3-(prop-2-enoyloxy)propanoic acid

• ChemBase ID: 144721
• Molecular Formular: C6H8O4
• Molecular Mass: 144.12532
• Monoisotopic Mass: 144.04225874
• SMILES: C=CC(=O)OCCC(=O)O
• Canonical SMILES: OC(=O)CCOC(=O)C=C
• InChI: InChI=1S/C6H8O4/c1-2-6(9)10-4-3-5(7)8/h2H,1,3-4H2,(H,7,8)
• InChIKey: CYUZOYPRAQASLN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(prop-2-enoyloxy)propanoic acid
• IUPAC Traditional name: 3-(prop-2-enoyloxy)propanoic acid
• Synonyms: 2-Carboxyethyl acrylate oligomers; 2-Carboxyethyl acrylate; β-(丙烯酰氧)丙酸低聚物; β-(丙烯酰氧)丙酸

Database IDs

• CAS Number: 24615-84-7
• MDL Number: MFCD00040709
• PubChem SID: 162238933; 24865464; 24879262
• PubChem CID: 90558

CALCULATED PROPERTIES

• Acid pKa: 4.101141
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7854834
• LogD (pH = 7.4): -2.471051
• Log P: 0.62717074
• Molar Refractivity: 32.8445 cm^3
• Polarizability: 12.94673 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Boiling Point: 103 °C/19 mmHg(lit.)
• Flash Point: 100 °C; 110 °C; 212 °F; 230 °F
• Density: 1.16 g/mL at 25 °C(lit.); 1.214 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.457(lit.)
• pH: 2.95 (10 wt. % in H2O)

Safety Information

• RTECS: UD3325250
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H314; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Grade: anhydrous
• Contains: 0.005% citric acid as inhibitor; 2000 ppm MEHQ; preserved with 0.01% BHA as inhibitor; 900-1100 ppm MEHQ as inhibitor
• Linear Formula: C3H3O2(C3H4O2)nH; CH2=CHCO2(CH2)2CO2H

DETAILS

Sigma Aldrich - 407585

Packaging
250 mL in poly bottle

Sigma Aldrich - 552348

Packaging
50, 500 mL in glass bottle
Application
Can be polymerized in solution or emulsion to produce acrylic, vinyl-acrylic, or styrenic-acrylic polymers with greater flexibility due to lower glass transition of itshomopolymer (<30C) and improved adhesion.
Features and Benefits
More reactive in its salt form than acylic acid, allowing high levels of incorporation over awide pH range. Also see Poly(2-carboxyethyl) acrylate, 407585.