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ニッケロセン

Nickelocene

HCID 62390
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
1271-28-9
標準SMILES
[Ni+2].c1cc[cH-]c1.c1cc[cH-]c1
InChIKey
KZPXREABEBSAQM-UHFFFAOYSA-N
分子式
C10H10Ni
平均分子量
188.88 g/mol
単同位体質量
188.013592

概要

Nickelocene can cause cancer according to California Labor Code.

名称と識別子

優先名称
Nickelocene
IUPAC
bis(cyclopenta-1,3-diene);nickel(2+)
現地名
ニッケロセン
英語名
Nickelocene
分子式
C10H10Ni10*
分子量
188.88

名称と別名

Nickelocene1271-28-9NikelocenBis(eta5-2,4-cyclopentadien-1-yl)nickelNickel biscyclopentadieneNikelocen [Czech]Bis(cyclopentadienyl)nickel(II)Di-pi-cyclopentadienylnickelCCRIS 430Bis(cyclopentadienyl)nickelEINECS 215-039-0JR8F745XV5
名称をさらに表示
ニッケロセンビス(5-2,4-シクロペンタジエン-1-イル)ニッケルジシクロペンタジエニルニッケル(II)ジ-π-クロペンタジエニルニッケルビス(シクロペンタジエニル)ニッケルビス(シクロペンタジエニル)ニッケル(II)Nickelocene,99%di(cyclopenta-1,3-dien-1-yl)nickelbis(B7Nickelocene>Nickelocene(NiCp2)nickelbiscyclopentadieneDI(CYCLOPENTADIENYL)NICKEL
Nickel, compd with pi-cyclopentadienyl (1:2)Nickel, di-pi-cyclopentadienyl-piCyclopentadienyl compd. With nickelBIS(CYCLOPENTADIENYL) NICKEL(II)BIS(ETA5-CYCLOPENTADIENYL)NICKELDipicyclopentadienylnickelRefChem:854087DTXCID101783329

データベース識別子

CAS
1271-28-9
PubChem CID
62390
UNII
JR8F745XV5
EC Number
215-039-0

物性

構造計算による物性

極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
11
形式電荷
0
複雑度
11.6

実験および物理化学的性質

Chemical Classes · 2 件

Metals -> Metals, Organic Compounds

Carcinogens

SolubilityInsoluble (<1 mg/ml at 75 °F) (NTP, 1992)
Flash Point · 2 件

39 °F (8-10% solution in toluene) (NTP, 1992)

39 °F (8-10% solution in toluene)

Melting Point340 to 343 °F (NTP, 1992)
Physical Description · 2 件

Nickelocene is a dark liquid in an 8-10% solution in toluene. Insoluble in water. (NTP, 1992)

Dark liquid in an 8-10% solution in toluene; [CAMEO] Dark green crystals; [Hawley]

物理化学的性質

融点
171 · 171-173 °C(lit.)
貯蔵温度
2 · 2-8°C
水溶解度
Insoluble in water
外見
結晶
色
濃い緑色
InChI
1S/2C5H5.Ni/c2*1-2-4-5-3-1;/h2*1-5H;
InChIKey
FOOKRXHSBKEWSE-UHFFFAOYSA-N
SMILES
[Ni].[CH]1[CH][CH][CH][CH]1.[CH]2[CH][CH][CH][CH]2
CAS データベース
1271 · 1271-28-9(CAS DataBase Reference)
NISTの化学物質情報
Nickelocene(1271-28-9)
EPAの化学物質情報
Nickelocene (1271-28-9)

化学的性質

化学的特性Nickelocene is a solid crystalline substance of dark green color, insoluble in water or carbon tetrachloride, slightly soluble in alcohol and liquid ammonia, and readily soluble in nonpolar organic solvents.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H228 (91.7%): Flammable solid [Danger Flammable solids]

P203, P210, P240, P241, P261, P264, P270, P272, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P370+P378, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 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

Regulatory Information · 3 件

Hazard Traits - Carcinogenicity

Restricted substance: Bis(η5-2,4-cyclopentadien-1-yl)nickel

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Solid
Fire HazardsThis chemical is flammable. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This chemical can be absorbed through the skin. (NTP, 1992)
Hazards Summary · 1 件

Toxic after inhalation or skin absorption; [Hawley] Toxic by ingestion; LD50 (rat) = 490 mg/kg; May cause skin sensitization; [MSDSonline] There is limited evidence that nickelocene is carcinogenic in experimental animals; [IARC] See Nickel and linked occupational diseases. See ORGANOMETALS.

Reactive GroupOrganometallics
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 件

Organometallics, such as NICKELOCENE, are reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents. Often reactive with water to generate toxic or flammable gases.

Air and Water ReactionsHighly flammable. The neat material is sensitive to air. (NTP, 1992). Insoluble in water.
Hazard Classes and Categories · 2 件

Flam. Sol. 1 (91.7%)

Carcinogens

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with toluene followed by washing with a strong soap and water solution. Do no reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 133 [Flammable Solids]:
Minimum Risk LevelIntermediate Inhalation: 0.0002 mg/m3 (L134) Chronic Inhalation: 0.00009 mg/m3 (L134)
Permissible Exposure Limit (PEL)1.0 [mg/m3], as Ni
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.
Immediately Dangerous to Life or Health (IDLH)10 mg Ni/m3 ; A potential occupational carcinogen. (NIOSH, 2024)

毒性情報

TreatmentExcess exposure to nickel is usually handled by preventing further exposure and symptomatic treatment. Nickel poisoning may also be treated using chelation therapy with sodium diethyldithiocarbamate. (L42)
Health Effects · 1 件

