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556-82-1

Basic Information
CAS No.: 556-82-1
Name: 2-Buten-1-ol, 3-methyl-
Article Data: 189
Cas Database
Molecular Structure:
Molecular Structure of 556-82-1 (2-Buten-1-ol, 3-methyl-)
Formula: C5H10O
Molecular Weight: 86.1338
Synonyms: 2-Methyl-2-buten-4-ol;3,3-Dimethylallyl alcohol;3-Methyl-2-buten-1-ol;3-Methyl-2-butene-1-ol;3-Methyl-2-butenol;3-Methyl-2-butenyl alcohol;3-Methylcrotyl alcohol;Dimethylallyl alcohol;Isopent-2-en-1-ol;NSC 158709;Prenol;Prenyl alcohol;g,g-Dimethylallyl alcohol;
EINECS: 209-141-4
Density: 0.844 g/cm3
Melting Point: -86oC
Boiling Point: 141.5 °C at 760 mmHg
Flash Point: 43.3 °C
Solubility: water: 170 g/L (20 °C)
Appearance: colorless liquid with fruity odor
Hazard Symbols: HarmfulXn
Risk Codes: 10-22-36/37/38-38-21/22
Safety: 26-36-37-23-16
Transport Information: UN 1987 3/PG 3
PSA: 20.23000
LogP: 0.94490
Synthetic route
107-86-8

3,3-dimethyl acrylaldehyde

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%
763-32-6

2-methyl-1-buten-4-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;
870-63-3

prenyl bromide

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
71821-61-9

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

556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With tris paraperiodate In benzene Heating;95%
1191-16-8

3-methylbut-2-enyl acetate

556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 2.5h;95%
503-60-6

3,3-dimethyl-allyl chloride

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
638-10-8

ethyl 3-methylbut-2-enoate

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℃;
54105-78-1

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

556-82-1

3-methyl-2-buten-1-ol

Conditions
ConditionsYield
With cerium(III) chloride In methanol at 20℃; for 1h; detetrahydropyranylation;90%
68480-28-4

formiate de methyl-3 butene-2 ol-1

556-82-1

3-methyl-2-buten-1-ol

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

3,3-dimethyl acrylaldehyde

A

123-51-3

i-Amyl alcohol

B

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;
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Chemistry

Molecular Structure of 3-Methyl-2-buten-1-ol (CAS No.556-82-1):

Molecular Formula: C5H10O
Molecular Weight: 86.13
IUPAC Name: 3-Methylbut-2-en-1-ol
CAS No: 556-82-1
EINECS: 209-141-4
H bond acceptors: 1
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 9.23 Å2
Index of Refraction: 1.435
Molar Refractivity: 26.64 cm3
Molar Volume: 101.9 cm3
Surface Tension: 26.4 dyne/cm
Density: 0.844 g/cm3
Flash Point: 43.3 °C
Enthalpy of Vaporization: 44.12 kJ/mol
Boiling Point: 141.5 °C at 760 mmHg
Vapour Pressure: 2.38 mmHg at 25°C
Refractive Index: 1.442-1.444
Water Solubility: 170 g/L (20 ºC)
Storage Temp.: Flammables area
Classification Code: Skin/Eye Irritant

Uses

   3-Methyl-2-buten-1-ol (CAS No.556-82-1) is used occasionally in perfumery.It occurs naturally in citrus fruits, cranberry, bilberry, currants, grapes, raspberry, blackberry, tomato, white bread, hop oil, coffee, arctic bramble, cloudberry and passion fruit.

Production

   3-Methyl-2-buten-1-ol (CAS No.556-82-1) is produced industrially by the reaction of formaldehyde with isobutene, followed by the isomerization of the resulting isoprenol (3-methyl-3-buten-1-ol).

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin 3900mg/kg (3900mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 895, 1979.
rat LD50 oral 810mg/kg (810mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 895, 1979.

Consensus Reports

  3-Methyl-2-buten-1-ol (CAS No.556-82-1) is reported in EPA TSCA Inventory.

Safety Profile

Safety Information of 3-Methyl-2-buten-1-ol (CAS No.556-82-1):
Hazard Codes: HarmfulXn
Risk Statements: 10-22-36/37/38-38-21/22 
R10:Flammable. 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R38:Irritating to skin. 
R21/22:Harmful in contact with skin and if swallowed.
Safety Statements: 26-36-37-23-16 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37:Wear suitable gloves. 
S23:Do not breathe vapour. 
S16:Keep away from sources of ignition.
RIDADR: UN 1987 3/PG 3
WGK Germany: 1
RTECS: EM9472500
HazardClass: 3
PackingGroup: III
HS Code: 29052990

Specification

  3-Methyl-2-buten-1-ol (CAS No.556-82-1), it also can be called 3,3-Dimethylallyl alcohol ; Prenyl alcohol ; 2-Buten-1-ol, 3-methyl- ; 2-Methyl-2-buten-4-ol ; 3-Methylbut-2-en-1-ol . It is clear colourless to very slightly yellow liquid. 3-Methyl-2-buten-1-ol (CAS No.556-82-1) is a natural alcohol. It is one of the most simple terpenes. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents.