2-Butenoic acid, 1,1'-anhydride
Basic information
- CAS
623-68-7- Standard SMILES
CC=CC(=O)OC(=O)C=CC- InChIKey
VJDDQSBNUHLBTD-UHFFFAOYSA-N- Molecular formula
- C8H10O3
- Average molar mass
- 154.16 g/mol
- Monoisotopic mass
- 154.06299418
Names & identifiers
- Preferred name
- 2-Butenoic acid, 1,1'-anhydride
- IUPAC
- but-2-enoyl but-2-enoate
- English name
- Crotonic anhydride
- Molecular formula
- C8H10O3
- Molecular weight
- 154.17
Names & synonyms
2-Butenoic acid, 1,1'-anhydrideRefChem:1062627623-68-7but-2-enoyl but-2-enoate2-Butenoic acid, anhydride2-Butenoic acid anhydrideButensaureanhydridSCHEMBL16505DTXSID10870711VJDDQSBNUHLBTD-UHFFFAOYSA-NAKOS025244034DB-054144
Show more names
Nsc97397Wln: 2U1vov1U2CROTONIC ANHYDRIDE2-ButensureanhydridCROTONSAEUREANHYDRID2-butenoic anhydrideDicrotonic anhydrideBiscrotonic anhydridecrotonicacidanhydrideBut-2-enoic anhydride
NS00043849
Database identifiers
- CAS
623-68-7- PubChem CID
- 12189
- DTXSID
DTXSID10870711- EC Number
- 210-807-1
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 179
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Acid Anhydrides, Other
OdorSLIGHT ODOR
Density1.0397 @ 20 °C
Color/FormCOLORLESS LIQUID
SolubilitySOL IN ETHER
Boiling Point246-248 °C @ 766 MM HG
Melting Point72 °C
Refractive IndexINDEX OF REFRACTION: 1.4745 @ 20 °C/D; SADTLER REFERENCE NUMBER: 17150 (IR, PRISM); 10049 (IR, GRATING); 4494 (NMR)
Physical DescriptionColorless liquid; [HSDB]
Other Experimental PropertiesDECOMPOSES IN WATER; ALCOHOL
Physicochemical properties
- Melting point
- -20 °C · -20 °C
- Boiling point
- 131 °C/20 · 131 °C/20 mmHg
- Density
- 1.04 · 1.04
- vapor pressure
- 1 hPa · 1 hPa (25 °C)
- refractive index
- 1.48 · 1.48
- Flash point
- 113 °C · 113 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- soluble in Ether
- form
- clear liquid
- color
- Colorless to Light orange to Yellow
- InChI
- 1S/C8H10O3/c1-3-5-7(9)11-8(10)6-4-2/h3-6H,1-2H3/b5-3+,6-4+
- InChIKey
- VJDDQSBNUHLBTD-GGWOSOGESA-N
- SMILES
- O(C(=O)\C=C\C)C(=O)\C=C\C
- CAS DataBase Reference
- 623 · 623-68-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 521 PMQ949 · N521PMQ949
- EPA Substance Registry System
- 2 · 2-Butenoic acid, anhydride (623-68-7)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS09
- Signal word
- Danger
- Hazard statements
- 314 · H314-H400
- Precautionary statements
- 273 · P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
- Hazard Codes
- C
- Risk Statements
- 34 · 34
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (97.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Butenoic acid, anhydride
REACH registered substance: 2-butenoic anhydride (EC: 210-807-1)
Crotonic anhydride: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryLiquid causes severe skin and eye burns; A lachrymator; Vapor may cause bronchial and lung injury; [HSDB] Corrosive; Causes burns; Inhalation may cause chemical pneumonitis; [MSDSonline]
Hazard Classes and CategoriesSkin Irrit. 2 (97.7%)
Skin, Eye, and Respiratory IrritationsPOTENT EYE IRRITANTS IN THE VAPOR PHASE... /ACID ANHYDRIDES/
Safety & protection
Personal Protective Equipment (PPE)...SUITABLE EYE PROTECTION EQUIPMENT & RESP PROTECTIVE EQUIPMENT ARE NECESSARY. /ACID ANHYDRIDES/
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts
CONTACT WITH THE LIQUID WILL PRODUCE SEVERE SKIN & EYE BURNS. DELAYED VESICANT OR BULLOUS RESPONSES MAY OCCUR IN THE SKIN FOLLOWING CONTACT OF CONTAMINATED CLOTHING WITH SKIN. THERE MAY BE LITTLE SENSATION OF PAIN AT THE TIME OF CONTACT.
