2,3-ジメチルマレイン酸無水物

Dimethylmaleic anhydride

HCID 13010CAS 766-39-2

基本情報

標準SMILES
CC1=C(C)C(=O)OC1=O
InChIKey
MFGALGYVFGDXIX-UHFFFAOYSA-N
分子式
C6H6O3
平均分子量
126.11 g/mol
単同位体質量
126.03169405

概要

2,3-Dimethylmaleic anhydride is a butenolide.

名称と識別子

優先名称
Dimethylmaleic anhydride
IUPAC
3,4-dimethylfuran-2,5-dione
現地名
2,3-ジメチルマレイン酸無水物
英語名
2,3-Dimethylmaleic anhydride
分子式
C6H6O3
分子量
126.11

名称と別名

2,3-DIMETHYLMALEIC ANHYDRIDE766-39-2Dimethylmaleic anhydride2,5-Furandione, 3,4-dimethyl-Pyrocinchonic anhydrideMaleic anhydride, dimethyl-Dimethylmaleic acid anhydridealpha,beta-Dimethylmaleic anhydride6PP3N541QADTXSID6061103NSC-92512RefChem:442539
名称をさらに表示
2,3-ジメチルマレイン酸無水物3,4-ジメチル-2,5-フランジオン3,4-ジメチルフラン-2,5-ジオンジメチル無水マレイン酸ピロシンコニン酸無水物3,4-ジメチル2,5-ジヒドロフラン-2,5-ジオン3,4-ジメチル-2,5-ジヒドロフラン-2,5-ジオンジメチルマレイン酸無水物無水2,3-ジメチルマレイン酸無水2,3‐ジメチルマレイン酸2,5-Furandione,3,4-dimethyl-2,2’-Dimethylmaleinsαureanhydrideic Anhydridepyrocinchonicanhydridedimethyl-maleicanhydrid3,4-dimethyl-5-furandioneTwoMethyl Maleic anhydride
2,3-dimethyl maleic anhydrideDTXCID5047902212-165-8DMMA3,4-dimethylfuran-2,5-dione3,4-Dimethyl-2,5-furandioneMFCD00005523HSDB 5517

データベース識別子

CAS
766-39-2
PubChem CID
13010
DTXSID
DTXSID6061103
ChEMBL
CHEMBL2270559
ChEBI
CHEBI:182178
UNII
6PP3N541QA
EC Number
212-165-8
Nikkaji
J36.810E

物性

構造計算による物性

XLogP
0.6
極性表面積
43.4 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
0
重原子数
9

実験および物理化学的性質

PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesChemical shift
Density1.107 AT 100 °C/4 °C
SolubilityVERY SOL IN ALCOHOL, ETHER, BENZENE, CHLOROFORM; SLIGHTLY SOL IN WATER
Boiling Point223 °C
Melting Point96 °C

物理化学的性質

融点
93 · 93-96 °C (lit.)
沸点
223 °C · 223 °C (lit.)
比重(密度)
1.107 g/cm3 · 1.107 g/cm3 (100℃)
屈折率
1.5627 · 1.5627 (estimate)
闪点
222 · 222-223°C
貯蔵温度
30 °C · Store below +30°C.

化学的性質

化学的特性white to beige crystals or cryst. powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (87.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazards SummaryMay decompose on exposure to moisture; May cause irritation; [MSDSonline] See ACID ANHYDRIDES.
Hazard Classes and CategoriesAcute Tox. 4 (87.8%)

毒性情報

Interactions · 1 件

Modification with succinic anhydride of Clostridium perfringens epsilon prototoxin or toxin resulted in a loss of activation by trypsin or lethal activity, respectively. The prototoxin was more sensitive to succinylation than the toxin. On the other hand, the succinylated prototoxin was activated and cleaved by chymotrypsin, but not by trypsin. The lethal activity of the toxin was also lost after treatment with 2,3-dimethylmaleic anhydride or 2,4,6-trinitrobenzenesulfonic acid. When the 2,3-dimethylmaleic anhydride treated toxin treated with succinic anhydride or 2,4,6-trinitrobenzenesulfonic acid was incubated under acidic condition, it regained lethal activity. Thus modification of amino groups (lysine residues) prevented activation of the prototoxin by trypsin, and abolished lethal activity of the toxin.

