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Succinic anhydride

pharmaceutical raw materials
Succinic anhydride structure

Succinic anhydride 

structure
  • CAS No:

    108-30-5

  • Formula:

    C4H4O3

  • Chemical Name:

    Succinic anhydride

  • Synonyms:

    2,5-Furandione,dihydro-;Succinic anhydride;Dihydro-2,5-furandione;Butanedioic anhydride;2,5-Diketotetrahydrofuran;Succinic acid anhydride;Succinyl oxide;Tetrahydro-2,5-dioxofuran;Succinyl anhydride;Tetrahydro-2,5-furandione;Rikacid SA;NSC 8518;Oxolane-2,5-dione;Rikacid;1123596-58-6

  • Categories:

    Pharmaceutical Intermediates  >  Blood Glucose Regulators

Description

Succinic anhydride is a cyclic anhydride and an ADC linker extracted from patent WO2009064913A1. It can react with compound 4 of the patent to link the prodrug to an amine or hydroxy 1 group of a targeting polypeptide[1].


Succinic anhydride, also called dihydro-2,5-furandione and butanedioic anhydride , is an organic compound with the molecular formula C4H4O3. This colorless solid is the acid anhydride of succinic acid.


Succinic anhydride appears as colorless needles or white crystalline solid. Melting point 237°F. Sublimes at 239°F at 5 mm Hg pressure; and at 198°F and 1 mm Hg pressure. Moderately toxic and an irritant.|PelletsLargeCrystals|Solid|COLOURLESS CRYSTALS OR FLAKES.


Succinic anhydride appears as colorless needles or white crystalline solid. Melting point 237°F. Sublimes at 239°F at 5 mm Hg pressure; and at 198°F and 1 mm Hg pressure. Moderately toxic and an irritant.|Succinic anhydride is a cyclic dicarboxylic anhydride and a tetrahydrofurandione. It derives from a succinic acid.

Succinic anhydride Basic Attributes

100.07300

100.07

203-570-0

6RF4O17Z8J

1312

8518

DTXSID7021287

NEEDLES FROM ALC; RHOMBIC PYRAMIDS FROM CHLOROFORM OR CARBON TETRACHLORIDE|COLORLESS OR LIGHT-COLORED NEEDLES OR FLAKES|Orthorhombic prisms from abs alc.|Succinic anhydride forms rhombic pyramidal or bipyramidal crystals.

2932999099

Characteristics

43.37000

-0.5

fine white crystalline solid

1.503 g/cm3

119.6 °C

261 °C @ Press: 760 Torr

157°C

1.497

H2O: <0.1 g/100 mL at 21 ºC (decomposes)

Store at 0-5ºC

1 mm Hg ( 92 °C)

3.5 (vs air)

ODORLESS

BURNING TART TASTE

Henry's Law constant = 1.6X10-5 atm-cu m/mol at 25 °C (est)

Sublimes at 115 °C and 5 mm pressure, at 92 °C and 1.0 mm pressure, respectively.|Reacts with sulfydryl group of cysteine in neutral aqueous solution|Hydrolyzes very slowly, requiring more than 30 min to convert agitated aqueous suspension to succinic acid at 21 °C|Sublimes at 115 °C and 5 mmHg pressure, at 92 °C and 1.0 mmHg pressure|Hydroxyl radical reaction rate constant = 4.6X10-13 cu cm/molecule-sec at 25 °C (est)

Reacts slowly with water. Insoluble in water.

Anhydrides

SUCCINIC ANHYDRIDE reacts exothermically with water. Reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

-1537.9 kJ/mol

Safety Information

UN 3261 8 / PGII

1

R22; R36/37

S25

WN0875000

Xn

Stable. Incompatible with oxidising agents, strong acids, strong bases, alcohols, amines. Avoid exposure to water or moisture.

P260-P280-P284-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

H302-H314-H317-H334-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Succinic anhydride is dimerized to 1,6-dioxaspiro[4.4]nonane-2,7dione by heating with sodium hydroxide.

DHHS/NTP; Toxicology & Carcinogenesis Studies of Succinic Anhydride in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 373 (1990) NIH Publication No. 90-2828

P260; P280; P284; P303 + P361 + P353; P304 + P340 + P310; P305 + P351 + P338

Flash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P280, P285, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P321, P330, P333+P313, P342+P311, P363, P405, and P501|H302 (98.68%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P285, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P330, P333+P313, P337+P313, P342+P311, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 1287 companies from 33 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501

Fires involving this compound should be controlled using a Halon, carbon dioxide, or dry chemical extinguisher. A water spray may also be used. (NTP, 1992)|Use water spray, powder, alcohol-resistant foam, carbon dioxide.

