Chloroacetic anhydride

Base Information

• Chemical Name: Chloroacetic anhydride
• CAS No.: 541-88-8
• Deprecated CAS: 39739-42-9
• Molecular Formula: C4H4Cl2O3
• Molecular Weight: 170.98
• Hs Code.: 29159000
• European Community (EC) Number: 208-794-2
• NSC Number: 71207
• UNII: 8Q7TXH7R5F
• DSSTox Substance ID: DTXSID701014649
• Nikkaji Number: J2.643C
• Wikidata: Q27270893
• Mol file: 541-88-8.mol

Synonyms:Aceticacid, chloro-, anhydride (6CI,7CI,8CI,9CI);2-Chloroacetic anhydride;Chloracetic anhydride;Chloroacetic acid anhydride;Chloroacetic anhydride;Chloroacetyl anhydride;NSC 71207;a,a'-Dichloroacetic anhydride;

Chemical Property of Chloroacetic anhydride

Chemical Property:

• Appearance/Colour: brownish semi-transparent crystals
• Vapor Pressure: <0.75 mm Hg ( 20 °C)
• Melting Point: 51 °C
• Refractive Index: 1.456
• Boiling Point: 203 °C at 760 mmHg
• Flash Point: 82.8 °C
• PSA: 43.37000
• Density: 1.449 g/cm³
• LogP: 0.53380
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Sensitive.: Moisture Sensitive
• Solubility.: Freely soluble in ether, chloroform. Slightly soluble in benzene
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 169.9537494
• Heavy Atom Count: 9
• Complexity: 109

Purity/Quality:

99% ^*data from raw suppliers

ChloroacetylAnhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, T
• Hazard Codes: C,T
• Statements: 34-36/37-43-25
• Safety Statements: 26-28-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Acid Anhydrides, Other
• Canonical SMILES: C(C(=O)OC(=O)CCl)Cl
• Uses: In N-acetylation of amino acids in alkaline solution; preparation of cellulose chloroacetates. Chloroacetic anhydride has been used in the synthesis of 3,3-bis(sulfonato)-4,4-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive and photo-switchable cross-linker, D,L-7-azatryptophan, 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2,1:4,5]-2-oxazoline.

Technology Process of Chloroacetic anhydride

There total 19 articles about Chloroacetic anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

sodium monochloroacetic acid (3926-62-3) + chloroacetyl chloride (79-04-9) → Chloroacetic anhydride (541-88-8)

Guidance literature:

In toluene; at 40 ℃; for 3h; Solvent; Temperature;

Reference yield: 91.0%

chloroacetic acid (79-11-8) → Chloroacetic anhydride (541-88-8)

Guidance literature:

With PEG-1000; sulfated zirconia; at 40 ℃; for 1.5h; neat (no solvent);

Reference yield:

sodium monochloroacetic acid (3926-62-3) → Chloroacetic anhydride (541-88-8)

Guidance literature:

With oxalyl dichloride; benzene;

upstream raw materials:

4-methyleneoxetan-2-one

chloroacetic acid

tetrakis(chloroacetoxy)silane

sodium monochloroacetic acid

Downstream raw materials:

2-chloro-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide

2-chloro-N-(6-ethoxy-1,3-benzothiazol-2-yl)acetamide

1-(9H-carbazol-9-yl)-2-chloro-1-ethanone

3,7-bis-chloroacetyl-1,5-diphenyl-3,7-diaza-bicyclo[3.3.1]nonan-9-one

Refernces

• 1、 Hu, Yu Lin,Zhao, Xing E.,Lu, Ming. "Efficient and convenient synthesis of symmetrical carboxylic anhydrides from carboxylic acids with sulfated zirconia by phase transfer catalysis". experimental part. p. 255 - 262. Retrieved 2012/04/17.
• 2、 Long, Ya-Qiu,Lung, Feng-Di T.,Roller, Peter P.. "Global optimization of conformational constraint on non-phosphorylated cyclic peptide antagonists of the Grb2-SH2 domain". . p. 3929 - 3936. Retrieved 2007/10/03.