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75-16-1 Usage

Chemical Properties

Clear brown solution when properly stored

Uses

Different sources of media describe the Uses of 75-16-1 differently. You can refer to the following data:
1. Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)
2. Methylmagnesium bromide is widely used in organic synthesis.

Application

Methylmagnesium bromide solution (3M in diethyl ether) be used to synthesize:3(4R)-{3(2R,3S)-[4′-(1′-triphenylmethyl)imidazole]-2-bromo-1-oxobutyl)-4-phenyl2-oxazolidinone.Benzyl 2-(2-oxopropyl)piperidine-1-carboxylate.(R*, R*) 1-[1-(1-phenylethyl)pyrrolidin-2-yl]propan-2-one).

Definition

Available in solution inether.

General Description

A colorless cloudy solution in diethyl ether. Flash point -49°F. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Reacts with water or moisture in the air to form flammable methane gas. The heat from this reaction may be sufficient to ignite the produced methane [AAR 1991]. Unstable peroxides may form with exposure of the ether to air. This is a slow process.

Reactivity Profile

Organometallics, such as METHYL MAGNESIUM BROMIDE, 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.

Health Hazard

Fire will produce irritating, corrosive and/or toxic gases. Inhalation of decomposition products may cause severe injury or death. Contact with substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.

Fire Hazard

Flammable/combustible material. May ignite on contact with moist air or moisture. May burn rapidly with flare-burning effect. Some react vigorously or explosively on contact with water. Some may decompose explosively when heated or involved in a fire. May re-ignite after fire is extinguished. Runoff may create fire or explosion hazard. Containers may explode when heated.

Safety Profile

May ignite spontaneously in air. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 75-16-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 75-16:
(4*7)+(3*5)+(2*1)+(1*6)=51
51 % 10 = 1
So 75-16-1 is a valid CAS Registry Number.
InChI:InChI=1/CH3.BrH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.BrH/c1-2;/h1H3;1H/q+1;/p-1

75-16-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M0362)  Methylmagnesium Bromide (12% in Tetrahydrofuran, ca. 1mol/L)  

  • 75-16-1

  • 250g

  • 620.00CNY

  • Detail
  • TCI America

  • (M2237)  Methylmagnesium Bromide (ca. 30% in 2-Methyltetrahydrofuran, ca. 3mol/L)  

  • 75-16-1

  • 250g

  • 1,850.00CNY

  • Detail
  • Alfa Aesar

  • (87324)  Methylmagnesium bromide, 3M in ether   

  • 75-16-1

  • 1mole

  • 1140.0CNY

  • Detail
  • Alfa Aesar

  • (41252)  Methylmagnesium bromide, 3M in ether, packaged under Argon in resealable ChemSeal? bottles   

  • 75-16-1

  • 0.25mole

  • 364.0CNY

  • Detail
  • Alfa Aesar

  • (41252)  Methylmagnesium bromide, 3M in ether, packaged under Argon in resealable ChemSeal? bottles   

  • 75-16-1

  • 1mole

  • 1099.0CNY

  • Detail
  • Aldrich

  • (302430)  Methylmagnesiumbromidesolution  1.0 M in dibutyl ether

  • 75-16-1

  • 302430-100ML

  • 1,503.45CNY

  • Detail
  • Aldrich

  • (302430)  Methylmagnesiumbromidesolution  1.0 M in dibutyl ether

  • 75-16-1

  • 302430-800ML

  • 5,819.58CNY

  • Detail
  • Aldrich

  • (282235)  Methylmagnesiumbromidesolution  1.4 M in THF: toluene (1:3)

  • 75-16-1

  • 282235-100ML

  • 596.70CNY

  • Detail
  • Aldrich

  • (282235)  Methylmagnesiumbromidesolution  1.4 M in THF: toluene (1:3)

  • 75-16-1

  • 282235-800ML

  • 1,177.02CNY

  • Detail
  • Aldrich

  • (703583)  Methylmagnesiumbromidesolution  ~3.4 M in 2-methyltetrahydrofuran

  • 75-16-1

  • 703583-100ML

  • 1,164.15CNY

  • Detail
  • Aldrich

  • (703583)  Methylmagnesiumbromidesolution  ~3.4 M in 2-methyltetrahydrofuran

  • 75-16-1

  • 703583-800ML

  • 5,218.20CNY

  • Detail

75-16-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methylmagnesium bromide

