Bromoacetic anhydride

Base Information

• Chemical Name: Bromoacetic anhydride
• CAS No.: 13094-51-4
• Molecular Formula: C4H4Br2O3
• Molecular Weight: 259.882
• Hs Code.: 29159000
• European Community (EC) Number: 624-068-1
• DSSTox Substance ID: DTXSID30401329
• Nikkaji Number: J364.710B
• Wikidata: Q72451217
• Mol file: 13094-51-4.mol

Synonyms:Bromoacetic anhydride;13094-51-4;2-Bromoacetic anhydride;(2-bromoacetyl) 2-bromoacetate;2-Bromoaceticanhydride;Bromoaceticanhydride;Acetic acid, bromo-, anhydride;SCHEMBL100137;DTXSID30401329;FUKOTTQGWQVMQB-UHFFFAOYSA-N;MFCD00045041;AKOS015836013;SB40392;Acetic acid, 2-bromo-, 1,1'-anhydride;AM806585;FT-0623216;FT-0623218;F87050

Chemical Property of Bromoacetic anhydride

Chemical Property:

• Melting Point: 31-36 °C(lit.)
• Boiling Point: 226.2 °C at 760 mmHg
• Flash Point: 90.6 °C
• PSA: 43.37000
• Density: 2.138g/cm³
• LogP: 0.84600
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 259.85067
• Heavy Atom Count: 9
• Complexity: 109

Purity/Quality:

98% ^*data from raw suppliers

2-bromoaceticanhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(=O)OC(=O)CBr)Br
• Uses: 2-Bromoacetic Anhydride can be used to prepare antibody-drug conjugates (ADCS) of KSP inhibitors with aglycosylated anti-TWEAKR antibodies.

Technology Process of Bromoacetic anhydride

There total 11 articles about Bromoacetic 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: 92.0%

bromoacetic acid (79-08-3) → bromoacetic anhydride (13094-51-4)

Guidance literature:

With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1055/s-1981-29544

Reference yield:

bromoacetic acid (79-08-3) + dicyclohexyl-carbodiimide (538-75-0) → bromoacetic anhydride (13094-51-4) + 1,3-Dicyclohexylurea (2387-23-7)

Guidance literature:

In dichloromethane; for 0.25h;

Reference yield:

acetic anhydride (108-24-7) → bromoacetic anhydride (13094-51-4)

Guidance literature:

With tetrachloromethane; aluminium trichloride; bromine;

DOI:10.1021/ja01651a070

upstream raw materials:

sodium 2-bromoacetate

acetic anhydride

bromoacetic acid

2-Bromoacetyl bromide

Downstream raw materials:

{[2-((2-Bromo-acetyl)-{2-[4-(2-methoxy-ethoxymethoxy)-phenyl]-ethyl}-amino)-acetyl]-isopropyl-amino}-acetic acid tert-butyl ester

BrCH₂C(O)-IGGF

Refernces

• 1、 Roy, Olivier,Dumonteil, Geoffrey,Faure, Sophie,Jouffret, Laurent,Kriznik, Alexandre,Taillefumier, Claude. "Homogeneous and Robust Polyproline Type i Helices from Peptoids with Nonaromatic α-Chiral Side Chains". . p. 13533 - 13540. Retrieved 2017.
• 2、 Likhosherstov,Novikova,Zheltova,Shibaev. "An improved procedure for the synthesis of N-bromoacetyl-β- glycopyranosylamines, derivatives of mono- and disaccharides". . p. 709 - 713. Retrieved 2004.
• 3、 Azam, Farzana,Bladon, Christine M.. "Synthetic approaches to macromolecular models for ion channel proteins". . p. 6377 - 6380. Retrieved 1998.
• 4、 Cadogan,J.I.G. et al.. "-". . p. 3950 - 3957. Retrieved 1965.
• 5、 -. "CHROMOGENIC PEROXIDASE SUBSTRATES". Paragraph 0412. . Retrieved 2017/07/14.