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4-Methyloctane, a member of the alkane family, is a saturated hydrocarbon compound characterized by a linear chain of eight carbon atoms with a methyl group attached to the fourth carbon. It is a colorless liquid with the molecular formula C9H20, a boiling point of 138.9°C, and a density of 0.737 g/cm3. Despite its low toxicity and non-hazardous classification, it should be handled with care and proper safety precautions.

2216-34-4

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2216-34-4 Usage

Uses

Used in Chemical Synthesis:
4-Methyloctane is utilized as a solvent in various chemical synthesis processes due to its ability to dissolve a wide range of compounds and facilitate reactions.
Used in Industrial Processes:
In the industrial sector, 4-Methyloctane serves as a solvent for numerous applications, including the production of chemicals, pharmaceuticals, and other products. Its properties make it suitable for use in various manufacturing processes.
Used in Laboratory Settings:
4-Methyloctane is employed as a solvent in laboratory experiments and research, where its ability to dissolve a variety of substances and its low toxicity make it a preferred choice for many applications.
Used in Fuel Additives:
Due to its compatibility with hydrocarbon fuels, 4-Methyloctane can be used as a component in fuel additives to improve combustion efficiency and reduce emissions.
Used in Cleaning Agents:
4-Methyloctane's solvent properties also make it suitable for use in cleaning agents, where it can effectively dissolve and remove contaminants and residues from various surfaces.

Check Digit Verification of cas no

The CAS Registry Mumber 2216-34-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,1 and 6 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2216-34:
(6*2)+(5*2)+(4*1)+(3*6)+(2*3)+(1*4)=54
54 % 10 = 4
So 2216-34-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H20/c1-4-6-8-9(3)7-5-2/h9H,4-8H2,1-3H3

2216-34-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-METHYLOCTANE

1.2 Other means of identification

Product number -
Other names Octane, 4-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2216-34-4 SDS

2216-34-4Synthetic route

2-iodopentane
637-97-8

2-iodopentane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With Li2[di-n-butylcyanocuprate] In tetrahydrofuran at -50℃; for 2h;99%
2-bromopentane
107-81-3

2-bromopentane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With Li2[di-n-butylcyanocuprate] In tetrahydrofuran 1) 0 deg C, 2h, 2) RT, 1h;94%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

2-bromopentane
107-81-3

2-bromopentane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With copper(I) thiocyanate In tetrahydrofuran at 0℃; for 3h; Mechanism; Product distribution; other reagents: CuI;63%
With copper(I) thiocyanate In tetrahydrofuran at 0℃; for 3h; other reagents: CuI;63%
With 1.) CuCN 1) THF, -78 deg C, 2) THF, 0 deg C, 2 h, RT, 1 h; Yield given. Multistep reaction;
2-methyl-1-chlorobutane
625-29-6

2-methyl-1-chlorobutane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With Li2[di-n-butylcyanocuprate] In tetrahydrofuran for 11h; Ambient temperature;28%
4-methyl-4-octanol
23418-37-3

4-methyl-4-octanol

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With naphthalene-2-sulfonate Hydrieren des erhaltenen Olefins an Platinoxyd in Eisessig;
aus dem durch Wasserabspaltung entstehenden Kohlenwasserstoff C9H18 durch Reduktion mit Wasserstoff und Nickel bei 160-180grad;
With aluminum oxide at 300 - 320℃; Beim Hydrieren des erhaltenen Olefin-Gemisches an Nickel/Kieselgur bei 140-180grad/175 at;
n-butylcyclopentane
2040-95-1

n-butylcyclopentane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With nickel-aluminium oxide; hydrogen at 250 - 305℃;
With platinum on activated charcoal; hydrogen at 305 - 315℃;
6-bromo-4-methyl-oct-2-ene
90675-89-1

6-bromo-4-methyl-oct-2-ene

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
(i) KOH, (ii) H2, Pd-CaCO3; Multistep reaction;
2-butyl-penta-1,4-diene
30479-99-3

