D(-)-Isovaline supplier | CasNO.3059-97-0

Name
D(-)-Isovaline
EINECS
CAS No. 3059-97-0
Article Data25
CAS DataBase
Density 1.07 g/cm³
Solubility freely soluble
Melting Point 276-278 °C (lit.)
Formula C₅H₁₁NO₂
Boiling Point 213.6 °C at 760 mmHg
Molecular Weight 117.148
Flash Point 83 °C
Transport Information
Appearance White needles or crystalline powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Isovaline,D- (8CI);(R)-Isovaline;a-Methyl-D-a-aminobutyric acid;
PSA 63.32000
LogP 0.89870

Synthetic route

: 1092559-79-9
benzyl (R)-2-azido-2-methylbutanoate

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With 1% Pd/C; hydrogen In methanol at 20℃;	100%
With 10% Pd/C; hydrogen In ethanol at 20℃; optical yield given as %ee;	97%

: 2583-48-4
(2R)-2-benzamido-2-methylbutanoic acid

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; for 16h;	99%

: (2R)-2-ethoxycarbonylamino-2-methylbutyronitrile

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; methyloxirane	93%

: (3R,6S)-3-Ethyl-6-isopropyl-3-methyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 150℃; for 24h;	89%

: 40916-97-0
(R)-2-Amino-2-methyl-butyric acid ethyl ester

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In ethanol for 4h; Reflux;	89%

: (R)-2-amino-2-methylbutanoic acid tert-butyl ester

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Stage #1: (R)-2-amino-2-methylbutanoic acid tert-butyl ester With methanesulfonic acid In 1,2-dichloro-ethane at 25 - 80℃; for 13h; Stage #2: With triethylamine In 1,2-dichloro-ethane at 25℃; for 16h;	76%

: 88082-98-8
(+/-)-2-amino-4-(benzylthio)-2-methylbutanoic acid

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With ranney nickel In water for 12h; Heating;	71%

: 86960-59-0
N-chloroacetyl-D-isovaline

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 595-39-1
DL-isovaline

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
durch Vergaerung mit Hefe unter Zusatz von Zucker;
Multi-step reaction with 2 steps 1: Ac2O 2: HCl / methanol View Scheme

: 2576-61-6
4-ethyl-4-methyl-2-phenyl-4H-oxazol-5-one

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
(i) (racemate resolution using l-menthol), (ii) aq. HBr; Multistep reaction;
Multi-step reaction with 2 steps 1: (i) Na, benzene, (ii) /BRN= 155858/ 2: aq. HBr / Heating View Scheme

: 2-Benzamido-2-methyl-buttersaeure-l-menthylester

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With hydrogen bromide Heating;

: (R)-2-Formylamino-2-methyl-butyric acid

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In methanol

: 74-96-4
ethyl bromide

: 10065-72-2
L-Alanine methyl ester

: 420-37-1
trimethoxonium tetrafluoroborate

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 59209-90-4
(RS)-2-amino-2-methylbutanamide

A: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

B: 595-40-4
L-isovaline

Conditions

Conditions	Yield
at 37℃; Mycobacterium neoaurum ATCC 25795, pH 8-8.5; Yield given. Title compound not separated from byproducts;

: (R)-2-Methyl-2-((R)-2-phenoxy-3-phenyl-propionylamino)-butyric acid

A: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

B: 64682-83-3, 120346-42-1
(R)-2-phenoxy-3-phenylpropionic acid

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 110℃;

: (R)-2-Methyl-2-((R)-2-phenoxy-3-phenyl-propionylamino)-butyric acid tert-butyl ester

A: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

B: 64682-83-3, 120346-42-1
(R)-2-phenoxy-3-phenylpropionic acid

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 110℃;

: (2R,3R)-2-Amino-3-hydroxy-2-methyl-butyric acid; hydriodide

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With phosphorus; hydrogen iodide In water at 160℃; for 5.5h; freeing from HI salt with Dowex 50 W*8;

: 177273-84-6
(R)-2-Methyl-2-(2,2,2-trichloro-acetylamino)-butyric acid

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
With potassium hydroxide at 50℃;

dl-isovaline: dl-isovaline

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
ueber das Chininsalz der Formylverbindung;
ueber das Brucinsalz der Formylverbindung;

