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GMBS

GMBS structure

GMBS 

structure
  • CAS No:

    80307-12-6

  • Formula:

    C12H12N2O6

  • Chemical Name:

    GMBS

  • Synonyms:

    GMBS;GMBS Crosslinker;CIVENTICHEM CV-2656;4-Maleimidobutyric acid NHS;4-Maleimidobutyric acid-NHS ester;N-SUCCINIMIDYL 4-MALEIMIDOBUTYRATE;N-(4-Maleimibutyryloxy)succinimide;N-(4-MALEIMIDOBUTYRYLOXY)SUCCINIMIDE;N-(4-MaleiMidebutyryloxy)succiniMide;N-GAMMA-MALEIMIDOBUTYRYLOXYSUCCINIMIDE

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

GMBS is a heterobifunctional cross-linker. GMBS is often used to prepare antibody-enzyme and hapten-carrier protein conjugates.

GMBS Basic Attributes

280.23

280.069550

DTXSID60230240

2925190090

Characteristics

101

-1.2

1.5±0.1 g/cm3

123-129ºC

461.3°C at 760 mmHg

232.8±29.3 °C

1.595

Safety Information

NONH for all modes of transport

3

R36/37/38

S26-S36

Xi

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

GMBS

GMBS Use and Manufacturing

Methods of Manufacturing

N-maleimidobutyric acid (99 g, 0.54 mol) and acetonitrile (300 ml) were placed in a500 ml three-necked flask andthionyl chloride (93.6 g, 0.82 mol) was added. The reaction was warmed to reflux and a large amount of gas was released .After the reaction was refluxed for 4h, the reaction became clear, acetonitrile and excess thionyl chloride were removed by concentration, and 200 ml of acetonitrile was added to remove the remaining acid in one pass to obtaincrudeN-maleimidobutyrylchloride.The crude product was dissolved in 200ml of acetonitrile was added dropwise to N- hydroxysuccinimide (69g, 0.6mol) and tri-n-butylamine (148g, 0.8mol) was dissolved in 300ml of acetonitrile, with ice water cooling to control the temperature does not exceed 20 , drip finished at room temperature for2h.The reaction solution was concentrated to remove acetonitrile, dissolved in 400 ml of methylene chloride, and dissolved in 200 ml of dichloromethane to remove tri-n-butylaminehydrochloride and 100 ml of 1N hydrochloric acid to remove excess tri-n-butylamine and 200 ml of saturated saline solution, Drywhite solid 139g, a mixed solvent of ethyl acetate and petroleum ether to give a white solid after recrystallization 104.2g, HPLC purity 98.9percent, 69.1percent yield.

Uses

A short, sulfhydryl and amino reactive heterobifunctional crosslinking reagent. Introduces maleimide groups into IgM

Computed Properties

Molecular Weight:280.23
XLogP3:-1.2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:280.06953611
Monoisotopic Mass:280.06953611
Topological Polar Surface Area:101
Heavy Atom Count:20
Complexity:490
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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