110-94-1

Basic information

• Product Name: Glutaric acid
• Synonyms: a,-Propanedicarboxylicacid;glutaric;Glutarsaure;1,3-PROPANEDICARBOXYLIC ACID;1,5-PENTADIOIC ACID;1,5-PENTANEDIOIC ACID;GLUTARIC ACID AND ANHYDRIDE;GLUTARIC ACID
• CAS NO: 110-94-1
• Molecular Formula: C₅H₈O₄
• Molecular Weight: 132.11
• EINECS: 203-817-2
• Product Categories: Pharmaceutical Intermediates;alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;C1 to C5;Carbonyl Compounds;Carboxylic Acids
• Mol File: 110-94-1.mol
• Article Data: 476

Chemical Properties

• Melting Point: 95-98 °C(lit.)
• Boiling Point: 302 °C
• Flash Point: 200°C/20mm
• Appearance: Orange/Crystalline Powder
• Density: 1,429 g/cm3
• Vapor Pressure: 0.000223mmHg at 25°C
• Refractive Index: nD106 1.41878
• Storage Temp.: 2-8°C
• Solubility: water: soluble5mg/mL, clear to slightly hazy, colorless to faint
• PKA: 4.31(at 25℃)
• Water Solubility: 430 g/L (20 ºC)
• Stability: Stable. Incompatible with bases, oxidizing agents, reducing agents.
• Merck: 14,4473
• BRN: 1209725
• CAS DataBase Reference: Glutaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Glutaric acid(110-94-1)
• EPA Substance Registry System: Glutaric acid(110-94-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-37/39-36-39
• WGK Germany: 1
• RTECS: MA3740000
• TSCA: Yes
• Hazardous Substances Data: 110-94-1(Hazardous Substances Data)

Usage

Chemical Properties

white or off-white crystals, usually containing 1mol crystal water. Soluble in water, alcohol, ether and chloroform, slightly soluble in petroleum ether.

Occurrence

Glutaric acid occurs in washings from fleece and, together with malonic acid, in the juice of unripened sugar beet.

Uses

Glutaric acid is used as the raw material for organic synthesis, pharmaceutical intermediate and synthetic resin. It serves as a precursor in the production of polyester polyols, polyamides, ester plasticizers and corrosion inhibitors. It is useful to decrease polymer elasticity and in the synthesis surfactants and metal finishing compounds. It acts as an intermediate during the catabolism of lysine in mammals.

Definition

ChEBI: glutaric acid is an alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid. It has a role as a human metabolite and a Daphnia magna metabolite. It is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid. It is a conjugate acid of a glutarate(1-) and a glutarate.

Preparation

glutaric acid is produced as a by-product of the production process of adipic acid (about 2% of the output of an adipic acid plant is glutaric); Glutaric acid can be produced through various chemical routes, for example, from cyclopentane by oxidation with molecular oxygen and cobalt (III) catalysts or by ozonolysis; and from cyclopentanol–cyclopentanone by oxidation with oxygen and Co(CH3CO2)2, with potassium peroxide in benzene, or with N2O4 or nitric acid. Together with succinic acid, glutaric acid is formed as a by-product during oxidation of cyclohexanol–cyclohexanone in the adipic acid production process.

Application

The applications of glutaric acid, e.g., as an intermediate, are limited. Its use as a starting material in the manufacture of maleic acid has no commercial importance. it does not usually reach the market because it is converted into dibasic esters and sold as environmentally friendly solvents.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2489, 1956 DOI: 10.1021/ja01592a042Organic Syntheses, Coll. Vol. 1, p. 290, 1941Synthetic Communications, 10, p. 205, 1980 DOI: 10.1080/00397918008064223

General Description

Glutaric acid appears as colorless crystals or white solid. (NTP, 1992)

Air & Water Reactions

Water soluble.

Reactivity Profile

1,5-Pentanedioic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 1,5-Pentanedioic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions 1,5-Pentanedioic acid reacts with bases, oxidizing agents and reducing agents.

