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3-Methyl-2-buten-1-ol is an organic compound with a distinctive phenolic, metallic odor that resembles iron gallate ink. It can be synthesized from isoprene through hydration via prenyl acetate or by rearrangement of 3-methyl-2-buten-3-ol.

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  • 556-82-1 Structure
  • Basic information

    1. Product Name: 3-Methyl-2-buten-1-ol
    2. Synonyms: 3-methyl-2-buten-1-o;3-Methyl-2-butenol;3-Methyl-2-butenyl alcohol;3-methyl-but-2-en-1-ol;3-methylbut-2-en-1-ol;dimethylallylalcohol;gamma,gamma-Dimethylallyl alcohol;gamma,gamma-dimethylallylalcohol
    3. CAS NO:556-82-1
    4. Molecular Formula: C5H10O
    5. Molecular Weight: 86.13
    6. EINECS: 209-141-4
    7. Product Categories: Pesticides intermediate
    8. Mol File: 556-82-1.mol
  • Chemical Properties

    1. Melting Point: 43.52°C
    2. Boiling Point: 140 °C(lit.)
    3. Flash Point: 110 °F
    4. Appearance: Clear colorless to very slightly yellow/Liquid
    5. Density: 0.848 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 1.4 mm Hg ( 20 °C)
    7. Refractive Index: n20/D 1.443(lit.)
    8. Storage Temp.: Flammables area
    9. Solubility: 64g/l
    10. PKA: 14.83±0.10(Predicted)
    11. Explosive Limit: 2.7-16.3%(V)
    12. Water Solubility: 170 g/L (20 ºC)
    13. BRN: 1633479
    14. CAS DataBase Reference: 3-Methyl-2-buten-1-ol(CAS DataBase Reference)
    15. NIST Chemistry Reference: 3-Methyl-2-buten-1-ol(556-82-1)
    16. EPA Substance Registry System: 3-Methyl-2-buten-1-ol(556-82-1)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 10-22-36/37/38-38-21/22
    3. Safety Statements: 26-36-37-23-16
    4. RIDADR: UN 1987 3/PG 3
    5. WGK Germany: 1
    6. RTECS: EM9472500
    7. TSCA: Yes
    8. HazardClass: 3
    9. PackingGroup: III
    10. Hazardous Substances Data: 556-82-1(Hazardous Substances Data)

556-82-1 Usage

Uses

Used in Chemical Synthesis:
3-Methyl-2-buten-1-ol is used as a reagent for the protection of carboxylic acids as their 3-methyl-2-buten-1-yl (Prenyl) esters. This protection allows for selective reactions to occur at other sites on a molecule, facilitating complex organic synthesis.
Used in Perfumery:
3-Methyl-2-buten-1-ol is utilized in the perfumery industry to create unique and complex fragrances. Its distinct metallic and phenolic odor adds depth and character to perfume compositions.
Used in Asymmetric Total Syntheses:
3-Methyl-2-buten-1-ol serves as a starting reagent in the asymmetric total syntheses of (R)-(+)and (S)-(-)-umbelactone via the Sharpless asymmetric epoxidation reaction. This reaction is a key step in the production of these valuable chiral compounds, which have potential applications in various fields, including pharmaceuticals and agrochemicals.

Flammability and Explosibility

Flammable

Check Digit Verification of cas no

The CAS Registry Mumber 556-82-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 6 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 556-82:
(5*5)+(4*5)+(3*6)+(2*8)+(1*2)=81
81 % 10 = 1
So 556-82-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

556-82-1 Well-known Company Product Price

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  • TCI America

  • (M0714)  3-Methyl-2-buten-1-ol  >98.0%(GC)

  • 556-82-1

  • 25mL

  • 195.00CNY

  • Detail
  • TCI America

  • (M0714)  3-Methyl-2-buten-1-ol  >98.0%(GC)

  • 556-82-1

  • 100mL

  • 530.00CNY

  • Detail
  • TCI America

  • (M0714)  3-Methyl-2-buten-1-ol  >98.0%(GC)

