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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 190
実験および物理化学的性質
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.
- 溶解性
- クロロホルム(微量)、酢酸エチル(微量)
- 外見
- 個体
- 色
- ホワイトからオフホワイト
- 水溶解度
- エタノール、エーテル、クロロホルムに可溶。水にわずかに溶ける。
- BRN
- 112044 · 112044
- InChI
- 1S/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3
- InChIKey
- MFGALGYVFGDXIX-UHFFFAOYSA-N
- SMILES
- CC1=C(C)C(=O)OC1=O
- LogP
- 0.183 · 0.183 (est)
- CAS データベース
- 766 · 766-39-2(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · 2,5-Furandione, 3,4-dimethyl-(766-39-2)
- EPAの化学物質情報
- 2 · 2,5-Furandione, 3,4-dimethyl- (766-39-2)
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
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
毒性情報
Interactions
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
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
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
- 化審法
- (9)-718
- hazard_code
- Xn,Xi
- safety_code
- 45-36/37/39-28A-26
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 766-39-2(Hazardous Substances Data)
化学と産業
用途と製造
Uses
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
(1979) NO EVIDENCE OF COMMERCIAL PRODN IN USA
(1981) NO EVIDENCE OF COMMERCIAL PRODN IN USA
応用分野
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
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
関連ノート
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