Fire Hazard

Flash point data for 1,5-Pentanedioic acid are not available; however, 1,5-Pentanedioic acid is probably combustible.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the acid from *benzene, CHCl3, distilled water or *benzene containing 10% (w/w) of diethyl ether. Dry it under vacuum. [Beilstein 2 IV 1934.]

InChI:InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)/p-2

Synthetic route

(+-)-1-(trimethylsilyl)ethanol (13246-39-4) + 5,5'-oxybis(5-oxopentanoic acid) (53715-97-2) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With dmap; triethylamine In dichloromethane	100%

1 ,5-pentanediol (111-29-5) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With C24H33IrN4O3; water; sodium hydroxide for 18h; Catalytic behavior; Reagent/catalyst; Reflux;	98%
In water for 48h; Ambient temperature; Gluconobacter roseus IAM 1841;	97%
With sodium hydroxide In water at 20℃; Temperature; Concentration; Electrochemical reaction;	91%

cis-1,2-cyclopentanediol (5057-98-7) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With dihydrogen peroxide; Na12[WZn3(H2O)2(ZnW9O34)2] at 75℃; for 7h;	98%

cyclohexane-1,2-dione (765-87-7) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With ozone In tetrachloromethane; water at 20℃; for 1h; UV-irradiation;	97%
With water; ozone at 25℃; under 760.051 Torr; for 1h; Irradiation;	95%
With oxygen; sodium hydroxide In water at 90℃; under 3000.3 Torr; for 3h; pH=7;	21%

trans-cyclopentane-1,2-diol (5057-99-8) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h;	96%

Cyclopentanol (96-41-3) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
Stage #1: Cyclopentanol With Oxone; ruthenium(III) chloride monohydrate In water at 70℃; for 8h; Stage #2: In ethanol Cooling;	95%
With nitric acid at 70 - 100℃;
With nitric acid; vanadia at 70 - 100℃;

cyclopentanone (120-92-3) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;	95%
Stage #1: cyclopentanone With Oxone; ruthenium(III) chloride monohydrate In water at 20℃; for 5h; Stage #2: In ethanol Cooling;	90%
With oxygen; copper dichloride In acetic acid at 80℃; for 6h; Oxidation;	84%

cyclopentene (142-29-0) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With potassium metaperiodate; potassium aquapentachlororuthenate(III) In dichloromethane; water; acetonitrile at 20℃; for 2h; Catalytic behavior; Sonication;	94%
With potassium permanganate; H-montmorillonite In water; benzene at 25 - 30℃; for 1h;	90%
With periodic acid; cis-[RuCl2(bipy)2]*2H2O In tetrachloromethane; water; acetonitrile at 20℃; for 2h;	85%

1,3-cylohexanedione (504-02-9) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With triethylmethylammonium iodide; water; dihydrogen peroxide In acetonitrile at 55℃; for 23h;	94%
With potassium carbonate In water at 25℃; Electrochemical reaction;	81%
With iodine; oxygen In ethyl acetate for 10h; Mercury lamp irradiation;	40%

cyclohexenone (930-68-7) + oxone + Os(VIII) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With hydrogenchloride; sodium sulfate; OsO4 In ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol	92%

Glutaraldehyde (111-30-8) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With tert.-butylhydroperoxide In water at 70℃; for 3.5h; Green chemistry;	91%
With tert.-butylhydroperoxide; copper(l) chloride In acetonitrile at 20℃; for 3.5h;	78%
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In acetonitrile at 60℃; for 8h; Reagent/catalyst; Time;	42%

Glutaraminsaeureethylester (56703-79-8) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With titanium tetrachloride In 1,4-dioxane; water for 20h; Heating;	90%

Dimethyl glutarate (1119-40-0) → 1,5-pentanedioic acid (110-94-1) + Pentanedioic acid, monomethyl ester (1501-27-5)