  • 556-82-1

  • 500mL

  • 995.00CNY

  • Detail
  • Alfa Aesar

  • (A16089)  3-Methyl-2-buten-1-ol, 98+%   

  • 556-82-1

  • 25g

  • 226.0CNY

  • Detail
  • Alfa Aesar

  • (A16089)  3-Methyl-2-buten-1-ol, 98+%   

  • 556-82-1

  • 100g

  • 455.0CNY

  • Detail
  • Alfa Aesar

  • (A16089)  3-Methyl-2-buten-1-ol, 98+%   

  • 556-82-1

  • 500g

  • 1562.0CNY

  • Detail

556-82-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name prenol

1.2 Other means of identification

Product number -
Other names 2-Buten-1-ol, 3-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:556-82-1 SDS

556-82-1Synthetic route

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); trifluorormethanesulfonic acid; carbon monoxide; N-(5-diphenylphosphanylpyrrole-2-carbonyl)guanidine; hydrogen In dichloromethane at 40℃; under 15001.5 Torr; for 20h; Autoclave;99%
With indium tri-isopropoxide supported on mesoporous SBA-15 In isopropyl alcohol at 80℃; for 7h; Reagent/catalyst; Meerwein-Ponndorf-Verley Reduction; Inert atmosphere; Schlenk technique; chemoselective reaction;89.6%
With Triisopropyl borate; isopropyl alcohol at 27℃; for 15h; Kinetics; Reagent/catalyst; Meerwein-Ponndorf-Verley reduction; Inert atmosphere; chemoselective reaction;87.9%
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With lithium hexafluorophosphate at 0℃; for 8h; Reagent/catalyst; Temperature; Irradiation; Inert atmosphere;97%
With palladium 10% on activated carbon; oxygen at 80℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Time; Concentration;53.05%
With pyridine; 2-methyl-2-phenyloxirane; iron pentacarbonyl; carbon monoxide at 70℃; under 3750.38 Torr; for 42h; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave;
With 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In acetone at 55℃; under 5250.53 Torr; for 1h; Temperature; Pressure; Autoclave;
prenyl bromide
870-63-3

prenyl bromide

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With Amberlyst A 26; carbonate form In tetrahydrofuran for 1h; Heating;95%
Multi-step reaction with 2 steps
1: NaBH4 / ethanol / 2 h / 15 - 20 °C
2: H2O2 / 2 h / 15 - 20 °C / var. oxidants and time.
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
2.1: potassium peroxomonosulfate / methanol; water / 12 h / 0 - 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: water; dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; hexane / 0.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
2.1: potassium peroxomonosulfate / methanol; water / 12 h / 0 - 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: water; dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; hexane / 0.5 h / 20 °C / Inert atmosphere
View Scheme
3-methyl-1-(trimethylsilyloxy)but-2-ene
71821-61-9

3-methyl-1-(trimethylsilyloxy)but-2-ene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With tris paraperiodate In benzene Heating;95%
3-methylbut-2-enyl acetate
1191-16-8

3-methylbut-2-enyl acetate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 2.5h;95%
3,3-dimethyl-allyl chloride
503-60-6

3,3-dimethyl-allyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium dodecylbenzenesulfonate In cyclohexane; water at 45℃; pH=8;92.9%
Multi-step reaction with 2 steps
2: aqueous KOH-solution
View Scheme
ethyl 3-methylbut-2-enoate
638-10-8

ethyl 3-methylbut-2-enoate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;91%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3h; Inert atmosphere;72%
With diisobutylaluminium hydride In toluene at -78 - 20℃;
1-[(tetrahydro-2H-pyran-2-yl)oxy]-3-methyl-2-butene
54105-78-1

1-[(tetrahydro-2H-pyran-2-yl)oxy]-3-methyl-2-butene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With cerium(III) chloride In methanol at 20℃; for 1h; detetrahydropyranylation;90%
formiate de methyl-3 butene-2 ol-1
68480-28-4

formiate de methyl-3 butene-2 ol-1

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With potassium carbonate In ethanol for 0.333333h;84%
With potassium hydroxide
3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