: 2-amino-2-methyl-butyric acid isopropyl ester; hydrochloride

A: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

B: 595-40-4
L-isovaline

Conditions

Conditions	Yield
With hydrogenchloride Heating;

: 52812-57-4
(Z)-1-iodo-2-methyl-1-butene

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) n-BuLi, 1/2CuBr-Me2S 2: DBU / CH2Cl2 / 1 h / -78 °C 3: 60 percent / xylene / 4 h / 140 °C 4: 81 percent / O3, Me2S / 12 h 5: Jones reagent / 0.33 h 6: KOH / 50 °C View Scheme

: 177273-81-3
2,2,2-Trichloro-N-((R)-1-formyl-1-methyl-propyl)-acetamide

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Jones reagent / 0.33 h 2: KOH / 50 °C View Scheme

: 2,2,2-Trichloro-N-((E)-(1R,4S)-1-ethyl-4-methoxymethoxy-1,5-dimethyl-hex-2-enyl)-acetamide

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / O3, Me2S / 12 h 2: Jones reagent / 0.33 h 3: KOH / 50 °C View Scheme

: 2,2,2-Trichloro-acetimidic acid (Z)-(S)-1-((S)-1-methoxymethoxy-2-methyl-propyl)-3-methyl-pent-2-enyl ester

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 60 percent / xylene / 4 h / 140 °C 2: 81 percent / O3, Me2S / 12 h 3: Jones reagent / 0.33 h 4: KOH / 50 °C View Scheme

: (Z)-(3S,4S)-3-Methoxymethoxy-2,6-dimethyl-oct-5-en-4-ol

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: DBU / CH2Cl2 / 1 h / -78 °C 2: 60 percent / xylene / 4 h / 140 °C 3: 81 percent / O3, Me2S / 12 h 4: Jones reagent / 0.33 h 5: KOH / 50 °C View Scheme

: 152033-17-5
(2R,5R)-2-(t-Butyl)-5-ethyl-3,5-dimethyl-4-oxo-1-imidazolidincarbonsaeure-t-butylester

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) 6N HCl; 2.) 1N NaOH / 1.) methanol, 24 h, reflux; 2.) 16 h 2: 90 percent / 4 N HCl / dioxane / 4 h / 80 °C 3: 99 percent / conc. aq. HCl / 16 h / 100 °C View Scheme

: 161956-11-2
N-benzoyl-D-isovaline-methylamide

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / 4 N HCl / dioxane / 4 h / 80 °C 2: 99 percent / conc. aq. HCl / 16 h / 100 °C View Scheme

: (R)-2-Methyl-2-((3R,4S)-2-oxo-3-phenoxy-4-phenyl-azetidin-1-yl)-butyric acid

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 2: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C View Scheme

: 110510-47-9
(R)-2-Methyl-2-((3R,4S)-2-oxo-3-phenoxy-4-phenyl-azetidin-1-yl)-butyric acid tert-butyl ester

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: CF3COOH 2: Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 3: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C View Scheme
Multi-step reaction with 2 steps 1: H2 / Pd-C 2: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C View Scheme

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 24424-99-5
di-tert-butyl dicarbonate

: 123254-58-0
(R)-2-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran Inert atmosphere;	97%

: 3934-20-1
2,6-Dichloropyrimidine

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: (R)-2-((2-chloropyrimidin-4-yl)amino)-2-methylbutanoic acid

Conditions

Conditions	Yield
With potassium carbonate In isopropyl alcohol at 90℃; for 5.5h;	93%

: 67-56-1
methanol

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 118725-00-1
methyl (R)-2-amino-2-methyl-butyrate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 3h; Reflux;	93%

: 590-28-3
potassium cyanate

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: (5R)-5-ethyl-5-methyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
Stage #1: potassium cyanate; (2R)-2-amino-2-methylbutanoic acid In water at 90℃; for 3h; Stage #2: With hydrogenchloride In water at 90℃; for 2h;	91%
Stage #1: potassium cyanate; (2R)-2-amino-2-methylbutanoic acid In water at 90℃; for 2h; Stage #2: With hydrogenchloride In water at 90℃; for 1h;	76%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 2493-02-9
4-bromophenyl isocyanate

: N-[(4-bromophenyl)carbamoyl]-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃;	85%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 404-71-7
1-fluoro-3-isocyanatobenzene

