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Maleimide

Maleimide structure

CAS No:
541-59-3
Formula:
C4H3NO2
Chemical Name:
Maleimide
Synonyms:
1H-Pyrrole-2,5-dione;Maleimide;Pyrrole-2,5-dione;3-Pyrroline-2,5-dione;Maleic imide;NSC 13684;2,5-Dioxo-2,5-dihydropyrrole;2,5-Dihydro-1H-pyrrole-2,5-dione
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

slight yellow crystalline powder

Maleimide is a cyclic dicarboximide in which the two carboacyl groups on nitrogen together with the nitogen itself form a 1H-pyrrole-2,5-dione structure. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a dicarboximide and a member of maleimides. It derives from a maleic acid. It derives from a hydride of a 1H-pyrrole.

Maleimide Basic Attributes

Molecular Weight：

97.07

Exact Mass：

97.07

BRN：

106910

EC Number：

208-787-4

UNII：

2519R1UGP8

NSC Number：

13684

DSSTox ID：

DTXSID3049417

HScode：

29251995

Characteristics

PSA：

46.2

XLogP3：

-0.3

Appearance：

White to slightly yellow Fine Crystalline Powder

Density：

1.4±0.1 g/cm3

Melting Point：

94 °C

Boiling Point：

120-125 °C @ Press: 10 Torr

Flash Point：

97-103°C/5mm

Refractive Index：

1.606

Water Solubility：

H2O: soluble

Storage Conditions：

Refrigerator

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 2923 8/PG 2

wgk germany：

hazard class code：

25-34-43-36/37/38-36

safety instructions：

26-36/37/39-45-37/39-28A-7/9

RTECS Number：

ON4800000

Marks：

T,C

Precautionary statement(s)：

P280-P301 + P310-P305 + P351 + P338-P310

Hazard Statements：

H301-H314-H317

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P363, P405, and P501|Aggregated GHS information provided by 48 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

maleimide

Maleimide Use and Manufacturing

Methods of Manufacturing

From the reaction of pyrrole and potassium dichromate. Dissolve 1177g of potassium dichromate in 1200ml of water and 712ml of concentrated sulfuric acid, heat to 35°C, slowly add 54g of pyrrole under stirring, and the temperature does not exceed 50°C. After the addition, keep the reaction at 40-50℃ until there is no odor of pyrrole. Cool, use glass wool to remove a small amount of tar generated by the reaction, and filter residue is washed with hot water. Filtration and washing liquid were extracted with ether. After the extract was dried over anhydrous sodium sulfate, ether was recovered by evaporation to obtain crude crystals. 7g pure white crystal product can be obtained by vacuum sublimation.

Uses

Rhodium-catalyzed conjugate arylation with arylboronic acids.1

Manufacturing Info：

1H-Pyrrole-2,5-dione: ACTIVE

Use Classification：

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Agrochemical：

Maleimide is a known environmental transformation product of Linuron.

Computed Properties

Molecular Weight:97.07
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:97.016378338
Monoisotopic Mass:97.016378338
Topological Polar Surface Area:46.2
Heavy Atom Count:7
Complexity:132
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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