The most common harmful health effect of nickel in humans is an allergic reaction. This usually manifests as a skin rash, although some people experience asthma attacks. Long term inhahation of nickel causes chronic bronchitis and reduced lung function, as well as damage to the naval cavity. Ingestion of excess nickel results in damage to the stomach, blood, liver, kidneys, and immune system, as well as having adverse effects on reproduction and development. (L41)

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesOral (L41) ; inhalation (L41) ; dermal (L41)
Toxicity Summary · 1 件

Nickel is known to substitute for other essential elements in certain enzmes, such as calcineurin. It is genotoxic, and some nickel compounds have been shown to promote cell proliferation. Nickel has a high affinity for chromatin proteins, particularly histones and protamines. The complexing of nickel ions with heterochromatin results in a number of alterations including condensation, DNA hypermethylation, gene silencing, and inhibition of histone acetylation, which have been shown to disturb gene expression. Nickel has also been shown to alter several transcription factors, including hypoxia-inducible transcription factor, activating transcription factor, and NF-KB transcription factor. There is also evidence that nickel ions inhibit DNA repair, either by directly inhibiting DNA repair enzymes or competing with zinc ions for binding to zinc-finger DNA binding proteins, resulting in structural changes in DNA that prevent repair enzymes from binding. Nickel ions can also complex with a number of cellular ligands including amino acids, peptides, and proteins resulting in the generation of oxygen radicals, which induce base damage, DNA strand breaks, and DNA protein crosslinks. (L41, A40)

Signs and SymptomsSymptoms of nickel poisoning include headache, nausea, vomiting, dizziness, irritability, and difficulty sleeping, followed by chest pains, sweating, rapid heart beat, and a dry cough. (L42)
Carcinogen Classification1, carcinogenic to humans. (L135)
RAIS Toxicity Values · 6 件

0.00026

CALEPA

0.0002

CALEPA

1.4e-05

CALEPA

Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 · 6 件

6.00e-01

2.50e+00

1.10e-02

4.70e-02

8.60e-02

4.0E+03(G)

Hazard Quotient Level 3 or Cancer Risk Level 1E-04 · 6 件

6.00e+01

2.50e+02

4.40e-02

1.80e-01

8.60e+00

4.0E+03 (G)

安全データ

F
10-23
wgk
3
tsca
TSCA listed
rtecs
QR6500000
ridadr
UN 1325 4.1/PG 2
毒性
mouse,LD50,intraperitoneal,86mg/kg (86mg/kg),Proceedings of the Western Pharmacology Society. Vol. 11, Pg. 39, 1968.
PRTR法
特定第一種指定化学物質
hs_code
29319090
risk_code
49-11-22-43
安衛法
特化則 特定化学物質(管理第2類)
hazard_code
F,T
safety_code
53-36/37/39-45
hazard_class
4.2
packing_group
I
Hazard Classifications
Acute Tox. 4 OralCarc. 1AFlam. Sol. 1Skin Sens. 1
ストレージクラス
4.1B - Flammable solid hazardous materials

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Nickel is absorbed mainly through the lungs and gastrointestinal tract. Once in the body it enters the bloodstream, where it binds to albumin, L-histidine, and _2-macroglobulin. Nickel tends to accumulate in the lungs, thyroid, kidney, heart, and liver. Absorbed nickel is excreted in the urine, wherease unabsorbed nickel is excreted in the faeces. (L41)

用途と製造

Uses · 2 件

Used as a catalyst and complexing agent; [Hawley]

Also known as bis(cyclopentadienyl)nickel or NiCp2, this bright green paramagnetic solid is found abundantly in nature in laterite ore minerals, such as limonite, garnierite, and pentlandite. Nickel has a biological role and is found in certain enzymes, including urease, hydrogenase, methylcoenzyme M reductase, and carbon monoxide dehydrogenase.

General Manufacturing InformationNickelocene: ACTIVE
応用分野 · 3 件

解説ビス(η5-シクロペンタジエニル)ニッケル(Ⅱ)ともいう.Ni(C5H5)2の組成式をもつニッケル化合物.ジエチルアミンのような塩基の存在下でシクロペンタジエンと塩化ニッケル(Ⅱ)とを反応させることにより合成される.フェロセンと同様,ニッケル原子が二つのシクロペンタジエニル環にはさまれた構造をしている.固体.融点171~173 ℃.ニッケロセンはフェロセンに比べてシクロペンタジエニル環と金属との結合距離が長く,フェロセンより不安定で化学反応性に富み,環への付加反応を受けやすい.[CAS 1271-28-9]森北出版「化学辞典(第2版)

使用Nickelocene is obtained through reacting nickel halides with sodium cyclopentadienide. It is used as a catalyst or as a complexing agent.

一般的な説明Dark liquid in an 8-10% solution in toluene. Insoluble in water.

調製方法 · 1 件

純化方法Dissolve the complex in Et2O, filter and evaporate in a vacuum. Purify it rapidly by recrystallisation from pet ether using a solid CO2/Me2CO bath, m 171-173o(in an evacuated tube). Also purify it by vacuum sublimation. [Wilkinson et al. J Am Chem Soc 76 1970 1954, Beilstein 16 IV 1831.]

上流・下流製品情報

上流原料

ジカルボニルビス(トリフェニルホスフィン)ニッケルジクロロニッケル(II)アンモニア2,4-シクロペンタジエン-1-イルナトリウムNickel dichlorideシクロペンタジエンニッケル クロリド ヘキサ水和物

下流製品

cyclopenta-1,3-dieneニッケル

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関連反応

1 件
反応記録を作成
HRID 1862195 の反応式
HRID 1862195生成物としてuspto-grants-2003_03

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート