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36282-40-3 Usage

Chemical Properties

Clear colorless to brown solution

Check Digit Verification of cas no

The CAS Registry Mumber 36282-40-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,2,8 and 2 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 36282-40:
(7*3)+(6*6)+(5*2)+(4*8)+(3*2)+(2*4)+(1*0)=113
113 % 10 = 3
So 36282-40-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H7O.BrH.Mg/c1-8-7-5-3-2-4-6-7;;/h2-3,5-6H,1H3;1H;/q;;+1/p-1/rC7H7BrMgO/c1-10-7-4-2-3-6(5-7)9-8/h2-5H,1H3

36282-40-3 Well-known Company Product Price

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  • Alfa Aesar

  • (H54780)  3-Methoxyphenylmagnesium bromide, 1.0 M in 2-MeTHF   

  • 36282-40-3

  • 100ml

  • 589.0CNY

  • Detail
  • Aldrich

  • (442194)  3-Methoxyphenylmagnesiumbromidesolution  1.0 M in THF

  • 36282-40-3

  • 442194-100ML

  • 912.60CNY

  • Detail
  • Aldrich

  • (442194)  3-Methoxyphenylmagnesiumbromidesolution  1.0 M in THF

  • 36282-40-3

  • 442194-800ML

  • 3,532.23CNY

  • Detail

36282-40-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-METHOXYPHENYLMAGNESIUM BROMIDE

1.2 Other means of identification

Product number -
Other names 3-Methoxyphenylmagnesium bromide

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:36282-40-3 SDS

36282-40-3Synthetic route

2,3-dihydro-4H-1-benzopyran-4-one
491-37-2

2,3-dihydro-4H-1-benzopyran-4-one

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

magnesium
7439-95-4

magnesium

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

Conditions
ConditionsYield
In tetrahydrofuran
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

Conditions
ConditionsYield
With magnesium; iodine In tetrahydrofuran at 20℃; Heating / reflux;
With magnesium In tetrahydrofuran Inert atmosphere;
With iodine; magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux;
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

cyclohexanone
108-94-1

cyclohexanone

1-(m-Methoxyphenyl)cyclohexanol
1884-42-0

1-(m-Methoxyphenyl)cyclohexanol

Conditions
ConditionsYield
Stage #1: (3-methoxyphenyl)magnesium bromide; cyclohexanone In diethyl ether at 0 - 20℃; for 4h;
Stage #2: With water at 0℃;
100%
In tetrahydrofuran for 0.333333h;
In tetrahydrofuran; toluene at 0℃; for 5.5h; Inert atmosphere;
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

3-bromo-α-(3-methoxyphenyl)benzenemethanol
76778-33-1

3-bromo-α-(3-methoxyphenyl)benzenemethanol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.25h;100%
Stage #1: m-bromobenzoic aldehyde; (3-methoxyphenyl)magnesium bromide In tetrahydrofuran at 80℃; for 3h; Grignard reaction; Inert atmosphere;
Stage #2: With water; sodium chloride In tetrahydrofuran at 20℃;
3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octan-8-one

3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octan-8-one

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

3-(4-methoxy-benzyl)-8-(3-methoxy-phenyl)-3-aza-bicyclo[3.2.1]octan-8-ol

3-(4-methoxy-benzyl)-8-(3-methoxy-phenyl)-3-aza-bicyclo[3.2.1]octan-8-ol

Conditions
ConditionsYield
Stage #1: 3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octan-8-one; (3-methoxyphenyl)magnesium bromide In tetrahydrofuran at -78 - 20℃;
Stage #2: With hydrogenchloride In water pH=1;
100%
ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate
150356-32-4

ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

Ethyl (1RS)-1-Hydroxy-1-(3-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indene-2-carboxylate
150356-38-0

Ethyl (1RS)-1-Hydroxy-1-(3-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indene-2-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran100%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

tert-butyl 2-oxopyrrolidine-1-carboxylate
85909-08-6

tert-butyl 2-oxopyrrolidine-1-carboxylate

tert-butyl (4-(3-methoxyphenyl)-4-oxobutyl)carbamate
914954-34-0

tert-butyl (4-(3-methoxyphenyl)-4-oxobutyl)carbamate

Conditions
ConditionsYield
In tetrahydrofuran at -40 - 0℃; for 3h;100%
In tetrahydrofuran at -78 - 20℃; for 14h; Inert atmosphere; Schlenk technique;45%
diethyl 2-(4-bromobenzylidene)malonate
22399-01-5

diethyl 2-(4-bromobenzylidene)malonate

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

2-[(4-bromo-phenyl)-(3-methoxy-phenyl)-methyl]-malonic acid diethyl ester

2-[(4-bromo-phenyl)-(3-methoxy-phenyl)-methyl]-malonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: diethyl 2-(4-bromobenzylidene)malonate; (3-methoxyphenyl)magnesium bromide In tetrahydrofuran; diethyl ether at 0℃; for 3.3h;
Stage #2: With water; ammonium chloride
100%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