A

i-Amyl alcohol
123-51-3

i-Amyl alcohol

B

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With dmap; formic acid; hexarhodium hexadecacarbonyl; carbon monoxide In tetrahydrofuran at 30℃; under 3800 Torr; for 20h;A 4 % Chromat.
B 81%
With dmap; formic acid; hexarhodium hexadecacarbonyl; carbon monoxide In tetrahydrofuran at 30℃; under 3800 Torr; Product distribution; base effect;
With Pt3Fe; hydrogen In ethanol at 70℃; under 750.075 Torr; for 5h; Catalytic behavior; Time;
With Pt0615Fe0385; hydrogen In ethanol at 100℃; under 1800.18 Torr;
2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With methanesulfonic acid In tetrahydrofuran; water at 20℃; for 12h;74%
With sulfuric acid
With dichloro-acetic acid und anschliessende Verseifung;
morpholide of 1-phenylthio-4-hydroxy-2-methylbut-2Z-ene-1-sulfonic acid
87791-06-8

morpholide of 1-phenylthio-4-hydroxy-2-methylbut-2Z-ene-1-sulfonic acid

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With lithium In ammonia at -70℃; for 0.0833333h;74%
1,7,7-trimethylbicyclo<2.2.1>hept-2-yl 3-methyl-2-butenoate

1,7,7-trimethylbicyclo<2.2.1>hept-2-yl 3-methyl-2-butenoate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With aluminium hydride In tetrahydrofuran at 0℃; for 2h;70%
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1.5h; ice bath;60%
With lithium aluminium tetrahydride In diethyl ether for 5h;54%
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In diethyl ether
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

A

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

B

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; oxygen at 80℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Time; Concentration;A 8.78%
B 53.06%
2-isopropyloxirane
1438-14-8

2-isopropyloxirane

A

3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

B

2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

C

2-isopropyl-5-methyl-hex-2-enal
35158-25-9

2-isopropyl-5-methyl-hex-2-enal

D

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With magnesium bromide In N,N-dimethyl-formamide at 130℃; for 0.666667h; Further byproducts given;A 52.2%
B 23.2%
C 8.7%
D 13.7%
trimethylsilyloxirane
16722-09-1

trimethylsilyloxirane

phenyl isopropyl sulfone
4238-09-9

phenyl isopropyl sulfone

A

3-Benzenesulfonyl-3-methyl-1-trimethylsilanyl-butan-1-ol
133827-98-2

3-Benzenesulfonyl-3-methyl-1-trimethylsilanyl-butan-1-ol

B

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -20 - 20℃; for 16h;A 45%
B 31%
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

sodium acetate
127-09-3

sodium acetate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sulfuric acid; hydrogen bromide; acetic acid das Acetat entsteht;
dichloro-acetic acid
79-43-6

dichloro-acetic acid

2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

A

Geraniol
106-24-1

Geraniol

B

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
bei folgendem Verseifen;
und Verseifen;
formaldehyd
50-00-0

formaldehyd

2-methylpropen-1-ylmagnesium bromide
38614-36-7

2-methylpropen-1-ylmagnesium bromide

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With diethyl ether
1-chloro-3-pentene
16435-50-0

1-chloro-3-pentene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With alkali
3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

aluminum isopropoxide
555-31-7

aluminum isopropoxide

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With isopropyl alcohol at 110℃;
at 110℃;
3-chloro-3-methyl-1-butene
2190-48-9

3-chloro-3-methyl-1-butene

sodium formate
141-53-7

sodium formate

A

2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

B

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With formic acid Erwaermen des Reaktionsprodukts mit wss.Kalilauge;
bromoethyl acetate
927-68-4

bromoethyl acetate

acetone
67-64-1

acetone

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With tetrahydrofuran; magnesium; mercury dichloride Erhitzen des Reaktionsprodukts mit wss.Kalilauge;
3,3-dimethyl-allyl chloride
503-60-6

3,3-dimethyl-allyl chloride

A

2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

B

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate at 50℃;
isoprene
78-79-5

isoprene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate; acetic acid at 20℃; das Acetat entsteht; Reagens 4: Hydrochinon;
With toluene-4-sulfonic acid; acetic acid das Acetat entsteht;
ueber das Dichloracetat;
With sulfuric acid; copper(II) sulfate; acetic acid at 20℃; das Acetat entsteht; Reagens 4: Hydrochinon;
ueber das Dichloracetat;
4,4-dimethyl-1,3-dioxane
766-15-4