1.2 Other means of identification

Product number -
Other names Methyl magnesium 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:75-16-1 SDS

75-16-1Synthetic route

1,2-dibromomethane
74-95-3

1,2-dibromomethane

A

propene
187737-37-7

propene

B

ethene
74-85-1

ethene

C

methylmagnesium bromide
75-16-1

methylmagnesium bromide

D

methylenedimagnesium dibromide
27329-47-1

methylenedimagnesium dibromide

E

MgBr2

MgBr2

Conditions
ConditionsYield
With amalgamated magnesium In diethyl ether; benzene at 0℃; special sealed glass apparatus; Further byproducts given;A n/a
B n/a
C n/a
D 50%
E n/a
methyl bromide
74-83-9

methyl bromide

methylmagnesium bromide
75-16-1

methylmagnesium bromide

Conditions
ConditionsYield
With magnesium In diethyl ether Thermodynamic data; -ΔH(reaction);
With magnesium at -258.2℃; Product distribution; codeposition with other metals under matrix isolation conditions;
With magnesium In diethyl ether
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

E-β-(dibenzylchlorosilyl)styrene

E-β-(dibenzylchlorosilyl)styrene

A

methylmagnesium bromide
75-16-1

methylmagnesium bromide

B

C15H14ClF3O3SSi

C15H14ClF3O3SSi

Conditions
ConditionsYield
In dichloromethane
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

E-β-(benzyldiphenylsilyl)styrene

E-β-(benzyldiphenylsilyl)styrene

A

methylmagnesium bromide
75-16-1

methylmagnesium bromide

B

C20H17F3O3SSi

C20H17F3O3SSi

Conditions
ConditionsYield
In dichloromethane
methyl bromide
74-83-9

methyl bromide

magnesium

magnesium

methylmagnesium bromide
75-16-1

methylmagnesium bromide

Conditions
ConditionsYield
With diethyl ether
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methylmagnesium bromide
75-16-1

methylmagnesium bromide

α,α-dimethyl-o-xylene α,α'-diol
55549-01-4

α,α-dimethyl-o-xylene α,α'-diol

Conditions
ConditionsYield
at -78 - 20℃;100%
In tetrahydrofuran; diethyl ether at 30℃; for 12.5h;88%
unter Wasserabgabe entsteht 1.1-Dimethyl-phthalan;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

α-methyl-trans-cinnamaldehyde
15174-47-7

α-methyl-trans-cinnamaldehyde

(E)-3-methyl-4-phenyl-but-3-en-2-ol
87422-10-4

(E)-3-methyl-4-phenyl-but-3-en-2-ol

Conditions
ConditionsYield
Stage #1: methylmagnesium bromide; α-methyl-trans-cinnamaldehyde In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
100%
With diethyl ether
4-iodobenzoic acid ethyl ester
51934-41-9

4-iodobenzoic acid ethyl ester

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-(4-iodophenyl)propan-2-ol
60514-82-1

2-(4-iodophenyl)propan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 72h;100%
3-methoxy-5H-dibenzo[a,d]cyclohepten-5-one
22725-38-8

3-methoxy-5H-dibenzo[a,d]cyclohepten-5-one

methylmagnesium bromide
75-16-1

methylmagnesium bromide

3-methoxy-5-methyl-5H-dibenzocyclohepten-5-ol
125025-18-5

3-methoxy-5-methyl-5H-dibenzocyclohepten-5-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 6h; Ambient temperature;100%
10-Undecenal
112-45-8

10-Undecenal

methylmagnesium bromide
75-16-1

methylmagnesium bromide

dodec-11-en-2-ol
21951-49-5

dodec-11-en-2-ol

Conditions
ConditionsYield
In diethyl ether at -40℃; Grignard reaction;100%
In tetrahydrofuran at 0℃; Grignard reaction;90%
In tetrahydrofuran; diethyl ether at -40 - 25℃; for 15h; Inert atmosphere;83%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-5-(N-benzyl-p-toluenesulfonamido)-3-methyl-6-phenylhex-3-on-2-one
82495-72-5

(E)-5-(N-benzyl-p-toluenesulfonamido)-3-methyl-6-phenylhex-3-on-2-one

(E)-5-(N-benzyl-p-toluenefulfonamido)-2,3-dimethyl-6-phenylhex-3-en-2-ol
82536-02-5

