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Tetrahydrofurfuryl bromide

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CAS:1192-30-9
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  • 2021-08-12
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Tetrahydrofurfuryl bromide Basic information
Product Name:Tetrahydrofurfuryl bromide
Synonyms:Tetrahydrofurfuryl Bromide=2-(Bromomethyl)tetrahydrofuran;2-(bromomethyl)tetrahydro-fura;tetrahydro-2-(bromomethyl)-fura;TETRAHYDROFRUFRYL BROMIDE;Tetrahydrofurfuryl bromide, pract., 95%;Tetrahydrofurfuryl bromide, tech., 90%;tetrahydro-2-(bromomethyl)-furan;A-(BROMOMETHYL)TETRA HYDROFURAN
CAS:1192-30-9
MF:C5H9BrO
MW:165.03
EINECS:214-750-3
Product Categories:Furans, Benzofurans & Dihydrobenzofurans;Methyl Halides;Furans;Aromatic Hydrocarbons (substituted) & Derivatives;Furans, Benzofurans & Dihydrobenzofurans;Methyl Halides;Furan&Benzofuran
Mol File:1192-30-9.mol
Tetrahydrofurfuryl bromide Structure
Tetrahydrofurfuryl bromide Chemical Properties
Boiling point 170-171 °C (755 mmHg)
density 1.45
refractive index 1.4853-1.4873
Fp 63 °C
storage temp. Refrigerator
solubility Chloroform (Slightly), Methanol (Slightly)
form Oil
color Clear Light Yellow
BRN 102717
InChIInChI=1S/C5H9BrO/c6-4-5-2-1-3-7-5/h5H,1-4H2
InChIKeyVOHILFSOWRNVJJ-UHFFFAOYSA-N
SMILESO1CCCC1CBr
CAS DataBase Reference1192-30-9(CAS DataBase Reference)
EPA Substance Registry SystemFuran, 2-(bromomethyl)tetrahydro- (1192-30-9)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 24/25
RIDADR 1993
WGK Germany WGK 3
RTECS LU6000000
TSCA TSCA listed
HS Code 29321900
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Toxicitymouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03416,
MSDS Information
ProviderLanguage
2-(Bromomethyl)tetrahydrofuran English
ACROS English
ALFA English
Tetrahydrofurfuryl bromide Usage And Synthesis
Chemical PropertiesColorless to light yellow liqui
Uses(±)-Tetrahydrofurfuryl Bromide is a general chemical reagent used in the synthesis of tubulin polymerization inhibitors.
SynthesisIn a 500-ml three-necked flask equipped with a stirrer, thermometer, dropping funnel, and calcium chloride tube, place 96 g of redistilled PBr₃ and 50 ml of dry benzene. Add 15 g of dry pyridine dropwise with stirring over 15 minutes.
Cool the flask in an ice-salt bath to -5°C. Then, slowly add a mixture of 102 g of tetrahydrofurfuryl alcohol and 5 g of dry pyridine over 4 hours, maintaining the internal temperature between -5° and -3°C. Stir for an additional hour and allow the mixture to warm to room temperature.
Let the mixture stand for 24-48 hours. Transfer it to a Claisen flask, rinse with a little benzene, and remove the benzene by distillation under reduced pressure (bath temperature ≤90°C). Finally, distill the product under high vacuum (5-10 mm Hg) with the bath temperature up to 150-155°C.
The crude product is redistilled to give pure tetrahydrofurfuryl bromide, boiling at 69-70°C/22 mm Hg. The yield is 90-102 g (53-61%)[1].
Tetrahydrofurfuryl bromide
References[1] Org. Synth. 1943, 23, 88. DOI: 10.15227/orgsyn.023.0088.
Tag:Tetrahydrofurfuryl bromide(1192-30-9) Related Product Information
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