Isobutyric anhydride

HCID 7346CAS 97-72-3

Basic information

Standard SMILES
CC(C)C(=O)OC(=O)C(C)C
InChIKey
LSACYLWPPQLVSM-UHFFFAOYSA-N
Molecular formula
C8H14O3
Average molar mass
158.19 g/mol
Monoisotopic mass
158.09429431

Overview

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

Names & identifiers

Preferred name
Isobutyric anhydride
IUPAC
2-methylpropanoyl 2-methylpropanoate
English name
Isobutyric anhydride
Molecular formula
C8H14O3
Molecular weight
158.2

Names & synonyms

Isobutyric anhydride97-72-3Isobutyric acid anhydride2-METHYLPROPANOIC ANHYDRIDEPropanoic acid, 2-methyl-, anhydrideIsobutyryl anhydride2-Methylpropionic anhydrideisobutanoic anhydride2-Methylpropanoic acid anhydrideDTXSID7026609N85A80FJDTHSDB 5309
Show more names
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]

Database identifiers

CAS
97-72-3
PubChem CID
7346
DTXSID
DTXSID7026609
ChEMBL
CHEMBL1871691
ChEBI
CHEBI:84261
UNII
N85A80FJDT
EC Number
202-603-6
Nikkaji
J38.161F

Properties

Computed structural properties

XLogP
2
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
11

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Acid Anhydrides, Other

Flammable agents - 2nd degree

SpringerMaterials PropertiesDielectric constant
Density · 2 items

0.9535 @ 20 °C/4 °C

0.9535 @ 20°C

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

139 °F (NFPA, 2010)

59.4 °C

139 °F

Physicochemical properties

Melting point
-56 °C · -56 °C (lit.)
Boiling point
182 °C · 182 °C (lit.)
Density
0.954 g/mL · 0.954 g/mL at 25 °C (lit.)
vapor density
5.45 · 5.45 (vs air)
vapor pressure
10 mm · 10 mm Hg ( 67 °C)
refractive index
20 · n20/D 1.406(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 5 items

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]:
Hazards Summary · 1 item

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

Safety & protection

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 items

6.7 [mg/m3]

74 [mg/m3]

440 [mg/m3]

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

Toxicology

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

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.

Safety data

F
13-21
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
NQ5550000
ridadr
2922

Chemistry & industry

Uses & manufacturing

Uses · 3 items

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 items

All Other Basic Organic Chemical Manufacturing

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

Applications

UsesIsobutyric 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.

General DescriptionIsobutyric anhydride is a colorless liquid. Flash point 139°F. Burns skin and eyes. Vapors are heavier than air.

Preparation methods

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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海伟聂化工科技有限公司13046668259 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]

Additional notes

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

Related reactions

34 records

Linked notes

Loading…