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4-Maleimidobutyric acid

4-Maleimidobutyric acid structure

CAS No:
57078-98-5
Formula:
C8H9NO4
Chemical Name:
4-Maleimidobutyric acid
Synonyms:
1H-Pyrrole-1-butanoic acid,2,5-dihydro-2,5-dioxo-;2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-butanoic acid;γ-Maleimidobutyric acid;4-Maleimidobutyric acid;ω-Maleimidobutyric acid;N-(3-Carboxypropyl)maleimide;4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid;4-Maleimidobutanoic acid
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

White Solid

4-Maleimidobutyric acid Basic Attributes

Molecular Weight：

183.16

Exact Mass：

183.16

EC Number：

1533716-785-6

DSSTox ID：

DTXSID90392183

HScode：

29251900

Characteristics

PSA：

74.7

XLogP3：

0.4 (LogP)

Density：

1.4±0.1 g/cm3

Melting Point：

93-94 °C @ Solvent: Ethyl acetate

Boiling Point：

400.1°C at 760 mmHg

Flash Point：

195.8±24.0 °C

Refractive Index：

1.553

Storage Conditions：

2-8°C

Safety Information

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

GHS Classification：

|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 40 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

4-Maleimidobutyric acid Use and Manufacturing

Methods of Manufacturing

A 1000 ml three-necked flask was charged with a compound of formula (II) (191 g, 0.95 mol, X = 3) and600 ml ofacetonitrilefollowed by diisopropylethylamine (363 g, 2.8 mol) , A solution of phenyl 4-nitro-trifluoroacetate(353.4g, 1.5mol) dissolved in 300ml acetonitrile was added dropwise and the temperature was controlled at -5-10 ° C.The reaction wasconcentrated to dryness, water was added 400ml, concentrated hydrochloric acid with stirring to adjust to pH 3-4, 4-nitrophenol was removed by filtration, filtrate was washed with methylenealkyl extracted three times, the organic phases were combined and washed with water, dried over anhydrous magnesium sulfate After concentration and dried to give a light yellow solid 129g, ethylacetate and petroleum ether solvent recrystallization to give a white solid 111g, after drying weighed 99g, HPLC purity 98.4percent, a yield of 57.0 percent.20.0 g (193.9 mmol) of 4-aminobutyric acid is mixed with 19 g of maleic acid anhydride, 290 ml of acetic acid, and it is heated for 4 hours in an oil bath at [130XB0;C.] It is azeotropically concentrated by evaporation with repeated addition of toluene, the residue is dissolved in dichloromethane and purified by chromatography on fine silica gel. 17.1 g (93.4 mmol, [48percent)] of the title compound is isolated as a crystalline solid. [1H-NMR] (CDC13): [8] = 1.93 (2H), 2.38 (2H), 3.60 (2H), 6.71 (2H) ppm.

Uses

A short crosslinking reagent Modification reagent for thiol groups in proteins Maleimide Derivatives MTS & Sulfhydryl Active Reagents

Computed Properties

Molecular Weight:183.16
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:183.05315777
Monoisotopic Mass:183.05315777
Topological Polar Surface Area:74.7
Heavy Atom Count:13
Complexity:264
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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4-MALEIMIDOBUTYRIC ACID

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