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79522

Sigma-Aldrich

tert-Butyl P,P-dimethylphosphonoacetate

≥97.0% (GC)

Synonym(s):

tert-Butyl ((oxo)dimethoxyphosphino)acetate, tert-Butyl (dimethoxyphosphinyl)acetate, Dimethyl (tert-butoxycarbonyl)methylphosphonate

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25 ML
$286.30

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25 ML
$286.30

About This Item

Linear Formula:
(CH3O)2P(O)CH2COOC(CH3)3
CAS Number:
62327-21-3
Molecular Weight:
224.19
Beilstein/REAXYS Number:
4861886
MDL number:
MFCD00042939
UNSPSC Code:
12352108
PubChem Substance ID:
57652799
NACRES:
NA.22

$286.30

List Price$409.00Save 30%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

Quality Level

100

assay

≥97.0% (GC)

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.434

bp

86-87 °C/0.02 mmHg (lit.)

density

1.131 g/mL at 20 °C (lit.)

functional group

ester
phosphonate

SMILES string

COP(=O)(CC(=O)OC(C)(C)C)OC

InChI

1S/C8H17O5P/c1-8(2,3)13-7(9)6-14(10,11-4)12-5/h6H2,1-5H3

InChI key

SAZYDWOWLRDDRQ-UHFFFAOYSA-N

Application

Reactant for:
  • Preparation of phosphonate terminated PPH dendrimers as anti-HIV-1 agents
  • Preparation of monodehydro diketopiperazines from ketoacyl amino acid amides via acid-catalyzed cyclization
  • Preparation of α,β-unsaturated esters for use in the guanidine-catalyzed oxa-Michael addition
  • Preparation of myxopyronin B and desmethyl myxopyronin B analogs, with antibacterial activity and inhibitory activity against bacterial RNA polymerase
  • Allylation and subsequent ring-closing metathesis in presence of Grubbs′ catalyst or intramolecular rhodium-catalyzed cyclopropanation reactions

Other Notes

Horner-Wittig reagent giving preferentially (E)-α,β-unsat. esters which are mildly saponified with acid[1][2][3]. Synthesis of derivatives by reductive alkylation[4]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110.0 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCBK8197V
1406137
1385357
043474/1
017502/1

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W.J. Guilford et al.
Journal of the American Chemical Society, 109, 5013-5013 (1987)
A novel synthesis of (+/-)-vermiculine.
Y Fukuyama et al.
Journal of the American Chemical Society, 99(2), 646-647 (1977-01-19)
G.W.J. Fleet et al.
Journal of the Chemical Society. Perkin Transactions 1, 905-905 (1984)
C. Kuroda et al.
The Journal of Organic Chemistry, 51, 956-956 (1986)

Questions

  1. What solution is this dissolved in? Is it DMSO?

    1 answer

    1. The composition of this product is considered proprietary.

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