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material at ambient temperatures, and protect it from moisture. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Combustible

Remove all ignition sources. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting.

Prevent dispersion of dust!|Inhalation /exposure can be prevented by/ local exhaust or breathing protection. Skin /exposure can be prevented by/ protective gloves. Eye /exposure can be prevented by/ safety goggles, or eye protection in combination with breathing protection if powder. /from table/|Do not eat, drink, or smoke during work. /from table/

The substance irritates the eyes, the skin and the respiratory tract.|A severe eye irritant.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is severely irritating to the eyes. The substance is irritating to the respiratory tract.

NO open flames.

PREVENT DISPERSION OF DUST! PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety goggles or eye protection in combination with breathing protection if powder.

Toxicity

LD50 Rat oral 1510 mg/kg

... Toxicology and carcinogenesis studies were conducted by administering suspensions of succinic anhydride (97% pure) in corn oil by gavage to groups of F344/N rats and B6C3F1 mice of each sex for ... 2 yr. ... Doses for the two yr studies were 0, 50, or 100 mg/kg to groups of 60 rats of each sex; 0, 38, or 75 mg/kg to groups of 50 male mice; and 0, 75, or 150 mg/kg to groups of 50 female mice. Succinic anhydride was administered as a suspension in corn oil by gavage, 5 days/wk week for 103 wk. Conclusions: Under the conditions of these 2 yr studies, there was no evidence of carcinogenic activity of succinic anhydride for male or female F344/N rats given 50 or 100 mg/kg succinic anhydride. There was no evidence of carcinogenic activity for male B6C3F1 mice given 38 or 75 mg/kg succinic anhydride or for female B6C3F1 mice given 75 or 150 mg/kg.

Succinic anhydride's production and use as a chemical reactant and intermediate, in the manufacture of pharmaceuticals and esters, as a hardener for resin(1), and as an acidulant in foods(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: The half-life for the hydrolysis of succinic anhydride is 4.3 minutes(SRC), based on a rate constant of 0.0027 1/sec at 25 °C(1). The major fate of succinic anhydride in soil is expected to be hydrolysis (SRC). Succinic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-3 mm Hg(2).|AQUATIC FATE: The half-life for the hydrolysis of succinic anhydride is 4.3 minutes(SRC), based on a rate constant of 0.0027 1/sec at 25 °C(1). The major fate of succinic anhydride in aquatic environments is expected to be hydrolysis(SRC). Bioconcentration of succinic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(SRC). Approximately 78% of the succinic anhydride added to activated sewage sludge was biodegraded within five days(2,3); however, hydrolysis is expected to be the principal fate of succinic anhydride in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), succinic anhydride, which has a vapor pressure of 1.5X10-3 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase succinic anhydride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 70 days (SRC), calculated from its rate constant of 4.56X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of succinic anhydride with photochemically-produced hydroxyl radicals has been estimated as 4.56X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 70 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Succinic anhydride hydrolyzes rapidly in water at room temperature to give succinic acid (half-life 4.3 min at 25 °C in initially neutral solution)(2).

Bioconcentration of succinic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(1). Experimental bioconcentration factors (chemical concentration in fish/chemical concentration in water) of succinic anhydride in fish (Golden ide) were less than 10(2,3).

Adsorption of succinic anhydride in soil is unlikely due its rapid hydrolysis(1).

Hydrolysis is expected to be the predominate fate of succinic anhydride in moist soil and water(1). Succinic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-3 mm Hg(2).

Occupational exposure to succinic anhydride may occur through inhalation of dust and dermal contact with this compound at workplaces where it is produced or used. Due to succinic anhydride's rapid hydrolysis, it is unlikely that the general population would be exposed to this chemical; however, succinic anhydride may exist as a vapor in dry air. (SRC)

Drug Information

SYMPTOMS: Symptoms of exposure to this chemical may include eye, skin, mucous membrane and respiratory tract irritation; it may blister and burn the skin on contact. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and fumes of carbon monoxide and carbon dioxide. It may cause eye, respiratory tract, mucous membrane and skin irritation. It is a suspected carcinogen. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest.


Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SIGNS AND SYMPTOMS/ The substance irritates the eyes, the skin and the respiratory tract.|/SIGNS AND SYMPTOMS/ Inhalation /may cause/ cough, shortness of breath, sore throat. Skin or eye /exposure may cause/ redness, pain. Ingestion /may cause/ diarrhea, nausea, vomiting. /from table/

succinic anhydride

The substance can be absorbed into the body by inhalation and by ingestion.

Cough. Shortness of breath. Sore throat.


Redness. Pain.

Succinic anhydride Use and Manufacturing

Methods of Manufacturing

Hydrogenation of maleic anhydride or fumaric acid; heating of succinic acid at elevated temperature and pressure.|...By treating succinic acid with diketene, succinyl chloride or acetic anhydride, or by reacting diethyl ester with boron chloride.|... Warming succinic acid with acetic anhydride, acetyl chloride, or phosphorus oxychloride.|Succinic anhydride is manufactured by catalytic hydrogenation of maleic anhydride. In the most widely used commercial process this reaction is performed in the liquid phase, at temperatures of 120-180 °C and at moderate pressures, in the range of 500-4000 kPa (72-580 psi). Catalysts mentioned in the patent literature include nickel, Raney nickel, palladium on different carriers, and palladium complexes.

Uses

It was used in the preparation of covalently cross-linked oxidized-alginate/N-succinyl-chitosan hydrogels, as injectable systems towards tissue engineering.It was also used in preparing functionalized oxide surfaces on a chip.


Adhesives and sealant chemicals


Adhesives and sealants

Production

2,5-Furandione, dihydro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1972) PROBABLY GREATER THAN 4.54X10+5 G|(1975) PROBABLY GREATER THAN 9.08X10+5 G|(1986) No Data|For more U.S. Production (Complete) data for SUCCINIC ANHYDRIDE (9 total), please visit the HSDB record page.

Grade: distilled.|...Available in US as commercial grade containing at least 99.5% of pure chemical, with maximum of 0.5% unsaturated compound...0.15% chlorides, 0.04% sulfates...and 20 mg/kg heavy metals.|Flake

Adhesive manufacturing|2,5-Furandione, dihydro-: ACTIVE|2,5-Furandione, dihydro-, mono-C11-13-alkenyl derivs.: ACTIVE|Anhydrous dentifrices containing an acid anhydride to maintain sweetener stability reported. Toothpaste containing 0.50 parts succinic anhydride is an example.|Succinic anhydride is...very useful dehydrating agent for removal of small amounts of moisture in...dry food mixtures which are later to be admixed with water. ...It is capable of taking up 20% of its weight of water, and the acid formed is desirable flavoring agent in many foods.

Titration method based on reaction of succinic anhydride with morpholine has been used for determining its purity, with an accuracy of +/-1%. Colorimetric determination is based on reaction of succinic anhydride with 2-nitrophenylhydrazine in basic medium.|Method for determining anhydrides...based on fluorescence of condensation product of succinic anhydride & 2-carboxy-isonitrosoacetanilide. Limits of detection are 5x10-10-5x10-9 M/liter, with error of 15-25%, Dziomko VM et al; New Luminescent Method For Determination of Acylating Agents, Zh Analyt Khim, 24, 1969, 927-930.|Techniques used for the determination of small concentrations of succinic acid or anhydride in various substances include gc or capillary gc in fruit and vegetables, eggs, rain, and liquors from wood; ion chromatography in rainwater, streams from the adipic acid process, and food; gc/ms in amber; hplc in wine and champagne, vinegar, beverages, apples, as well as milk and cheese; and polarography in -butyrolactone.

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Normal alkane RI, non-polar column, custom temperature program Capillary 1022. custom temperature program Program: not specified Brandi, F.Bar, E.Mourgues, F.Horvath, G.Turcsi, E.Giuliano, G.Liverani, A.Tartarini, S.Lewinsohn, E.Rosati, C.Study of Redhaven peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolismBMC Plant Biol.2011, 11, 24, 1-14.

Computed Properties

Molecular Weight:100.07
XLogP3:-0.5
Hydrogen Bond Acceptor Count:3
Exact Mass:100.016043985
Monoisotopic Mass:100.016043985
Topological Polar Surface Area:43.4
Heavy Atom Count:7
Complexity:102
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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  • Data: 2026-08-08
  • Price: 21000.00Yuan/ton
  • Change: 0

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