: N-[(3-fluorophenyl)carbamoyl]-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 3h;	77%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 104-12-1
p-chlorphenylisocyanate

: N-[(4-chlorophenyl)carbamoyl]-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 4.5h;	77%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 108282-38-8
4-amino-5-chloro-2-ethoxybenzoic acid

: (+)-N-(4-amino-5-chloro-2-ethoxybenzoyl)-L-isovaline

Conditions

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 50℃; for 5h;	74%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 2909-38-8
m-chlorophenyl isocyanate

: N-[(3-chlorophenyl)carbamoyl]-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 2h;	71%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 35290-97-2
4-amino 5-bromo 2-methoxy benzoic acid

: (+)-N-(4-amino-5-bromo-2-methoxybenzoyl)-L-isovaline

Conditions

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 50℃; for 5h;	71%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 35037-73-1
1-isocyanato-4-trifluoromethoxy-benzene

: (-)-N-{[4-(trifluoromethoxy)phenyl]carbamoyl}-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃;	68%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 58417-15-5
1-(difluoromethoxy)-4-isocyanatobenzene

: N-{[4-(difluoromethoxy)phenyl]carbamoyl}-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 3.5h;	64%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 15845-62-2
1-iodo-4-isocyanatobenzene

: N-[(4-iodophenyl)carbamoyl]-D-isovaline

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃;	62%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 4-amino-2-ethoxy-5-fluorobenzoic acid

: (+)-N-(4-amino-2-ethoxy-5-fluorobenzoyl)-L-isovaline

Conditions

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 50℃; for 5h;	40%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 7206-70-4
4-amino-5-chloro-2-methoxybenzoic acid

: (+)-N-(4-amino-5-chloro-2-methoxybenzoyl)-L-isovaline

Conditions

Conditions	Yield
Stage #1: 4-amino-5-chloro-2-methoxybenzoic acid With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: (2R)-2-amino-2-methylbutanoic acid In N,N-dimethyl-formamide at 50℃; for 3h;	33%

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 591-18-4
1-Bromo-3-iodobenzene

: (R)-2-((3-bromophenyl)amino)-2-methylbutanoic acid

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	27.02%

: 75-15-0
carbon disulfide

: 74-96-4
ethyl bromide

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 27539-03-3
(R)-N-Dithiocarbethoxyisovalin

Conditions

Conditions	Yield
(i) aq. K2CO3, EtOH, (ii) /BRN= 1209224/; Multistep reaction;

...Expand

: 3059-97-0
(2R)-2-amino-2-methylbutanoic acid

: 10196-30-2
(R)-2-amino-2-methylbutan-1-ol

Conditions

Conditions	Yield
(i) EtOH, SOCl2, (ii) NaBH4; Multistep reaction;

D(-)-Isovaline Specification

The D-Isovaline, belongs to the following product categories: (1)Amino Acid Derivatives; (2)Valine [Val, V]. It has the systematic name of D-isovaline. And its IUPAC name is (2R)-2-azaniumyl-2-methylbutanoate. This chemical is a kind of white needles or crystalline powder. When use it, avoid contact with skin and eyes.

Physical properties of D-Isovaline: (1)ACD/LogP: 0.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.3; (4)ACD/LogD (pH 7.4): -2.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.465; (14)Molar Refractivity: 30.27 cm³; (15)Molar Volume: 109.4 cm³; (16)Polarizability: 12×10^-24cm³; (17)Surface Tension: 41 dyne/cm; (18)Enthalpy of Vaporization: 49.58 kJ/mol; (19)Vapour Pressure: 0.0633 mmHg at 25°C.

Preparation: this chemical can be prepared by (R)-2-amino-4-benzylthio-2-methylbutanoic acid. This reaction will need reagent Ranney nickel and solvent H₂O. The reaction time is 12 hour(s). The yield is about 71%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@@](N)(C)CC
(2)InChI: InChI=1/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m1/s1
(3)InChIKey: GCHPUFAZSONQIV-RXMQYKEDBV
(4)Std. InChI: InChI=1S/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m1/s1
(5)Std. InChIKey: GCHPUFAZSONQIV-RXMQYKEDSA-N

Product Name

D(-)-Isovaline

Synthetic route

D(-)-Isovaline Specification

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