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Isobuttersäureanhydrid

Isobutyric anhydride

HCID 7346
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Grundinformationen

CAS
97-72-3
Standard-SMILES
CC(C)C(=O)OC(=O)C(C)C
InChIKey
LSACYLWPPQLVSM-UHFFFAOYSA-N
Summenformel
C8H14O3
Durchschnittliche Molmasse
158,19 g/mol
Monoisotopische Masse
158,09429431

Überblick

Isobutyric anhydride appears as a colorless liquid. Burns skin and eyes. Vapors are heavier than air.

Namen und Bezeichner

Bevorzugter Name
Isobutyric anhydride
IUPAC
2-methylpropanoyl 2-methylpropanoate
Lokaler Name
Isobuttersäureanhydrid
Englischer Name
Isobutyric anhydride
Summenformel
C8H14O3
Molmasse
158.2

Namen und Synonyme

Isobutyric anhydride97-72-3Isobutyric acid anhydride2-METHYLPROPANOIC ANHYDRIDEPropanoic acid, 2-methyl-, anhydrideIsobutyryl anhydride2-Methylpropionic anhydrideisobutanoic anhydride2-Methylpropanoic acid anhydrideDTXSID7026609N85A80FJDTHSDB 5309
Weitere Namen anzeigen
Isobutylic anhydrideDi(isobutyric acid)anhydrideIsobutyric anhydride, distilled(iso-C3H7CO)2OisobutyryloxideIsobutyl Anhydridesobutyric anhydride
Propanoic acid, 2-methyl-, 1,1'-anhydrideEINECS 202-603-6UN2530AI3-28521DTXCID406609CHEBI:84261EC 202-603-6ISOBUTYRIC ACID ANHYDRIDE [HSDB]

Datenbank-Bezeichner

CAS
97-72-3
PubChem CID
7346
DTXSID
DTXSID7026609

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2
Polarare Oberfläche (TPSA)
43,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
11
Formalladung
0
Komplexität
141

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Acid Anhydrides, Other

Flammable agents - 2nd degree

SpringerMaterials PropertiesDielectric constant
Density · 2 Einträge

0.9535 @ 20 °C/4 °C

0.9535 @ 20°C

Color/FormLIQUID
SolubilitySOL IN ALL PROP IN ETHER
Flash Point · 3 Einträge

139 °F (NFPA, 2010)

59.4 °C

139 °F

Boiling Point181.5 °C @ 734 MM HG
Melting Point · 2 Einträge

-53.5 °C

-53.5 °C

Vapor Pressure0.5 [mmHg]
Refractive Index

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 9.8% (37 of 376) of reports.

Danger

H301 (17.3%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 376 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Propanoic acid, 2-methyl-, anhydride

Propanoic acid, 2-methyl-, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanoic acid, 2-methyl-, 1,1'-anhydride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 09-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13208

2-Methylpropionic anhydride: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid Corrosive
Fire HazardsExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Health HazardsExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

Used as a chemical intermediate and flavor/aroma enhancer; [HSDB] Used for the esterification of cellulose and sucrose and to make odorants, peroxide catalysts, flavors, and perfumes; [CHEMINFO]

CHEMICAL INTERMEDIATE

Patented for use as flavor and/or aroma enhancer

U.S. Production2023: 8,500,000 - <25,000,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
General Manufacturing Information · 2 Einträge

All Other Basic Organic Chemical Manufacturing

Propanoic acid, 2-methyl-, 1,1'-anhydride: ACTIVE

Anwendungen

VerwendenIsobutyric anhydride was used in the synthesis of 4-O-isobutyryl derivative via reaction with octyl β-D-glucopyranoside in the presence of C2-symmetric chiral 4-pyrrolidinopyridine as a catalyst.

Darstellung

synthetischeIsobutyric anhydride is prepared from iso-Butyryl chloride and Sodium acetate, or: from iso-Butyryl chloride and Butyric acid with a catalyst.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

IsobuttersäureDichlormethanDicyclohexylcarbodiimid

Nachgelagerte Produkte

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 3027
HRID 3027als Eduktuspto-grants-1998_03
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Reaktionsgleichung von HRID 356809
HRID 356809als Eduktuspto-grants-1998_11
Reaktionsgleichung von HRID 363288
HRID 363288als Eduktuspto-grants-1999_02
Reaktionsgleichung von HRID 518749
HRID 518749als Eduktuspto-grants-2015_08
Reaktionsgleichung von HRID 552088
HRID 552088als Eduktuspto-grants-2011_05
Reaktionsgleichung von HRID 596981
HRID 596981als Eduktuspto-grants-1977_03
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ChEMBL
CHEMBL1871691
ChEBI
CHEBI:84261
UNII
N85A80FJDT
EC Number
202-603-6
Nikkaji
J38.161F
SADTLER REF NUMBER: 11317 (IR, PRISM), V516 (NMR); INDEX OF REFRACTION: 1.4061 AT 20 °C/D
Physical Description · 3 Einträge

Isobutyric anhydride appears as a colorless liquid. Burns skin and eyes. Vapors are heavier than air.

