20485-53-4

Basic information

• Product Name: (1Z)-3-chloro-1-diazonioprop-1-en-2-olate
• Synonyms: 1-Chloro-3-diazo-2-propanone
• CAS NO: 20485-53-4
• Molecular Formula: C₃H₃ClN₂O
• Molecular Weight: 118.5217
• Mol File: 20485-53-4.mol

Chemical Properties

• Melting Point: 3 °C
• Boiling Point: 75 °C(Press: 13 Torr)
• CAS DataBase Reference: (1Z)-3-chloro-1-diazonioprop-1-en-2-olate(CAS DataBase Reference)
• NIST Chemistry Reference: (1Z)-3-chloro-1-diazonioprop-1-en-2-olate(20485-53-4)
• EPA Substance Registry System: (1Z)-3-chloro-1-diazonioprop-1-en-2-olate(20485-53-4)

Safety Data

• Hazardous Substances Data: 20485-53-4(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 79-04-9 chloroacetyl chloride 
• 15018-06-1 chloroacetyl bromide 

Downstream Products

• 534-07-6 1,3-Dichloroacetone 
• 60378-99-6 O,O-dimethyl 3-chloro-2-oxopropylphosphonate 
• 937-38-2 1-chloro-3-phenylpropan-2-one 
• 159301-44-7 3-chloro-2-oxopropyl p-toluenesulfonate 
• 57892-76-9 2-chloromethylimidazo[1,2-a]pyridine 
• 121332-43-2 3-bromo-2-oxopropyl 2-<4-(3-chloro-5-trifluoromethyl-2-pyridinyloxy)phenoxy>propionate 

Relevant articles and documents

Improved arndt-eistert synthesis of α-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger

A practical methodology to obtain α-diazoketones through an improved Arndt-Eistert synthesis is described. The method allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, witho

N-isocyanotriphenyliminophosphorane; a convenient reagent for the conversion of acyl chlorides into α-diazoketones

Aliphatic, aromatic and vinylic acid chlorides were converted into the corresponding α-diazoketones in synthetically useful yields by reaction with N-isocyanotriphenyliminophosphorane followed by treatment of the resulting N- unsubstituted α-ketohydrazido

Efficient routes to isotopically labelled epichlorohydrins ((chloromethyl) oxiranes)

Efficient routes are developed for the synthesis of variously labelled 2H- and 13C- labelled epichlorohydrins prepared from appropriately labelled acetic acids and sodium borodeuteride. The route is versatile and can be used for strategic location of isotopes at C-I, C-2 and C-3 of epichlorohydrin. By way of demonstration [2-13C]-, [2-2H]-, [3-2H2] and [2-2H, 3-2H2]-epithlorohydrins have been prepared. In addition the syntheses can be adapted for the preparation of enantiomerically pure and isotopically labelled epichlorohydrins.

P-H INTERNAL CARBENES. IV. FORMATION OF O,O-DIMETHYL-3-CHLORO-2-OXOPROPYLPHOSPHONATE

In reactions of ω-polychloro-substituted diazoacetones with dimethyl phosphite catalyzed by copper acetyloacetonate, products of carbenoid P-H introduction are formed. Reduction of the chlorine atoms in them is brought about as a result of a copper-catalyzed Atherton-Todd reaction.

INSERTION OF CARBENES INTO P-H BONDS. 5. SYNTHESIS OF NEW PHOSPHONATES AND PHOSPHINATES IN REACTIONS CATALYSED BY Cu, Pd, Rh, Ni COMPLEXES

Cu(OTf)2 and Cu(acac)2 were found to be the most effective catalysts in the reaction of diazo compounds Ph2CN2 (1a), EtOC(O)CHN2 (1b), MeOC(O)CHN2 (1c), MeC(O)CN2C(O)OMe (1d), ClCH2C(O)CHN2 (1e) and CH2N2 (1f) with hydrophosphoryl compounds (MeO)2P(O)H (2a), (t-BuO)2P(O)H (2b), Ph(MeO)P(O)H (2c), (EtO)2P(O)H (2d) and P(O)H (2e) resulting in P-C bond formations.Cu, Pd and Rh acetates and Ni(acac)2 have a much lower efficiency.Chlorines in Cl3CC(O)CH2P(O)(OMe)2 (3k) and Cl2CHC(O)CH2P(O)(OMe)2 (3l) are reduced in the copper catalysed Atherton-Todd reaction.Key words: Catalyst; diazo compound; hydrophosphoryl compound; insertion; phosphonate; phosphinate.

Alkylation of Benzene with α-Diazoketones via Cycloheptatrienyl Intermediates

Benzyl ketones can be synthesised efficiently from benzene and α-diazoketones with sequential catalysis by rhodium(II) trifluoroacetate and trifluoroacetic acid; the process involves cycloheptatrienyl intermediates.