trans-4-(Maleimidomethyl)cyclohexanecarboxylic acid

Base Information

• Chemical Name: trans-4-(Maleimidomethyl)cyclohexanecarboxylic acid
• CAS No.: 69907-67-1
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• Hs Code.: 2928009090
• European Community (EC) Number: 835-612-4,835-889-1
• UNII: 7CN76JAX09
• DSSTox Substance ID: DTXSID801145980
• Nikkaji Number: J2.951.386D
• Wikidata: Q27268077
• Mol file: 69907-67-1.mol

Synonyms:69907-67-1;64987-82-2;TRANS-4-(MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLIC ACID;trans-4-((2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylic acid;N-[4-(-Carboxycyclohexylmethyl)]maleimide;Mal-AMCHC-OH;4-(Maleimidomethyl)cyclohexanecarboxylic acid;N-(4-Carboxycyclohexylmethyl)maleimide;4-((2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylic acid;4-((2,5-dioxo-2H-pyrrol-1(5H)-yl)methyl)cyclohexanecarboxylic acid;4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylic Acid;7CN76JAX09;MFCD03093740;MFCD11519178;Cyclohexanecarboxylic acid, 4-((2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl)-;Cyclohexanecarboxylic acid, 4-((2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl)-, trans-;4-(n-maleimidomethyl)cyclohexane-1-carboxylic acid;trans-4-(N-Maleimidomethyl)cyclohexane-1-carboxylic Acid;4-(Maleimidomethyl)cyclohexanecarboxylicAcid;(1R,4R)-4-((2,5-DIOXO-2,5-DIHYDRO-1H-PYRROL-1-YL)METHYL)CYCLOHEXANECARBOXYLIC ACID;Mal-AMCHC;UNII-7CN76JAX09;trans-4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexanecarboxylic acid;Trans-4-(Maleimidomethyl)cyclohexanecarboxylicAcid;4-(Maleimidomethyl)cyclohexanecarboxylic acid, E-;SCHEMBL159817;SCHEMBL890390;(Discontinued, see C177860);DTXSID801145980;AMY13237;AMY21605;FD6031;AKOS015995272;AKOS016014251;CS-W006952;DS-6035;4-[(2,5-DIHYDRO-2,5-DIOXO-1H-PYRROL-1-YL)METHYL]CYCLOHEXANECARBOXYLIC ACID;N-(4-carboxycyclohexylmethyl)-maleimide;AC-32531;BP-20232;BS-29029;HY-42359;SY069051;SY247856;TRIALLYL1,2,4-BENZENETRICARBOXYLATE;A8847;CS-0021355;FT-0604025;FT-0604080;M3218;M3219;A19079;C70531;EN300-6487298;EN300-7363655;J-513759;Q27268077;trans-4-(maleimidomethyl)cyclohexane-1-carboxylic acid;Z1793625431;4-(MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLIC ACID, TRANS-;4-((2,5-DIOXO-2H-PYRROL-1(5H)-YL)METHYL)CYCLOHEXANECARBOXYLICACID;(1r,4r)-4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylic acid;4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylic acid

Chemical Property of trans-4-(Maleimidomethyl)cyclohexanecarboxylic acid

Chemical Property:

• Melting Point: 144 °C(Solv: benzene (71-43-2))
• Boiling Point: 433.6±18.0 °C(Predicted)
• PKA: 4.80±0.10(Predicted)
• Density: 1.329
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 362

Purity/Quality:

NLT 98% ^*data from raw suppliers

trans-4-(N-Maleimidomethyl)cyclohexane-1-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)O
• Description: Trans-4-(Maleimidomethyl) cyclohexanecarboxylic Acid is a kind of carboxylate, being well known for its N-hydroxysuccinimide ester derivative (SMCC), which is a useful cross-linking reagent. SMCC is widely used for the generation of stable maleimide-activated carrier proteins, enzyme immunoconjugates and hapten carrier molecule conjugates. It can be used for the coupling of a peptide to an amino group.

Technology Process of trans-4-(Maleimidomethyl)cyclohexanecarboxylic acid

There total 5 articles about trans-4-(Maleimidomethyl)cyclohexanecarboxylic acid 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:

C12H17NO5 (953817-12-4) → (1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid (69907-67-1,64987-82-2)

Guidance literature:

With sodium acetate; acetic anhydride; at 120 ℃; for 3h; Sealed tube;

Reference yield:

maleic anhydride (108-31-6) + trans-4-aminomethyl-cyclohexyl-carboxylic acid (1197-18-8) → (1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid (69907-67-1,64987-82-2)

Guidance literature:

In N,N-dimethyl-formamide; for 6h;

Reference yield:

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid (69907-68-2) → (1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid (69907-67-1,64987-82-2)

Guidance literature:

With sodium acetate; acetic anhydride; at 100 ℃; for 2h;

DOI:10.1016/j.bmcl.2007.04.014

upstream raw materials:

maleic anhydride

trans-4-aminomethyl-cyclohexyl-carboxylic acid

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

C₁₂H₁₇NO₅

Refernces

• 1、 Zhang, Yue,Zhang, Qing,Wong, Clarence T. T.,Li, Xuechen. "Chemoselective Peptide Cyclization and Bicyclization Directly on Unprotected Peptides". supporting information. p. 12274 - 12279. Retrieved 2019/08/20.
• 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.