Liquid

Colorless liquid; [CHEMINFO]

Autoignition Temperature625 °F (329 °C)

Physikochemische Eigenschaften

Schmelzpunkt
-56 °C · -56 °C (lit.)
Siedepunkt
182 °C · 182 °C (lit.)
Dichte
0.954 g/mL · 0.954 g/mL at 25 °C (lit.)
Dampfdichte
5.45 · 5.45 (vs air)
Dampfdruck
10 mm · 10 mm Hg ( 67 °C)
Brechungsindex
20 · n20/D 1.406(lit.)
Flammpunkt
152 °F · 152 °F
storage temp.
30 °C · Store below +30°C.
Aggregatzustand
Liquid
Farbe
Clear colorless
Explosionsgrenze
1.09 %, · 1.09%, 87°F
Wasserlöslichkeit
decomposes
BRN
386267 · 386267
Dielectric constant
13.9 · 13.9(20℃)
InChI
1S/C8H14O3/c1-5(2)7(9)11-8(10)6(3)4/h5-6H,1-4H3
InChIKey
LSACYLWPPQLVSM-UHFFFAOYSA-N
SMILES
CC(C)C(=O)OC(=O)C(C)C
LogP
1.1 at · 1.1 at 25℃
CAS Datenbank
97 · 97-72-3(CAS DataBase Reference)
NIST chemische Informationen
2 · Propanoic acid, 2-methyl-, anhydride(97-72-3)
EPA chemische Informationen
Isobutyric anhydride (97-72-3)
Hazards Summary · 1 Eintrag

May cause burns to skin and eyes; [CAMEO] Reacts with moisture of the body to form butyric acid; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; [CHEMINFO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; Can be absorbed through skin; [MSDSonline]

Reactive GroupAnhydrides
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 Eintrag

ISOBUTYRIC ANHYDRIDE reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with a cids, strong oxidizing agents, alcohols, amines, and bases.

DOT Emergency Guidelines · 5 Einträge

/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Fire or Explosion: Flammable/combustible materials. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Health: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.

/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing is recommended for fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

For more DOT Emergency Guidelines (Complete) data for 2-METHYLPROPANOIC ANHYDRIDE (8 total), please visit the HSDB record page.

Air and Water ReactionsFlammable. Reacts exothermically with water or moisture-containing materials to form isobutyric acid.
Hazard Classes and Categories · 3 Einträge

Acute Tox. 3 (17.3%)

Flammable liquids - Category 4

Flammable agents - 2nd degree, Reactive agents - 1st degree

Shipment Methods and Regulations · 3 Einträge

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
First AidExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Nonfire Spill ResponseExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Isolation and EvacuationExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Protective Action Criteria (PAC) · 3 Einträge

6.7 [mg/m3]

74 [mg/m3]

440 [mg/m3]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts · 3 Einträge

THEIR PHYSIOLOGICAL EFFECTS GENERALLY RESEMBLE THOSE OF CORRESPONDING ACIDS, THEY ARE MORE POTENT EYE IRRITANTS IN VAPOR PHASE, & MAY PRODUCE CHRONIC CONJUNCTIVITIS. /ACID ANHYDRIDES/

REPEATED EXPOSURE TO ANHYDRIDES OF ORGANIC ACIDS CAN BE THE CAUSE OF ALLERGIC CONTACT DERMATITIS. /ANHYDRIDES OF ORG ACID/

STRONG IRRITANT TO TISSUE.

Sicherheitsdaten

F
13-21
wgk
3
tsca
TSCA listed
ridadr
2922
hs_code
2915 90 70
RTECS-Nr.
NQ5550000
risk_code
34-21/22
Toxizität
LD50 orally in Rabbit: 266 mg/kg LD50 dermal Rabbit 475 mg/kg
hazard_code
C
safety_code
26-36/37/39-45
hazard_class
8
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
97-72-3(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 OralSkin Corr. 1B
Selbstentzündungstemperatur
624 °F
IbudilastNERYL ISOBUTYRATESucrosedi(acetat)hexaisobutyrat1,5-Dimethyl-1-vinylhex-4-enylisobutyrat1-Boc-4-(4-methoxycarbonylphenyl)piperazinetert-Butyl 4-(2-cyanophenyl)piperazine-1-carboxylate4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid1-Boc-4-(4-carboxy-2-nitrophenyl)piperazine(S)-1-(3-Pyridyl)ethanol3,7-Dimethyloct-6-enylisobutyrat2,6-Dimethylheptan-3,5-dion1-(isobutyryl)pyrrolidin-2-one4-iodo-3-isopropyl-1H-pyrazolo[3,4-b]pyridineCHEMBRDG-BB 4002112

Ergänzende Hinweise

DefinitionChEBI: An acyclic carboxylic anhydride of isobutyric acid. Metabolite observed in cancer metabolism.