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(R)-Glycidyl butyrate

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Name

(R)-Glycidyl butyrate

EINECS -0
CAS No. 60456-26-0 Density 1.069 g/cm3
PSA 38.83000 LogP 1.11860
Solubility insoluble in water Melting Point N/A
Formula C7H12O3 Boiling Point 196.3 °C at 760 mmHg
Molecular Weight 144.17 Flash Point 85 °C
Transport Information UN 2810 Appearance Colorless to light yellow liquid
Safety 23-36/37-45-36/37/39-26 Risk Codes 22-36/37/38-42/43
Molecular Structure Molecular Structure of 60456-26-0 ((R)-Glycidyl butyrate) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Butanoicacid, (2R)-oxiranylmethyl ester (9CI);Butanoic acid, oxiranylmethyl ester,(R)-;(-)-Glycidyl butyrate;(2R)-(-)-Glycidyl butyrate;(R)-(-)-Glycidylbutyrate;

Article Data 12

(R)-Glycidyl butyrate Synthetic route

890051-54-4

butyric acid-3-chloro-(S)-2-hydroxy-propyl ester

60456-26-0

(R)-glycidyl butyrate

Conditions
ConditionsYield
With sodium hydroxide for 12h; Reflux;90%
With potassium phosphate; [(S,S)-(salen)Co(II)]2*Al(NO3)3 In various solvent(s) at 20℃;40%
With potassium tert-butylate In 1,2-dichloro-ethane at 0℃; for 1h;72.0 %Chromat.
141-75-3

butyryl chloride

60456-23-7

(S)-oxiranemethanol

60456-26-0

(R)-glycidyl butyrate

Conditions
ConditionsYield
With calcium oxide In 2-methyltetrahydrofuran at 20℃; for 6h; Green chemistry; chemoselective reaction;89%
2461-40-7

(+/-)-glycidyl butyrate

A

5309-42-2

1-sn-monobutyroylglycerol

B

60456-26-0

(R)-glycidyl butyrate

C

126254-87-3

(S)-2,3-dihydroxypropyl butyrate

Conditions
ConditionsYield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;A n/a
B 46%
C n/a
2461-40-7

(+/-)-glycidyl butyrate

A

60456-26-0

(R)-glycidyl butyrate

B

126254-87-3

(S)-2,3-dihydroxypropyl butyrate

Conditions
ConditionsYield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;A 46%
B n/a
2461-40-7

(+/-)-glycidyl butyrate

A

60456-26-0

(R)-glycidyl butyrate

B

57044-25-4

(R)-oxiranemethanol

Conditions
ConditionsYield
With sodium phosphate buffer; 25 kDa lipase-like enzyme immobilized on DEAE-Sepharose In 1,4-dioxane; water at 25℃; for 10h; pH=7.00;A n/a
B 45%
With thermomyces lanuginosa In 1,4-dioxane; aq. phosphate buffer at 30℃; for 2h; pH=7; Temperature; Resolution of racemate; Enzymatic reaction;A n/a
B n/a
2461-40-7

(+/-)-glycidyl butyrate

A

890051-54-4

butyric acid-3-chloro-(S)-2-hydroxy-propyl ester

B

890051-57-7

butyric acid-3-chloro-(R)-2-hydroxy-propyl ester

C

60456-26-0

(R)-glycidyl butyrate

D

65031-96-1

(S)-glycidyl butyrate

Conditions
ConditionsYield
With hydrogenchloride; (R,R)-[Co(salen)]2*GaCl3 In diethyl ether at 0 - 4℃; for 4h;A 45%
B n/a
C n/a
D 43%
2461-40-7

(+/-)-glycidyl butyrate

A

60456-26-0

(R)-glycidyl butyrate

B

126254-87-3

(S)-2,3-dihydroxypropyl butyrate

C

65031-96-1

(S)-glycidyl butyrate

Conditions
ConditionsYield
With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water In tetrahydrofuran at 0℃; for 12h; Jacobsen rearrangement; optical yield given as %ee;A 40%
B n/a
C n/a
2461-40-7

(+/-)-glycidyl butyrate

A

60456-26-0

(R)-glycidyl butyrate

B

57044-25-4

(R)-oxiranemethanol

C

60456-23-7

(S)-oxiranemethanol

Conditions
ConditionsYield
With Rhizopus oryzae lipase on dextran sulfate coated Sepabeads In water at 25℃; pH=7; Enzymatic reaction; Title compound not separated from byproducts;
106-31-0

butanoic acid anhydride

60456-23-7

(S)-oxiranemethanol

60456-26-0

(R)-glycidyl butyrate

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 1h; Product distribution / selectivity;n/a
123-20-6

vinyl n-butyrate

60456-23-7

(S)-oxiranemethanol

60456-26-0

(R)-glycidyl butyrate

Conditions
ConditionsYield
With Rhizopus oryzae lipase/polystyrene fibers at 35℃; for 1h; Kinetics;

(R)-Glycidyl butyrate Chemical Properties

IUPAC Name:[(2R)-oxiran-2-yl]methyl butanoate
Molecular Formula:C7H12O3
Molecular Weight:144.168380 g/mol
Appearance:Yellow liquid
Boiling Point:197 °C(lit.)
Flash Point:185 °F
alpha:-30 °(c=neat)
density:1.032 g/mL at 20 °C(lit.)
refractive index:n20/D 1.428(lit.)
storage temp.:  2-8°C
Water Solubility:insoluble
BRN:5246881
CAS DataBase Reference:60456-26-0(CAS DataBase Reference)
Synonyms of (R)-4-Glycidyl butyrate(60456-26-0):
(2R)-(-)-GLYCIDYL BUTYRATE;BUTYRIC ACID (R)-GLYCIDYL ESTER;(R)-(-)-GLYCIDYL BUTYRATE;(R)-GLYCIDYL BUTYRATE;(R)-OXIRANE-2-METHANOL BUTYRATE;R(-)-OXIRANE-2-METHANOL BUTYRATE;(R)-4-GLYCIDYL BUTYRATE;(R)-2,3-EPOXYPROPYL N-BUTYRATE
Categories of (R)-4-Glycidyl butyrate(60456-26-0):
Small molecule;chiral;API intermediates;CHIRAL COMPOUNDS;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound;Esters;Ring Systems

(R)-Glycidyl butyrate Uses

(R)-4-Glycidyl butyrate(60456-26-0) is used as a  intermediate for synthesis of linezolid.

(R)-Glycidyl butyrate Safety Profile

Safety Information of (R)-4-Glycidyl butyrate(60456-26-0):
Hazard Codes:Xn,Xi 
Risk Statements:22-36/37/38-42/43
22:Harmful if swallowed 
36/37/38:Irritating to eyes, respiratory system and skin 
42/43:May cause sensitization by inhalation and skin contact  
Safety Statements:23-36/37-45-36/37/39-26
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 
36/37:Wear suitable protective clothing and gloves 
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
36/37/39:Wear suitable protective clothing, gloves and eye/face protection 
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice  
RIDADR:2810
WGK Germany:3
F:10-21
HazardClass:6.1
PackingGroup:III

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