(E)-5-(N-benzyl-p-toluenefulfonamido)-2,3-dimethyl-6-phenylhex-3-en-2-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 1h; -78 deg C -> 0 deg C;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

3-fluoro-5H-dibenzocyclohepten-5-one
93559-82-1

3-fluoro-5H-dibenzocyclohepten-5-one

3-fluoro-5-methyl-5H-dibenzocyclohepten-5-ol
125025-39-0

3-fluoro-5-methyl-5H-dibenzocyclohepten-5-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 6h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

6-(benzyloxy)-2,4-dimethylfuro<2,3-b>pyridine-5-carboxaldehyde
124098-64-2

6-(benzyloxy)-2,4-dimethylfuro<2,3-b>pyridine-5-carboxaldehyde

5-(1-hydroxyethyl)-6-(benzyloxy)-2,4-dimethylfuro<2,3-b>pyridine
124098-67-5

5-(1-hydroxyethyl)-6-(benzyloxy)-2,4-dimethylfuro<2,3-b>pyridine

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃; for 0.25h;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

N-methoxy-N-methylcinnamamide
80783-99-9, 124931-15-3, 113474-86-5

N-methoxy-N-methylcinnamamide

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;98%
Stage #1: N-methoxy-N-methylcinnamamide With methyl 4-bromocinnamate; triethylsilyl trifluoromethyl sulfonate; triethylphosphine In toluene at 110℃; for 5h; Inert atmosphere;
Stage #2: methylmagnesium bromide In tetrahydrofuran; toluene at -78℃; Inert atmosphere;
Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene for 0.5h; Inert atmosphere;
83%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

Benzoic acid (2S,3S)-2-formyl-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl ester

Benzoic acid (2S,3S)-2-formyl-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl ester

Benzoic acid (2R,3S)-2-(1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl ester

Benzoic acid (2R,3S)-2-(1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl ester

Conditions
ConditionsYield
In tetrahydrofuran at -45℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-3-(furan-2-yl)-N-methoxy-N-methylprop-2-enamide
134197-98-1

(E)-3-(furan-2-yl)-N-methoxy-N-methylprop-2-enamide

(E)-4-(furan-2-yl)but-3-en-2-one
623-15-4

(E)-4-(furan-2-yl)but-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-N-methoxy-N-methyl-3-(thiophen-2-yl)acrylamide
134197-97-0

(E)-N-methoxy-N-methyl-3-(thiophen-2-yl)acrylamide

(E)-4-(2-thienyl)but-3-en-2-one
874-83-9, 33603-63-3

(E)-4-(2-thienyl)but-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(1S,3R)-2,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid methoxy-methyl-amide
134197-91-4

(1S,3R)-2,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid methoxy-methyl-amide

[(1RS,3SR)-2,2-dimethyl-3-phenylcyclopropyl]ethanone
134197-90-3

[(1RS,3SR)-2,2-dimethyl-3-phenylcyclopropyl]ethanone

Conditions
ConditionsYield
100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-N-Methoxy-3-(6-methoxy-naphthalen-2-yl)-N-methyl-acrylamide
134197-96-9

(E)-N-Methoxy-3-(6-methoxy-naphthalen-2-yl)-N-methyl-acrylamide

4-(6'-methoxy-2'-naphthyl)-3-buten-2-one
127053-22-9

4-(6'-methoxy-2'-naphthyl)-3-buten-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-N-Methoxy-N-methyl-3-(3-phenoxy-phenyl)-acrylamide
134197-94-7

(E)-N-Methoxy-N-methyl-3-(3-phenoxy-phenyl)-acrylamide

(E)-1-(3-Phenoxyphenyl)buten-3-one
121488-67-3

(E)-1-(3-Phenoxyphenyl)buten-3-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-3-(4-(benzyloxy)phenyl)-N-methoxy-N-methylacrylamide
134197-95-8

(E)-3-(4-(benzyloxy)phenyl)-N-methoxy-N-methylacrylamide

1-(4-benzyloxyphenyl)but-1-en-3-one
75676-91-4

1-(4-benzyloxyphenyl)but-1-en-3-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(E)-N-Methoxy-N-methyl-3-[4-(1-phenyl-ethoxy)-phenyl]-acrylamide
134197-93-6

