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Cas Database

108-55-4

108-55-4

Identification

  • Product Name:2H-Pyran-2,6(3H)-dione,dihydro-

  • CAS Number: 108-55-4

  • EINECS:203-593-6

  • Molecular Weight:114.101

  • Molecular Formula: C5H6O3

  • HS Code:29171990

  • Mol File:108-55-4.mol

Synonyms:Glutaricanhydride (6CI,7CI,8CI);Dihydro-2H-pyran-2,6(3H)-dione;Dihydro-3H-pyran-2,6-dione;Dihydropyran-2,6-dione;Glutaric acid anhydride;NSC 16640;Oxacyclohexane-2,6-dione;Pentanedioic acid anhydride;Pentanedioicanhydride;Pyroglutaric acid;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H318 Causes serious eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Glutaric Anhydride
  • Packaging:5g
  • Price:$ 312
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  • Manufacture/Brand:TRC
  • Product Description:Glutaric Anhydride
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  • Price:$ 50
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Glutaric Anhydride >98.0%(T)
  • Packaging:25g
  • Price:$ 20
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Glutaric Anhydride >98.0%(T)
  • Packaging:100g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Glutaric Anhydride >98.0%(T)
  • Packaging:500g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Glutaric Anhydride 95%
  • Packaging:100 g
  • Price:$ 144
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Glutaric Anhydride 95%
  • Packaging:500 g
  • Price:$ 224
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Glutaric anhydride 95%
  • Packaging:500g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Glutaric anhydride for synthesis. CAS 108-55-4, molar mass 114.1 g/mol., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Glutaric anhydride for synthesis
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Relevant articles and documentsAll total 23 Articles be found

Lactones as minor products of the electrochemical reduction of glutaryl dichloride at mercury cathodes in acetonitrile

Urove, Greg A.,Peters, Dennis G.

, p. 1271 - 1274 (1993)

Electrochemical reduction of glutaryl dichloride at a mercury electrode in acetonitrile containing 0.1 M tetraethylammonium perchlorate results in the formation of 5-chlorovalerolactone, valerolactone, and a polymeric species.

Remote stereocontrol as a synthetic strategy: Diastereoselective annulations on an arene tricarbonylchromium template

Sur, Surojit,Ganesh, Sambasivam,Puranik, Vedavati G.,Sarkar, Amitabha

, p. 977 - 982 (1998)

Stereoselective annulations on Cr(CO)3 complexed tetralone and benzosuberone derivatives have been achieved. Diastereomeric products are shown to be related by an epimerisable chiral centre. An unusually facile de-ethoxycarbonylation has been observed.

A NEW SYNTHESIS OF CARBOXYLIC AND CARBONIC ACID ANHYDRIDES USING PHASE TRANSFER REACTIONS

Plusquellec, Daniel,Roulleau, Fabienne,Lefeuvre, Martine,Brown, Eric

, p. 2471 - 2476 (1988)

Acyl chlorides and alkylchloroformates smoothly reacted with one molar equivalent of sodium hydroxide, using liquid-liquid phase transfer conditions to afford high yields of the corresponding symmetrical carboxylic and carbonic hemiester anhydrides.Unstable anhydrides such as 4-nitrobenzoic, 2-furoic and methacrylic anhydrides, which are otherwise difficult to obtain, were easily prepared by this method.The reaction mechanism does not seem to involve intermediate hydrolysis of half the acid chloride into the corresponding sodium carboxylate.

METHOD FOR PRODUCING CARBOXYLIC ACID ANHYDRIDE OR SULFONIC ACID ANHYDRIDE

-

Paragraph 0042-0045; 0048-0049, (2021/02/25)

To provide a method for producing carboxylic acid anhydride or sulfonic acid anhydride in which carboxylic acid anhydride or sulfonic acid anhydride is produced in a simple or easy process using carboxylic acid or sulfonic acid as raw material, and using an industrially available raw material and in an efficient process in industrial practice.SOLUTION: Provided is a method for producing carboxylic acid anhydride or sulfonic acid anhydride, which is a method for producing an acid anhydride by reacting carboxylic acid or sulfonic acid and a halogenating agent, and in which a solvent containing a phosphoric acid ester such as the formula (1) is used. (R1, R2 and R3 are the same or non-identical alkyl group or fluorine-containing alkyl group having 1 to 10 carbon atoms, and at least one is fluorine-containing alkyl group.).SELECTED DRAWING: None

Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production

Rashed, Md. N.,Siddiki,Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Kon, Kenichi,Toyao, Takashi,Shimizu, Ken-Ichi

, p. 3238 - 3242 (2017/07/28)

Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.

