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369799

Sigma-Aldrich

(tert-Butoxycarbonylmethylene)triphenylphosphorane

98%

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Synonym(s):
tert-Butyl(triphenylphosphoranylidene)acetate
Linear Formula:
(C6H5)3P=CHCO2C(CH3)3
CAS Number:
35000-38-5
Molecular Weight:
376.43
EC Number:
412-880-7
MDL number:
MFCD00075545
UNSPSC Code:
12352108
PubChem Substance ID:
24863043
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

152-155 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C24H25O2P/c1-24(2,3)26-23(25)19-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-19H,1-3H3

InChI key

ZWZUFQPXYVYAFO-UHFFFAOYSA-N

Related Categories

Application

Wittig reagent used in the synthesis of aldose reductase inhibitors, a podophyllotoxin derivative, and tautomycin.
Versatile Wittig reagent used in medicinal chemistry.

Signal Word

Danger

Hazard Statements

H301,H317,H319,H373,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1 - STOT RE 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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B L Mylari et al.
Journal of medicinal chemistry, 35(12), 2155-2162 (1992-06-12)
Benzothiazole side chains featured in zopolrestat (1a) and its congeners were incorporated into oxophthalazineacetic acid replacements, including indazole, pyridazinone, and pyridopyridazinone with a pendant acetic acid moiety. Potent aldose reductase inhibition activity among resulting compounds is as widespread as it
George Kokotos et al.
Journal of medicinal chemistry, 47(14), 3615-3628 (2004-06-25)
The Group IVA cytosolic phospholipase A(2) (GIVA PLA(2)) is a particularly attractive target for drug development because it is the rate-limiting provider of proinflammatory mediators. We previously reported the discovery of novel 2-oxoamides that inhibit GIVA PLA(2) [Kokotos, G.; et
The Journal of Organic Chemistry, 57, 2922-2922 (1992)
Tetrahedron Letters, 35, 4809-4809 (1994)
Fritz Sieber et al.
Phosphorus, sulfur, and silicon and the related elements, 180(3-4), 647-657 (2006-02-24)
Elemental selenium generated by the photobleaching of selenomerocyanine dyes forms conjugates with serum albumin and serum lipoproteins that are toxic to leukemia and selected solid tumor cells but well tolerated by normal CD34-positive hematopoietic stem and progenitor cells. Serum albumin

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