(BROMOMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE Chemical Properties

Melting point:

234-236 °C (lit.)

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

Light beige to pink

Water Solubility 

almost transparency

BRN 

3579901

InChI

InChI=1S/C19H17BrP.BrH/c20-16-21(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19;/h1-15H,16H2;1H/q+1;/p-1

InChIKey

YFTMLUSIDVFTKU-UHFFFAOYSA-M

SMILES

[P+](CBr)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br-]

CAS DataBase Reference

1034-49-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-28

WGK Germany 

3

F 

3-10

HS Code 

29319019

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(BROMOMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE Usage And Synthesis

Chemical Properties

Light beige to pink powder

Uses

Reactant or reagent for synthesis of:

• Vernonia allenes and sesquiterpenoids
• Monohalovinylated pyrethoids with insecticidal activity
• Vitamin D analogs with anticancer activity

• Asymmetric substitution affecting optical properties of boradiazaindacene dyes
• Carbanionic rearrangements of halomethylenecyclobutanes

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Triphenylphosphine (15.00 g, 57.25 mmol) and dibromomethane (19.92 g, 114.48 mmol) were dissolved in dry toluene (125 mL). The reaction mixture was heated to reflux for 7 days. Upon completion of the reaction, the mixture was cooled to 0 °C, the precipitated white crystals were collected by filtration and washed with toluene to give the final bromomethyltriphenylphosphonium bromide (16.50 g, 66% yield).

References

[1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8180 - 8187
[2] Journal of the American Chemical Society, 2005, vol. 127, # 41, p. 14182 - 14183
[3] Chemistry - A European Journal, 2010, vol. 16, # 19, p. 5803 - 5811
[4] Journal of Organic Chemistry, 2012, vol. 77, # 5, p. 2149 - 2158
[5] Tetrahedron, 2003, vol. 59, # 7, p. 1021 - 1032

(BROMOMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE(1034-49-7)Related Product Information

• Bromomethyl methyl ether
• Bromomethylboronic acid, pinacol ester
• (Carbethoxymethyl)triphenylphosphonium bromide
• Tetrakis(hydroxymethyl)phosphonium sulfate
• Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate
• Triphenylphosphine hydrobromide
• SALOR-INT L159980-1EA
• (BROMOMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
• TETRAMETHYLPHOSPHONIUM BROMIDE
• Methyltriphenylphosphonium bromide
• (BROMODIFLUOROMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE