2-Carboxyethyl acrylate

HCID 90558
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Basic information

CAS
24615-84-7
Standard SMILES
C=CC(=O)OCCC(=O)O
InChIKey
CYUZOYPRAQASLN-UHFFFAOYSA-N
Molecular formula
C6H8O4
Average molar mass
144.12 g/mol
Monoisotopic mass
144.04225873

Names & identifiers

Preferred name
2-Carboxyethyl acrylate
IUPAC
3-prop-2-enoyloxypropanoic acid
English name
2-Carboxyethyl acrylate
Molecular formula
C6H8O4
Molecular weight
144.13

Names & synonyms

2-Carboxyethyl acrylate24615-84-72-Propenoic acid, 2-carboxyethyl ester3-Acryloyloxypropionic acidbeta-Carboxyethyl acrylate2-Carboxyethyl 2-propenoatebeta-(Acryloyloxy)propionic acidDTXSID2027834KM1E1216WRARONIX M 566C 800 (ACRYLATE)DTXCID807834
Show more names
B-CEAβ-Carboxyethyl acrylateβ-Carboxyethyl AcrylateL-61045sipomerb-ceaSolvay β-CEAEinecs 246-359-9RARECHEM AL BO 0311
EBECRYL BETA-CEARefChem:4681802-carboxyethyl ester 2-propenoic acid246-359-93-prop-2-enoyloxypropanoic acid3-(acryloyloxy)propanoic acid2-carboxyethylacrylateHydracrylic acid acrylate

Database identifiers

CAS
24615-84-7
PubChem CID
90558
DTXSID
DTXSID2027834
ChEMBL
CHEMBL3185107
UNII
KM1E1216WR
EC Number
246-359-9
Nikkaji
J52.386K

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
63.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
10

Experimental & physicochemical properties

Physical DescriptionLiquid

Physicochemical properties

Boiling point
103 °C/19 · 103 °C/19 mmHg (lit.)
Density
1.214 g/mL · 1.214 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.457(lit.)
Flash point
230 °F · >230 °F
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: soluble

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 7.1% (55 of 775) of reports.

Danger

H302 (71.2%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (57.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H314 (77.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H315 (14.8%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (73%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H319 (14.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P337+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 775 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 55 of 775 reports by companies.；There are 13 notifications provided by 720 of 775 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: 2-Propenoic acid, 2-carboxyethyl ester

2-Propenoic acid, 2-carboxyethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-carboxyethyl ester 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)

2-Propenoic acid, 2-carboxyethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (71.2%)；Acute Tox. 4 (57.7%)；Skin Corr. 1B (77.8%)；Skin Irrit. 2 (14.8%)；Eye Dam. 1 (73%)；Eye Irrit. 2 (14.8%)

Regulatory information

Regulatory Information · 3 items

Chemical: 2-Propenoic acid, 2-carboxyethyl ester

2-Propenoic acid, 2-carboxyethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-carboxyethyl ester 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)

2-Propenoic acid, 2-carboxyethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
UD3325250
ridadr
UN 3265 8/PG 2
hs_code
29161290

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 10,000,000 - <50,000,000 lb；2022: 10,000,000 - <50,000,000 lb；2021: 10,000,000 - <50,000,000 lb；2020: 10,000,000 - <50,000,000 lb
Consumer UsesMonomers
Industry UsesMonomers；Intermediate
General Manufacturing Information · 2 items

Paint and Coating Manufacturing；All Other Chemical Product and Preparation Manufacturing；Printing and Related Support Activities；Adhesive Manufacturing；Miscellaneous Manufacturing；All Other Basic Organic Chemical Manufacturing

2-Propenoic acid, 2-carboxyethyl ester: ACTIVE

Applications · 2 items

Description2-Carboxyethyl acrylate is a highly versatile monomer extensively used to produce diverse polymers. It can be polymerized in solution or emulsion, producing vinyl-acrylic, acrylic, or styrenic-acrylic polymers with greater flexibility due to lower glass transition of itshomopolymer (<30C) and improved adhesion. It finds applications in various polymer production processes, including those geared towards optical applications like optical fibers, optical waveguides, and optical lenses. Moreover, 2-Carboxyethyl acrylate is instrumental in synthesizing polymers used in energy storage applications, such as fuel cells, batteries, and supercapacitors. 2-carboxyethyl acrylate could be used as a new monomer in the gel casting of alumina. This low-toxic, water-soluble monomer modifies the ceramic suspensions' rheological properties and minimizes the oxygen inhibition's negative effect [1-3].

Uses2-Carboxyethyl Acrylate is used in the preparation of DNase enzyme derivatives that act as potent preventative material of bacterial adhesion and biofilm formation in biomaterials.

Preparation methods · 1 item

PreparationSynthesis of 1-ethoxyethyl acrylate (EEA) and protected 2-carboxyethyl acrylate (proCEA)EEA and proCEA were synthesized following a previously published procedure and distilled prior to use. For the synthesis of proCEA (Figure 1), phosphoric acid (109 mg, 1.11 mmol) was weighed into a dry round bottom flask in a glovebox and then taken outside the glovebox, taking care that the phosphoric acid stayed dry. 2-Carboxyethyl acrylate (80 g, 555 mmol) and ethyl vinyl ether (48 g, 666 mmol) were added and the reaction was stirred for two days at room temperature. Hydrotalcite (Mg6Al2(OH)16CO3·4H2O, ~1 g) was added, stirred for one hour and filtered off. Excess ethyl vinyl ether was removed under reduced pressure and the product was distilled under reduced pressure (80 °C, 1.3 mbar).Figure 1 Synthesis of proCEA

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

5 records
New reaction record

Compound notes

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