(E)-N-Methoxy-N-methyl-3-[4-(1-phenyl-ethoxy)-phenyl]-acrylamide

(E)-4-[4-(1-Phenyl-ethoxy)-phenyl]-but-3-en-2-one
134197-92-5

(E)-4-[4-(1-Phenyl-ethoxy)-phenyl]-but-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-<(trimethylsilyl)methyl>-2-butenal
122421-16-3

2-<(trimethylsilyl)methyl>-2-butenal

(Z)-3-((trimethylsilyl)methyl)pent-3-en-2-ol
141023-16-7

(Z)-3-((trimethylsilyl)methyl)pent-3-en-2-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 0.333333h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

C26H24O2S
136964-79-9

C26H24O2S

11-methyl-12-phenyl-9,10-dihydro-9,10-etheno-anthracene
79979-60-5

11-methyl-12-phenyl-9,10-dihydro-9,10-etheno-anthracene

Conditions
ConditionsYield
palladium(II) acetylacetonate In tetrahydrofuran Heating;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

Methyl (1R,2S)-2-<2-(3-Isopropylphenyl)ethyl>-1-methyl-3-oxo-1-cyclohexanecarboxylate
134454-00-5

Methyl (1R,2S)-2-<2-(3-Isopropylphenyl)ethyl>-1-methyl-3-oxo-1-cyclohexanecarboxylate

Methyl (1R,2S,3R)-1,3-Dimethyl-1-hydroxy-2<2-(3-isopropylphenyl)-ethyl>cyclohexanecarboxylate
134365-17-6

Methyl (1R,2S,3R)-1,3-Dimethyl-1-hydroxy-2<2-(3-isopropylphenyl)-ethyl>cyclohexanecarboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 2h;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl
141807-44-5, 126613-06-7, 128544-05-8, 128575-34-8

(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; for 24h; Reflux;100%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 20℃;99%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 20℃; for 1h; Substitution;99%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

8-oxabicyclo<3.2.1>oct-6-en-2-one
154811-20-8

8-oxabicyclo<3.2.1>oct-6-en-2-one

(1R,2R,5R)-2-Methyl-8-oxa-bicyclo[3.2.1]oct-6-en-2-ol

(1R,2R,5R)-2-Methyl-8-oxa-bicyclo[3.2.1]oct-6-en-2-ol

Conditions
ConditionsYield
In diethyl ether at 0℃;100%
In diethyl ether at 0℃;
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

methylmagnesium bromide
75-16-1

methylmagnesium bromide

Conditions
ConditionsYield
In diethyl ether at 0℃; for 2h;100%
In diethyl ether at 0 - 5℃; for 2h; Inert atmosphere;61%
Yield given;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(3aS,5R,5aR,6aS,9aS,9bS,9cS)-5-Methoxy-1,1,8,8,9c-pentamethyl-decahydro-4,7,9-trioxa-cyclopenta[e]acenaphthylen-6-one
161659-30-9

(3aS,5R,5aR,6aS,9aS,9bS,9cS)-5-Methoxy-1,1,8,8,9c-pentamethyl-decahydro-4,7,9-trioxa-cyclopenta[e]acenaphthylen-6-one

1,2,3,3aβ,5aβ,6,6aα,9aα,9bα,9c-decahydro-6α-hydroxy-5β-methoxy-1,1,6β,8,8,9cβ-hexamethyl-5H-furo<4',3',2':4,5>naphtho<1,2-d><1,3>dioxolane
161659-31-0

1,2,3,3aβ,5aβ,6,6aα,9aα,9bα,9c-decahydro-6α-hydroxy-5β-methoxy-1,1,6β,8,8,9cβ-hexamethyl-5H-furo<4',3',2':4,5>naphtho<1,2-d><1,3>dioxolane

Conditions
ConditionsYield
In diethyl ether for 1h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

7-(4-chlorophenylthio)-6,7-dihydro-1-(phenylsulfonyl)-1H-indol-4(5H)-one
157396-11-7

7-(4-chlorophenylthio)-6,7-dihydro-1-(phenylsulfonyl)-1H-indol-4(5H)-one

1-Benzenesulfonyl-7-(4-chloro-phenylsulfanyl)-4-methyl-4,5,6,7-tetrahydro-1H-indol-4-ol
146564-05-8

1-Benzenesulfonyl-7-(4-chloro-phenylsulfanyl)-4-methyl-4,5,6,7-tetrahydro-1H-indol-4-ol

