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BIS(1,5-CYCLOOCTADIENE)NICKEL(0)

Product Name
BIS(1,5-CYCLOOCTADIENE)NICKEL(0)
CAS No.
1295-35-8
Chemical Name
BIS(1,5-CYCLOOCTADIENE)NICKEL(0)
Synonyms
NI(COD)2;Bis(1,5-cyclooctadiene)nickel;Bis(cyclooctadiene)nickel;Bis(1,5-cycL;NICKEL(COD)2;ooctadiene)nickeL;Nickel dicyclooctadiene;Dicyclooctadiene nickel;Bis(1,5-cyclooctadiene)nick;Di(1,5-cyclooctadiene)nickel
CBNumber
CB9303298
Molecular Formula
C16H24Ni
Formula Weight
275.06
MOL File
1295-35-8.mol
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BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Property

Melting point:
60 °C (dec.)(lit.)
storage temp. 
-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.
Sensitive 
Air Sensitive
Exposure limits
NIOSH: IDLH 10 mg/m3; TWA 0.015 mg/m3
Stability:
Air Sensitive
CAS DataBase Reference
1295-35-8(CAS DataBase Reference)
NIST Chemistry Reference
Nickel, bis[(1,2,5,6-«eta»)-1,5-cyclooctadiene]-(1295-35-8)
EPA Substance Registry System
Bis[(1,2,5,6-.eta.)-1,5-cyclooctadiene]nickel (1295-35-8)
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Safety

Hazard Codes 
F,Xn,T
Risk Statements 
11-40-45
Safety Statements 
36/37-45-16-53
RIDADR 
UN 1325 4.1/PG 2
WGK Germany 
3
RTECS 
QR6135000
TSCA 
No
HazardClass 
4.2
PackingGroup 
I
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H228Flammable solid

H317May cause an allergic skin reaction

H351Suspected of causing cancer

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
244988
Product name
Bis(1,5-cyclooctadiene)nickel(0)
Packaging
2g
Price
$95.8
Updated
2024/03/01
TCI Chemical
Product number
B3095
Product name
Bis(1,5-cyclooctadiene)nickel(0)
Purity
>97.0%(T)
Packaging
5g
Price
$491
Updated
2023/06/20
TCI Chemical
Product number
B5417
Product name
Bis(1,5-cyclooctadiene)nickel(0) (Wax encapsulated) (ca. 0.05mmol/capsule)
Packaging
5each
Price
$261
Updated
2024/03/01
Alfa Aesar
Product number
039234
Product name
Bis(1,5-cyclooctadiene)nickel(0)
Packaging
2g
Price
$108
Updated
2024/03/01
Alfa Aesar
Product number
039234
Product name
Bis(1,5-cyclooctadiene)nickel(0)
Packaging
0.5g
Price
$31.6
Updated
2021/12/16
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BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Chemical Properties,Usage,Production

Chemical Properties

Light yellow to Brown powder to crystal.

Uses

Bis(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.

Preparation

Bis(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 + C2H4
Ni(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.

Reactions

Catalyst for Grignard metathesis chain-growth polymerization of Poly(bithienylmethylene)s
Catalyst for neopentylglycolborylation of ortho-substituted aryl halides
Catalyst for Suzuki-Miyaura coupling reactions of heteroaryl ethers with arylboronic acids
Catalyst for carboxylation of naphthyl pivalates with CO2
Catalyst decarboxylative C?P cross-coupling of alkenyl acids with P(O)H compounds
Catalyst for direct amination of phenols via C–O Bond Activation using 2,4,6-Trichloro-1,3,5-triazine as reagent
Catalyst for conversion of aryl, heteroaryl and pharmaceutically relevant chlorides to the corresponding trifluoromethyl sulphides
Catalytic precursor for Suzuki–Miyaura cross-coupling reactions in water under very mild reaction conditions: (a) aryl–heteroaryl cross-couplings; (b) Hetero–heteroaryl cross-couplings

General Description

Yellow crystals or yellowish green solid.

Reactivity Profile

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is extremely air and moisture sensitive. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is sensitive to exposure to light. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is incompatible with oxidizing agents, acids and acid fumes.

Fire Hazard

Flash point data for BIS(1,5-CYCLOOCTADIENE)NICKEL(0) are not available. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is probably combustible.

Purification Methods

It is available in sealed ampoules under N2. All procedures should be carried out in a dry box and in an atmosphere of N2 or Argon in subdued light because the complex is light and oxygen sensitive, and flammable. The solid is washed with dry Et2O (under Ar) and separates from toluene as yellow crystals. Filter this under Ar gas pressure, place the crystals in a container and dry under a vacuum of 0.01mm to remove adhered toluene, flush with Ar and seal them under Ar or N2 in glass ampoules. [Semmelhack Org Reactions 19 115 and 178 1972, Wilke et al. Justus Liebigs Ann Chem 699 1 1966, Wender & Jenkins J Am Chem Soc 111 6432 1989, Fieser & Fieser Reagents for Org Synth 4 33, 16 29, 17 32.] SUSPECTED CARCINOGEN.

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Preparation Products And Raw materials

Raw materials

Preparation Products

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BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Suppliers

Sinocompound Catalysts Co., Ltd.
Tel
0512-67216630 18962121273
Fax
0512-56316689
Email
sales@sinocompound.com
Country
China
ProdList
278
Advantage
64
LaaJoo
Tel
021-60702684 18516024827
Email
huang.jiayi@sinocompound.com
Country
China
ProdList
2654
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Beijing Donghualituo Techonlogy Development Co.,Ltd.
Tel
010-88425576
Fax
(+86)-10-88425546
Email
sales@dhltchem.com
Country
China
ProdList
793
Advantage
59
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3572
Advantage
66
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8415
Advantage
55
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
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View Lastest Price from BIS(1,5-CYCLOOCTADIENE)NICKEL(0) manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Bis(1,5-cyclooctadiene)nickel (0) 1295-35-8
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
10000KG
Release date
2024-09-02
Career Henan Chemical Co
Product
BIS(1,5-CYCLOOCTADIENE)NICKEL(0) 1295-35-8
Price
US $9.80/KG
Min. Order
1g
Purity
≥99%
Supply Ability
100kg
Release date
2020-01-08

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