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15486-96-1 - 3-Bromopropionyl chloride, tech. 90% - A10846 - Alfa Aesar

A10846 3-Bromopropionyl chloride, tech. 90%

CAS Number
15486-96-1
Synonyms

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3-Bromopropionyl chloride, tech. 90%

MDL
MFCD00000746
EINECS
239-515-2

Chemical Properties

Formula
C3H4BrClO
Formula Weight
171.43
Boiling Point
54-56°/14mm
Flash Point
79°(174°F)
Density
1.72
Refractive Index
1.4950
Sensitivity
Moisture Sensitive
Solubility
Reacts with water.

Applications

3-Bromopropionyl chloride acts as an acrylate synthon by reaction with 2-oxazolidinone, followed by base-promoted elimination to form a Diels-Alder dienophile. Brominated poly (ethylene glycol) methacrylate (v-PEG-Br) which was synthesized by the reaction of poly (ethyleneglycol) methacrylate, v-PEG-OH with Mn = 526 Dalton and 3-bromopropionyl chloride. Used in the reduction of organic compounds by mixed hydrides. Used as reagent in Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists. Reaction of veratrole with 3- bromopropionyl chloride led to the formation of 15 in 82% yield, which on treatment with the Tebbe reagent13 led to the formation of styryl bromide 16 in 93% yield. Used in the preparation of ome new mono- and di-nitrogen-containing monobenzo-crowns. 3-Bromopropionyl chloride was used in the preparation of 1-chloro-4-bromo-2-butanone.

Notes

Moisture Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents, water, moisture, bases.

Literature References

Jeffrey D. Winkler,; Cheryl L. Muller,; Robert D. Scott. A new method for the formation of nitrogen-containing ring systems via the intramolecular photocycloaddition of vinylogous amides. A synthesis of mesembrine. J. Am. Chem. Soc.,1998, 110 (14), 4831-4832.

Robert F. Nystrom.Reduction of Organic Compounds by Mixed Hydrides. III. 3-Bromopropionic Acid, 3-Bromopropionyl Chloride, Methyl 3-Bromopropionate and Halides. J. Am. Chem. Soc.,1959, 81(3), 610-612.

Acts as an acrylate synthon by reaction with 2-oxazolidinone, followed by base-promoted elimination to form a Diels-Alder dienophile: Org. Synth. Coll., 9, 67 (1998).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H227

Causes severe skin burns and eye damage. Causes serious eye damage. Combustible liquid.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
605453
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2915.90
TSCA
Yes

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