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592684

Sigma-Aldrich

Bis(dimethylphosphino)methane

97%

Synonym(s):

DMPM

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About This Item

Linear Formula:
(CH3)2PCH2P(CH3)2
CAS Number:
64065-08-3
Molecular Weight:
136.11
MDL number:
MFCD00058731
UNSPSC Code:
12352001
PubChem Substance ID:
24881405
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

refractive index

n20/D 1.5060 (lit.)

bp

42 °C/12 mmHg (lit.)

density

0.86 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CP(C)CP(C)C

InChI

1S/C5H14P2/c1-6(2)5-7(3)4/h5H2,1-4H3

InChI key

MRNJHNUEBDGNEL-UHFFFAOYSA-N

Application

Reactant for:
  • Preparation of ruthenium carbonyl hydrido phosphanido diphosphine dinuclear complexes
  • Luminescent face-to-face dinuclear platinum(II) alkynyl phosphine complexes
  • Phosphorus-phosphorus bond and nuclear spin-spin coupling
  • Formation of a catalytic ruthenium(II)-triphos complex

Catalyst for:
  • Asymmetric alkylation of racemic secondary phosphines
  • Palladium-diphosphine catalyzed carbonylation of ethene

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H250

Precautionary Statements

P222 - P231 - P422

Hazard Classifications

Pyr. Liq. 1

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBG2515V
56496HKV
56496HK
15917CB
23019BB

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Graziella Cimino-Reale et al.
Journal of hematology & oncology, 10(1), 140-140 (2017-07-19)
Understanding the molecular/cellular underpinnings of diffuse malignant peritoneal mesothelioma (DMPM), a fatal malignancy with limited therapeutic options, is of utmost importance for the fruitful management of the disease. In this context, we previously found that telomerase activity (TA), which accounts
Giovanna Li Petri et al.
British journal of cancer, 123(4), 644-656 (2020-06-05)
Expression of proton-coupled folate transporter (PCFT) is associated with survival of mesothelioma patients treated with pemetrexed, and is reduced by hypoxia, prompting studies to elucidate their correlation. Modulation of glycolytic gene expression was evaluated by PCR arrays in tumour cells
Jana Elias et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(26), 6553-6561 (2019-03-02)
A new boron-boron dehydrocoupling strategy was established, providing convenient access to some diborane(4) compounds starting from simple borane adducts under mild conditions. In contrast to the traditional pathway using a reducing reagent, the reduction from BIII to BII was paradoxically
Sophie Vermersch et al.
Pediatric blood & cancer, 67(6), e28286-e28286 (2020-04-12)
Malignant and multicystic peritoneal mesotheliomas are extremely rare tumors in children, developing from mesothelial cells. No specific guidelines are available at this age. We performed a retrospective analysis of all identified children (< 18-year-old) treated in France from 1987 to 2017 for
Michelandrea De Cesare et al.
Oncotarget, 6(15), 13119-13132 (2015-05-08)
Survivin, which is highly expressed and promotes cell survival in diffuse malignant peritoneal mesothelioma (DMPM), exclusively relies on exportin 1 (XPO1/CRM1) to be shuttled into the cytoplasm and perform its anti-apoptotic function. Here, we explored the efficacy of Selective Inhibitors

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