(R)-2-Methylbutanol supplier

Name
(R)-2-Methylbutanol
EINECS
CAS No. 616-16-0
Article Data70
CAS DataBase
Density 0.809
Solubility
Melting Point
Formula C₅H₁₂O
Boiling Point 129 ºC
Molecular Weight 88.1497
Flash Point 43 ºC
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Butanol,2-methyl-, (R)-;1-Butanol, 2-methyl-, (R)-(+)- (8CI);1-Butanol, 2-methyl-, d-(4CI);(+)-2-Methyl-1-butanol;(+)-2-Methylbutanol;(R)-(+)-2-Methyl-1-butanol;(R)-2-Methyl-1-butanol;
PSA 20.23000
LogP 1.02480

Synthetic route

: 32231-50-8
(R)-2-methylbutyric acid

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
Stage #1: (R)-2-methylbutyric acid With lithium aluminium tetrahydride In diethyl ether at 0 - 5℃; for 1h; Stage #2: With hydrogenchloride; water In diethyl ether Cooling with ice;	100%
Stage #1: (R)-2-methylbutyric acid With lithium aluminium tetrahydride In diethyl ether at 0 - 5℃; for 1h; Stage #2: With water In diethyl ether	100%
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 1h;	93%

: (R)-(-)-2-methyl-1-(tetrahydro-2-pyranyloxy)-butan-1-ol

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With Amberlyst(R) In methanol at 45℃; for 0.666667h;	100%

: 130856-00-7
(R)-2-methyl-1-(2-tetrahydropyranyloxy)butane

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol for 12h; Ambient temperature;	95%
With toluene-4-sulfonic acid In methanol for 3h; Decomposition; Heating;	57%
With toluene-4-sulfonic acid In methanol for 4h; Heating;

: 1174752-30-7
1-methoxy-4-((R)-(-)-2-methylbutoxymethyl)benzene

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In dichloromethane under 760.051 Torr;	93%
With palladium on carbon; hydrogen In dichloromethane at 20℃;	64%

: 474828-48-3
(R)-4-benzyl-3-((R)-2-methylbutanoyl) oxazolidin-2-one

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With lithium borohydride In methanol; diethyl ether at -30℃; Inert atmosphere; Cooling with ice;	92%
With lithium borohydride In methanol; diethyl ether at -30 - 0℃; for 12.5h; Inert atmosphere;	92%
With methanol; lithium borohydride In tetrahydrofuran at 0 - 20℃; for 3h;
With lithium aluminium tetrahydride In diethyl ether at -20 - 0℃; for 2h;
Multi-step reaction with 2 steps 1: lithium hydroxide; dihydrogen peroxide / water / 16 h / 0 - 20 °C 2: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 - 20 °C View Scheme

: 33204-48-7
(R)-2-methylbutanal

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With dimethylsulfide borane complex 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 0.5 h;	90%
With sodium tetrahydroborate In tetrahydrofuran; water for 4h; Ambient temperature;

: 13602-09-0, 115166-86-4, 115166-89-7
Acetaldehyde O-ethyl O'-(R)-2-methylpropyl acetal

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In tetrahydrofuran; water for 2h; Heating;	88%
With pyridinium p-toluenesulfonate In tetrahydrofuran; water Heating; Yield given;

: 474828-48-3
(R)-4-benzyl-3-((R)-2-methylbutanoyl) oxazolidin-2-one

A: 616-16-0
(R)-2-Methyl-1-butanol

B: 40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7
(R)-4-(phenylmethyl)-2-oxazolidinone

Conditions

Conditions	Yield
With lithium borohydride In methanol; diethyl ether at -20 - 0℃; for 2h; Inert atmosphere;	A 86% B 72%
Stage #1: (R)-4-benzyl-3-((R)-2-methylbutanoyl) oxazolidin-2-one With lithium borohydride In methanol; diethyl ether at -20 - 0℃; for 2h; Inert atmosphere; Stage #2: With sodium hydroxide In methanol; diethyl ether for 0.5h; Inert atmosphere;	A 86% B 72%

: 1068600-85-0
(2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl-2-methylbutanamide

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 23℃; for 2h;	85%
With n-butyllithium; ammonia borane; diisopropylamine In tetrahydrofuran; hexane at -78 - 25℃; for 2h;	76%
With lithium amidotrihydridoborate In tetrahydrofuran; hexane at 20℃;