4-Biphenylalanine- and 3-Phenyltyrosine-Derived Hydroxamic Acids as Inhibitors of the JumonjiC-Domain-Containing Histone Demethylase KDM4A

Morera, Ludovica,Roatsch, Martin,Fürst, Michael C. D.,Hoffmann, Inga,Senger, Johanna,Hau, Mirjam,Franz, Henriette,Schüle, Roland,Heinrich, Markus R.,Jung, Manfred

, p. 2063 - 2083 (2016/10/22)

Overexpression of the histone lysine demethylase KDM4A, which regulates H3K9 and H3K36 methylation states, has been related to the pathology of several human cancers. We found that a previously reported hydroxamate-based histone deacetylase (HDAC) inhibitor (SW55) was also able to weakly inhibit this demethylase with an IC50value of 25.4 μm. Herein we report the synthesis and biochemical evaluations, with two orthogonal in vitro assays, of a series of derivatives of this lead structure. With extensive chemical modifications on the lead structure, also by exploiting the versatility of the radical arylation with aryldiazonium salts, we were able to increase the potency of the derivatives against KDM4A to the low-micromolar range and, more importantly, to obtain demethylase selectivity with respect to HDACs. Cell-permeable derivatives clearly showed a demethylase-inhibition-dependent antiproliferative effect against HL-60 human promyelocytic leukemia cells.

Reactions of hydrogen peroxide with acetylacetone and 2- acetylcyclopentanone

Novikov,Shestak

, p. 2171 - 2190 (2014/11/07)

A reaction of acetylacetone with equimolar amount of concentrated aqueous H2O2 in both organic solvents (ButOH, AcOH) and water at various temperatures gave the corresponding 3,5-dihydroxy-1,2- dioxolanes with different configuration of stereogenic centers. In the pres-ence of an excess of H2O2, 3,5-dihydroxy-1,2-dioxolanes were converted to a mixture of 5-hydroperoxy-3-hydroxy-1,2-dioxolanes and further to a mixture of dimeric 1,2-dioxolan-3-ylperoxides. All the peroxides formed exist in solutions as equilibrium mixtures with the starting reagents. A prolonged reflux of solutions of 3,5-dihydroxy-1,2-dioxolanes in ButOH in the presence of a large excess of H2O2 led to the skeletal rearrangements of the substrates to a mixture of propionic acid and hydroxyacetone, which underwent further oxidative transfor-mations. Unlike acetylacetone, 2-acetylcyclopentanone reacted with H2O2 in aqueous phase or in solutions in ButOH under thermodynamic or kinetic control with the formation of the corresponding 5-hydroperoxy-3-hydroxy- 1,2-dioxolanes, rather than 3,5-dihydroxy-1,2-di-oxolanes. Thermodynamically controlled process in solution in AcOH gave a mixture of all four possible hydroperoxyhydroxy-1,2-dioxolanes. These cyclic peroxides in solutions in ButOH or AcOH readily converted to a mixture of AcOH, glutaric, α-methyladipic, and α-hydroxy-α-methyladipic acids. An active α-hydroxylation of the substrate was observed upon reflux of a solution of 2-acetylcyclopentanone and H2O2 in AcOH.