2-butyl-penta-1,4-diene

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In acetic acid
5-methyl-nonanal
52432-75-4

5-methyl-nonanal

A

5-methylnonane
15869-85-9

5-methylnonane

B

4-methyloctane
2216-34-4

4-methyloctane

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

2-methyl-1-chlorobutane
625-29-6

2-methyl-1-chlorobutane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With 1.) CuCN 1) THF, -78 deg C, 2) THF, RT, 11 h; Yield given. Multistep reaction;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

2-iodopentane
637-97-8

2-iodopentane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With 1.) CuCN 1) THF, -78 deg C, 2) THF, -50 deg C, 2 h; Yield given. Multistep reaction;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

2-pentyl tosylate
3813-69-2

2-pentyl tosylate

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With 1.) CuCN 1) THF, -78 deg C, 2) THF, RT, 7 h; Yield given. Multistep reaction;
1-<2-thienyl>-butan-1-one

1-<2-thienyl>-butan-1-one

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With methyl magnesium iodide; diethyl ether Beim Erwaermen des Reaktionsprodukts mit Oxalsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit Raney-Nickel in Dioxan;
n-butylcyclopentane
2040-95-1

n-butylcyclopentane

nickel-aluminium oxide

nickel-aluminium oxide

hydrogen

hydrogen

A

4-methyloctane
2216-34-4

4-methyloctane

B

2-Ethyltoluene
611-14-3

2-Ethyltoluene

Conditions
ConditionsYield
at 250 - 305℃;
n-butylcyclopentane
2040-95-1

n-butylcyclopentane

hydrogen

hydrogen

platinum-coal

platinum-coal

A

4-methyloctane
2216-34-4

4-methyloctane

B

2-Ethyltoluene
611-14-3

2-Ethyltoluene

Conditions
ConditionsYield
at 305 - 315℃;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

1-n-butylcyclopentene
2423-01-0

1-n-butylcyclopentene

hydrogen

hydrogen

nickel-aluminium-alloy

nickel-aluminium-alloy

A

2-Methylhexane
591-76-4

2-Methylhexane

B

3-methylheptane
589-81-1

3-methylheptane

C

4-methyloctane
2216-34-4

4-methyloctane

D

n-butylcyclopentane
2040-95-1

n-butylcyclopentane

Conditions
ConditionsYield
at 200℃;
2-Pentanone
107-87-9

2-Pentanone

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aluminium oxide / 300 - 320 °C / Beim Hydrieren des erhaltenen Olefin-Gemisches an Nickel/Kieselgur bei 140-180grad/175 at
View Scheme
n-hexan-2-one
591-78-6

n-hexan-2-one

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aus dem durch Wasserabspaltung entstehenden Kohlenwasserstoff C9H18 durch Reduktion mit Wasserstoff und Nickel bei 160-180grad
View Scheme
Multi-step reaction with 2 steps
2: aus dem durch Wasserabspaltung entstehenden Kohlenwasserstoff C9H18 durch Reduktion mit Wasserstoff und Nickel bei 160-180grad
View Scheme
2-bromopent-3-ene
1809-26-3

2-bromopent-3-ene

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SnCl4
2: (i) KOH, (ii) H2, Pd-CaCO3
View Scheme
2-n-butyl-dimethoxy(1,4-pentadienyl)borane
21223-14-3

2-n-butyl-dimethoxy(1,4-pentadienyl)borane

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AcOH, MeOH
2: H2 / PtO2 / acetic acid
View Scheme
hex-1-yne
693-02-7

hex-1-yne

tertiary amine

tertiary amine

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) , (ii) /BRN= 1098229/, isopentane
2: AcOH, MeOH
3: H2 / PtO2 / acetic acid
View Scheme
propene
187737-37-7

