine (139024-81-0) + 1,4-phenylenediacetic acid (7325-46-4) → C38H64N6O10

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In acetonitrile at 0 - 20℃; Reflux;	97%

1,4-phenylenediacetic acid (7325-46-4) → phenylenediacetic acid-2,2,2',2'-d4 (104183-03-1)

Conditions	Yield
With potassium hydroxide; water-d2 at 160℃; for 28h;	95%

1,4-phenylenediacetic acid (7325-46-4) + 2,3-dihydro-1H-isoindole-5,6-dicarboxylic acid 5-{[2-(4-fluoro-phenyl)-ethyl]-amide} 6-(4-methyl-benzylamide) → C62H58F2N6O6

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 12h;	94%

1,2-bis(5-methylisoxazol-3-yl)hydrazine (2632-99-7) + 1,4-phenylenediacetic acid (7325-46-4) + zinc(II) acetate dihydrate (5970-45-6) → [Zn(μ4-1,4-phenylenediacetate)(μ-4,4′-azobis(pyridine))0.5]n

Conditions	Yield
In water at 70 - 120℃; for 72.5h;	93%

1,4-phenylenediacetic acid (7325-46-4) → 2-[4-(2-hydroxyethyl)phenyl]ethan-1-ol (5140-03-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;	92%
Stage #1: 1,4-phenylenediacetic acid With dimethyl sulfide borane In tetrahydrofuran for 18h; Stage #2: With hydrogenchloride In tetrahydrofuran; water	87%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;	81.8%

1,4-phenylenediacetic acid (7325-46-4) + 4'-methoxy-N-(azulen-1-ylmethylene)aniline (854154-95-3) → 1,4-bis[(E)-2-(azulen-1-yl)vinyl]benzene

Conditions	Yield
for 10h; Heating;	91%

pyrrolidine (123-75-1) + trimethylsilyl cyanide (7677-24-9) + 1,4-phenylenediacetic acid (7325-46-4) → C20H26N4

Conditions	Yield
Stage #1: pyrrolidine; 1,4-phenylenediacetic acid With (dimethoxy)methylsilane; molybdenum hexacarbonyl at 65℃; Stage #2: trimethylsilyl cyanide In 2,2,2-trifluoroethanol at 20℃; for 1h; chemoselective reaction;	91%

ethanol (64-17-5) + 1,4-phenylenediacetic acid (7325-46-4) → diethyl 2,2'-(1,4-phenylene)diacetate (36076-26-3)

Conditions	Yield
With sulfuric acid for 15h; Reflux;	90%
With sulfuric acid at 80℃;	87%
With sulfuric acid for 18h; Heating;	74%
acetyl chloride for 18h; Heating / reflux;

1,4-phenylenediacetic acid (7325-46-4) → 1,4-benzenediacetaldehyde (39246-00-9)

Conditions	Yield
With triethylsilane; tris(pentafluorophenyl)borate In benzene at 23℃; for 6h; Schlenk technique; Inert atmosphere;	90%
Multi-step reaction with 3 steps 1: 74 percent / aq. H2SO4 / 18 h / Heating 2: 84 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 62 percent / Dess-Matin periodinane / CH2Cl2 / 4 h / 20 °C View Scheme

europium(III) nitrate hexahydrate + 1,4-phenylenediacetic acid (7325-46-4) → [(europium(III))2(1,4-phenylenediacetate)3(H2O)] dihydrate

Conditions	Yield
In N,N-dimethyl acetamide; water High Pressure; mixt. of Eu(NO3)3*6H2O (0.4 mmol), H2pda (0.6 mmol), H2O and dimethylacetamide heated in Teflon-lined autoclave at 105°C for 2 d, cooled slowly to room temp.; elem. anal.;	90%

yttrium(lll) nitrate hexahydrate + 1,4-phenylenediacetic acid (7325-46-4) → [Y2(1,4-phenylenediacetate)3(H2O)1]*2H2O