Thermal and photochemical oxidation of 2-acetylcyclopentanone with atmospheric oxygen

Novikov,Shestak

, p. 1099 - 1110 (2013/07/26)

The major products of thermal (acetone, CaCl2 excess, reflux) and photochemical (acetone or CCl4, room temperature) oxidation of 2-acetylcyclopentanone with atmospheric oxygen are 2-acetyl-2- hydroxycyclopentanone, 2-acetyl-2-hydroxy

Process route upstream and downstream products

Process route

(1,2-bis(diphenylphosphino)ethane)NiCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>COO
82840-52-6

(1,2-bis(diphenylphosphino)ethane)NiCH2CH2CH2COO

glutaric anhydride,
108-55-4

glutaric anhydride,

2-methylsuccinic anhydride
4100-80-5

2-methylsuccinic anhydride

Conditions
Conditions Yield
In hexane; for 48h; Ambient temperature;
8%
41%
gloutaric dichloride
2873-74-7

gloutaric dichloride

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9,26354-94-9

3,4,5,6-tetrahydro-2H-pyran-2-one

glutaric anhydride,
108-55-4

glutaric anhydride,

5-Chlorovalerolactone

5-Chlorovalerolactone

Conditions
Conditions Yield
With tetraethylammonium perchlorate; In acetonitrile; -1.45 V, mercury pool electrode;
14 % Chromat.
34 % Chromat.
18 % Chromat.
With tetraethylammonium perchlorate; In acetonitrile; Product distribution; Mechanism; -1.45 V, mercury pool cathode; other potential, variation of dichloride concentration;
14 % Chromat.
18 % Chromat.
34 % Chromat.
2-acetylcyclopentanaone
1670-46-8

2-acetylcyclopentanaone

1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

4-butanolide
96-48-0

4-butanolide

glutaric anhydride,
108-55-4

glutaric anhydride,

formic acid
64-18-6

formic acid

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

4-Hydroxy-4-methyl-2-pentanone
123-42-2

4-Hydroxy-4-methyl-2-pentanone

4-acetoxybutyric acid
26976-72-7

4-acetoxybutyric acid

5,6-dioxo-n-heptanoic acid
85951-55-9

5,6-dioxo-n-heptanoic acid

2-acetyl-2-hydroxycyclopentanone
1262892-77-2

2-acetyl-2-hydroxycyclopentanone

2-acetoxycyclopentanone
52789-75-0

2-acetoxycyclopentanone

2-acetyl-2-hydroxymethylcyclopentanone
1167443-17-5

2-acetyl-2-hydroxymethylcyclopentanone

1,1'-diacetyl-1,1'-bicyclopentyl-2,2'-dione
1426960-55-5

1,1'-diacetyl-1,1'-bicyclopentyl-2,2'-dione

2-acetyl-2,3-epoxycyclopentanone
89540-15-8

2-acetyl-2,3-epoxycyclopentanone

acetic acid
64-19-7,77671-22-8

acetic acid

Conditions
Conditions Yield
With oxygen; calcium chloride; In acetone; at 57 ℃; for 30h;
11%
1%
7%
2%
2%
38%
2%
5%
0.014 g
13%
2%
7%
2-acetylcyclopentanaone
1670-46-8

2-acetylcyclopentanaone

1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

4-butanolide
96-48-0

4-butanolide

glutaric anhydride,
108-55-4

glutaric anhydride,

formic acid
64-18-6

formic acid

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

2-acetyl-2-hydroxycyclopentanone
1262892-77-2

2-acetyl-2-hydroxycyclopentanone

2-acetoxycyclopentanone
52789-75-0

2-acetoxycyclopentanone

2-acetyl-2-hydroxymethylcyclopentanone
1167443-17-5

2-acetyl-2-hydroxymethylcyclopentanone

2-acetyl-2,3-epoxycyclopentanone
89540-15-8

2-acetyl-2,3-epoxycyclopentanone

acetic acid
64-19-7,77671-22-8

acetic acid

Conditions
Conditions Yield
With oxygen; In acetone; at 20 ℃; for 6h; Irradiation;
2%
5%
4%
2%
18%
3%
17%
30%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