propene

A

3,5-dimethylheptane
926-82-9

3,5-dimethylheptane

B

3,4-dimethylheptane
922-28-1

3,4-dimethylheptane

C

nonane
111-84-2

nonane

D

2-methyloctane
3221-61-2

2-methyloctane

E

3,3,4-trimethylhexane
16747-31-2

3,3,4-trimethylhexane

F

2,3,5-trimethylhexane
1069-53-0

2,3,5-trimethylhexane

G

3-ethyl-2-methyl-hexane
16789-46-1

3-ethyl-2-methyl-hexane

H

2,2,4-trimethylhexane
16747-26-5

2,2,4-trimethylhexane

I

2,5-dimethylheptane
2216-30-0, 132854-35-4

2,5-dimethylheptane

J

4-ethyl-2-methylhexane
3074-75-7

4-ethyl-2-methylhexane

K

2,4-dimethylheptane
2213-23-2

2,4-dimethylheptane

L

4-methyloctane
2216-34-4

4-methyloctane

M

3-ethylheptane
15869-80-4

3-ethylheptane

N

2,6-dimethylheptane
1072-05-5

2,6-dimethylheptane

O

3-methyloctane
2216-33-3, 116783-15-4

3-methyloctane

P

2,3-dimethylheptane
3074-71-3

2,3-dimethylheptane

Q

2,4-dimethyl-3-ethylpentane
1068-87-7

2,4-dimethyl-3-ethylpentane

R

2,2,5-trimethylhexane
3522-94-9

2,2,5-trimethylhexane

S

2,2-dimethylheptane
1071-26-7

2,2-dimethylheptane

Conditions
ConditionsYield
Stage #1: propene With water at 25 - 40℃;
Stage #2: at 125 - 172℃; under 52505.3 Torr;
Stage #3: With hydrogen; 0.5% Pt/Al2O3
non-1-ene
124-11-8

non-1-ene

A

2-methyloctane
3221-61-2

2-methyloctane

B

4-methyloctane
2216-34-4

4-methyloctane

C

3-methyloctane
2216-33-3, 116783-15-4

3-methyloctane

Conditions
ConditionsYield
WO3/ZrO2 catalyst at 199.84℃; for 0.266667h; Product distribution;A 36.2 % Chromat.
B 8.3 % Chromat.
C 25.8 % Chromat.
cis-bicyclo[4.4.0]decane

cis-bicyclo[4.4.0]decane

trans-bicyclo[4.4.0]decane

trans-bicyclo[4.4.0]decane

B

3,4-diethylhexane
19398-77-7

3,4-diethylhexane

C

octane, 4-ethyl-
15869-86-0

octane, 4-ethyl-

D

4,5-dimethyloctane
15869-96-2

4,5-dimethyloctane

E

decane
124-18-5

decane

F

5-methylnonane
15869-85-9

5-methylnonane

G

4-methyloctane
2216-34-4

4-methyloctane

H

3-ethylheptane
15869-80-4

3-ethylheptane

I

4-ethyl-3-methylheptane
52896-89-6

4-ethyl-3-methylheptane

J

4-(1-methylethyl)-heptane
52896-87-4

4-(1-methylethyl)-heptane

Conditions
ConditionsYield
With 2.59 wt.% iridium on non-acidic silica; hydrogen at 290℃; under 39003.9 Torr; Autoclave;
1-(furan-2-yl)-2-methylpent-1-en-3-one
131375-70-7

1-(furan-2-yl)-2-methylpent-1-en-3-one

A

4-methylnonane
17301-94-9, 108266-42-8

4-methylnonane

B

4-methyloctane
2216-34-4

4-methyloctane

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 349.84℃; under 45004.5 Torr; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;
nonane
111-84-2

nonane

A

3,5-dimethylheptane
926-82-9

3,5-dimethylheptane

B

2-methyloctane
3221-61-2

2-methyloctane

C

4-methyloctane
2216-34-4

4-methyloctane

D

3-methyloctane
2216-33-3, 116783-15-4

3-methyloctane

Conditions
ConditionsYield
With conventional isomerization catalyst In neat (no solvent, gas phase) at 330℃; under 30003 Torr; Flow reactor;A 7 %Chromat.
B 16 %Chromat.
C 26 %Chromat.
D 25 %Chromat.
propane
74-98-6