: 69743-62-0
(R)-2-methylbutyl benzoate

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water for 2h; Heating;	84%

: 1499185-56-6
(R)-2-(iodomethyl)butyl acetate

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride Inert atmosphere;	82%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 23℃; for 2h;	82%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 23℃; for 2h;	82%

: 75-16-1
methylmagnesium bromide

: 155674-95-6
(2S)-3-iodo-2-methyl-1-propanol

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With dilithium tetrachlorocuprate(II) Inert atmosphere;	77%

: 676-58-4
methylmagnesium chloride

: 155674-95-6
(2S)-3-iodo-2-methyl-1-propanol

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran; diethyl ether at 0 - 23℃; for 3h;	77%
With dilithium tetrachlorocuprate In tetrahydrofuran; diethyl ether at 0 - 23℃; for 3h;	77%

: 108-05-4
vinyl acetate

: 137-32-6
(+/-)-2-methyl-1-butanol

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With vinyl acetate; pseudomonas fluorescens lipase In dichloromethane Enzymatic reaction;	30%

: 137-32-6
(+/-)-2-methyl-1-butanol

A: 616-16-0
(R)-2-Methyl-1-butanol

B: 1565-80-6
(2S)-2-methyl-1-butanol

Conditions

Conditions	Yield
Stage #1: (+/-)-2-methyl-1-butanol With (R,R,R,R)-(-)-trans,trans-2,3,10,11-tetrakis(hydroxydiphe.. at 20℃; for 24h; inclusion complexation; resolution of racemate; Stage #2: at 180℃; under 30 Torr; decomposition of complex;	A n/a B 5%
Stage #1: (+/-)-2-methyl-1-butanol With chiral Zn*salen complex at 40℃; for 2h; Stage #2: at 60℃; Further stages.;
With C14H15NO8Zn2 for 48h; Resolution of racemate; optical yield given as %ee;

: 96-17-3, 57456-98-1
2-Methylbutyraldehyde

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
bei der Einw.von Termobacterium mobile Lindner; teilweise racemisierte Praeparat entsteht;

: 96-17-3, 57456-98-1
2-Methylbutyraldehyde

A: 616-16-0
(R)-2-Methyl-1-butanol

B: 802294-64-0
propionic acid

Conditions

Conditions	Yield
bei der Einw. von Aceton-Trockenpreparaten aus B.pasteuranium;
bei der Einw. von B. pasteurianum;

: 137-32-6
(+/-)-2-methyl-1-butanol

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
ueber den Tartranilsaeureester; teilweise racemisierte Praeparat entsteht;
ueber das Brucin- oder Strychninsalz des sauren Schwefelsaeureesters; teilweise racemisierte Praeparat entsteht;

: 75-09-2
dichloromethane

: 97235-22-8
(R)-(-)-2-(1-methylpropyl)-1,3,2-dioxaborinane

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With n-butyllithium; K-tetrakis(isopropoxy)borate; hydroxide; dihydrogen peroxide; trimethyleneglycol Yield given. Multistep reaction;

: 109686-80-8
(R)-2-Methylbutyrat

A: 616-16-0
(R)-2-Methyl-1-butanol

B: 1565-80-6
(2S)-2-methyl-1-butanol

Conditions

Conditions	Yield
With carbon monoxide; Paraquat In water at 40℃; pH: 5.5; Clostridium thermoaceticum;

: 69743-61-9
(R)-2-methylbutyl acetate

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; diethyl ether; water at 25℃; for 1h; Yield given;

: 32793-87-6
(R)-1-<(2-methylbutoxy)methyl>benzene

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In tetrahydrofuran under 760 Torr; for 3h;

: 79563-31-8
(4R,5S)-4-methyl-3-[2(R)-methyl-1-oxobutyl]-5-phenyloxazolidin-2-one

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With lithium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide 2) Et2O; Yield given. Multistep reaction;

: (2R,3S)-3-Methanesulfonyloxy-2-methyl-butyric acid ethyl ester

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With sodium tetrahydroborate at 85 - 90℃; for 20h;

