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D(-)-Isovaline

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Name

D(-)-Isovaline

EINECS N/A
CAS No. 3059-97-0 Density 1.07 g/cm3
PSA 63.32000 LogP 0.89870
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 N/A Appearance White needles or crystalline powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 3059-97-0 (D(-)-Isovaline) Hazard Symbols N/A
Synonyms

Isovaline,D- (8CI);(R)-Isovaline;a-Methyl-D-a-aminobutyric acid;

Article Data 25

D(-)-Isovaline Synthetic route

1092559-79-9

benzyl (R)-2-azido-2-methylbutanoate

3059-97-0

(2R)-2-amino-2-methylbutanoic acid

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

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

3059-97-0

(2R)-2-amino-2-methylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride; methyloxirane93%

(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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride
595-39-1

DL-isovaline

3059-97-0

(2R)-2-amino-2-methylbutanoic acid

Conditions
ConditionsYield
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
ConditionsYield
(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

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

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