Conditions	Yield
Stage #1: Dimethyl glutarate With potassium hydroxide In tetrahydrofuran; water at 0℃; for 0.166667h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃;	A 13.2% B 86.8%
Stage #1: Dimethyl glutarate With lithium hydroxide; water In tetrahydrofuran at 0℃; for 0.333333 - 0.583333h; Stage #2: With water Product distribution / selectivity; Acidic conditions;
Stage #1: Dimethyl glutarate With potassium hydroxide; water In tetrahydrofuran at 0℃; for 0.166667 - 0.416667h; Stage #2: With water Product distribution / selectivity; Acidic conditions;
Stage #1: Dimethyl glutarate With cesium hydroxide; water In tetrahydrofuran at 0℃; for 0.166667 - 0.416667h; Stage #2: With water Product distribution / selectivity; Acidic conditions;
Stage #1: Dimethyl glutarate With sodium hydroxide; water In tetrahydrofuran at 0℃; for 0.333333 - 0.583333h; Stage #2: With water Product distribution / selectivity; Acidic conditions;

4-(1,1-dimethylethyl)-cyclohexanol (98-52-2) → 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + succinic acid (110-15-6) + 2-tert-butyl-1,4-butanedicarboxylic acid (10347-88-3)

Conditions	Yield
With ammonium vanadate; nitric acid at 95 - 100℃; for 1h;	A n/a B n/a C n/a D 85%

Cyclopentanol (96-41-3) → 1,5-pentanedioic acid (110-94-1) + cyclopentanone (120-92-3)

Conditions	Yield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 12.25h; Product distribution / selectivity;	A 85% B 10%

N,N,N',N'-tetraethyl glutaramide (17642-87-4) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
Stage #1: N,N,N',N'-tetraethyl glutaramide With sodium hydroxide In water at 110℃; for 12h; Stage #2: With hydrogenchloride; magnesium oxide In water; ethyl acetate pH=Ca. 4; Stage #3: With sulfuric acid In water; ethyl acetate pH=Ca. 4;	85%

L-glutamic acid (56-86-0) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With sulfuric acid; hypophosphorous acid; sodium nitrite In water at -5 - 0℃; for 10 - 12h; Reagent/catalyst;	80%

cyclohexene (110-83-8) → 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + hexanedial (1072-21-5) + succinic acid (110-15-6) + 1-cyclopentene-1-carboxaldehyde (6140-65-4) + 1,2-Cyclohexanediol (931-17-9) + cyclohexanone-2-ol (533-60-8)

Conditions	Yield
With dihydrogen peroxide; ortho-tungstic acid In water at 140℃; for 0.333333h; Mechanism; Flow reactor; Microwave irradiation; Sealed tube; Green chemistry; chemoselective reaction;	A n/a B 74% C n/a D n/a E n/a F n/a G n/a

cyclohexanone-2-ol (533-60-8) → 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9)

Conditions	Yield
With oxygen; sodium hydroxide In water at 90℃; for 3h; pH=> 13;	A 7% B 73%
With oxygen; H5PV2Mo10O40(1,11) In acetic acid at 60℃; under 750.06 Torr; for 10h; Yield given. Yields of byproduct given;
With oxygen; H7*10H2O In acetic acid at 60℃; under 750.06 Torr; for 10h; Yield given. Yields of byproduct given;

carbon monoxide (201230-82-2) + allyl alcohol (107-18-6) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	73%

1-(trimethylsilyloxy)cyclopentene (19980-43-9) → 1,5-pentanedioic acid (110-94-1) + 2-hydroxycyclopentanone (99440-98-9)

Conditions	Yield
With tert.-butylhydroperoxide; titanium silicate for 24h; Heating;	A 72% B 6%

Glutaronitrile (544-13-8) → 1,5-pentanedioic acid (110-94-1) + 4-cyanobutyric acid (39201-33-7)

Conditions	Yield
With water; nitrile hydratase SP361 at 30℃; for 40h; in potassium phosphate buffer (pH = 7);	A 9% B 70%
With water Product distribution; bacterial hydrolysis of aliphatic dinitriles with cells of Rhodococcus rhodochrous NCIB 11,216; 0.25 M phosphate buffer, pH 7;