: (2R,3S)-2-Methyl-3-(toluene-4-sulfonyloxy)-butyric acid ethyl ester

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In dimethyl sulfoxide at 85 - 90℃; for 20h;

dl-methylethylacetaldehyde: dl-methylethylacetaldehyde

A: 116-53-0, 600-07-7
2-Methylbutanoic acid

B: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
bei der Einw. von Bact.pasteurianum oder daraus hergestellten Acetontrockenpraeparaten;

(-)-3-bromo-2-methyl-butyric acid methyl ester: (-)-3-bromo-2-methyl-butyric acid methyl ester

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride ein partiell racemisches Praeparat;
With hydrogen iodide; zinc ein partiell racemisches Praeparat;

(-)(R)-methylethylacetic acid ethyl ester: (-)(R)-methylethylacetic acid ethyl ester

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With CuO/Cr2O3 at 250℃; under 147102 - 202265 Torr; Hydrogenation.teilweise racemisierte Praeparat entsteht;

rac2-methyl-butan-1-ol: rac2-methyl-butan-1-ol

: 616-16-0
(R)-2-Methyl-1-butanol

Conditions

Conditions	Yield
With water durch Einwirkung einer Schimmelpilzkultur;

dl-methylethylacetaldehyde: dl-methylethylacetaldehyde

A: 616-16-0
(R)-2-Methyl-1-butanol

B d,l-amyl alcohol: d,l-amyl alcohol

Conditions

Conditions	Yield
durch Einw. von Bacterium pasteurianum oder des daraus hergestellten Acetonpraeparats; Nebenprod.2:Methylaethylessigsaeure;

: 616-16-0
(R)-2-Methyl-1-butanol

: 98-59-9
p-toluenesulfonyl chloride

: 46481-05-4
(R)-2-methyl-1-butanol 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With pyridine at 0 - 5℃; for 12h;	99%
With pyridine at 0 - 5℃; for 2h;	95%
With pyridine at 0 - 5℃;	86%

: tricarbonyl(cyclohexadienyl)iron tetrafluoroborate

: 616-16-0
(R)-2-Methyl-1-butanol

: (CO)3Fe(C6H7OCH2CH(CH3)C2H5)

Conditions

Conditions	Yield
With N(C2H5)(CH(CH3)2)2 In dichloromethane under N2, to stirred suspn. of Fe-complex and HOCH2CH(Me)Et (molar ratio 1:2) in CH2Cl2 was added 1.19 equiv of NEt(i-Pr)2, stirred for 40 min at room temp.; product contained two diastereoisomers; elem. anal.;	98%

: 616-16-0
(R)-2-Methyl-1-butanol

: 86-93-1
1-Phenyl-1H-tetrazole-5-thiol

: (R)-5-([2-methylbutyl]thio)-1-phenyl-1H-tetrazole

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -20 - 20℃; for 10h; Mitsunobu Displacement; Inert atmosphere;	98%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 8h; Mitsunobu Displacement; Inert atmosphere; Cooling with ice;	87.3%

: 616-16-0
(R)-2-Methyl-1-butanol

: 124-63-0
methanesulfonyl chloride

: 104418-39-5
(R)-1-Methylsulfonyloxy-2-methylbutane

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 25℃; for 1h;	94%
With triethylamine In dichloromethane at 0℃; for 2h;	83%

: 616-16-0
(R)-2-Methyl-1-butanol

: 33204-48-7
(R)-2-methylbutanal

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 1.5h;	88%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.25h;	52%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1) CH2Cl2, -78 deg C, 2) CH2Cl2, -78 to 0 deg C; Multistep reaction;

: 616-16-0
(R)-2-Methyl-1-butanol

: 87106-25-0
(R)-(+)-1-iodo-2-methylbutane

Conditions

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 23℃; for 2h;	85%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0℃; for 3h; Inert atmosphere;	74%
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 5 °C 2: 80 percent / NaI / acetone / 6 h / Heating View Scheme