(4-bromo-phenyl)-(3-methoxy-phenyl)-methanol
134446-26-7

(4-bromo-phenyl)-(3-methoxy-phenyl)-methanol

Conditions
ConditionsYield
Stage #1: (3-methoxyphenyl)magnesium bromide; 4-bromo-benzaldehyde In tetrahydrofuran at 80℃; for 3h; Grignard reaction; Inert atmosphere;
Stage #2: With water; sodium chloride In tetrahydrofuran at 20℃;
100%
1-Chlorohexane
544-10-5

1-Chlorohexane

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

3-n-hexyl-1-methoxybenzene

3-n-hexyl-1-methoxybenzene

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 20℃; for 20h; Kumada coupling;99%
With 1,3-bis(mesityl)imidazolium chloride; palladium diacetate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Kumada reaction;99%
C17H16O3

C17H16O3

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

C24H24O4

C24H24O4

Conditions
ConditionsYield
Stage #1: C17H16O3; (3-methoxyphenyl)magnesium bromide In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran at 0℃; diastereoselective reaction;
99%
3-iodo-1,2-dicarba-closo-dodecaborane
137495-63-7

3-iodo-1,2-dicarba-closo-dodecaborane

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

A

3-meta-hydroxyphenyl-o-carborane

3-meta-hydroxyphenyl-o-carborane

B

3-meta-methoxyphenyl-o-carborane
1159494-39-9

3-meta-methoxyphenyl-o-carborane

Conditions
ConditionsYield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran Ar, a soln. of Mg compd. (8.5 equiv.) added dropwise to a soln. of B compd., CuI and catalyst, refluxed for 34 h; quenched (dilute HCl), extd. (ethyl acetate), washed (water), dried (MgSO4), concd., chromy. (silica gel);A 0%
B 99%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

1-[1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl]ethanone

1-[1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl]ethanone

1-(1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl)-1-m-tolylethanol

1-(1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl)-1-m-tolylethanol

Conditions
ConditionsYield
at 20℃; for 13h; Inert atmosphere;99%
8-methoxy-3,4-dihydroisocoumarin
30404-50-3

8-methoxy-3,4-dihydroisocoumarin

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

[2-(2-hydroxy-ethyl)-6-methoxy-phenyl]-(3-methoxy-phenyl)-methanone
891829-94-0

[2-(2-hydroxy-ethyl)-6-methoxy-phenyl]-(3-methoxy-phenyl)-methanone

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane at -78 - 20℃;98%
3-bromobenzoyl chloride
1711-09-7

3-bromobenzoyl chloride

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

(3-bromophenyl)-(3-methoxyphenyl)-methanone
750633-66-0

(3-bromophenyl)-(3-methoxyphenyl)-methanone

Conditions
ConditionsYield
Stage #1: 3-bromobenzoyl chloride With tributylphosphine In tetrahydrofuran at 20℃; for 0.333333h;
Stage #2: (3-methoxyphenyl)magnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
98%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

(2-isocyanophenyl)(phenyl)methanone
521270-76-8

(2-isocyanophenyl)(phenyl)methanone

2-(3-methoxyphenyl)-3-phenyl-3H-indol-3-ol
1253396-21-2

2-(3-methoxyphenyl)-3-phenyl-3H-indol-3-ol

Conditions
ConditionsYield
Stage #1: (3-methoxyphenyl)magnesium bromide; (2-isocyanophenyl)(phenyl)methanone In tetrahydrofuran; diethyl ether at 0℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 0℃;
98%
quinolin-6-yl 4-methylbenzene-1-sulfonate
426265-40-9

quinolin-6-yl 4-methylbenzene-1-sulfonate

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

6-(3'-methoxyphenyl)quinoline
1023531-31-8

6-(3'-methoxyphenyl)quinoline

Conditions
ConditionsYield
Stage #1: (3-methoxyphenyl)magnesium bromide With C24H52Cl2O12P4Pd2 In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.0833333h; Kumada-Corriu cross-coupling reaction; Inert atmosphere;
Stage #2: quinolin-6-yl 4-methylbenzene-1-sulfonate In tetrahydrofuran; 1,4-dioxane at 80℃; for 24h; Kumada-Corriu cross-coupling reaction; Inert atmosphere; regioselective reaction;
98%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

cyclohept-1-en-1-yl dimethylcarbamate

cyclohept-1-en-1-yl dimethylcarbamate

(E)-1-(3-methoxyphenyl)cyclohept-1-en
75209-54-0

(E)-1-(3-methoxyphenyl)cyclohept-1-en

Conditions
ConditionsYield
With N,N'-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene hydrochloride; palladium diacetate In tetrahydrofuran at 50℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube;98%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

