基本情報
- 標準SMILES
N#CCC(N)=O- InChIKey
DGJMPUGMZIKDRO-UHFFFAOYSA-N- 分子式
- C3H4N2O
- 平均分子量
- 84.08 g/mol
- 単同位体質量
- 84.03236275
概要
cyanoacetamide has been reported in Apis with data available.
名称と識別子
- 優先名称
- Cyanoacetamide
- IUPAC
- 2-cyanoacetamide
- 現地名
- 2-シアノアセトアミド
- 英語名
- 2-Cyanoacetamide
- 分子式
- C3H4N2O
- 分子量
- 84.08
名称と別名
名称をさらに表示
データベース識別子
- CAS
107-91-5- PubChem CID
- 7898
- DTXSID
DTXSID2051552- ChEMBL
CHEMBL2333142- UNII
- YBK38G2YXH
- EC Number
- 203-531-8
- Nikkaji
- J4.067C
物性
構造計算による物性
- XLogP
- -1
- 極性表面積
- 66.9 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 1
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 98.6
実験および物理化学的性質
Color/Form
NEEDLES FROM ALCOHOL
PLATES (WATER)
WHITE POWDER
Melting Point
119.5 °C
121.5 °C
物理化学的性質
- 融点
- 119 · 119-121 °C(lit.)
- 沸点
- 154.34 °C · 154.34°C (rough estimate)
- 比重(密度)
- 1 · 1,4 g/cm3
- 屈折率
- 1.511 · 1.5110 (estimate)
- 闪点
- 419 °F · 419 °F
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- 6.5 mlに1gm可溶 · 冷水:6.5mlに1gm可溶
- 酸解離定数(Pka)
- -1.27 · -1.27±0.10(Predicted)
- 外見
- 結晶性粉末
- 色
- ホワイト~ライトクリーム
- 臭い (Odor)
- 無臭
- 水溶解度
- 溶ける
- Merck
- 14 · 14,2688
- BRN
- 878221 · 878221
- InChI
- 1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
- InChIKey
- DGJMPUGMZIKDRO-UHFFFAOYSA-N
- SMILES
- NC(=O)CC#N
- CAS データベース
- 107 · 107-91-5(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · Acetamide, 2-cyano-(107-91-5)
- EPAの化学物質情報
- 2 · 2-Cyanoacetamide (107-91-5)
化学的性質
化学的特性White or light yellow needle crystal or powder. Slightly soluble in water, easily soluble in ethanol.
安全と法規制
GHS分類
GHS Classification
Warning
H302 (77.4%): 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 62 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Acetamide, 2-cyano-
Status: Active Update: 26-05-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/11828
Acetamide, 2-cyano-: Does not have an individual approval but may be used under an appropriate group standard
安全と保護具
Storage Conditions
SEE CYANIDES. ...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED FROM EACH OTHER. /CYANIDES/
Protective Action Criteria (PAC)
0.81 [mg/m3]
8.7 [mg/m3]
52 [mg/m3]
毒性情報
Treatment
Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Toxicity Summary
Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Non-Human Toxicity Values
LD50 RATS ORAL MORE THAN 3200 MG/KG
LD50 RATS INTRAPERITONEAL MORE THAN 800 MG/KG
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AB5950000
- ridadr
- UN 3439 6.1/PG 3
- hs_code
- 29269095
- risk_code
- 22-36/37/38-20/21/22
- 化審法
- (2)-1550
- hazard_code
- Xn
- safety_code
- 22-26-28A
- packing_group
- III
- 毒劇物取締法
- 劇物
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 107-91-5(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
用途と製造
Uses
Used in the synthesis of pharmaceuticals and plastics; [Hawley]
IN ORGANIC SYNTHESES (EG STARTING MATERIAL FOR VITAMIN B6 SYNTHESIS)
応用分野
用途有機合成原料。
使用2-Cyanoacetamide was used in spectrofluorimetric method for the determination of some antihistaminic H1 receptor antagonist drugs such as ebastine, cetirizine dihydrochloride and fexofenadine hydrochloride. It may be used in fluorometric determination of 3,4-dihydroxyphenylalanine. It was used as post column fluorigenic derivatizing agent for the bio-analysis and pharmacokinetics of chitosan ester in rabbit serum. Cyanoacetamide is the starting reagent for vitamin B6 synthesis. It reacts with reducing carbohydrates in borate buffer to give intense fluorescence and is useful for the automated analysis of carbohydrates as borate complexes. It can also be used in the synthesis of heterocyclic compounds such as pyrazole, pyridine and pyrimidine derivatives. Moreover, it can also be applied for the spectrophotometric assay of the enzyme activity of cellulose in related host cells.
一般的な説明Cyanoacetamide is the starting reagent for vitamin B6 synthesis. It reacts with reducing carbohydrates in borate buffer to give intense fluorescence andis useful for the automated analysis of carbohydrates as borate complexes.
調製方法
製造方法Cyanoacetamide can be prepared from ethyl cyanoacetate and ammonia. Cool the ethyl cyanoacetate to below 200°C, add concentrated ammonia water to react, and the mixture turns from turbid to clear. After cooling in cold water for 20 minutes, a precipitate is precipitated. After filtration and drying, the crude product is obtained, and then the crude product of cyanoacetamide is added. In the boiling ethanol, after dissolving it, add a small amount of activated carbon for decolorization and purification, filter, cool the filtrate to separate out the precipitate, and dry it at 80-100 ℃ to obtain the fine cyanoacetamide.
純化方法Crystallise the amide from MeOH/dioxane (6:4), then water and dry it over P2O5 under vacuum. [Beilstein 2 IV 1891.]
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2-Cyanoacetamide is an acetic amide with a nitrile functional group. It is a codon of glutamine that directs the placement of glutamine into a polypeptide.
関連反応
関連ノート
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