...KNOWN TO BE A SEVERE EYE AND SKIN IRRITANT. ...16 CASES OF CORNEAL BURNS /REPORTED/ IN HUMANS, 1 OF WHICH RESULTED IN LOSS OF VISION. /ACETIC ANHYDRIDE/
CONTAMINATION OF EYE BY SMALL AMT OF LIQ CAUSING...BURNING DISCOMFORT... FOLLOWED...BY INCR SEVERITY OF REACTION, WITH CORNEAL & CONJUNCTIVAL EDEMA. INTERSTITIAL CORNEAL OPACITY MAY DEVELOP... /ACETIC ANHYDRIDE/
/INVESTIGATORS/...MENTION...NOSE...IRRITATION & SUGGEST THAT BRONCHIAL & LUNG INJURY ARE LIKELY TO OCCUR FROM INHALATION OF ACETIC ANHYDRIDE VAPOR. ...MARKED LACRIMATOR... /ACETIC ANHYDRIDE/
POTENT EYE IRRITANTS IN THE VAPOR PHASE... /ACID ANHYDRIDES/
Non-Human Toxicity Excerpts
RATED 10 ON RABBIT EYES. 10= THE MOST SEVERE INJURIES OBSERVED AFTER 24 HR.
...INHALATION OF 2000 PPM BY RATS FOR 4 HOURS CAUSED DEATHS. IT CAUSED SEVERE EYE BURNS IN RABBITS. /ACETIC ANHYDRIDE/
...PENETRATE/S/ INTACT CORNEAL EPITHELIUM RAPIDLY & REACH IRIS IN CONCN HIGH ENOUGH TO CAUSE IRITIS. /ACETIC ANHYDRIDE/
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GQ6125000
- ridadr
- UN 3265 8/PG 3
- hs_code
- 2916 19 95
- Toxicity
- LD50 orally in Rabbit: 2061 mg/kg
- risk_code
- 34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS09
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible, corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H314-H400
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Eye Dam. 1Skin Corr. 1B
- Autoignition Temperature
- 290 °C
- Precautionary statements
- P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
- Hazardous Substances Data
- 623-68-7(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used in the production of organic chemicals; [HSDB]
IN SYNTHESES
General Manufacturing Information2-Butenoic acid, 1,1'-anhydride: ACTIVE
Applications
UsesCrotonic anhydride belongs to the organic chemical intermediates, is an important organic chemical raw materials, in the dyestuff industry is used as fur dyes, reactive dyestuffs intermediates; in the cosmetic industry is used as a high-grade cosmetics, such as skin creams, hair conditioners, shampoos, creams, and other additives; in the pharmaceutical industry as a pharmaceutical antimicrobial drugs, sulfonamides as raw materials for drugs. Crotonic anhydride can also be used in the preparation of butenoic acid fiber and coal dye, hair dye, color developer, epoxy resin curing agent, petroleum additives, rubber antioxidants and other synthetic.
UsesCrotonic anhydride is also known as 2-butenoic anhydride is commonly used as a precursor in the synthesis of polymers. Its reactive anhydride group makes it an effective acylating agent in esterification reactions, facilitating the formation of esters by reacting with alcohols.
Upstream & downstream products
Downstream products
Related reactions
0 records
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Compound notes
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