Conditions	Yield
In ethanol; water at 180℃; for 1.16667h;	90%

1,4-phenylenediacetic acid (7325-46-4) + (3S,4S)-N3,N4-bis(((1S,2R)-2-phenylcyclopropyl)carbamoyl)pyrrolidine-3,4-dicarboxamide hydrochloride → (3S,3’S,4S,4’S)-1,1’-((1,4-phenylene)diacetyl)-bis(N3,N4-bis((1S,2R)-2-phenylcyclopropyl)pyrrolidine-3,4-dicarboxamide)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 18h;	89%

1,4-phenylenediacetic acid (7325-46-4) + phenylglyoxylic acid potassium salt (63468-90-6) → 1,4-Phenylene bis(phenylmaleic anhydride) (104595-14-4)

Conditions	Yield
With acetic anhydride for 1h; Heating;	88%

nickel(II) nitrate hexahydrate + 1,4-phenylenediacetic acid (7325-46-4) + 1,3-bis(1H-imidazol-4-yl)benzene (794485-43-1) + water (7732-18-5) → C12H10N4*C10H8O4(2-)*H2O*Ni(2+)

Conditions	Yield
With sodium hydroxide at 120℃; for 72h; Sealed tube; Autoclave;	88%

1,4-phenylenediacetic acid (7325-46-4) + Diphenylphosphine oxide (4559-70-0) → (1,4-phenylenebis(methylene))bis(diphenylphosphine oxide) (38661-56-2)

Conditions	Yield
With sodium persulfate; silver carbonate In acetonitrile at 80℃;	88%

1,4-phenylenediacetic acid (7325-46-4) → 1,4-benzenediacetyl dichloride (21062-19-1)

Conditions	Yield
With Vilsmeier reagent In toluene at 35 - 40℃; for 0.25h;	87%
With thionyl chloride
With phosphorus pentachloride

1,4-phenylenediacetic acid (7325-46-4) + L-Leu-L-Pro-OMe (72087-28-6) → 1,4-phenylenedi(acetyl-L-leucyl-L-proline methyl ester) (668479-44-5)

Conditions	Yield
Stage #1: 1,4-phenylenediacetic acid With diisopropyl-carbodiimide In dichloromethane for 0.75h; Stage #2: L-Leu-L-Pro-OMe In dichloromethane for 16h;	86%

gadolinium(III) nitrate hexahydrate + 1,4-phenylenediacetic acid (7325-46-4) → [(gadolinium(III))2(1,4-phenylenediacetate)3(H2O)] dihydrate

Conditions	Yield
In N,N-dimethyl acetamide; water High Pressure; mixt. of Gd(NO3)3*6H2O (0.4 mmol), H2pda (0.6 mmol), H2O and dimethylacetamide heated in Teflon-lined autoclave at 105°C for 2 d, cooled slowly to room temp.; elem. anal.;	86%

1,4-phenylenediacetic acid (7325-46-4) + zinc(II) nitrate hexahydrate + 4,4'-di(4-pyridyl)stilbene → [Zn(1,4-pda)(4,4'-di(4-pyridyl)stilbene)]n

Conditions	Yield
In water for 72h; Autoclave; High pressure;	86%

cobalt(II) chloride hexahydrate + 1,4-phenylenediacetic acid (7325-46-4) + water (7732-18-5) → [Co(1,4-phenylenediacetate)(H2O)2]

Conditions	Yield
With sodium carbonate In water High Pressure; addn. of aq. soln. of sodium carbonate to aq. soln. of carbon compd., addn. of aq. soln. of cobalt compd. at room temp., sealing in stainless steel reactor, heating at 120°C for 48 h; cooling, isolation of crystals by hand, washing with water, drying over filter paper, elem. anal.;	85%

yttrium(lll) nitrate hexahydrate + europium(III) nitrate hexahydrate + 1,4-phenylenediacetic acid (7325-46-4) → [Y1.8Eu0.2(1,4-phenylenediacetate)3(H2O)1]*2H2O

Conditions	Yield
In ethanol; water at 180℃; for 1.16667h; Milling;	85%

1,4-phenylenediacetic acid (7325-46-4) + Benzoylformic acid (611-73-4) → 1,4-Phenylene bis(phenylmaleic anhydride) (104595-14-4)