glutaric anhydride,
108-55-4

glutaric anhydride,

Conditions
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%
at 250 ℃; under 20 Torr; Rate constant; Equilibrium constant; var. temperature, var. pressure;
88%
With thionyl chloride; tris(2,2,2-trifluoroethyl)phosphite; In water; at 20 - 90 ℃; for 28h; Alkaline conditions;
85%
With acetic anhydride; for 1.5h; Reflux;
78%
With acetic anhydride; for 1h; Reflux;
67%
With acetyl chloride; at 40 ℃;
under 10 Torr;
With phosphorus pentachloride; at 110 ℃; anschliessend Erhitzen mit Glutarsaeure;
With thionyl chloride;
With methanesulfonic acid; 1,1'-oxalyldiimidazole; Yield given. Multistep reaction; 1.) acetonitrile, 40 deg C, 1 h; 2.) reflux, 2 h;
With 4-methyl-morpholine; methyl chloroformate; In tetrahydrofuran; at 20 ℃; for 1.5h;
under 10 Torr; beim mehrstuendigem Erhitzen;
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 80 ℃; for 24h; under 22501.8 Torr;
79 % Chromat.
With trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; for 2h;
With 2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid; In pentanonitrile; for 24h;
73 %Spectr.
gloutaric dichloride
2873-74-7

gloutaric dichloride

glutaric anhydride,
108-55-4

glutaric anhydride,

Conditions
Conditions Yield
With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; at -10 ℃; for 0.5h;
76%
(2,2'-bipyridine)Ni(II)((CH<sub>2</sub>)3COO)

(2,2'-bipyridine)Ni(II)((CH2)3COO)

glutaric anhydride,
108-55-4

glutaric anhydride,

Ni(CO)2(2,2'-bipyridine)
14917-14-7

Ni(CO)2(2,2'-bipyridine)

Conditions
Conditions Yield
With carbon monoxide; In dichloromethane; Schlenk tube contg. CH2Cl2 soln. of nickel complex evacuated and 1 atm of CO introduced; analyzed by GLC, GC-mass, and IR;
29%
2-acetylcyclopentanaone
1670-46-8

2-acetylcyclopentanaone

glutaric anhydride,
108-55-4

glutaric anhydride,

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

5,6-dioxo-n-heptanoic acid
85951-55-9

5,6-dioxo-n-heptanoic acid

2-acetyl-2-hydroxycyclopentanone
1262892-77-2

2-acetyl-2-hydroxycyclopentanone

2-acetoxycyclopentanone
52789-75-0

2-acetoxycyclopentanone

2-acetyl-2,3-epoxycyclopentanone
89540-15-8

2-acetyl-2,3-epoxycyclopentanone

Conditions
Conditions Yield
With oxygen; In tetrachloromethane; at 20 ℃; for 3h; Irradiation;
20%
2%
2%
8%
9%
43%
2-acetylcyclopentanaone
1670-46-8

2-acetylcyclopentanaone

1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

4-butanolide
96-48-0

4-butanolide

glutaric anhydride,
108-55-4

glutaric anhydride,

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

2-acetyl-2-hydroxycyclopentanone
1262892-77-2

2-acetyl-2-hydroxycyclopentanone

2-acetoxycyclopentanone
52789-75-0

2-acetoxycyclopentanone

2-acetyl-2-hydroxymethylcyclopentanone
1167443-17-5

2-acetyl-2-hydroxymethylcyclopentanone

2-acetyl-2,3-epoxycyclopentanone
89540-15-8

2-acetyl-2,3-epoxycyclopentanone

Conditions
Conditions Yield
With oxygen; In acetone; at 20 ℃; for 4h; Irradiation;
36%
22%
2%
1%
3%
3%
1%
13%
2-acetylcyclopentanaone
1670-46-8

2-acetylcyclopentanaone

4-butanolide
96-48-0

4-butanolide

glutaric anhydride,
108-55-4

glutaric anhydride,

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

4-acetoxybutyric acid
26976-72-7

4-acetoxybutyric acid

2-methylhexane-1,6-dioic acid
626-70-0

2-methylhexane-1,6-dioic acid

2-hydroxycyclopentanone
99440-98-9,473-84-7

2-hydroxycyclopentanone

Conditions
Conditions Yield
With dihydrogen peroxide; In tert-butyl alcohol; at 20 ℃; for 120h;
4%
2%
3%
2%
40%
40%

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