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Dimethyl (1-diazo-2-oxopropyl)phosphonate




Molecular Formula:C5H9N2O4P

Molecular Weight:192.1097

UN Number:

Haz Class:

Packing Group:

Synonyms: Dimethyl (1-Diazo-2-oxopropyl)phosphonate; 90965-06-3; dimethyl 1-diazo-2-oxopropylphosphonate; SQHSJJGGWYIFCD-UHFFFAOYSA-N; 96G79J0LR6; PHOSPHONIC ACID, P-(1-DIAZO-2-OXOPROPYL)-, DIMETHYL ESTER; (Z)-1-diazonio-1-dimethoxyphosphoryl-prop-1-en-2-olate; Dimethyl(1-diazo-2-oxopropyl)phosphonate; 1-Diazoacetonylphosphonic Acid Dimethyl Ester; Phosphonic acid, (1-diazo-2-oxopropyl)-, dimethyl ester; Dimethyl 1-Diazoacetonylphosphonate; 1-Diazo-1-dimethoxyphosphoryl-propan-2-one; OHIRA-BESTMANN REAGENT; alp.-Azido-alp.-(dimethyl phosphono)acetone; Bestmann-ohira reagent [MI]; Bestmann ohira reagent; Ohira Bestmann reagent; PubChem16454; alpha-Azido-alpha-(dimethyl phosphono)acetone; Ohira-Bestmann's reagent;; DIMETHYL (ACETYLDIAZOMETHYL)PHOSPHONATE; ACMC-209r7p; SCHEMBL17772; Bestmann reagent; C5H9N2O4P; P-(1-Diazo-2-oxopropyl)phosphonic acid dimethyl ester; CTK3J6757; DTXSID70455381; EBD5184; ACN-S001947; ACT02841; BCP08419; ANW-39539; STL433300; Ohira's reagent; ZINC40435381; AKOS006344979; dimethyl 1-diazo-2-oxopropylphoshonate; AB32016; ACN-001947; AM85386; AN-2426; LS40070; RP25148; RTC-069742; Ohira-bestmann phosphonate; WT81745; KS-000000Y8; dimethyl 1-diazo-2-oxopropylphos-phonate; dimethyl 2-oxo-1-diazo-propylphosphonate; AS-17907; SC-14491; AB0021208; AB2000720; DB-009693; dimethyl (1-diazo-2-oxopropyl)-phosphonate; (1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester; TC-069742; CS-0044356; D3546; D5048; dimethyl (1-diazo-2-oxo-propyl)-phosphonate; FT-0083406; V2455; A-2199; A843684; 1-diazo-2-oxo-propyl)-phosphonic acid dimethyl est; UNII-96G79J0LR6; J-520342; (1-diazo-2-oxopropyl)-phosphonic acid dimethyl ester; Ohira-Bestmann Reagent solution(~10% in acetonitrile); (Z)-1-diazonio-1-dimethoxyphosphoryl-1-propen-2-olate; p-(1-Diazo-2-oxopropyl)-phosphonic acid, dimethyl ester; Dimethyl (1-Diazo-2-oxopropyl)phosphonate (10% in Acetonitrile); 1-Diazoacetonylphosphonic Acid Dimethyl Ester; (1-Diazo-2-oxopropyl)phosphonic Acid Dimethyl Ester; Dimethyl 1-Diazoacetonylphosphonate; Ohira-Bestmann Reagent; Dimethyl (1-diazo-2-oxopropyl)phosphonate solution, ~10% in acetonitrile (H-NMR), >=96% (HPLC); BESTMANN-OHIRA REAGENT; -PHOSPHONICACIDDIMETHYLESTER; (1-Diazo-2-oxopropyl)phosphonic Acid Dimethyl Ester; CID11106189; Dimethyl (2-oxopropanimidoyl)phosphonate; Dimethyl (1-diazo-2-oxopropyl)phosphonate, 97% - 1G 1g; (1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester, 99+%; ? (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER; (Z)-1-diazonio-1-dimethoxyphosphorylprop-1-en-2-olate; (1-Diazo-2-oxopropyl)phosphonic Acid Dimethyl Ester; 1-Diazoacetonylphosphonic Acid Dimethyl Ester; Dimethyl (1-Diazo-2-oxopropyl)phosphonate; Dimethyl 1-Diazoacetonylphosphonate; Ohira-bestmann phosphonate; Dimethyl (1-diazo-2-oxo-propyl)phosphonate;

Keywords: 90965-06-3,MFCD07368360,1P0036MO,Dimethyl (1-diazo-2-oxopropyl)phosphonate,C5H9N2O4P

Catalog# Purity Size Price Dis. Price Availability Quantity
1P0036MO 97% 1g $14.00 $11.00 In Stock USA ADD TO CART BUY NOW
1P0036MO 97% 5g $42.00 $31.00 In Stock USA ADD TO CART BUY NOW
1P0036MO 97% 25g $165.00 $124.00 In Stock USA ADD TO CART BUY NOW

  • Dimethyl (1-diazo-2-oxopropyl)phosphonate, often referred to as the Bestmann-Ohira reagent, is a versatile compound in organic chemistry used primarily for the synthesis of alkynes. Its utility in chemical synthesis lies in its ability to act as a substitute for the traditional Horner-Wadsworth-Emmons (HWE) reaction.
    The Bestmann-Ohira reagent allows for the conversion of aldehydes into terminal alkynes. When reacted with an aldehyde, it undergoes a Wolff rearrangement to produce a carbene intermediate. This carbene can then insert into an O-H bond of methanol to give rise to an intermediate which eventually collapses to form the alkyne product upon base treatment. The phosphonate group stabilizes the diazo functionality and is an essential part of the mechanism that leads to the creation of the carbon-carbon triple bond.
    One of the key applications of this reagent is the synthesis of propargylic alcohols, which are useful intermediates for a multitude of derivatization reactions. These reactions can lead to the creation of complex molecules, ranging from pharmaceuticals to materials sciences. The high degree of functional group tolerance and the ability to introduce complex substituents onto the alkyne make this reagent particularly useful in the field of synthetic organic chemistry. Additionally, the Bestmann-Ohira reagent has been utilized in the construction of heterocycles, which are rings containing at least one atom other than carbon. These heterocycles are found in many biologically active molecules.
    Moreover, with the growing importance of click chemistry, the alkyne functionality introduced by the Bestmann-Ohira reagent is invaluable as it can be used in subsequent azide-alkyne cycloaddition reactions, which are pivotal for the synthesis of various polymeric materials, bioconjugates, and surface modifications.

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