4,4-dimethyl-1,3-dioxane

A

4-methyl-3,6-dihydro-2H-pyran
16302-35-5

4-methyl-3,6-dihydro-2H-pyran

B

2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

C

3-methyl-butane-1,3-diol
2568-33-4

3-methyl-butane-1,3-diol

D

4-hydroxy-4-methyltetrahydropyran
7525-64-6

4-hydroxy-4-methyltetrahydropyran

E

2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

F

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sulfuric acid at 120℃; for 3h; Product distribution; various catalyst, various temperature, various time, extent of conversion, solvent cyclohexane;
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen In tetrahydrofuran at 23℃; for 0.5h;100%
With [Os(η(5)-C5,κ-N-Cp(N))(CH3CN)2]PF6 In tetrahydrofuran-d8 at 60℃; for 1.33333h; Inert atmosphere;93%
With {(η6-p-cymene)RuCl2}{[3-(3,5-diaza-1-azonia-7-phosphatricyclo[3.3.1.13,7]decan-1-yl)propyl]silanetriyltrioxy} supported on silica-coated ferrite nanoparticles In water at 150℃; under 5171.62 - 6205.94 Torr; for 14h; Inert atmosphere; Microwave irradiation;87%
phenyl isocyanate
103-71-9

phenyl isocyanate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-en-1-yl phenylcarbamate
105902-61-2

3-methylbut-2-en-1-yl phenylcarbamate

Conditions
ConditionsYield
In acetonitrile at 70℃; for 23h; Inert atmosphere;100%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;88%
With triethylamine In dichloromethane at 20℃;88%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

1-[(tetrahydro-2H-pyran-2-yl)oxy]-3-methyl-2-butene
54105-78-1

1-[(tetrahydro-2H-pyran-2-yl)oxy]-3-methyl-2-butene

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;100%
With pyridinium p-toluenesulfonate In tetrahydrofuran100%
With Aluminum(III) chloride hexahydrate at 30℃; for 0.5h;98%
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

(3,3-dimethyloxiranyl)methanol
18511-56-3

(3,3-dimethyloxiranyl)methanol

Conditions
ConditionsYield
With dihydrogen peroxide; {[CF3(CF2)7(CH2)3]3N(+)}12[WZn3(H2O)2(ZnW9O34)2] In ethyl acetate at 22℃; for 8h;100%
With 3,3-dimethyldioxirane In acetone at 23℃; Kinetics; Further Variations:; Solvents;100%
With tetrabutylphosphonium peroxotantalate; dihydrogen peroxide In water at 0℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Schlenk technique; chemoselective reaction;100%
acetic anhydride
108-24-7

acetic anhydride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-enyl acetate
1191-16-8

3-methylbut-2-enyl acetate

Conditions
ConditionsYield
indium(III) chloride In acetonitrile at 20℃; for 0.5h;100%
With zirconium(IV) chloride In dichloromethane at 20℃; for 1h;100%
With pyridine at 20℃; for 2.5h;99%
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

1-((tert-butyldiphenylsilyl)oxy)-3-methyl-2-butene
188263-82-3

1-((tert-butyldiphenylsilyl)oxy)-3-methyl-2-butene

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 0.5h;98%
With dmap; triethylamine In dichloromethane for 2h; Ambient temperature;82%
Phenylselenyl chloride
5707-04-0

Phenylselenyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methyl-2-(phenylselenyl)-1,3-butanediol
99018-46-9

3-methyl-2-(phenylselenyl)-1,3-butanediol

Conditions
ConditionsYield
With water In acetonitrile at 20℃; for 24h;100%
In water; acetonitrile for 2h; Ambient temperature;86%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

tert-butyldimethyl((3-methylbut-2-en-1-yl)oxy)silane
114701-65-4

tert-butyldimethyl((3-methylbut-2-en-1-yl)oxy)silane

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6h;94%
With 1H-imidazole In dichloromethane at 0 - 20℃;93%
trityl chloride
76-83-5

trityl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

(((3-methylbut-2-en-1-yl)oxy)methanetrityl)tribenzene
141561-63-9

(((3-methylbut-2-en-1-yl)oxy)methanetrityl)tribenzene

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 23℃;100%
With dmap; triethylamine In dichloromethane at 0 - 23℃; Inert atmosphere;100%
With dmap; 4 A molecular sieve; triethylamine In dichloromethane at 20℃; for 12h;65%
1,1-dimethoxyethylene
922-69-0