TETRAHYDROPYRANE (142-68-7) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9) + 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With sodium bromate; potassium hydrogensulfate In water at 25 - 30℃; for 20h; Oxidation;	A 69% B 16%
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 20h; Reagent/catalyst; Inert atmosphere;	A 56% B 16%

TETRAHYDROPYRANE (142-68-7) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With ruthenium tetroxide In tetrachloromethane; water for 95h;	68%
With lithium nitrate In water; acetonitrile at 25℃; anodic oxidation;	66%
With hydrogenchloride
With nitric acid at 25 - 35℃;

2-acetylcyclopentanaone (1670-46-8) → 1,5-pentanedioic acid (110-94-1) + 2-methylhexane-1,6-dioic acid (626-70-0) + 2-acetyl-2-hydroxycyclopentanone (1262892-77-2)

Conditions	Yield
With dihydrogen peroxide In acetic acid at 20℃; for 240h;	A 67% B 30% C 0.5%

cyclohexane (110-82-7) → 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9)

Conditions	Yield
With N-hydroxyphthalimide; nitric acid; trifluoroacetic acid at 20℃; under 760.051 Torr; for 18h; Catalytic behavior; Reagent/catalyst;	A 5 %Spectr. B 66%
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid; cobalt acetylacetonate at 80℃; under 760.051 Torr; for 24h;
Multi-step reaction with 2 steps 1: N-hydroxyphthalimide; oxygen; acetic acid; bis(acetylacetonato)manganese(II) / 6 h / 100 °C / 760.05 Torr 2: oxygen; acetic acid; bis(acetylacetonato)manganese(II) / 6 h / 100 °C / 760.05 Torr View Scheme

cyclohexanol (108-93-0) → 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + monocyclohexyl adipate (54812-72-5) + cyclohexanone (108-94-1)

Conditions	Yield
With oxygen at 120℃; for 4.33333h; Further byproducts given;	A 3.1% B 12.4% C 8.9% D 65%
With oxygen at 120℃; for 4.33333h; Further byproducts given;	A 3.1% B 12.4% C 8.9% D 65%

cyclohexane (110-82-7) → 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + succinic acid (110-15-6) + cyclohexanone (108-94-1)

Conditions	Yield
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid at 80℃; under 760.051 Torr; for 14h; Time;	A 9% B 65% C 6% D 19%

glutaric anhydride, (108-55-4) → 1,5-pentanedioic acid (110-94-1)

Conditions	Yield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 25℃; for 12h; Ring cleavage;	64%
Multi-step reaction with 2 steps 1: sodium; alcohol 2: chromic acid View Scheme

methanol (67-56-1) + 1,5-pentanedioic acid (110-94-1) → Dimethyl glutarate (1119-40-0)

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
With phosphorus trichloride Cooling;	92%
With hydrogenchloride

1,5-pentanedioic acid (110-94-1) + 2-(vinyloxy)ethyl isothiocyanate (59565-09-2) → pentanedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

Conditions	Yield
trifluoroacetic acid at 55 - 60℃;	100%

1,5-pentanedioic acid (110-94-1) + zinc(II) oxide → zinc glutarate (331968-18-4)

Conditions	Yield
In toluene (Ar) suspn. ZnO and glutaric acid in toiluene was heated at 80°C for 1 day; react. mixt. was cooled, ppt. was filtered, washed with acetone and dried in vacuo at 130°C; powder X-ray diffraction;	100%
In ethanol; toluene at 60℃; for 10h; Solvent;	97%
In toluene at 60℃;	85%
In toluene byproducts: H2O; powdered ZnO added to soln. of org. compd., slurry stirred vigorously at55°C for 2 h then refluxed until no more H2O in trap; cooled to room temp., filtered, washed with acetone, powdered product dried in vac. at 100°C for 5 d; detn. FTIR, XANES EXAFS, (13)C NMR;
In toluene heating (3 h, 45°C); filtration, drying (overnight, vac., 90°C);

