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61477-40-5

61477-40-5 structural image
Product Name: (R)-3-amino-1-butanol
Formula: C4H11NO
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SAFETY INFORMATION

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

Molecular Weight 89.14 g/mol
XLogP3 -0.6
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 2
Rotatable Bond Count 2
Exact Mass 89.084063974 g/mol
Monoisotopic Mass 89.084063974 g/mol
Topological Polar Surface Area 46.2 Ų
Heavy Atom Count 6
Formal Charge 0
Complexity 30.7
Isotope Atom Count 0
Defined Atom Stereocenter Count 1
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

PRODUCT INTRODUCTION

Description

(R)-3-amino-1-butanol is the most essential building block for synthesising pharmaceuticals, including Dolutegravir, penicillium antibiotics and anti-tumor drug 4-methylcyclophosphamide. Particularly, Dolutegravir is a new-generation integrase inhibitor for the treatment of HIV infection. Currently, the synthesis of (R)-3-amino-1-butanol is mainly achieved by chemical methods. Early production of (R)-3-amino-1-butanol was carried out by reaction between (R)-(+)-1-phenylethylamine and crotonates, generating a set of epimers with two chiral centers. After separation by silica gel column chromatography, a single isomer was obtained, which was further reduced and debenzylated to give (R)-3-amino-1-butanol. However, this route suffered from low yield and purity of product, requirement of substantial quantities of organic eluents, and use of expensive reducing agent LiAlH4, leading to problems of poor processing economics and environmental unfriendliness. The biosynthesis of (R)-3-amino-1-butanol by transferring the amino group from isopropylamine to 4-hydroxy-2-butanone. After optimization of the reaction condition, (R)-3-amino-1-butanol with a maximum yield of 29.6 g/L and 99.9% e.e. value was obtained.

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