(S)-diethyl 5-phenyl-1-(trimethylsilyl)pent-1-yn-3-yl phosphate

(S)-diethyl 5-phenyl-1-(trimethylsilyl)pent-1-yn-3-yl phosphate

(S)-1-(3-methoxyphenyl)-5-phenyl-1-trimethylsilylpenta-1,2-diene

(S)-1-(3-methoxyphenyl)-5-phenyl-1-trimethylsilylpenta-1,2-diene

Conditions
ConditionsYield
With copper acetylacetonate In tetrahydrofuran at -18 - 0℃; for 2h; enantiospecific reaction;98%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

allyl bromide
106-95-6

allyl bromide

1-allyl-3-methoxybenzene
24743-14-4

1-allyl-3-methoxybenzene

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;97%
In tetrahydrofuran; toluene at 0 - 20℃; for 18h;81%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

bis(3-methoxyphenyl)methanol
55360-45-7

bis(3-methoxyphenyl)methanol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h; Grignard Reaction;97%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

propionic acid anhydride
123-62-6

propionic acid anhydride

1-(3-methoxyphenyl)propan-1-one
37951-49-8

1-(3-methoxyphenyl)propan-1-one

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -70℃;97%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

(1E)-4,4-bis(methylthio)-2-nitro-1-pyrrolidino-1,3-butadiene
389838-05-5

(1E)-4,4-bis(methylthio)-2-nitro-1-pyrrolidino-1,3-butadiene

(E)-4-(3-methoxyphenyl)-1,1-bis(methylthio)-3-nitro-1,3-butadiene
467421-88-1

(E)-4-(3-methoxyphenyl)-1,1-bis(methylthio)-3-nitro-1,3-butadiene

Conditions
ConditionsYield
In tetrahydrofuran at -78℃;97%
4-benzyloxy-6-bromo-3-methoxybenzaldehyde
40705-22-4

4-benzyloxy-6-bromo-3-methoxybenzaldehyde

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

[4-(benzyloxy)-2-bromo-5-methoxyphenyl](3-methoxyphenyl)methanol
1569316-45-5

[4-(benzyloxy)-2-bromo-5-methoxyphenyl](3-methoxyphenyl)methanol

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere;97%
1-bromo-3,5-dimethoxybenzene
20469-65-2

1-bromo-3,5-dimethoxybenzene

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

3,3',5-trimethoxy-1,1'-biphenyl
33580-34-6

3,3',5-trimethoxy-1,1'-biphenyl

Conditions
ConditionsYield
With nickel(II) fluoride; 1,3-bis(3,6-diisopropylphenyl)imidazolium hydrochloride In tetrahydrofuran at 0 - 80℃; for 12.5h; Inert atmosphere;97%
(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

3,3'-dimethoxybiphenyl
6161-50-8

3,3'-dimethoxybiphenyl

Conditions
ConditionsYield
With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 20℃; for 0.166667h;96%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In tetrahydrofuran at 66℃; for 0.166667h; Inert atmosphere;87%
With 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl In tetrahydrofuran at 66℃; for 0.166667h; Inert atmosphere;87%
(4aR*,6R*,7R*)-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4,4a,5,6,7-octahydronaphthalene-4a-carbaldehyde

(4aR*,6R*,7R*)-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4,4a,5,6,7-octahydronaphthalene-4a-carbaldehyde

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

C30H52O4Si2

C30H52O4Si2

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h; Grignard reaction;96%
(triphenylphosphine)gold(I) chloride
14243-64-2

(triphenylphosphine)gold(I) chloride

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

(3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold
870485-34-0

(3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold

Conditions
ConditionsYield
In tetrahydrofuran 3-methoxyphenylmagnesium bromide added dropwise at -78°C to soln.ClAuPPh3 in THF in Schlenk techniques under Ar; mixt. warmed to room te mp., mixed for 16 h; treated with satd. soln. of NH4Cl, extd. with Et2O; org. layers washed with satd. soln. of NaCl, dried over MgSO4; solvents removed under vac.; crystals obtained via crystn. from CHCl3;96%
(1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione

