Ethyl diazoacetate (HCID 12192)

名称と識別子

優先名称: Ethyl diazoacetate
IUPAC: ethyl 2-diazoacetate
現地名: ジアゾ酢酸エチル
英語名: Ethyl diazoacetate
分子式: C4H6N2O2
分子量: 114.1

名称と別名

Ethyl diazoacetate623-73-4Diazoacetic esterEthyldiazoacetateDAAEEthoxycarbonyldiazomethaneDiazoacetic acid, ethyl esterN84B835FMRNSC-79147DTXSID10878732RefChem:132757DTXCID201016771

名称をさらに表示

2-ジアゾ酢酸エチルジアゾ酢酸エチルEthyl diazoethanoateEthyl diazoatediazoaceticesterdiazoacetate soL

210-810-8Ethyl 2-diazoacetateethyl2-diazoacetateDiazoacetic acid ethyl esterEthyl-2-diazoacetateACETIC ACID, DIAZO-, ETHYL ESTERdiazo-acetic acid ethyl esterEthyl Diazoacetate (>90%)

データベース識別子

CAS: 623-73-4
PubChem CID: 12192
ChEMBL: CHEMBL4212182
UNII: N84B835FMR
EC Number: 210-810-8
Nikkaji: J2.294.246H、J25.573D、J3.230.208D、J3.230.209B

物性

構造計算による物性

XLogP: 0.7
極性表面積: 28.3 Å²
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: 3
重原子数: 8
形式電荷: 0
複雑度: 126

実験および物理化学的性質

Density1.085 @25 °C

Physical DescriptionYellow liquid with a pungent odor; [Merck Index] Light to dark yellow liquid; [Sigma-Aldrich MSDS]

物理化学的性質

融点: -22 °C · -22 °C (lit.)
沸点: 140 · 140-141 °C/720 mmHg (lit.)
比重(密度): 1.085 g/mL · 1.085 g/mL at 25 °C (lit.)
屈折率: 20 · n20/D 1.46(lit.)
闪点: 115 °F · 115 °F
貯蔵温度: 2 · 2-8°C
溶解性: Chloroform (Slightly), DMSO (Soluble), Hexane (Slightly), Methanol (Slightly)
外見: Oil
色: Light Yellow to Orange
Merck: 13 · 13,3021
BRN: 107654 · 107654
InChI: InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3
InChIKey: YVPJCJLMRRTDMQ-UHFFFAOYSA-N
SMILES: C(=O)(OCC)C=[N+]=[N-]
NISTの化学物質情報: Ethyl diazoacetate(623-73-4)

化学的性質

化学的特性Liquid.

安全と法規制

GHS分類

GHS Classification · 5 件

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]；H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory InformationAcetic acid, diazo-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Highly volatile and explosive; [Merck Index] May explode on heating; An irritant; May cause nervous system disturbances; Possible carcinogen and mutagen; Targets the liver and pancreas; Harmful by ingestion, inhalation, and skin absorption; [Sigma-Aldrich MSDS] See Diazodinitrophenol.

Hazard Classes and CategoriesFlam. Liq. 3 (100%)；Acute Tox. 4 (100%)

安全と保護具

Protective Action Criteria (PAC) · 3 件

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

毒性情報

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

法規制情報

Regulatory InformationAcetic acid, diazo-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

安全データ

wgk: 3
rtecs: AG5775000
ridadr: UN 1993 3/PG 3
hs_code: 29270000
risk_code: 5-10-22-40-67-65-48/20-38-11-63
hazard_code: Xn,F
safety_code: 36/37-62-16
hazard_class: 3.2
packing_group: III
Hazard Classifications: Acute Tox. 4 OralCarc. 2Eye Irrit. 2Flam. Liq. 3Self-react. ESkin Irrit. 2
ストレージクラス: 5.2 - Organic peroxides and self-reacting hazardous materials

化学と産業

応用分野 · 2 件

解説C4H6N2O2(114.11)．N2CHCOOC2H5．ジアゾ酢酸エチルは，グリシンエチルエステルの塩酸塩に亜硝酸カリウムを作用させてつくる．刺激臭のある黄色の液体．融点－22 ℃，沸点141 ℃(96 kPa，不純なものは分解する)，84 ℃(8.1 kPa)．d201.083．エタノール，ベンゼン，エーテル，リグロインなどに可溶，水に難溶．非常に反応性に富み，加熱や濃塩酸，濃硫酸によって爆発的に分解する．また，水と煮沸するか，痕跡の硫酸の作用でグリコール酸エステルとなる．フェーリング液や硝酸銀を還元する．非常に多くの有機化学反応および合成に利用されている．なお，遊離のジアゾ酢酸(N2CHCOOH)はまだ知られていない．森北出版「化学辞典（第2版）

使用Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.1

調製方法 · 1 件

純化方法It is a very volatile yellow oil with a strong pungent odour. EXPLOSIVE [distillation even under reduced pressure is dangerous and may result in an explosion — TAKE ALL THE NECESSARY PRECAUTIONS IF DISTILLATION IS TO BE CARRIED OUT]. It explodes in contact with conc H2SO4-trace acid causes rapid decomposition. It is slightly soluble in H2O, but is miscible with EtOH, *C6H6, pet ether and Et2O. To purify, dissolve it in Et2O [using CH2Cl2 instead of Et2O, protects the ester from acid], wash it with 10% aqueous Na2CO3, dry (MgSO4), filter and repeat as many times as possible until the Et2O layer loses its yellow colour, then remove the solvent below 20o (vacuum). Note that prolonged heating may lead to rapid decomposition and low yields. It can also be purified by steam distillation under reduced pressure but with considerable loss in yield. Place the residual oil in a brown bottle, keep below 10o, and use as soon as possible without distilling. For preparing esters usually the ethereal solution is used directly without purification. [Womack & Nelson Org Synth Coll Vol III 392 1955, UV: Miller & White J Am Chem Soc 79 5974 1957, Fieser 1 367 1967, Beilstein 3 IV 1495.]