1,1-dimethoxyethylene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

C9H18O3
76347-60-9

C9H18O3

Conditions
ConditionsYield
at 20℃; for 0.5h; Inert atmosphere; neat (no solvent);100%
TrocNHOSO2NH2
1310054-46-6

TrocNHOSO2NH2

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

C8H13Cl3N2O5S
1310054-26-2

C8H13Cl3N2O5S

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; Cooling with ice;100%
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

isopentanoyl chloride
108-12-3

isopentanoyl chloride

3-methyl-2-buten-1-yl 3-methylbutanoate
89026-29-9

3-methyl-2-buten-1-yl 3-methylbutanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 2.5h;100%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

ethyl 3,3-dimethylpent-4-enoate
7796-72-7

ethyl 3,3-dimethylpent-4-enoate

Conditions
ConditionsYield
With phenol at 130 - 160℃; for 16h; Johnson-Claisen Rearrangement; Inert atmosphere;100%
2,6-dichloro-N-cyclohexyl-pyridine-3-carboxamide
1003872-51-2

2,6-dichloro-N-cyclohexyl-pyridine-3-carboxamide

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

6-chloro-N-cyclohexyl-2-(3-methylbut-2-enoxy)pyridine-3-carboxamide

6-chloro-N-cyclohexyl-2-(3-methylbut-2-enoxy)pyridine-3-carboxamide

Conditions
ConditionsYield
Stage #1: 3-methyl-2-buten-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.75h; Inert atmosphere;
Stage #2: 2,6-dichloro-N-cyclohexyl-pyridine-3-carboxamide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 4h; Inert atmosphere;
100%
dioctyltin dilaurate

dioctyltin dilaurate

methyl 2-methylbut-2-enoate
41725-90-0

methyl 2-methylbut-2-enoate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methyl-2-butenyl angelate
765300-33-2

3-methyl-2-butenyl angelate

Conditions
ConditionsYield
In toluene99.8%
BOC-glycine
4530-20-5

BOC-glycine

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

tert-butoxycarbonylamino-acetic acid 3-methyl-but-2-enyl ester
82706-45-4

tert-butoxycarbonylamino-acetic acid 3-methyl-but-2-enyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -5 - 25℃; for 8h;99.15%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;91%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Solvent; Large scale;129 kg
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

Conditions
ConditionsYield
With bis(acetylacetonato)dioxidomolybdenum(VI); dimethyl sulfoxide at 100℃; for 7h;99%
With oxygen; Pd561phen60(OAc)180 In benzene at 60℃; for 24h;99%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In acetonitrile at 75℃; under 760.051 Torr; for 11h;99%
benzoyl chloride
98-88-4

benzoyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methyl-2-butenyl benzoate
5205-11-8

3-methyl-2-butenyl benzoate

Conditions
ConditionsYield
Stage #1: benzoyl chloride; 3-methyl-2-buten-1-ol In dichloromethane at 20℃;
Stage #2: With poly{trans-bicyclo[2.2.1]hept-5-ene-2,3-di(chlorocarbonyl)} In dichloromethane Heating;
99%
With dmap; triethylamine In dichloromethane at 0 - 20℃;91%
With pyridine at 20℃; for 0.5h;89%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

2-iodo-1-(3-methylbut-2-enyl)oxy-1-(4-methoxyphenyl)ethane

2-iodo-1-(3-methylbut-2-enyl)oxy-1-(4-methoxyphenyl)ethane

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at -78 - 0℃;99%
Stage #1: 4-Methoxystyrene; 3-methyl-2-buten-1-ol In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With N-iodo-succinimide In dichloromethane at -78 - 0℃; Further stages.;
99%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

