Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

Base Information

• Chemical Name: Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS
• CAS No.: 71875-81-5
• Molecular Formula: C16H18 N2 O6
• Molecular Weight: 334.329
• Hs Code.: 2925190090
• Mol file: 71875-81-5.mol

Synonyms:1H-Pyrrole-2,5-dione,1-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]-, trans-;1H-Pyrrole-2,5-dione,1-[[trans-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]- (9CI)

Chemical Property of Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

Chemical Property:

• Melting Point: 171-174 °C(Solv: acetone (67-64-1); methanol (67-56-1))
• Boiling Point: 501.7±42.0 °C(Predicted)
• PKA: -2.24±0.20(Predicted)
• PSA: 101.06000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 0.20080
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

99% ^*data from raw suppliers

Mal-AMCHC-OSu ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

There total 8 articles about Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS 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: 89.0%

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid (69907-68-2) + N-trifluoroacetoxy succinimide (5672-89-9) → 4-(N-maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (71875-81-5)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1080/00397910701750151

Reference yield: 71.4%

trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate (1337538-63-2) → 4-(N-maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (71875-81-5)

Guidance literature:

In acetonitrile; at 72 - 82 ℃;

Reference yield: 60.0%

maleic anhydride (108-31-6) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + trans-4-aminomethyl-cyclohexyl-carboxylic acid (1197-18-8) → 4-(N-maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (71875-81-5)

Guidance literature:

maleic anhydride; trans-4-aminomethyl-cyclohexyl-carboxylic acid; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

1-hydroxy-pyrrolidine-2,5-dione; With 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride; at 0 - 20 ℃;

DOI:10.1021/acs.chemmater.9b02485

upstream raw materials:

maleic anhydride

1-hydroxy-pyrrolidine-2,5-dione

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid

Downstream raw materials:

cyclo(L-Arginyl-glycyl-L-asparagyl-D-phenylalanyl-L-[εN-(trans-[4-(1-maleimido)methyl]cyclohexylcarbonyl)]lysine) trifluoroacetate

C₂₂H₂₉N₃O₇

6-((1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid

Refernces

• 1、 -. "Refining method of SMCC". . . Retrieved 2019/05/08.
• 2、 Su, Yu-Chih,Lo, Yu-Lun,Hwang, Chi-Ching,Wang, Li-Fang,Wu, Min Hui,Wang, Eng-Chi,Wang, Yun-Ming,Wang, Tzu-Pin. "Azide-alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates". . p. 6624 - 6633. Retrieved 2014/08/18.