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(R)-Glycidyl butyrate

Product Name(R)-Glycidyl butyrate
CAS60456-26-0
MFC7H12O3
MW144.17
EINECS611-977-3
MOL File60456-26-0.mol

Chemical Properties

alpha	-30 º (c=neat)
Boiling point	197 °C(lit.)
Density	1.032 g/mL at 20 °C(lit.)
refractive index	n20/D 1.428(lit.)
Flash point	185 °F
storage temp.	Inert atmosphere,2-8°C
solubility	Chloroform, Ethyl Acetate
form	Liquid
Specific Gravity	1.018
color	Clear colorless to slightly yellow
optical activity	[α]25/D 31°, neat
Water Solubility	insoluble
BRN	5246881
InChI	1S/C7H12O3/c1-2-3-7(8)10-5-6-4-9-6/h6H,2-5H2,1H3/t6-/m1/s1
InChIKey	YLNSNVGRSIOCEU-ZCFIWIBFSA-N
SMILES	CCCC(=O)OC[C@H]1CO1
CAS DataBase Reference	60456-26-0(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	22-36/37/38-42/43
Safety Statements	23-36/37-45-36/37/39-26
RIDADR	2810
WGK Germany	3
F	10-21
HazardClass	6.1
PackingGroup	III
HS Code	29156000
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Resp. Sens. 1 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
(R)-Glycidyl butyrate	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(R)-Glycidyl butyrate is a reagent used in the synthesis of glycidol, a stabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraul ic fluids; epoxy resin diluent.

Uses

(2R)-2-Oxiranylmethyl Ester Butanoic Acid is a reagent used in the synthesis of glycidol, a stabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraulic fluids; epoxy resin diluent.

Reactions

Research demonstrate that phosphonium tetraborane Lewis pair (P4B-Br) enables the ring-opening polymerization (ROP) of (R)-Glycidyl butyrate (RGB) at room temperature with a turnover number (TON) of 200, yielding α-Br/ω-OH and α-OH/ω-OH terminated poly(glycidyl butyrate) (PRGB)^[4].

Synthesis

Butanoic acid, (2S)-3-chloro-2-hydroxypropyl ester

890051-54-4

60456-26-0

(S)-3-Chloro-1,2-propanediol 1-(n-butyrate) (50.0 g, 0.277 mol, optical purity 99% ee) was used as a raw material and dissolved in 1,2-dichloroethane (200 ml). Potassium tert-butoxide (32.6 g, 0.291 mol) was added to the solution under cooling conditions in an ice bath. The reaction mixture was stirred for 1 hour. After completion of the reaction, the mixture was transferred to a partition funnel and washed twice with water (200 ml). The organic layer was concentrated under reduced pressure to give (R)-glycidyl butyrate (28.7 g, 72.0% yield). The optical purity of the target product was 99% ee as determined by HPLC.

References

[1] Letters in Organic Chemistry, 2011, vol. 8, # 4, p. 242 - 243
[2] Tetrahedron Letters, 2006, vol. 47, # 20, p. 3453 - 3457
[3] Patent: US2004/24254, 2004, A1. Location in patent: Page 6
[4] Li, L., Liu, M., Wang, Z., Wang, X., & Li, Z. (2026). Synthesis of glycerol-based (co)polyethers via ring-opening polymerization of glycidyl butyrate catalyzed by a one-component phosphonium tetraborane Lewis pair. Polymer Chemistry, 17 8, Pages 856-864. https://doi.org/10.1039/d5py01129a

(R)-Glycidyl butyrate

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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