C23H24OSi

C23H24OSi

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 22h;99%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

tert-butyl (3-methylbut-2-en-1-yl)carbonate

tert-butyl (3-methylbut-2-en-1-yl)carbonate

Conditions
ConditionsYield
Stage #1: 3-methyl-2-buten-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.5h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane at 0 - 24℃; for 20h;
99%
isobutyryl chloride
79-30-1

isobutyryl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methyl-2-butenyl isobutanoate
76649-23-5

3-methyl-2-butenyl isobutanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 2.5h;99%
With dmap; triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;
vinyl laurate
2146-71-6

vinyl laurate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Dodecanoic acid 3-methyl-but-2-enyl ester

Dodecanoic acid 3-methyl-but-2-enyl ester

Conditions
ConditionsYield
With carbon dioxide at 46.02℃; under 66081.6 Torr; for 3.5h; Reagent/catalyst; High pressure; Supercritical conditions; Green chemistry;99%
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

(R,S)-3-methyl-1,2,3-butanetriol
62875-08-5

(R,S)-3-methyl-1,2,3-butanetriol

Conditions
ConditionsYield
Stage #1: 3-methyl-2-buten-1-ol With dihydrogen peroxide; bis(2,4-pentanedionato)dioxomolybdenum(VI) In acetonitrile at 30℃;
Stage #2: With diphenyl sulfide regioselective reaction;
99%
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 168 h / 20 °C
2: water; perchloric acid / 0.17 h
View Scheme
vinyl acetate
108-05-4

vinyl acetate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-enyl acetate
1191-16-8

3-methylbut-2-enyl acetate

Conditions
ConditionsYield
With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes at 50℃; for 4h; Green chemistry;99%
4-Methoxyphenyl isocyanate
5416-93-3

4-Methoxyphenyl isocyanate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-en-1-yl (4-methoxyphenyl)carbamate

3-methylbut-2-en-1-yl (4-methoxyphenyl)carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;99%
In acetonitrile at 70℃; for 23h; Inert atmosphere;78%
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-en-1-yl 4-methoxybenzoate

3-methylbut-2-en-1-yl 4-methoxybenzoate

Conditions
ConditionsYield
With pyridine at 0 - 24℃; for 24.5h; Inert atmosphere;99%
With pyridine at 0 - 24℃; for 24.5h;99%
2-(4-bromophenyl)acrylic acid
28131-17-1

2-(4-bromophenyl)acrylic acid

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-en-1-yl 2-(4-bromophenyl)acrylate

3-methylbut-2-en-1-yl 2-(4-bromophenyl)acrylate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;99%
C18H16O8

C18H16O8

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-enyl 4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-oxobutanoate
1334485-04-9

3-methylbut-2-enyl 4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-oxobutanoate

Conditions
ConditionsYield
In toluene at 55℃; Inert atmosphere; Schlenk technique;99%
In toluene at 55℃; for 4h; regioselective reaction;4.33 g

556-82-1Relevant articles and documents

Configurational Stability of a Cyclopropyl Grignard Reagent Containing a Metalated 2-Hydroxymethyl Group

Richey, Herman G.,Moses, L. Meredith

, p. 4013 - 4017 (1983)

Mixtures of cis- and trans-2-bromo-3-(hydroxymethyl)-1,1-dimethylcyclopropane were treated with methylmagnesium bromide to metalate the hydroxyl groups and then with magnesium to form metalated Grignard reagents.The compositions of products obtained upon hydrolysis with D2O indicated that the metalated Grignard reagents in refluxing diethyl ether did not undergo significant cis-trans isomerization.This work provides an example of the configurational stability of a cyclopropyl Grignard reagent with a secondary rather than a tertiary α-carbon.Because of these resultswith cyclopropyl Grignard reagents containing a metalated hydroxyl group, prior observations on additions of allylic Grignard reagents to 3-(hydroxymethyl)cyclopropenes only of products resulting from a cis relationship of magnesium and hydroxymethyl must be due to the stereochemistry of the addition process rather than to a subsequent isomerization.

Reaction of Methylbutenol with Hydroxyl Radical: Mechanism and Atmospheric Implications

Rudich, Yinon,Talukdar, Ranajit,Burkholder, James B.,Ravishankara, A. R.