(1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

(1RS,4SR,5SR,6RS,7RS)-4-hydroxy-3-methoxy-4-(3-methoxyphenyl)-7-methyl-6-phenylbicyclo[3.2.1]oct-2-en-8-one

(1RS,4SR,5SR,6RS,7RS)-4-hydroxy-3-methoxy-4-(3-methoxyphenyl)-7-methyl-6-phenylbicyclo[3.2.1]oct-2-en-8-one

Conditions
ConditionsYield
Stage #1: (1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione; (3-methoxyphenyl)magnesium bromide In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran at 0℃; diastereoselective reaction;
96%
1-bromocyclohexane
108-85-0

1-bromocyclohexane

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

1-cyclohexyl-3-methoxybenzene
41876-58-8

1-cyclohexyl-3-methoxybenzene

Conditions
ConditionsYield
With Iron(III) amine-bis(phenolate) complex In diethyl ether at 20℃; for 0.5h; Inert atmosphere;96%
With C54H80Cl2Fe2N2O4 In diethyl ether at 22℃; for 0.5h; Inert atmosphere;> 95 %Chromat.
With [Fe(n-propylamino-N,N-bis(2-methylene-4-tert-butyl-6-methylphenolate))(chloride)]2 In diethyl ether at 22℃; for 0.5h; Catalytic behavior;> 95 %Chromat.
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

C15H14O
244159-74-8

C15H14O

Conditions
ConditionsYield
Stage #1: 4-vinylbenzyl chloride With cobalt(III) acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 30℃; for 1h;
Stage #2: (3-methoxyphenyl)magnesium bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 30℃; for 0.333333h;
96%
5-benzyloxy-2-bromo-4-methoxybenzaldehyde
6451-86-1

5-benzyloxy-2-bromo-4-methoxybenzaldehyde

(3-methoxyphenyl)magnesium bromide
36282-40-3

(3-methoxyphenyl)magnesium bromide

[5-(benzyloxy)-2-bromo-4-methoxyphenyl](3-methoxyphenyl)methanol
1569316-44-4

[5-(benzyloxy)-2-bromo-4-methoxyphenyl](3-methoxyphenyl)methanol

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere;96%

36282-40-3Relevant articles and documents

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.

supporting information, p. 19257 - 19262 (2019/12/02)

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates

Eno, Meredith S.,Lu, Alexander,Morken, James P.

supporting information, p. 7824 - 7827 (2016/07/11)

Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.

Use of73Ge NMR Spectroscopy and X-ray Crystallography for the Study of electronic interactions in substituted tetrakis(phenyl)-, -(phenoxy)-, and -(thiophenoxy)germanes

Yoder, Claude H.,Agee, Tamara M.,Griffith, Allison K.,Schaeffer Jr., Charles D.,Carroll, Mary J.,Detoma, Alaina S.,Fleisher, Adam J.,Gettel, Cameron J.,Rheingold, Arnold L.

experimental part, p. 582 - 590 (2010/04/25)

NMR chemical shifts of 1H, 13C, and 73Ge, molecular modeling, and single-crystal X-ray diffraction results are reported for a series of substituted tris- and tetrakis(phenyl)germanes of the type (XC6H4)3GeY and (XC6H 4)4Ge, where X = o-, m-, and p-OCH3, o-, m-, and p-OC2H5, m- and p-CF3, H, p-C(CH 3)3, p-Cl; and Y = Cl and H. Chemical shifts and X-ray data are also reported for o-CH3 and o-OCH3 tetrakis(phenoxy)- ((XC6H4O)4Ge) and thiophenoxygermanes ((XC6H4S)4Ge). For tetrakis derivatives, 73Ge resonances are observed for all but the o-methoxyphenoxy compound, for which the inability to detect a resonance is attributed to rapid quadrupolar relaxation caused by intramolecular interactions of the methoxy oxygen with the central atom. The observation of a relatively broad, slightly upfield 73Ge resonance in the analogous phenyl and thiophenoxy derivatives suggests, as do the results of molecular modeling, that in these compounds there is some hypercoordination. The solid-state structures show bond angles at the aromatic carbon bearing the alkoxy group that suggest an interaction of the alkoxy oxygen with germanium. Oxygen-germanium bond distances are about 17% shorter than the sum of the van der Waals radii.

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