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Nickelocene

HCID 62390
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
1271-28-9
Standard SMILES
[Ni+2].c1cc[cH-]c1.c1cc[cH-]c1
InChIKey
KZPXREABEBSAQM-UHFFFAOYSA-N
Molecular formula
C10H10Ni
Average molar mass
188.88 g/mol
Monoisotopic mass
188.013592

Overview

Nickelocene can cause cancer according to California Labor Code.

Names & identifiers

Preferred name
Nickelocene
IUPAC
bis(cyclopenta-1,3-diene);nickel(2+)
English name
Nickelocene
Molecular formula
C10H10Ni10*
Molecular weight
188.88

Names & synonyms

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
Show more names
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

Database identifiers

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

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
11
Formal charge
0
Complexity
11.6

Experimental & physicochemical properties

Chemical Classes · 2 items

Metals -> Metals, Organic Compounds

Carcinogens

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

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 items

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]

Physicochemical properties

Melting point
171 · 171-173 °C(lit.)
storage temp.
2 · 2-8°C
Water Solubility
Insoluble in water
form
crystal
color
dark green
Sensitive

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 3 items

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 item

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

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

Uses · 2 items

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
Applications · 4 items

UsesCatalyst, complexing agent.

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

UsesThis metal alkyl may be used to synthesize hybrid organic-inorganic polymeric molecular layer deposition (MLD). Bis(cyclopentadienyl) nickel (Cp 2 Ni) may be used as a Ni precursor for the atomic layer deposition (ALD) of NiO/carbon nanotubes hybrids.

General DescriptionDark liquid in an 8-10% solution in toluene. Insoluble in water.

Preparation methods · 1 item

It is obtained by reacting nickel chloride with potassium cyclopentadienyl chloride in liquid ammonia or with sodium cyclopentadienyl chloride in diethyl ether. It can also be prepared by reacting sodium cyclopentadienyl chloride with nickel dichloride in an ether solvent. Alternatively, it can be prepared by reacting sodium cyclopentadienyl chloride with nickel chloride, or by reacting cyclopentadiene with nickel chloride hexahydrate in dimethyl sulfoxide. To obtain a pure product, it can be purified with petroleum ether or by sublimation under vacuum at 130°C.

Related reactions

1 records
New reaction record
HRID 1862195 reaction equation
HRID 1862195As productuspto-grants-2003_03

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Air & Moisture Sensitive
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
REACH Annex XVII Substances List
Bis(η5-2,4-cyclopentadien-1-yl)nickel (1271-28-9)
CAS DataBase Reference
1271 · 1271-28-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
8 F745XV5 · JR8F745XV5
Proposition 65 List
Nickelocene
NIST Chemistry Reference
Nickelocene(1271-28-9)
EPA Substance Registry System
Nickelocene (1271-28-9)
UNSPSC Code
12352103 · 12352103
NACRES
23 · NA.23
Symbol(GHS)
2 · GHS02,GHS07,GHS08
Signal word
Danger
Hazard statements
228 · H228-H302-H317-H350
Precautionary statements
201 · P201-P210-P280-P301+P312+P330-P302+P352-P308+P313
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
F,T
Risk Statements
49 · 49-11-22-43
Safety Statements
53 · 53-36/37/39-45
RIDADR
1325 · UN 1325 4.1/PG 2
WGK Germany
3 · 3
RTECS
6500000 · QR6500000
F
10 · 10-23
TSCA
TSCA listed
HazardClass
4.2 · 4.2
PackingGroup
I
HS Code
29319090 · 29319090
Storage Class
4.1 B · 4.1B - Flammable solid hazardous materials
Hazard Classifications
4 OralCarc · Acute Tox. 4 OralCarc. 1AFlam. Sol. 1Skin Sens. 1
Toxicity
50 · mouse,LD50,intraperitoneal,86mg/kg (86mg/kg),Proceedings of the Western Pharmacology Society. Vol. 11, Pg. 39, 1968.
Reactivity Profile · 1 item

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 items

Flam. Sol. 1 (91.7%)

Carcinogens

Safety & protection

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

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 item

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)

Toxicology

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 item

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 item

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 items

0.00026

CALEPA

0.0002

CALEPA

1.4e-05

CALEPA

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

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 items

6.00e+01

2.50e+02

4.40e-02

1.80e-01

8.60e+00

4.0E+03 (G)

Safety data

F
10-23
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
QR6500000
ridadr
UN 1325 4.1/PG 2
hs_code
29319090
Toxicity
mouse,LD50,intraperitoneal,86mg/kg (86mg/kg),Proceedings of the Western Pharmacology Society. Vol. 11, Pg. 39, 1968.
risk_code
49-11-22-43
Signal word
Danger
Symbol(GHS)
GHS02,GHS07,GHS08
hazard_code
F,T
safety_code
53-36/37/39-45
hazard_class
4.2
Storage Class
4.1B - Flammable solid hazardous materials
packing_group
I
Hazard statements
H228-H302-H317-H350
Hazard Classifications
Acute Tox. 4 OralCarc. 1AFlam. Sol. 1Skin Sens. 1
Precautionary statements
P201-P210-P280-P301+P312+P330-P302+P352-P308+P313
Preparation

Upstream & downstream products

Upstream raw materials

Bis(triphenylphosphine)dicarbonylnickelNickle chlorideAmmoniaSodium cyclopentadienideNickel dichloride1,3-CyclopentadieneNickel(II) chloride hexahydrate

Downstream products

cyclopenta-1,3-dieneNickel

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
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Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
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