propane

A

2,3,3-trimethyloctane

2,3,3-trimethyloctane

B

2-Methylhexane
591-76-4

2-Methylhexane

C

2,3,3-Trimethyl-pentane
560-21-4

2,3,3-Trimethyl-pentane

D

3,3-dimethylhexane
563-16-6

3,3-dimethylhexane

E

2,3,5-trimethylhexane
1069-53-0

2,3,5-trimethylhexane

F

4,4-dimethyloctane
15869-95-1

4,4-dimethyloctane

G

2,3,5-trimethylheptane
20278-85-7

2,3,5-trimethylheptane

H

2,2,4-trimethylheptane
14720-74-2

2,2,4-trimethylheptane

I

2,3-dimethyl pentane
565-59-3

2,3-dimethyl pentane

J

2,3-dimethylhexane
584-94-1, 116724-01-7

2,3-dimethylhexane

K

2,4-dimethylhexane
589-43-5

2,4-dimethylhexane

L

2-Methylpentane
107-83-5

2-Methylpentane

M

triptane
464-06-2

triptane

N

4-methyloctane
2216-34-4

4-methyloctane

O

3-methyloctane
2216-33-3, 116783-15-4

3-methyloctane

P

2,3,3-trimethylhexane
16747-28-7

2,3,3-trimethylhexane

Q

2,3-dimethylheptane
3074-71-3

2,3-dimethylheptane

R

2,4,6-trimethyloctane
62016-37-9

2,4,6-trimethyloctane

S

tetramethyl-2,3,6,7 octane
52670-34-5

tetramethyl-2,3,6,7 octane

T

3,6-dimethyldecane
17312-53-7

3,6-dimethyldecane

Conditions
ConditionsYield
at 20℃; under 760.051 Torr; Electric arc;
propane
74-98-6

propane

A

nonane
111-84-2

nonane

B

2,3,5-trimethylhexane
1069-53-0

2,3,5-trimethylhexane

C

3-methylheptane
589-81-1

3-methylheptane

D

2,2-dimethyl-3-pentanol
3970-62-5

2,2-dimethyl-3-pentanol

E

2,4-dimethylheptane
2213-23-2

2,4-dimethylheptane

F

4-methyloctane
2216-34-4

4-methyloctane

G

2,4-dimethyl-3-ethylpentane
1068-87-7

2,4-dimethyl-3-ethylpentane

H

S-(-)-dihydrocitronellol
68680-98-8

S-(-)-dihydrocitronellol

Conditions
ConditionsYield
at 20℃; under 760.051 Torr; Electric arc;
propane
74-98-6

propane

A

2,3,5-trimethylhexane
1069-53-0

2,3,5-trimethylhexane

B

2,4-dimethylheptane
2213-23-2

2,4-dimethylheptane

C

4-methyloctane
2216-34-4

4-methyloctane

D

2,4-dimethyl-3-ethylpentane
1068-87-7

2,4-dimethyl-3-ethylpentane

E

2-methyl-3-prop-2-enoxyprop-1-ene
14289-96-4

2-methyl-3-prop-2-enoxyprop-1-ene

F

4-methylpentyl trichloroacetic acid ester

4-methylpentyl trichloroacetic acid ester

G

2,5,6-trimethyloctane

2,5,6-trimethyloctane

Conditions
ConditionsYield
at 20℃; under 760.051 Torr; Electric arc;
4-methyloctane
2216-34-4

4-methyloctane

platinum

platinum

coal

coal

A

1-Methyl-3-ethylbenzene
620-14-4

1-Methyl-3-ethylbenzene

B

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
at 305 - 310℃;

2216-34-4Relevant academic research and scientific papers

UPGRADING 5-NONANONE

-

Paragraph 0104-0108, (2018/04/20)

Provided are fuel components, a method for producing fuel components, use of the fuel components and fuel containing the fuel components based on 5-nonanone.

