32315-10-9 Usage
Chemical Description
Triphosgene is a chemical compound with the formula C3Cl6O3, which is used as a reagent in organic synthesis.
Chemical Description
Triphosgene is a highly electrophilic reagent that is used to activate the carboxylate group in the alkali metal salt, leading to lactamization.
Chemical Description
Triphosgene is a reagent used to convert amines to isocyanates.
Uses
Used in Organic Synthesis:
Triphosgene is used as a carbonylating agent for aza-peptide synthesis, reacting with several alpha-amino acids to produce the corresponding N-carboxyanhydrides. It is also involved in the preparation of the esterification coupling reagent, di-2-thienyl carbonate, from 2(5H)-thiophenone.
Used in the Preparation of Thiocarbonates:
Triphosgene can be employed as a reagent to prepare thiocarbonates from thiols and alcohols through a one-pot, three-component reaction.
Used in the Synthesis of Substituted Azetidin-2-ones:
It is used in the synthesis of substituted azetidin-2-ones from acids and imines via ketene-imine cycloaddition reaction.
Used in the Production of Methyl (S)-2-Isocyanato-3-Phenylpropanoate:
Triphosgene is used to produce methyl (S)-2-isocyanato-3-phenylpropanoate from L-phenylalanine methyl ester hydrochloride in the presence of sodium bicarbonate.
Used in the Formation of Acyl Azides Derivatives:
It is employed in the preparation of acyl azides derivatives from various carboxylic acids and sodium azide.
Used in the Synthesis of Immunosuppressant Agent Cyclosporin:
Triphosgene is used in the solid-phase peptide synthesis of the immunosuppressant agent cyclosporin.
Used in the Production of Allyl Azides:
It is used in the synthesis of allyl azides from allyl alcohols and sodium azide in a one-pot method.
Used as a Useful Substitute for Phosgene:
Triphosgene is considered a useful substitute for phosgene in various chemical reactions, including chloroformylations, carbonylations, chlorinations, and dehydration reactions.
Used in the Preparation of 2-Chloronicotinaldehydes:
It is employed in the preparation of 2-chloronicotinaldehydes through cyclization of the corresponding enamides.
Toxicity
As a common production raw material for chemical enterprises, Sanguang gas is not listed in the list of hazardous chemicals, and its risk is not familiar and understood by many users, which often leads to decomposition and poisoning accidents. Therefore, it is of great practical significance to study the hazards and safety measures in the use of Triphosgene. Based on the characteristic identification of triphosgene, the hazards in the process of dissolution and reaction are identified and analyzed, and the corresponding safety measures in the use of Triphosgene are put forward according to the results of hazard identification and analysis. Triphosgene has gradually become the raw material for acyl chlorination in many enterprises because it is a non hazardous chemical, relatively stable material properties, easy transportation and easy treatment of tail gas. However, if the safety measures are not appropriate during the transportation, storage and use of triphosgene, it is very easy to cause poisoning accidents.
Reactions
The Triphosgene reaction is quenched very carefully by dropwise addition of 75 mL of saturated aqueous sodium sulfate solution ?(Notes 5 and 6). The resulting white granular precipitate or slurry is ?removed by vacuum filtration through Celite, and the filter cake is ?washed with three portions of 75 mL of chloroform .
Safety
Triphosgene's low vapor pressure makes it possible for it to reach concentrations that are considered toxicologically unsafe. While several properties of triphosgene are not yet readily available, it is known that it is extremely toxic if inhaled. A toxic gas is emitted if it comes in contact with water. There is a lack of information and variability regarding the proper handling of triphosgene. It is assumed to have the same risks as phosgene.
Synthesis
Triphosgene?is synthesized by exhaustive free radical chlorination of dimethyl carbonate:CH3OCO2CH3 + 6 Cl2 → CCl3OCO2CCl3 + 6 HClTriphosgene can be easily recrystallized from hot hexanes.