Conditions	Yield
With acetic anhydride; sodium hydride Reflux;	85%

Upstream product

• 201230-82-2 carbon monoxide 
• 589-29-7 p-xylylene glycol 
• 77295-67-1 1,4-bis(2,2-dibromoethenyl)benzene 
• 935-14-8 1,4-diethynylbenzene 
• 36076-26-3 diethyl 2,2'-(1,4-phenylene)diacetate 
• 623-25-6 p-Xylylene dichloride 
• 105077-01-8 diethyl α-methylthio-1,4-benzenediacetate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 623-24-5 1,4-bis(bromomethyl)benzene 
• 106-42-3 para-xylene 
• 622-75-3 1,4-phenylenediacetonitrile 
• 1528-42-3 ethyl 4-acetylphenylacetate 
• 7398-52-9 4-acetyl-phenylacetic acid 
• 111-65-9 octane 

Downstream Products

• 104595-25-7 C₁₆H₁₀O₆ 
• 104595-14-4 1,4-Phenylene bis(phenylmaleic anhydride) 
• 104595-20-2 C₃₀H₁₈O₆ 
• 104595-22-4 C₂₆H₁₄O₈ 
• 104595-23-5 C₂₆H₁₄O₆S₂ 
• 128822-56-0 C₃₄H₃₀O₆ 
• 5140-03-4 2-[4-(2-hydroxyethyl)phenyl]ethan-1-ol 
• 104183-05-3 1,4-phenylenediacetic acid-d4 
• 104183-03-1 phenylenediacetic acid-2,2,2',2'-d4 
• 909778-31-0 [4-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylmethyl)phenyl]acetic acid 
• 36076-25-2 (4-methoxycarbonylmethylphenyl)acetic acid methyl ester 
• 1258790-96-3 [Cd(1,4-phenylenediacetate)(bis-(4-pyridylformyl)piperazine)(H₂O)] 

Relevant articles and documents

Method for preparing carboxylic acid by one-pot method

The invention discloses a method for preparing carboxylic acid by a one-pot method, which comprises the steps of carrying out a Corey-Fuchs process on 1,1-dibromo olefin under the action of n-butyllithium, reacting with isopropanol pinacol borate, quenching with hydrogen chloride, oxidizing with an oxidant, separating and purifying to obtain carboxylic acid. The method disclosed by the invention is a one-pot preparation method, is simple and convenient to operate, does not need to use metal catalysis, uses cheap and easily available reagents for reaction, is green and environment-friendly, hasmild reaction conditions and wide substrate applicability, and provides a new way for rapidly preparing a series of carboxylic acids containing different functional groups.

Preparation method of acid with different substituent groups

The invention discloses a preparation method of an acid with different substituent groups. A terminal alkyne is lithiated with n-butyllithium, and then reacts with isopropoxyboronic acid pinacol ester, hydrogen chloride is added to achieve quenching, then the obtained reaction product is oxidized by an oxidizing agent, and the oxidized reaction product is separated and purified to obtain the acid.The method of the invention has the advantages of simplicity in operation, one-pot process preparation, no metal catalysis, nontoxic reagents, greenness, environmental friendliness and high atomic utilization rate, and provides a novel and quick way for preparing the acid with different substituent groups; and the obtained acid is an important fine chemical product, and can be widely used in fields of medicines, pesticides, spices and other industries.

The selenium-containing complexes in the phenylacetic acid and its derivatives or its application in the synthesis of (by machine translation)

The present invention provides a kind of structural formula (I) indicated by the 2 - (2 - carboxyl phenyl) benzothiazole of selenium-containing complexes of, this kind of selenium-containing complex can be applied to the catalytic benzyl chloride rigid synthetic phenylacetic acid or derivatives thereof in the reaction, in the reaction, the less the amount of catalyst, the catalytic activity is high, simple operation, conducive to such synthetic method in industry popularization and application. (by machine translation)