(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide
• CAS No.: 59159-39-6
• Molecular Formula: C24H26 O2 P . Br
• Molecular Weight: 457.347
• Hs Code.: 29319019
• European Community (EC) Number: 628-357-3
• NSC Number: 82468
• DSSTox Substance ID: DTXSID00370018
• Mol file: 59159-39-6.mol

Synonyms:59159-39-6;(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide;(2-(tert-Butoxy)-2-oxoethyl)triphenylphosphonium bromide;(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide;MFCD00075527;[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-triphenylphosphanium;bromide;Phosphonium, [2-(1,1-dimethylethoxy)-2-oxoethyl]triphenyl-, bromide;(tert-Butoxycarbonylmethyl)tripheenyphosphonium bromide;[2-(tert-Butoxy)-2-oxoethyl]triphenylphosphonium Bromide;BARIUMHYDRIDE;SCHEMBL629737;DTXSID00370018;NSC82468;NSC-82468;AKOS008901294;CS-W009646;SY060199;B3928;FT-0640586;H11313;carbo-t-butoxymethyl triphenylphosphonium bromide;A832189;(2-tert-butoxy-2-oxoethyl)triphenylphosphonium bromide;(2-(tert-butoxy)-2-oxoethyl)triphenylphosphanium bromide;(2-(tert-Butoxy)-2-oxoethyl)triphenylphosphoniumbromide;(2-tert-Butoxy-2-oxoethyl)(triphenyl)phosphanium bromide;(tert-butoxycarbonylmethyl)-triphenylphosphonium bromide;(tert-butoxy carbonyl methyl) triphenyl phosphonium bromide;[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-triphenylphosphonium bromide;[2-[(2-methylpropan-2-yl)oxy]-2-oxidanylidene-ethyl]-triphenyl-phosphanium bromide

Chemical Property of (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide

Chemical Property:

• Melting Point: 178oC (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 39.89000
• Density: g/cm³
• LogP: 1.32620
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 456.08538
• Heavy Atom Count: 28
• Complexity: 418

Purity/Quality:

98%,99%, ^*data from raw suppliers

(Boc-methyl)triphenylphosphoniumBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: Reactant for:Rhodium-catalyzed asymmetric hydrogenation reactionsWittig reactionWittig methylenationPreparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via double aza-Michael addition reactionStereoselective preparation of of α-fluoro-α,β-unsaturated esters via deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydesWittig chain extension reactions

Technology Process of (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide

There total 2 articles about (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide 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: 99.0%

bromoacetic acid tert-butyl ester (5292-43-3) + triphenylphosphine (603-35-0) → (tert-butoxycarbonylmethyl)triphenylphosphonium bromide (59159-39-6)

Guidance literature:

In benzene; at 20 ℃; for 12h;

Reference yield:

→ (tert-butoxycarbonylmethyl)triphenylphosphonium bromide (59159-39-6)

Guidance literature:

Reference yield: 100.0%

(tert-butoxycarbonylmethyl)triphenylphosphonium bromide (59159-39-6) → (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 5h;

upstream raw materials:

bromoacetic acid tert-butyl ester

triphenylphosphine

Downstream raw materials:

(tert-Butoxycarbonylmethylene)triphenylphosphorane

4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester

tert-butyl (Z)-5-phenyl-2-pentenoate

5-phenyl-2(E)-pentenoic acid tert-butyl ester

Refernces

• 1、 Liu, Xin,Werner, Thomas. "Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides". . p. 1096 - 1104. Retrieved 2020/12/31.
• 2、 Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.. "Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes". supporting information. p. 9413 - 9418. Retrieved 2021/12/09.