(2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM TRIBROMIDE Property

Melting point:

158-160°C (dec.)

Water Solubility 

It reacts with water. Soluble in THF (25 g/100 mL), dichloromethane, insoluble in alcohol.

Sensitive 

Moisture Sensitive

BRN 

6262851

Safety

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

3261

HazardClass 

8

PackingGroup 

II

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Hazard statements

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

Precautionary statements

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

(2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM TRIBROMIDE Chemical Properties,Usage,Production

Uses

(2-Carboxyethyl)triphenylphosphonium tribromide, is a fine chemical and pharmaceutical intermediate. It is a bromine transfer agent for selective α-bromination of ketones and ketone acetals in the presence of double bonds, activated aromatic rings, esters or another free enolic position.

Synthesis

Synthesis of (2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM TRIBROMIDE: Ph3P (26.2 g, 0.1 mol), acrylic acid (7.2 g, 0.1 mol) and 49% HBr (50 mL) were stirred at rt until a homogeneous solution was obtained, then heated at 95-100 °C for 10 min, whereupon the mixture was cooled and glacial HOAc (240 mL) was added; bromine (9.8 mL) was added slowly with stirring to this mixture at 0 °C; after 0.5 h, the product was filtered and recrystallized from MeCN to give the perbromide (52.5 g, 91%);¹ a two step procedure involving bromination of the isolated intermediate monobromide can also be used.

Synthesis Reference(s)

1. Armstrong, V. W.; Chishti, N. H.; Ramage, R. TL 1975, 373

storage

(2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM TRIBROMIDE is irritant and moisture sensitive solid; store in a dry place. It should be handled in a fume hood.