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Chemical Structure| 71875-81-5 Chemical Structure| 71875-81-5
Chemical Structure| 71875-81-5

Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

CAS No.: 71875-81-5

SMCC is a linker for antibody-drug-conjugation (ADC).

Synonyms: SMCC

4.5 *For Research Use Only !

Cat. No.: A283587 Purity: 95%

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Product Details of Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

CAS No. :71875-81-5
Formula : C16H18N2O6
M.W : 334.32
SMILES Code : O=C([C@H]1CC[C@H](CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O
Synonyms :
SMCC
MDL No. :MFCD08274640
Boiling Point : No data available
InChI Key :JJAHTWIKCUJRDK-UHFFFAOYSA-N
Pubchem ID :125175

Safety of Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 71875-81-5 ]

[ 71875-81-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 6066-82-6 ]
  • [ 69907-67-1 ]
  • [ 71875-81-5 ]
YieldReaction ConditionsOperation in experiment
39% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;Inert atmosphere; The product of the preceding step B (10.0 g, 42.1 mmol) was dissolved in dichioromethane (50 mL) under Ar, treated with N-hydroxysuccinimide (7.27 g, 63.2 mmol) and 1 -(3 -dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (EDAC, 12.4 g, 64.5 mmol), and the reaction was stirred at ambient temperature overnight. The resulting brown solution was diluted with dichloromethane, washed with water and brine, dried over Na2SO4, filtered over a sintered glass funnel, and the filtrate concentrated and dried in vacuo. This product was then dissolved in hot ethyl acetate, treated with activated charcoal (1.5 g), filtered, and the filtrate cooled. Filtration of the crystalline product, washing with cold ethyl acetate, and suction drying then gave the title compound as a tan solid (5.52 g, 39%). 1H NMR (300 MHz, CDC13) 5 6.72 (s, 2H), 3.42 (m, 2H), 2.85 (br s, 4H), 2.56 (tt, 1H, J= 12Hz, 4Hz), 2.18 (m, 2H), 1.80 (m, 2H),1.70 (m, 1H), 1.56 (m, 2H), 1.09 (m, 2H).
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 4h; To a solution of 6 (0.387 g, 1.60 mmol) and N-hydroxysuccinimide (HOSu) (0.562 g, 4.90 mmol) in 19.6 mL of DCM was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI·HCl) (0.939 g, 4.90 mmol) at room temperature and stirred for 4 h. The solvent was removed and the residue was dissolved in ethyl acetate. The solution was washed with 10% citric acid (three times), satd NaHCO3 (three times) and brine, dried over MgSO4 and concentrated to afford crude product 7 which was used without further purification. To a solution of c(RGDfK)·2TFA (50 mg, 0.06 mmol) and 7 (13.4 mg, 0.04 mmol) in 2 mL of DMF was added DIPEA (34.8 muL, 0.20 mmol) and the solution was stirred at room temperature. After 9 h, the solvent was removed in vacuo. Purification of the crude product by preparative RP-HPLC afforded 8 (19.1 mg, 40% for two-steps) as trifluoroacetate salt of colorless freeze-dried amorphous. HRMS (FAB) m/z: calcd for C39H55N10O10+ [M+H]+ 823.4097, found 823.4091.
 

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