: 616-16-0
(R)-2-Methyl-1-butanol

: 149-30-4
2-Mercaptobenzothiazole

A: (R)-2-(2-methylbutylthio)benzo[d]thiazole

B: (S)-2-(2-methylbutylthio)benzo[d]thiazole

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h;	A 82% B n/a

...Expand

: 616-16-0
(R)-2-Methyl-1-butanol

: 149-30-4
2-Mercaptobenzothiazole

: (R)-2-(2-methylbutylthio)benzo[d]thiazole

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement;	82%

: 616-16-0
(R)-2-Methyl-1-butanol

: 99032-67-4
(S)-(+)-1-bromo-2-methylbutane

Conditions

Conditions	Yield
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; Mukaiyama reaction; Inert atmosphere;	80%
With triphenyl phosphite; bromine In dichloromethane for 3h; Ambient temperature;	49%
With bromine; triphenylphosphine In N,N-dimethyl-formamide at 0℃;	44%

: 616-16-0
(R)-2-Methyl-1-butanol

: 32231-50-8
(R)-2-methylbutyric acid

Conditions

Conditions	Yield
With chromium(VI) oxide In acetone Oxidation;	75%

: 616-16-0
(R)-2-Methyl-1-butanol

: 21988-87-4
1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene

: 2,4,6-Tris[(2'R)-2'-methylbutyloxymethyl]mesitylene

Conditions

Conditions	Yield
Stage #1: (R)-2-Methyl-1-butanol With sodium hydride In tetrahydrofuran for 0.5h; Metallation; Stage #2: 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene With tetra-(n-butyl)ammonium iodide In tetrahydrofuran Etherification;	71%

: 616-16-0
(R)-2-Methyl-1-butanol

: 407-25-0
trifluoroacetic anhydride

: 195305-45-4
(2R)-2-methylbutyl trifluoromethanesulfonate

Conditions

Conditions	Yield
With pyridine In dichloromethane at -78℃; for 2h;	71%

: 616-16-0
(R)-2-Methyl-1-butanol

: 99-93-4
4-Hydroxyacetophenone

: 4'-hydroxyacetophenone (S)-2-methyl-1-butyl ether

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;	57%

: 616-16-0
(R)-2-Methyl-1-butanol

: 471-25-0
Propiolic acid

: (R)-2-methyl-1-butyl propiolate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Reflux; Dean-Stark;	50%

: 75-47-8
iodoform

: 616-16-0
(R)-2-Methyl-1-butanol

: 944271-63-0
C6H11I

Conditions

Conditions	Yield
Stage #1: (R)-2-Methyl-1-butanol With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.5h; Stage #2: iodoform With chromium chloride; lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5h; Takai reaction; Further stages.;	33%

(R)-2-Methylbutanol Specification

The (R)-2-Methylbutanol, with the cas registry number of 616-16-0, has the systematic name of (2R)-2-methylbutan-1-ol. And the molecular formula of the chemical is C₅H₁₂O.

The characteristics of this chemical are as followings: (1)ACD/LogP: 1.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.22; (4)ACD/LogD (pH 7.4): 1.22; (5)ACD/BCF (pH 5.5): 5; (6)ACD/BCF (pH 7.4): 5; (7)ACD/LogP: 1.22; (8)# of Rule of 5 Violations: 0; (9)ACD/LogD (pH 5.5): 1.22; (10)ACD/LogD (pH 7.4): 1.22; (11)ACD/BCF (pH 5.5): 5; (12)ACD/BCF (pH 7.4): 5; (13)ACD/KOC (pH 5.5): 110.18; (14)ACD/KOC (pH 7.4): 110.18; (15)#H bond acceptors: 1; (16)#H bond donors: 1; (17)#Freely Rotating Bonds: 3; (18)Polar Surface Area: 9.23 Å²; (19)Index of Refraction: 1.405; (20)Molar Refractivity: 26.7 cm³; (21)Molar Volume: 108.9 cm³; (22)Polarizability: 10.58×10^-24cm³; (23)Surface Tension: 25.6 dyne/cm; (24)Density: 0.809 g/cm³; (25)Flash Point: 43.3 °C; (26)Enthalpy of Vaporization: 42.7 kJ/mol; (27)Boiling Point: 128.7 °C at 760 mmHg; (28)Vapour Pressure: 4.76 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: OC[C@H](C)CC
(2)InChI: InChI=1/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3/t5-/m1/s1
(3)InChIKey: QPRQEDXDYOZYLA-RXMQYKEDBU

Product Name

(R)-2-Methylbutanol

Synthetic route

(R)-2-Methylbutanol Specification

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