1,5-pentanedioic acid (110-94-1) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) + (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine (151433-25-9) → [(1-RR)-(Glutaric acid)]

Conditions	Yield
Stage #1: cobalt(II) acetate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In ethanol for 5h; Heating / reflux; Stage #2: 1,5-pentanedioic acid With oxygen In dichloromethane; acetone at 20℃; for 3h;	100%

1,5-pentanedioic acid (110-94-1) + meloxicam (71125-38-7) → meloxicam glutaric acid (1246227-11-1)

Conditions	Yield
In chloroform for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

1,5-pentanedioic acid (110-94-1) + carbonic acid dimethyl ester (616-38-6) → Dimethyl glutarate (1119-40-0)

Conditions	Yield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;	99%

1,5-pentanedioic acid (110-94-1) + copper (12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8) → [Cu(pentanedioate)]n (7268-93-1)

Conditions	Yield
With ozone In water for 6h; Time;	98.97%

1,5-pentanedioic acid (110-94-1) + 1,2-diamino-benzene (95-54-5) → 2,2'-(1,3-propanediyl)bis(1H-benzimidazole) (7147-66-2)

Conditions	Yield
With tetrafluoroboric acid In water at 150℃; for 2h;	98%
With polyphosphoric acid at 120℃;	79%
With polyphosphoric acid at 180℃;	65%

1,5-pentanedioic acid (110-94-1) + 4-nitro-2-trifluoromethyl-aniline (121-01-7) → 1-(4-nitro-2-trifluoromethyl-phenyl)-piperidine-2,6-dione

Conditions	Yield
With PPA at 80℃; for 12h;	98%

1,5-pentanedioic acid (110-94-1) + 2-methyl-4-nitro-benzenamine (99-52-5) → 1-(2-methyl-4-nitro-phenyl)-piperidine-2,6-dione

Conditions	Yield
With PPA at 80℃; for 12h;	98%

1,5-pentanedioic acid (110-94-1) + (3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine (99135-90-7) → δ-<(3R,4R)-3,4-Bis(diphenylphophino)pyrrolidino>-δ-oxopentansaeure (104351-44-2)

Conditions	Yield
In diethyl ether; dichloromethane	98%

1,5-pentanedioic acid (110-94-1) + camostat (59721-28-7) → N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate glutarate

Conditions	Yield
In ethanol at 20 - 65℃;	98%

1,5-pentanedioic acid (110-94-1) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6,5',6'-tetramethyl-2,2'-(1,3-propanediyl) bis-(1H-benzimidazole) (1171054-64-0)

Conditions	Yield
With tetrafluoroboric acid In water at 150℃; for 2h;	98%

4,4'-bipyridine (553-26-4) + 1,5-pentanedioic acid (110-94-1) + copper nitrate hemi(pentahydrate) → Cu2(glutarate)2(4,4'-bipyridine)

Conditions	Yield
With sodium hydroxide In water at 70℃; for 1h;	98%

1,5-pentanedioic acid (110-94-1) + 4-nitro-aniline (100-01-6) → 1-(4-nitro-phenyl)-piperidine-2,6-dione (139776-02-6)

Conditions	Yield
With PPA at 80℃; for 12h;	97%

1,5-pentanedioic acid (110-94-1) + 2-methoxy-4-nitrophenylamine (97-52-9) → 1-(2-methoxy-4-nitro-phenyl)-piperidine-2,6-dione

Conditions	Yield
With PPA at 80℃; for 12h;	97%

1,5-pentanedioic acid (110-94-1) + (S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carbaldehyde → (C20H11CHO(OH)OCO)2C3H6 (1002101-64-5)

Conditions	Yield
Stage #1: 1,5-pentanedioic acid; (S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carbaldehyde With dmap In dichloromethane at 20℃; for 0.25h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	97%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 3h;	96%

1,5-pentanedioic acid (110-94-1) + N,0-dimethylhydroxylamine (1117-97-1) → N1,N5-dimethoxy-N1,N5-dimethylglutaramide (259236-21-0)

