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670359

Sigma-Aldrich

Acetylthiomethyl-diphenylphosphine borane complex

≥98.0%

Synonym(s):

(T-4)-[S-[(Diphenylphosphino-κP)methyl] ethanethioate]trihydroboron

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About This Item

Empirical Formula (Hill Notation):
C15H18BOPS
CAS Number:
Molecular Weight:
288.15
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

Assay

≥98.0%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: ligand
reaction type: Staudinger Reaction

mp

52-55 °C

functional group

phosphine

storage temp.

2-8°C

SMILES string

B.CC(=O)SCP(c1ccccc1)c2ccccc2

InChI

1S/C15H15OPS.BH3/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3;1H3

InChI key

MXPNVFCCEGQGEN-UHFFFAOYSA-N

Application

  • Traceless Staudinger ligation reagent with borane protecting group.
  • The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.
  • After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.
  • Used in the synthesis of cyclic peptides.
Acetylthiomethyl-diphenylphosphine borane complex Ligation with DABCO

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

Sold under license for research and development purposes only. US Patent 6,974,884 and related patents apply

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

670359-250MG:
670359-BULK:
670359-1G:
670359-VAR:


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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