(R)-3-amino-1-butanol
- CAS NO.:61477-40-5
- Empirical Formula: C4H11NO
- Molecular Weight: 89.14
- MDL number: MFCD13184351
- EINECS: 640-387-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-21 17:11:28
What is (R)-3-amino-1-butanol ?
Description
(R)-3-amino-1-butanol is an alcohol organic compound, which is a key intermediate for many chiral drugs.
The Uses of (R)-3-amino-1-butanol
(R)-3-Aminobutan-1-ol, can be used as an intermediate in the preparation of compounds having HIV integrase inhibitory activity.
Definition
(R)-3-amino-1-butanol is the most critical building block for synthesizing pharmaceuticals, including Dolutegravir, penicillium antibiotics, and anti-tumor drug 4-methylcyclophosphamide. Mainly, Dolutegravir is a new-generation integrase inhibitor for the treatment of HIV infection[1]. Currently, this compound is mainly achieved by chemical methods. A ruthenium complex could be used to catalyze the hydrogen reduction of (R)-3-aminobutyric acid ester to (R)-3-amino-1-butanol[2].
Synthesis
The (S)-mandelic salt of (R)-3-amino-1-butanol (372 g, 1.54 mol) was suspended in triethanolamine (1 I) at 80° C., and the slurry was admixed with sodium methoxide (277.6 g, 1.54 mol; 30% in methanol), which gave a clear solution. This was heated to 100° C. and vacuum was applied. In a stepwise manner, a pressure of 750, 500, 250, 100, 50 and finally 20 mbar was applied. Through an attached Claisen distillation head (no return stream, no column), a clear distillate distilled over at a top temperature of 50 to 60° C., which was predominantly methanol. The pressure was then lowered further to 5 mbar, and (R)-3-amino-1-butanol distilled over at a top temperature of 76° C. The product was distilled once again in a water jet pump vacuum, in the course of which (R)-3-amino-1-butanol distilled over at 93° C. and 26 mbar. This gave 125 g (91% of theory) of (R)-3-amino-1-butanol as a colorless liquid with an optical purity of 99.6% ee.
References
[1] TangXiao-Ling. "Efficient biosynthesis of (R)-3-amino-1-butanol by a novel (R)-selective transaminase from Actinobacteria sp." Journal of biotechnology 295 (2019): 49–54.
[2] HhneMatthias. "Rational assignment of key motifs for function guides in silico enzyme identification." Nature chemical biology 6 11 (2010): 807–13.
Properties of (R)-3-amino-1-butanol
Boiling point: | 168℃ |
Density | 0.927 |
refractive index | 1.4530 to 1.4570 |
Flash point: | 56℃ |
storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
solubility | soluble in Dichloromethane, DMSO |
pka | 15.00±0.10(Predicted) |
form | clear liquid |
color | Colorless to Light orange to Yellow |
InChI | InChI=1S/C4H11NO/c1-4(5)2-3-6/h4,6H,2-3,5H2,1H3/t4-/m1/s1 |
CAS DataBase Reference | 61477-40-5 |
Safety information for (R)-3-amino-1-butanol
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Corrosion Corrosives GHS05 |
GHS Hazard Statements |
H226:Flammable liquids H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P242:Use only non-sparking tools. P243:Take precautionary measures against static discharge. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P370+P378:In case of fire: Use … for extinction. P405:Store locked up. P403+P235:Store in a well-ventilated place. Keep cool. |
Computed Descriptors for (R)-3-amino-1-butanol
InChIKey | AGMZSYQMSHMXLT-SCSAIBSYSA-N |
SMILES | C(O)C[C@H](N)C |
(R)-3-amino-1-butanol manufacturer
Ceyone Life Sciences
Aether Industries Limited
Besil Chem LLP
Inventys Research Company Pvt Ltd
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