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

Bis-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-methanone
161227-56-1

Bis-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-methanone

C28H50N2Si2
161227-57-2

C28H50N2Si2

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 2h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-Benzyl-6-methyl-1-phenyl-3,4-dihydro-isoquinolinium; iodide

2-Benzyl-6-methyl-1-phenyl-3,4-dihydro-isoquinolinium; iodide

2-benzyl-1,6-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline
174784-47-5

2-benzyl-1,6-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-Benzyl-1-cyclohexyl-3,4-dihydro-isoquinolinium; bromide

2-Benzyl-1-cyclohexyl-3,4-dihydro-isoquinolinium; bromide

2-benzyl-1-cyclohexyl-1-methyl-1,2,3,4-tetrahydroisoquinoline
126115-25-1

2-benzyl-1-cyclohexyl-1-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(1S,2R,5S)-2-Benzyloxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-one

(1S,2R,5S)-2-Benzyloxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-one

(1R,2S,5R,6R)-2-Benzyloxy-1,5,6-trimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

(1R,2S,5R,6R)-2-Benzyloxy-1,5,6-trimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

Conditions
ConditionsYield
In diethyl ether100%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

N-(tert-butoxycarbonyl)-D-alanine methyl ester
91103-47-8

N-(tert-butoxycarbonyl)-D-alanine methyl ester

((R)-2-hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester
186466-64-8

((R)-2-hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: methylmagnesium bromide; N-(tert-butoxycarbonyl)-D-alanine methyl ester In tetrahydrofuran at 0 - 20℃; for 16h;
Stage #2: With water In tetrahydrofuran Cooling with ice;
100%
Stage #1: methylmagnesium bromide; N-(tert-butoxycarbonyl)-D-alanine methyl ester In tetrahydrofuran at 0 - 20℃; for 3h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
99%
In tetrahydrofuran; diethyl ether at 0 - 25℃; for 2h;99%

75-16-1Relevant articles and documents

Low-Temperature Reactions of Metal Atoms with Methyl Bromide

Tanaka, Yasutaka,Davis, Stephen C.,Klabunde, Kenneth J.

, p. 1013 - 1016 (1982)

The atoms of a series of metals were codeposited with CH3Br under matrix conditions (argon diluent at 12 K and pure CH3Br at 77 K).Oxidative addition of CH3Br to Fe, Co, Ni, and Pd did not occur upon simple codeposition or upon matrix photolysis, which is rationalized by the formation of a favored CH3Br-M complex.Cu, Ag, and Au behaved similary.Main-group metals Mg, Al, Ga, and In did react to form CH3MBr whereas Zn, Tl, Ge, Sn, and Pb did not.For the group 1B - 4B (Cu, Zn, B, C) families the most important reactivity parameter is a low ionization potential.However, a high heat of vaporization of the element also has a positive effect on reactivity.In the case of Mg, clusters may be necessary for high reactivity.

Cross-coupling of aryl/alkenyl silyl ethers with grignard reagents through nickel-catalyzed CO bond activation

Zhao, Fei,Yu, Da-Gang,Zhu, Ru-Yi,Xi, Zhenfeng,Shi, Zhang-Jie

supporting information; experimental part, p. 1001 - 1003 (2011/12/05)

CO activation and its application have drawn much attention since oxygen-based electrophiles are easily available, less toxic, and more environmentally benign. This letter presents systematically results on the Ni-catalyzed KumadaTamaoCorriu coupling based on siloxy arenes/alkenes, which provides a new strategy of silyl protection/CC bond formation sequence in organic synthesis.

Interior surface modifications of molecular sieves with organometallic reagents and the use thereof for the conversion of oxygenates to olefins

-

, (2008/06/13)

A method for making an organometallic treated molecular sieve is described in which a molecular sieve having at least one hydroxyl group and at least [AlO2] and [PO2] tetrahedral units and having an average pore dimension less than or equal to about 5? is contacted with a solution comprising an organometallic compound and a non-proton donating solvent. The resulting organometallic treated molecular sieve has enhanced ethylene and/or propylene selectivity when used in the conversion of organic oxygenates to olefins. The ethylene and/or propylene selectivity, as well as catalyst life, are further enhanced when the resulting organometallic treated molecular sieve is combined with an oxide of at least one metal selected from Groups 2, 3 and Group 4 of the Periodic Table.

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