Conditions	Yield
Stage #1: 1,5-pentanedioic acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h; Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h;	97%

1,5-pentanedioic acid (110-94-1) + metformin hydrochloride (1115-70-4) → metformin glutarate (2:1)

Conditions	Yield
Stage #1: metformin hydrochloride With sodium hydroxide In methanol; chloroform; water at 20℃; Stage #2: 1,5-pentanedioic acid In methanol; chloroform at 20℃; Product distribution / selectivity;	96.9%
Stage #1: metformin hydrochloride With sodium hydroxide In tetrahydrofuran; water at 20℃; Stage #2: 1,5-pentanedioic acid In tetrahydrofuran; water at 10℃; Product distribution / selectivity;	96.7%
Stage #1: metformin hydrochloride With sodium hydroxide In methanol; chloroform; water at 20℃; Stage #2: 1,5-pentanedioic acid In methanol; chloroform; water at 20℃; Product distribution / selectivity;	96.9%

1,5-pentanedioic acid (110-94-1) + dimethylbiguanide (657-24-9) → metformin glutarate (2:1)

Conditions	Yield
Stage #1: dimethylbiguanide In water; acetone at 40℃; Stage #2: 1,5-pentanedioic acid In water; acetone at 10℃; Product distribution / selectivity;	95.3%
In water; acetone at 10 - 40℃; Product distribution / selectivity;	95.3%
In ethanol at 10 - 20℃; Product distribution / selectivity;	62.8%
With sodium hydroxide In ethanol at 70℃; Product distribution / selectivity;	57.7%
In methanol at 40℃; Product distribution / selectivity;	43.8%

1,5-pentanedioic acid (110-94-1) + 2-Ethylhexyl alcohol (104-76-7) → glutaric acid bis-(2-ethyl-hexyl ester) (21302-20-5)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h;	95%
With Candida antarctica lipase B In cyclohexane at 45℃; for 24h;	68%
With sulfuric acid; toluene

1,5-pentanedioic acid (110-94-1) → glutaric anhydride, (108-55-4)

Conditions	Yield
With Isopropenyl acetate; Montmorillonite KSF for 0.0666667h; Irradiation;	95%
With PEG-1000; sulfated zirconia at 40℃; for 1.5h; neat (no solvent);	95%
With niobium(V) oxide hydrate In 1,3,5-trimethyl-benzene at 200℃; for 60h; Inert atmosphere; Molecular sieve;	92%

Upstream product

• 1191-99-7 2,3-Dihydrofuran 
• 544-13-8 Glutaronitrile 
• 504-63-2 1,3-Propanediol 
• 120-92-3 Cyclopentanone 
• 108-94-1 Cyclohexanone 
• 124-04-9 Adipic acid 
• 8002-74-2 Paraffin wax 
• 96-48-0 gamma-Butyrolactone 

Downstream Products

• 87818-31-3 Cinmethylin 
• 60687-93-6 LACCAIC ACID 
• 108-55-4 Glutaric anhydride 
• 123-99-9 Azelaic acid 
• 36505-84-7 Buspirone 
• 1134-47-0 Baclofen 

Recommend Products

• 5260-04-8  N,N'-bis[4-(dimethylamino)phenyl]urea 
• 110-86-1  pyridine 
• 738-65-8  bis-(4-dimethylamino-phenyl)-carbodiimide 
• 71-43-2  benzene 
• 110-87-2  3,4-dihydro-2H-pyran 
• 96-48-0  4-butanolide 
• 151-50-8  potassium cyanide 
• 542-28-9  3,4,5,6-tetrahydro-2H-pyran-2-one 
• 100-73-2  acrolein dimer 
• 1501-27-5  Pentanedioic acid, monomethyl ester 
• 67-56-1  methanol 
• 1119-40-0  Dimethyl glutarate 
• 1724-48-7  pentanedioic acid dipropyl ester 
• 71-23-8  propan-1-ol 

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