3-Butenoic acid (Vinylacetic acid) may be utilized to prepare bicyclic 3,6-dihydro-1,2-oxazine. Strained bicyclic 3,6-dihydro-1,2-oxazine is a substrate for reaction with external olefins in the domino metathesis reaction.

Physicochemical Properties

Molecular Formula	C4H6O2
Molecular Weight	86.09
Exact Mass	86.036
CAS #	625-38-7
Related CAS #	28391-17-5
PubChem CID	32743
Appearance	Colorless to light yellow liquid（Density：1.013 g/cm3）
Density	1.0±0.1 g/cm3
Boiling Point	170.6±9.0 °C at 760 mmHg
Melting Point	−39 °C(lit.)
Flash Point	65.6±0.0 °C
Vapour Pressure	0.7±0.7 mmHg at 25°C
Index of Refraction	1.432
LogP	0.54
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Heavy Atom Count	6
Complexity	65.9
Defined Atom Stereocenter Count	0
SMILES	O([H])C(C([H])([H])C([H])=C([H])[H])=O
InChi Key	PVEOYINWKBTPIZ-UHFFFAOYSA-N
InChi Code	InChI=1S/C4H6O2/c1-2-3-4(5)6/h2H,1,3H2,(H,5,6)
Chemical Name	but-3-enoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References	[1]. Géraldine Calvet, et al. Domino metathesis of 3,6-dihydro-1,2-oxazine: access to isoxazolo[2,3-a]pyridin-7-ones. Org Lett. 2007 Apr 12;9(8):1485-8. [2]. M A Casado-Rodriguez, et al. Synthesis of vinyl-terminated Au nanoprisms and nanooctahedra mediated by 3-butenoic acid: direct Au@pNIPAM fabrication with improved SERS capabilities. Nanoscale. 2016 Feb 28;8(8):4557-64.
Additional Infomation	But-3-enoic acid is that isomer of butenoic acid having the double bond at position C-3. It is a conjugate acid of a but-3-enoate.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (1161.58 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (29.04 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (29.04 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	11.6158 mL	58.0788 mL	116.1575 mL
	5 mM	2.3232 mL	11.6158 mL	23.2315 mL
	10 mM	1.1616 mL	5.8079 mL	11.6158 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.