, p. 12188 - 12194 (1995)

The tropospheric fate of 2-methyl-3-buten-2-ol (methylbutenol, MBO), a recently identified emission by vegetation, was investigated by measuring its UV absorption cross sections (210-300 nm) and the rate coefficient for its reaction with hydroxyl free radicals.UV absorption cross sections were found to be too small for photolysis to be an important removal pathway for MBO in the troposphere.The rate constant applicable under tropospheric conditions for the reaction of OH with MBO was determined to be k=(8.2 +/- 1.2) * 10-12 e((610 +/- 50)/T) cm3 molecule-1 s-1.The OH reaction proceeds mainly via addition of the OH to the double bond in MBO.In the absence of O2, about 15-20percent of the adducts eliminate the alcohol-OH group.However, O2 can scavenge the adduct before it decomposes at T 300 K.This mechanism was confirmed by measuring the rate coefficients for the reactions of OD and 18OH and determining the rate coefficient for the OH reaction in the presence of 7-13 Torr of O2 and in SF6 buffer gas.The elimination of alcohol-OH group was substantiated by observing OH production in the reactions of 18OH and OD.The obtained OH reaction rate coefficient suggests that the primary daytime loss of MBO in the troposphere is via its reaction with OH.

Cationic Ru complexes anchored on POM via non-covalent interaction towards efficient transfer hydrogenation catalysis

Chen, Manyu,Cui, Kai,Hou, Zhenshan,Peng, Qingpo,Wang, Jiajia,Wei, Xinjia,Zhao, Xiuge

, (2021/12/22)

The ionic materials consisting of cationic Ru complexes and Wells-Dawson polyoxometalate anion (POM, K6P2W18O62) have been constructed via a non-covalent interaction. The as-synthesized catalysts have been characterized thoroughly by NMR, XRD, FESEM, and FT-IR, etc. The characterization suggested that a hydrogen bond interaction occurred between the proton of the amine ligand in the cationic Ru complexes and the oxygen atom of the POM anion. The hydrogen bond played an important role in enhancing catalytic activity for the transfer hydrogenation of methyl levulinate (ML) to γ-valerolactone (GVL) under very mild conditions. Especially, the transfer hydrogenation reaction proceeded via a heterogeneous catalysis approach and the heterogenized catalysts even afforded much better catalytic performance than homogeneous analogs. Notably, the catalysts can be recycled without an obvious loss of activity, and further extended to highly selective transfer hydrogenation of α,β-unsaturated ketones and aldehydes, etc. into the corresponding α,β-unsaturated alcohols without any base external additives. The high catalytic performance of these anchored catalysts was highly related to the hydrogen bond interaction and the basicity of the polyanion. The obtained knowledge from this work could lead us to a new catalysis concept of tethering active homogeneous complexes for constructing highly active anchored Ru complex catalysts for hydrogenation reaction.

Metal oxide coated ceramic corrugated plate catalyst, preparation and application in preparation of key intermediates of citral

-

Page/Page column 9, (2021/04/14)

The present disclosure belongs to the technical field of catalysis, and particularly relates to a metal oxide coated ceramic corrugated plate catalyst, its preparation method and application thereof in preparation of key intermediates of citral. The catalyst consists of a ceramic corrugated plate carrier and a metal oxide active layer coated on a surface of the carrier, wherein the metal oxide active layer is a metal oxide formed by active ingredient titanium and at least four other metal elements selected from vanadium, chromium, manganese, iron, zirconium, niobium and molybdenum.

Ir nanoclusters confined within hollow MIL-101(Fe) for selective hydrogenation of α,β-unsaturated aldehyde

Chen, Yurong,Li, Guangqin,Li, Yinle,Liu, Qian,Liu, Qinghua,Liu, Qinglin,Su, Hui

supporting information, (2021/08/13)

