541-88-8 Usage
Description
Chloroacetic anhydride is an organic compound with the chemical formula (ClCH2CO)2O. It is a brownish semi-transparent crystalline solid that is commonly used in various chemical reactions and synthesis processes.
Uses
1. Used in the Chemical Industry:
Chloroacetic anhydride is used as a reagent for the N-acetylation of amino acids in alkaline solutions. This process is essential for the modification of amino acid properties and their subsequent use in various applications.
2. Used in the Textile Industry:
Chloroacetic anhydride is used as a reactant in the preparation of cellulose chloroacetates. These derivatives are important for the development of new materials with specific properties, such as increased water solubility and improved reactivity.
3. Used in the Pharmaceutical Industry:
Chloroacetic anhydride has been utilized in the synthesis of various pharmaceutical compounds, such as 3,3-bis(sulfonato)-4,4-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive, and photo-switchable cross-linker. This cross-linker is valuable for the development of new drug candidates and the study of protein-protein interactions.
4. Used in the Synthesis of D,L-7-azatryptophan:
Chloroacetic anhydride is employed in the synthesis of D,L-7-azatryptophan, a modified tryptophan derivative with potential applications in the pharmaceutical and biotechnology industries.
Chloroacetic anhydride is also used in the synthesis of 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2,1:4,5]-2-oxazoline, a complex organic molecule with potential applications in the development of new drugs and bioactive compounds.
Preparation
chloroacetic anhydride Synthesis: Powdered s odium monochloroacetate(113.3g, 1.138 mol) was added slowly for a period of 15 min at room temperature (which slowly raises to 60°C) to a stirred solution of commercially available chloroaceyl chloride (127.5g, 1mol) in dry benzene (136mL) was refluxed for 9h. Salts were filtered off, the filtrate was cooled to room temperature, diluted with n-hexane and further cooled to 0°C. The solid separated was then filtered, washed with dry hexane and dried to yield chloroacetic anhydride as white crystalline compound in 60% yield (80g); mp=46-49°C [Lit. mp=46°C]. Alternatively, the benzene layer was directly subjected to high vacuum distillation.The product collected at 109-10°C at 10mm vacuum on cooling chloroacetic anhydride in lump form in 70 % yield (93g). It was observed that, the latter method gives anhydride in lump form while the former method gives in crystalline form.
Purification Methods
Crystallise the it from *benzene. [Eglinton et al. J Chem Soc 1860 1954, Beilstein 2 IV 487.]
Check Digit Verification of cas no
The CAS Registry Mumber 541-88-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 1 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 541-88:
(5*5)+(4*4)+(3*1)+(2*8)+(1*8)=68
68 % 10 = 8
So 541-88-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H4Cl2O3/c5-1-3(7)9-4(8)2-6/h1-2H2
541-88-8Relevant articles and documents
Synthesis process of chloroacetic anhydride
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Paragraph 0018-0031, (2018/07/30)
The invention discloses a synthesis process of chloroacetic anhydride, and relates to the technical field of medicine synthesis. The problems that the existing process can easily generate corrosion onthe equipment, and the high-temperature and high-vacuum conditions are needed are solved. The process comprises the following steps of chloroacetic anhydride solution preparation: dripping sodium chloroacetate and aprotic solvents into a reaction bottle; performing heating to 40 to 50 DEG C; performing stirring; slowly dripping chloroacetyl chloride; completing the dripping in 2 to 3 hours; continuously performing stirring for 1 to 2 hours under the condition of 40 to 50 DEG C; performing filtering; washing filter cake with aprotic solvents; performing filtering; merging filter liquid to obtain a chloroacetic anhydride solution; purifying the chloroacetic anhydride; adding the chloroacetic anhydride solution into a reactor; adding petroleum ether; performing cooling to 35 to 40 DEG C; continuously performing stilling until solid is separated out; lowering the temperature to 0 to 5 DEG C; performing heat insulation stirring for 1 to 2 hours; performing filtering; washing the filter cake with petroleum ether; drying the filter cake to obtain white crystal solid products which are chloroacetic anhydride. The process has the advantages that hydrogen chloride gas is not generated; theanti-corrosion requirement on the equipment is low; the reaction conditions are mild; the energy consumption is reduced.
GLUCOKINASE ACTIVATORS
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Page/Page column 60, (2009/04/24)
Compounds are provided for use with glucokinase that comprise the formula: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.
Detection of Elusive Chloro- and Bromo Substituted Ozonides by Nucleophilic Substitution Reactions
Griesbaum, Karl,Schlindwein, Konrad,Bettinger, Herbert
, p. 307 - 310 (2007/10/03)
Ozonolyses of 2,3-dichloro-2-butene (4), 4,5-dichloro-4-octene (9) and 2,3-dibromo-1,4-dichloro-2-butene (12) on polyethylene gave the corresponding ozonides 5,10 and 13a, respectively, which could not be isolated or unequivocally identified. Their identity could be proven, however, via substitution of the chloro- or bromo substituents at the ozonide rings by stabilizing substituents and subsequent isolation of the substituted ozonides 6, 11, 13b and 13c. Ozonolysis of 2,3-diacetoxy-2-butene (14) on polyethylene, in dichloro methane and in pentane gave mixtures of 16 and 17 but not ozonide 6.