Human Toxicity Excerpts · 1 件

THE MALEIC ANHYDRIDES, A SERIES OF REVERSIBLE ACYLATING AGENTS, PRODUCED THE ASPIRIN-TYPE DEFECT IN PLATELET AGGREGATION. UNLIKE THE ANTIPLATELET EFFECT OF ASPIRIN WHICH WAS IRREVERSIBLE, THE ANTIPLATELET EFFECT OF 2,3-DIMETHYLMALEIC ANHYDRIDE DISAPPEARED IN APPROXIMATELY 80 MINUTES AT 25 DEG.

Non-Human Toxicity Excerpts · 3 件

2,3-DIMETHYLMALEIC ANHYDRIDE, A REAGENT REMOVING POSITIVE CELL SURFACE CHARGES, DECREASED THE AGGREGATION OF CHICK EMBRYO NEURAL RETINA CELLS IN CULTURE. TWENTY-FOUR HOURS AFTER 2,3-DIMETHYLMALEIC ANHYDRIDE WAS REMOVED FROM THE MEDIUM, THE MOBILITIES OF THE CELLS WERE SIMILAR TO THOSE OF THE CONTROLS.

ALPHA,BETA-DIMETHYLMALEIC ANHYDRIDE INDUCED SARCOMAS IN 3 OF 5 RATS. ARACHIS OIL, USED AS THE VEHICLE, WAS NONCARCINOGENIC IN 0.5 ML DOSES IN RATS.

THE REACTION OF DIMETHYLMALEIC ANHYDRIDE WITH AMINO GROUPS AT SURFACE OF THE EGGS OF SEA URCHIN DID NOT PREVENT FERTILIZATION.

安全データ

F
9-21
wgk
3
tsca
TSCA listed
rtecs
ON4025000
hs_code
2917 19 80
risk_code
22

化学と産業

用途と製造

Uses · 2 件

Used as a research chemical; No known commercial production in the US; [HSDB]

RESEARCH CHEM (CHEM INT FOR ORG SYNTH; PROTEIN REAGENT)

U.S. Production · 2 件

(1979) NO EVIDENCE OF COMMERCIAL PRODN IN USA

(1981) NO EVIDENCE OF COMMERCIAL PRODN IN USA

Methods of ManufacturingDECARBOXYLATIVE DIMERIZATION OF MALEIC ANHYDRIDE IN THE PRESENCE OF 2-AMINOPYRIDINE
General Manufacturing Information2,5-Furandione, 3,4-dimethyl-: ACTIVE
応用分野 · 3 件

解説2,3-ジメチルマレイン酸無水物,ジメチルマレインサンムスイブツ,3,4-dimethyl-2,5-furandione.C6H6O3(126.11).2,3-ジメチルマレイン酸と塩化アセチルとを加熱すると得られる.板状晶または葉状晶.融点93 ℃,沸点223 ℃.d1940.9092.エタノール,エーテル,クロロホルム,ベンゼンに可溶,冷水に難溶.水蒸気蒸留される.アルカリで処理すると2,3-ジメチルフマル酸を与える.殺菌剤,殺虫剤,除草剤,枯葉剤などの合成原料に用いられる.

用途有機合成原料。

使用2,3-Dimethylmaleic anhydride can be usually used in the synthesis of maleimides and as an amino group protecting agent for superoxide dismutase. It is also used in the preparation of dimethylmaleic acid dimethyl ester. Further, it serves as a reactant in the dissociation of ribosomal proteins. In addition to this, The isolated molecule 2, 3-dimethylmaleic anhydride showed potent insecticidal activity in fumigation bioassay against several insect species, viz., adults of houseflies, cockroaches and stored-product insects.

調製方法

純化方法Distil the anhydride from *benzene/ligroin and sublime in a vacuum. [Beilstein 17/11 V 69.]

サプライヤー50 社

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補足説明 · 1 件

定義ChEBI: 2,3-Dimethylmaleic anhydride is a butenolide. It is a 5-membered cyclic anhydride with a double bond between carbon atoms C2 and C3. The double bond locks the molecule in a planar conformation and stabilizes the acid anhydride against hydration. It was used as linker to a cell penetrating peptidebased nanoparticle.

関連反応

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