Bromomethyltriphenylphosphonium

Base Information

• Chemical Name: Bromomethyltriphenylphosphonium
• CAS No.: 1034-49-7
• Molecular Formula: C19H17 Br P . Br
• Molecular Weight: 436.126
• Hs Code.: 2931900090
• Nikkaji Number: J232.006A
• Mol file: 1034-49-7.mol

Synonyms:bromomethyltriphenylphosphonium;EINECS 213-857-2;NSC 193751;SCHEMBL3347;FKDAUYUOARWXGL-UHFFFAOYSA-N

Chemical Property of Bromomethyltriphenylphosphonium

Chemical Property:

• Appearance/Colour: Light beige to pink powder
• Melting Point: 234-236oC(lit.)
• PSA: 13.59000
• LogP: 1.33690
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: almost transparency
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 355.02513
• Heavy Atom Count: 21
• Complexity: 253

Purity/Quality:

98% ^*data from raw suppliers

(Bromomethyl)triphenylphosphonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](CBr)(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Reactant or reagent for synthesis of: Vernonia allenes and sesquiterpenoidsMonohalovinylated pyrethoids with insecticidal activityVitamin D analogs with anticancer activityReactant for: Asymmetric substitution affecting optical properties of boradiazaindacene dyesCarbanionic rearrangements of halomethylenecyclobutanesUsed for diferrocenyl molecular wires

Technology Process of Bromomethyltriphenylphosphonium

There total 6 articles about Bromomethyltriphenylphosphonium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

triphenylphosphine (603-35-0) + 1,1-dibromomethane (74-95-3) → (bromomethyl)triphenyl phosphonium bromide (1034-49-7)

Guidance literature:

In toluene; for 24h; Heating;

DOI:10.1021/jo0006223 DOI:10.1021/ja053431w

Reference yield: 52.0%

ethylene dibromide (106-93-4) + triphenylphosphine (603-35-0) → (bromomethyl)triphenyl phosphonium bromide (1034-49-7)

Guidance literature:

In toluene; for 24h; Heating;

Reference yield:

Methylenetriphenylphosphorane (19493-09-5) → (bromomethyl)triphenyl phosphonium bromide (1034-49-7) + Methyltriphenylphosphonium bromide (1779-49-3) + tribromomethyltriphenylphosphonium bromide (56506-89-9) + (dibromomethyl)(triphenyl)phosphonium bromide (56506-90-2)

Guidance literature:

With 1,2-dibromo-1,1,2,2-tetrafluoroethane; In diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)91362-0

upstream raw materials:

Hydroxymethyl-triphenyl-phosphonium-bromid

ethylene dibromide

triphenylphosphine

1,1-dibromomethane

Downstream raw materials:

9-(bromomethylene)-9H-fluorene

1,1,3-Trimethyl-2-(4-brom-3-methyl-butadien-1,3-yl)-cyclohexen-2, β-Ionyliden-brommethan

9-{2-[1-Bromo-meth-(Z)-ylidene]-4,4-diphenyl-but-3-enylidene}-9H-fluorene

1,3-di-tert-butyl-5-ethynylbenzene

Refernces

• 1、 Hatzimarinaki, Maria,Roubelakis, Manolis M.,Orfanopoulos, Michael. "Biradical intermediate in the [2 + 2] photocycloaddition of dienes and alkenes to [60]fullerene". . p. 14182 - 14183. Retrieved 2005.
• 2、 Li, Bi-Jie,Zhang, Su-Lei,Zhang, Wen-Wen. "Highly Enantioselective Synthesis of Propargyl Amide with Vicinal Stereocenters through Ir-Catalyzed Hydroalkynylation". supporting information. p. 6874 - 6880. Retrieved 2020/03/19.
• 3、 Feng, Xiujuan,Zhang, Haixia,Lu, Wenbo,Yamamoto, Yoshinori,Almansour, Abdulrahman I.,Arumugam, Natarajan,Kumar, Raju Suresh,Bao, Ming. "Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction". supporting information. p. 2727 - 2732. Retrieved 2017/06/13.