(Benzyloxycarbonylmethyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (Benzyloxycarbonylmethyl)triphenylphosphonium bromide
• CAS No.: 78385-36-1
• Molecular Formula: C27H24BrO2P
• Molecular Weight: 491.364
• Hs Code.: 2931900090
• European Community (EC) Number: 625-922-6
• DSSTox Substance ID: DTXSID20458943
• Mol file: 78385-36-1.mol

Synonyms:78385-36-1;(Benzyloxycarbonylmethyl)triphenylphosphonium bromide;(2-(Benzyloxy)-2-oxoethyl)triphenylphosphonium bromide;(2-oxo-2-phenylmethoxyethyl)-triphenylphosphanium;bromide;Phosphonium, [2-oxo-2-(phenylmethoxy)ethyl]triphenyl-, bromide;SCHEMBL180801;(2-benzyloxy-2-oxo-ethyl)-triphenyl-phosphonium bromide;DTXSID20458943;AVQABZVTPWROCF-UHFFFAOYSA-M;MFCD00191780;AKOS015913459;CS-W009621;(Cbz-methyl)triphenylphosphonium bromide;FT-0641674;E76046;(Benzyloxycarbonylmethyl)triphenyl-phosphonium br;A839407;(benzyloxycarbonyl)methyltriphenylphosphonium bromide;(2-(Benzyloxy)-2-oxoethyl)triphenylphosphoniumbromide;(benzyloxycarbonylmethyl)-triphenyl-phosphoniumbromide;[2-(Benzyloxy)-2-oxoethyl](triphenyl)phosphanium bromide

Chemical Property of (Benzyloxycarbonylmethyl)triphenylphosphonium bromide

Chemical Property:

• Melting Point: 124 °C (dec.)(lit.)
• PSA: 39.89000
• LogP: 1.72790
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 490.06973
• Heavy Atom Count: 31
• Complexity: 463

Purity/Quality:

98% ^*data from raw suppliers

(Benzyloxycarbonylmethyl)triphenylphosphonium bromide 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]
• Uses: Reactant for:Atypical aza-Morita-Baylis-Hillman mechanismThermal decompositionDouble aza-Michael reactionCyclodextrin derivativesStereoselective preparation of α,β-unsaturated carbonyl compounds via stereoselective Wittig olefination with aldehydes under solventless conditions or ultrasonicationSynthesis of [difluoro(alkenylphenyl)methyl]phosphonic acids on non-crosslinked polystyrene as inhibitors of PTP-1B via Wittig reaction

Technology Process of (Benzyloxycarbonylmethyl)triphenylphosphonium bromide

There total 3 articles about (Benzyloxycarbonylmethyl)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: 96.0%

triphenylphosphine (603-35-0) + Benzyl bromoacetate (5437-45-6) → benzyloxycarbonylmethyltriphenylphosphonium bromide (78385-36-1)

Guidance literature:

In toluene; at 20 ℃;

DOI:10.3987/COM-07-S(U)56

Reference yield: 96.0%

Benzyl bromoacetate (5437-45-6) → benzyloxycarbonylmethyltriphenylphosphonium bromide (78385-36-1)

Guidance literature:

With triphenylphosphine; In toluene; at 20 ℃; for 72h;

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyloxycarbonylmethyltriphenylphosphonium bromide (78385-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: sodium hydroxide / dichloromethane

With triethylamine; sodium hydroxide; In dichloromethane;

DOI:10.1021/acs.orglett.6b00981

upstream raw materials:

triphenylphosphine

Benzyl bromoacetate

benzyl alcohol

Downstream raw materials:

benzyl 4-(indan-2-yl)-2-butenoate

(E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester

(E)-(4R,5R)-4,5-Bis-benzyloxy-hex-2-enoic acid benzyl ester

(2E,6E)-(4R,5R)-4,5-Bis-benzyloxy-nona-2,6-dienoic acid benzyl ester

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