Although the selective hydrogenation of α,β-unsaturated aldehyde to unsaturated alcohol (UOL) is an extremely important transformation, it is still a great challenge to achieve high selectivity to UOL due to thermodynamic favoring of the C[dbnd]C hydrogenation over the C[dbnd]O hydrogenation. Herein, we report that iridium nanoclusters (Ir NCs) confined within hollow MIL-101(Fe) expresses satisfied reaction activity (93.9%) and high selectivity (96.2%) for the hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL) under 1 bar H2 atmosphere and room temperature. The unique hollow structure of MIL-101(Fe) benefits for the fast transport of reactant, ensuring the comparable reaction activity and better recyclability of Ir@MIL-101(Fe) than the counterparts which Ir NCs were on the surface of MIL-101(Fe). Furthermore, The X-ray photoelectron spectroscopy data indicates the electropositive Ir NCs, owing to the electron transfer from Ir to MIL-101(Fe), can interact with oxygen lone pairs, and Fourier transform infrared spectrum shows the Lewis acid sites in MIL-101(Fe) can strongly interact with C[dbnd]O bond, which contributes to a high selectivity for COL. This work suggests the considerable potential of synergetic effect between hollow MOFs and metal nanoclusters for selective hydrogenation reactions.

Preparation method of 3-methyl-2-butenol

-

Paragraph 0026-0027; 0028-0029; 0030-0031; 0032-0049, (2020/12/08)

The invention provides a preparation method of 3-methyl-2-butenol. The preparation method comprises the following steps: carrying out an isomerization reaction on 2-methyl-3-butene-2-ol in a tubular reactor under the catalysis of a ruthenium catalyst to obtain the 3-methyl-2-butenol. No solvent is added in a reaction process, 2-methyl-3-butene-2-ol is subjected to the isomerization reaction in thetubular reactor to obtain a mixture of the 3-methyl-2-butene-2-ol and the 2-methyl-3-butene-2-ol, the mixture is rectified and separated to obtain the pure 3-methyl-2-butene-2-ol, and the 3-methyl-2-butene-2-ol obtained through recovery is returned to a reaction process, and continues to participate in the reaction. The method has the advantages of simple process flow, few side reactions, high reaction selectivity and high conversion rate.

Method for preparing 3-methyl-2-butenol through photocatalysis

-

Paragraph 0037-0053, (2021/01/04)

The invention discloses a method for preparing 3-methyl-2-butenol through photocatalysis. The 3-methyl-3-butenol is efficiently subjected to isomerization reaction through photocatalysis reaction to obtain the 3-methyl-2-butenol. The method solves the problem of generation of isoamyl alcohol in the traditional preparation process of 3-methyl-2-butenol, and has the advantages of mild reaction conditions, simple operation, high product yield and easy separation.

Preparation method of allylic alcohol

-

Paragraph 0023-0036, (2020/02/20)

The invention belongs to the technical field of fine chemical industry. A heterogeneous catalyst technology is adopted, a complex catalyst is of a chelate structure and is formed by diphosphine ligandand transition metal compounds, the complex catalyst is used for catalyzing heterogeneous rearrangement of 3-methyl-3-butene-1-alcohol, production of by-products such as isoamyl alcohol and isopreneare inhibited at the same time, the conversion rate of raw materials is increased, and the product selectivity is improved. The invention provides a preparation method of the catalyst. The invention relates to a preparation method of allylic alcohol. Preparation is carried out by adopting a 3-methyl-3-butene-1-alcohol heterogeneous rearrangement technology. The preparation method is characterizedin that heterogeneous rearrangement is completed with the 1,3-bi(diphenylphosphine)propane-palladium-acetate chelate complex as the catalyst and on the conditions that hydrogen exists, the temperatureranges from 50 DEG C to 80 DEG C, and the time ranges from 20 minutes to 2 hours. According to the preparation method, the raw materials are easy to get, the cost is low, the repeated usage time number of catalysts is large, no three wastes are produced, and the energy consumption is low; and because of energy saving, consumption reduction and environmental protection, and the high conversion rate of the raw materials and the high product selectivity, the preparation method is suitable for preparing allylic alcohol and is especially suitable for preparing high-quality allylic alcohol.

Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes

He, Jun,Xue, Yuhang,Han, Bo,Zhang, Chunzhu,Wang, You,Zhu, Shaolin

supporting information, p. 2328 - 2332 (2020/01/08)

Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis.

Engineering Catalysts for Selective Ester Hydrogenation

Dub, Pavel A.,Batrice, Rami J.,Gordon, John C.,Scott, Brian L.,Minko, Yury,Schmidt, Jurgen G.,Williams, Robert F.

, p. 415 - 442 (2020/03/04)

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.

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