Bis(1,5-cyclooctadiene)nickel

HCID 6433264CAS 1295-35-8

Basic information

Standard SMILES
C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
InChIKey
JRTIUDXYIUKIIE-KZUMESAESA-N
Molecular formula
C16H24Ni
Average molar mass
275.05 g/mol

Overview

Bis(1,5-cyclooctadiene)nickel appears as yellow crystals or yellowish green solid. (NTP, 1992)

Names & identifiers

Preferred name
Bis(1,5-cyclooctadiene)nickel
IUPAC
bis((1Z,5Z)-cycloocta-1,5-diene);nickel
English name
Bis(1,5-cyclooctadiene)nickel(0)
Molecular formula
C16H24Ni
Molecular weight
275.06

Names & synonyms

Bis(1,5-cyclooctadiene)nickel(0)1295-35-8Bis(1,5-cyclooctadiene)nickelCCRIS 5973Nickel, bis(1,5-cyclooctadiene)-EINECS 215-072-0Bis(cyclooctadiene)nickel(0)Bis((1,2,5,6-eta)-1,5-cyclooctadiene)nickelbis((1Z,5Z)-cycloocta-1,5-diene) nickelRefChem:120008bis(1,5-cyclooctadiene)-NickelNickel, bis(1,5cyclooctadiene)
Show more names
NI(COD)2Bis(cyclooctadiene)nickelBis(1,5-cycLNICKEL(COD)2ooctadiene)nickeLNickel dicyclooctadieneDicyclooctadiene nickelBis(1,5-cyclooctadiene)nickDi(1,5-cyclooctadiene)nickel
JRTIUDXYIUKIIE-UHFFFAOYSA-NNICKEL BIS(CYCLOOCATADIENE)1,5-CYCLOOCTADIENE, NICKEL COMPLEXBIS(ETA4-1,5-CYCLOOCTADIENE)NICKELBis((1,2,5,6eta)1,5cyclooctadiene)nickelNickel, bis((1,2,5,6eta)1,5cyclooctadiene)BIS((1,2,5,6,ETA)-1,5-CYCLOOCTADIENE)NICKEL215-072-0

Database identifiers

CAS
1295-35-8
PubChem CID
6433264
EC Number
215-072-0

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
17

Experimental & physicochemical properties

Chemical ClassesMetals -> Metals, Organic Compounds
SolubilityDecomposes (NTP, 1992)
Boiling PointDecomposes (NTP, 1992)
Melting Point284 to 288 °F (NTP, 1992)
Physical Description · 2 items

Bis(1,5-cyclooctadiene)nickel appears as yellow crystals or yellowish green solid. (NTP, 1992)

Yellow or yellowish-green solid; [CAMEO] Yellow crystalline solid; [MSDSonline]

Physicochemical properties

Melting point
60 °C · 60 °C (dec.)(lit.)
storage temp.
-20 °C · -20°C
solubility
Benzene (Partially Dissolved), THF (Slightly)
form
Shiny Crystalline Powder
color
Gold
Water Solubility
Soluble in benzene, toluene, terahydrofuran, ether, dimethyl formamide, hexamethylphosphoramide, N-methylpyrrolidinone. Insoluble in water.

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H228 (100%): Flammable solid [Danger Flammable solids]

P203, P210, P233, P240, P241, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P318, P321, P333+P317, P342+P316, P362+P364, P370+P378, P403, 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.

Hazard information

Regulatory InformationRestricted substance: Bis(1,5-cyclooctadiene)nickel
DOT LabelFlammable Solid
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Similar compounds cause irritation of the eyes, nose, throat and skin.
Hazards Summary · 1 item

A strong reducing agent; Reacts with air and water; Similar compounds are skin, eye, nose, and throat irritants; [CAMEO] Spontaneously flammable on exposure to air; An irritant; May cause skin sensitization; [MSDSonline] See Nickel and the linked occupational diseases.

Reactive GroupHydrocarbons, Aliphatic Unsaturated

Safety & protection

Fire FightingFires involving this compound can be controlled using 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 a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not 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 LevelChronic Inhalation: 0.0001 mg/m3 (L134) Intermediate Oral: 0.01 mg/kg/day (L134)
Permissible Exposure Limit (PEL)1.0 [mg/m3], as Ni

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 RoutesInhalation (L41) ; oral (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)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
No
rtecs
QR6135000
ridadr
UN 1325 4.1/PG 2
hs_code
29319090

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

UsesBis(cyclooctadiene)nickel(0) is a common source of Ni(0) in chemical synthesis. (L498)
Applications · 2 items

UsesBis(1,5-cyclooctadiene)nickel(0) is used as a catalyst for the cycloaddition of 1,3-dienes and is used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. Also, it is involved as a catalyst for asymmetric alpha-arylation and heteroarylation of ketones with chloroarenes, stereoselective borylative ketone-diene coupling, cycloaddition of benzamides with internal alkynes and methyl carboxylation of homopropargylic alcohols.

General DescriptionYellow crystals or yellowish green solid.

Preparation methods · 1 item

PreparationBis(1,5-cyclooctadiene)nickel(0) is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:Ni(acac)2 + 2 cod + 2 AlEt3 → Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4Ni(cod)2 is moderately soluble in several organic solvents. One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides. If exposed to air, the solid oxidizes to nickel(II) oxide. As a result, this compound is generally handled in a glovebox.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
杭州奥得科技有限公司0571-88772972-0 15057128248 · [email protected]

Related reactions

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Linked notes

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