Purification Methods
It is a good solid substitute for phosgene (using a third mol per mol). Crystallise it from pet ether (b 60-80o), wash it with anhydrous cold Et2O, de-gas it at 200mm then dry at 0.1mm (over H2SO4). It has IR: max 900 and 1900 cm-1 . It is a lachrymator, is TOXIC and should be handled with gloves and in an efficient fume hood. [Hales et al. J Chem Soc 620 1957, Eckert & Forster Angew Chem, Int Ed Engl 26 894 1987, Aldrichimica Acta 21 47 1988, Beilstein 3 H 17, 3 I 8, 3 II 16, 3 III 36, 3 IV 33.]
Check Digit Verification of cas no
The CAS Registry Mumber 32315-10-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,2,3,1 and 5 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 32315-10:
(7*3)+(6*2)+(5*3)+(4*1)+(3*5)+(2*1)+(1*0)=69
69 % 10 = 9
So 32315-10-9 is a valid CAS Registry Number.
InChI:InChI=1/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
32315-10-9Relevant articles and documents
PROCESS FOR SYNTHESIS OF FIPRONIL
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Page/Page column 22-23, (2011/10/03)
A process for preparation of a trifluoromethylsulfinyl pyrazole compound of formula (I) from a compound of formula (III) is provided, wherein R, R1 and R2 represent a group containing halogen respectively and R3 represents a perhaloalkyl.
Synthesis of new fluorine substituted hydrazinecarboxamides and hydrazine carbothioamides having antitubercular and fungicidal activity
Madhukar Nalavde,Joshi
, p. 634 - 637 (2007/10/03)
3-(Trifluoromethyl)phenylhydrazine 3 on condensation with substituted phenylisocyanates 2a-f and phenylisothiocyanates 2g-1 gives N,2-diphenylhydrazinecarboxamides 4a-f and N,2-diphenylhydrazine carbothioamides 4g-1 which have been found to show antitubercular and antifungal activity.
Carbamazepine derivatives
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, (2008/06/13)
The present invention provides a novel carbamazepine hydrazide compound suitable for covalent attachment to a polymer particle reagent, having the general formula STR1 The present invention also provides a novel carbamazepine acid compound suitable for attachment to proteins for the production of carbamazepine immunogens. The carbamazepine antigen of the present invention has the following general structure: STR2 where X is C=O, CH2 or SO2 ; Y is C=O, CH2, SO2 ; R is an alkyl and P is a protein or a hapten.
A convenient synthesis of chiral oxazolidin-2-ones and thiazolidin-2-ones and an improved preparation of triphosgene
Falb,Nudelman,Hassner
, p. 2839 - 2844 (2007/10/02)
Oxazolidin-2-ones and thiazolidin-2-ones are conveniently prepared by condensation of L-serine, L-threonine and L-cysteine, respectively with triphosgene. The corresponding methyl esters may be subsequently obtained by quenching the reaction mixture with methanol, without prior need for the isolation of the free acids. An improved procedure for preparation of triphosgene using an internal cooling system is described.
Physostigmine derivatives.
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, (2008/06/13)
Physostigmine derivatives are described of the general formula: in which R is a linear or branched alkyl with three to nine C atoms, or benzyl, and their slats with pharmaceutically acceptable acids, which are particularly useful for the preparation of pharmaceutical compositions having a acetylcholinesterase inhibiting function
Nucleophilic Substitutions at Carbonic Acid Derivatives. XIX. Alcoholysis and Hydrolysis of Bis(trichloromethyl)carbonate
Cotarca, Livius,Bacaloglu, Radu,Marcu, Nicolae,Tarnaveanu, Alexandru
, p. 881 - 886 (2007/10/02)
The rate constants of hydrolysis and alcoholysis of bis(trichlormethyl)carbonate in dioxane have been determinated conductometrically.The effects of the water and alcohol concentrations, the temperature and deuterium have been studied.By the hydrolysis and alcoholysis of bis(trichlormethyl)carbonate the nucleophilic attack of water and alcohol is the rate-determining step, followed by a fast elimination of unstable trichloromethanol.