GAS-TO-LIQUID REACTOR AND METHOD OF USING

-

Paragraph 0143, (2019/08/15)

A device and a process to propagate molecular growth of hydrocarbons, either straight or branched chain structures, that naturally occur in the gas phase to a molecular size sufficient to shift the natural occurring phase to a liquid or solid state is provided. According to one embodiment, the device includes a grounded reactor vessel having a gas inlet, a liquid outlet, and an electrode within the vessel; a power supply coupled to the electrode for creating an elecirostatic field within the vessel for converting the gas to a liquid and or solid state.

Solvent-free synthesis of C9 and C10 branched alkanes with furfural and 3-pentanone from lignocellulose

Chen, Fang,Li, Ning,Li, Shanshan,Yang, Jinfan,Liu, Fei,Wang, Wentao,Wang, Aiqin,Cong, Yu,Wang, Xiaodong,Zhang, Tao

, p. 229 - 232 (2015/01/09)

Jet fuel range branched alkanes were first synthesized under solvent-free conditions by the aldol condensation of furfural and 3-pentanone from lignocellulose followed by the one-step hydrodeoxygenation (HDO). Among the investigated solid base catalysts,

Ring opening of decalin via hydrogenolysis on Ir/- and Pt/silica catalysts

Haas, Andreas,Rabl, Sandra,Ferrari, Marco,Calemma, Vincenzo,Weitkamp, Jens

experimental part, p. 97 - 109 (2012/07/13)

The catalytic conversion of cis-decalin was studied at a hydrogen pressure of 5.2 MPa and temperatures of 250-410 °C on iridium and platinum supported on non-acidic silica. The absence of catalytically active Br?nsted acid sites was indicated by both FT-IR spectroscopy with pyridine as a probe and the selectivities in a catalytic test reaction, viz. the hydroconversion of n-octane. On iridium/silica, decalin hydroconversion starts at ca. 250-300 °C, and no skeletal isomerization occurs. The first step is rather hydrogenolytic opening of one six-membered ring to form the direct ring-opening products butylcyclohexane, 1-methyl-2-propylcyclohexane and 1,2- diethylcyclohexane. These show a consecutive hydrogenolysis, either of an endocyclic carboncarbon bond into open-chain decanes or of an exocyclic carboncarbon bond resulting primarily in methane and C9 naphthenes. The latter can undergo a further endocyclic hydrogenolysis leading to open-chain nonanes. All individual C10 and C9 hydrocarbons predicted by this direct ring-opening mechanism were identified in the products generated on the iridium/silica catalysts. The carbon-number distributions of the hydrocracked products C9- show a peculiar shape resembling a hammock and could be readily predicted by simulation of the direct ring-opening mechanism. Platinum on silica was found to require temperatures around 350-400 °C at which relatively large amounts of tetralin and naphthalene are formed. The most abundant primary products on Pt/silica are spiro[4.5]decane and butylcyclohexane which can be readily accounted for by the well known platinum-induced mechanisms described in the literature for smaller model hydrocarbons, namely the bond-shift isomerization mechanism and hydrogenolysis of a secondary-tertiary carboncarbon bond in decalin.

Activation and isomerization of hydrocarbons over WO3/ZrO2 catalysts. II. Influence of tungsten loading on catalytic activity: Mechanistic studies and correlation with surface reducibility and tungsten surface species

Di Gregorio, Francois,Keller, Nicolas,Keller, Valerie

, p. 159 - 171 (2008/09/21)

We studied the correlation among the catalytic behavior of WO3/ZrO2 samples toward unsaturated and saturated hydrocarbons transformation, tungsten surface species oxidation states, and the crystallographic structure of the zirconia support. Different tungsten-loaded catalysts were studied, from 9 wt% (near-monolayer coverage) to 30 wt%. The resulting WO3/ZrO2 materials were obtained by impregnation of a tungsten salt on either a commercially available monoclinic zirconia or an amorphous hydroxide, ZrOx(OH)4-2x, followed by a calcination step (according to the Hino and Arata procedure), leading to a tetragonal structure. In contrast to previous works, here we demonstrate that the crystallographic structure of zirconia has no influence on catalytic properties. Correlations with XPS analyses revealed two aspects of catalytic behavior that depend strongly on the catalyst reducibility and thus on the W surface species oxidation states. First, on hardly reducible (tungsten loadings a purely acidic monomolecular mechanism for both isomerization (largely predominant) and cracking reactions, associated with W6+ and W5+ surface species, was demonstrated. Second, on easily reducible (tungsten loadings >15 wt%) or deeply reduced (over 723 K) surfaces, a bifunctional mechanism associating dehydrogenating/hydrogenating properties occurring on metallic tungsten and acidic isomerization and cracking on W5+ and W6+ surface species was observed. However, in this last case, we could not exclude the participation of a purely metallic isomerization mechanism occurring through σ-alkyl adsorbed species on the β-W metallic phase. A more pronounced reduction then led to an increase in the extensive hydrogenolysis mechanism, causing catalyst deactivation.

Alkene oligomerization process

-

Page 4-5, (2008/06/13)

A process for oligomerising alkenes having from 3 to 6 carbon atoms which comprises contacting a feedstock comprising a) one or several alkenes having x carbon atoms, and, b) optionally, one or several alkenes having y carbon atoms, x and y being different, with a catalyst containing a zeolite of the MFS structure type, under conditions to obtain selectively oligomeric product containing predominant amounts of certain oligomers. The process is carried out at a temperature comprised between 125 and 175° C. when the feedstock contains only alkenes with 3 carbon atoms and between 140 and 240° C., preferably between 140 and 200° C. when the feedstock contains comprises at least one alkene with 4 or more carbon atoms.

Substitution Reactions of Secondary Halides and Epoxides with Higher Order, Mixed Organocuprates, R2Cu(CN)Li2: Synthetic, Stereochemical, and Mechanistic Aspects

Lipshutz, Bruce H.,Wilhelm, Robert S.,Kozlowski, Joseph A.,Parker, David

, p. 3928 - 3938 (2007/10/02)

Higher order cuprates, represented by the general formula R2Cu(CN)Li2, are readily prepared from copper cyanide and 2 equiv of an organolithium.These novel reagents react readily and efficiently with secondary unactivated iodides and bromides affording products of substitution.Likewise, mono-, di-, and trisubstituted epoxides undergo ring opening leading to the corresponding alcohols in excellent yields.The effects of solvent, temperature, gegenion, and variations in ligands are discussed.Replacement of the second equivalent of RLi by CH3Li strongly encouragestransfer of R over CH3 in R(CH3)Cu(CN)Li2 with halides.Use of PhLi as RRLi in place of one RTLi (i.e.RT(Ph)Cu(CN)Li2) is suggested for oxirane cleavage.The stereochemical implications associated with both couplings are also addressed.

Chemistry of Higher Order, Mixed Organocuprates. 5. On the Choice of the Copper(I) Salt for the Formation of R2CuLi

Lipshutz, Bruce H.,Kozlowski, Joseph A.,Wilhelm, Robert S.

, p. 546 - 550 (2007/10/02)

Chemical and spectroscopic studies are presented that have been designed to manifest differences in reagent composition and reactivity between mixtures of CuI/2RLi and CuSCN/2RLi.The results indicate that while both Cu(I) salts are reported to serve as precursors to lower order cuprates R2CuLi, CuSCN may actually be forming a higher order, mixed species R2Cu(SCN)Li2.This would explain the discrepancy in coupling reactions of each solution with similar organic substrates under otherwise identical conditions.The presence of added lithium salts demonstrates that while Li I added to CuSCN/2RLi has essentially no effect, introduction of an equivalent of LiSCN to CuI/2RLi dramatically alters the efficiency of ligand transfer.

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