ChemicalBook > CAS DataBase List > (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL

(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL

Product Name
(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL
CAS No.
58577-87-0
Chemical Name
(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL
Synonyms
SERINOL(BZL);H-SER(BZL)-OL;H-D-SER(BZL)-OL;Ser(bzl)-OL.HCL;Serinol(Bzl)·HCl;H-Ser(Bzl)-ol.HCl;O-BENZYL-L-SERINOL;O-BENZYL-D-SERINOL;H-L-Ser(Bzl)-ol·HCl;L-Serinol(Bzl) hydrochloride
CBNumber
CB5115532
Molecular Formula
C10H15NO2
Formula Weight
181.23
MOL File
58577-87-0.mol
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(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL Property

Melting point:
34-37 °C (lit.)
Boiling point:
307 °C (lit.)
Density 
1.0918 (rough estimate)
refractive index 
1.5464 (estimate)
Flash point:
>230 °F
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
form 
Oil
pka
12.53±0.10(Predicted)
color 
Clear Colourless
optical activity
[α]20/D +4°, c = 1 in methylene chloride
Sensitive 
Air Sensitive
InChI
InChI=1S/C10H15NO2/c11-10(6-12)8-13-7-9-4-2-1-3-5-9/h1-5,10,12H,6-8,11H2/t10-/m1/s1
InChIKey
ZJUOMDNENVWMPL-SNVBAGLBSA-N
SMILES
C(O)[C@@H](N)COCC1=CC=CC=C1
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Safety

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
26-27-36/37/39-45
RIDADR 
3267
WGK Germany 
3
HazardClass 
8
HS Code 
29221990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
473758
Product name
(R)-(+)-2-Amino-3-benzyloxy-1-propanol
Purity
97%
Packaging
1g
Price
$105
Updated
2023/06/20
TRC
Product number
A600205
Product name
(R)-(+)-2-Amino-3-benzyloxy-1-propanol
Packaging
1g
Price
$95
Updated
2021/12/16
Apolloscientific
Product number
OR40517
Product name
(2R)-(+)-2-Amino-3-(benzyloxy)propan-1-ol
Packaging
5g
Price
$428
Updated
2021/12/16
Chem-Impex
Product number
03219
Product name
O-Benzyl-L-serinolhydrochloride,98%(HPLC)
Purity
98%(HPLC)
Packaging
5G
Price
$168
Updated
2021/12/16
Chem-Impex
Product number
03219
Product name
O-Benzyl-L-serinolhydrochloride,≥98%(HPLC)
Purity
≥98%(HPLC)
Packaging
250MG
Price
$36.22
Updated
2021/12/16
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(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL Chemical Properties,Usage,Production

Chemical Properties

Colorless to yellow liquid or low melting solid

Uses

(R)-(+)-2-Amino-3-benzyloxy-1-propanol is used as a reagent to synthesize beta-amino alcohols, compounds that are used as therapeutic agents to treat heart disease. (R)-(+)-2-Amino-3-benzyloxy-1-propanol is also used as a reagent to synthesize 15-membered macrolide antibiotics, drugs that are used to treat respiratory tract infections.

Synthesis

4726-96-9

58577-87-0

General procedure for the synthesis of O-benzyl-L-serinol from (S)-2-amino-3-(benzyloxy)propionic acid: O-benzyl-L-serine (15.0 g, 76.8 mmol) was slowly added to a tetrahydrofuran (THF, 150 mL) suspension of lithium aluminum hydride (4.37 g, 115.3 mmol) under reflux conditions. The reaction mixture was stirred at reflux temperature for 1.5 h. After cooling in an ice bath, distilled water (4.4 mL), 10% NaOH aqueous solution (4.4 mL), and distilled water (4.4 mL) were added sequentially. After stirring for 18 h at room temperature, the mixture was filtered and the filter cake was washed with THF. The filtrate was concentrated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent ratio CHCl3/MeOH/NH4OH = 10:1:0.1) to afford the target product, O-benzyl-L-serinol (6.43 g, 69% yield), as a colorless foamy substance. Its physical properties were as follows: [α]27D -5.0 (c 0.760, methanol); 1H NMR (CDCl3) δ 7.27-7.41 (m, 5H), 4.53 (s, 2H), 3.39-3.67 (m, 4H), 3.03-3.17 (m, 1H), 1.85 (br s, 3H); 13C NMR (CDCl3) δ 137.9, 128.2, 127.55, 127.50, 73.1, 72.5, 63.7, 52.3; MS (ESI) m/z 182.2 [M + H]+. The NMR data are in agreement with literature reports.

References

[1] Liebigs Annalen der Chemie, 1988, p. 851 - 854
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5787 - 5801
[3] Tetrahedron, 2002, vol. 58, # 46, p. 9387 - 9401
[4] Tetrahedron, 1975, vol. 31, p. 2629 - 2632
[5] Molecules, 2009, vol. 14, # 12, p. 5124 - 5143

(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL Preparation Products And Raw materials

Raw materials

Preparation Products

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(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL Suppliers

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View Lastest Price from (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL 58577-87-0
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1000kg
Release date
2025-09-28
Sichuan HongRi Pharma-Tech Co.,Ltd
Product
H-L-Ser(Bzl)-OL.HCl 58577-87-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1T+
Release date
2024-01-19
Sichuan Jiaying Lai Technology Co.,LTD
Product
H-Ser(Bzl)-Ol.HCl 58577-87-0
Price
US $1.00/g
Min. Order
1g
Purity
98%
Supply Ability
100KG
Release date
2019-07-25

58577-87-0, (R)-2-AMINO-3-BENZYLOXY-1-PROPANOLRelated Search:

BENZYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE 3-FLUORO-5-(TRIFLUOROMETHYL)PHENOL O-BENZYL-L-SERINE Boc-Thr(Bzl)-OH Z-SER(BZL)-OH FMOC-SER(BZL)-OH N-Boc-(S)-2-amino-3-benzyloxy-1-propanol 3-Benzyloxy-1-propanol Benzyl 2-AcetaMido-2-deoxy-3-O-(β-D-galactopyranosyl) α-D-galactopyranoside L-THREONINE BENZYL ESTER BOC-SER(P-CHLORO-BZL)-OH DCHA BENZYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE BENZYL 2-ACETAMIDO-2-DEOXY-3,6-DI-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE BOC-THR(BZL)-ONP AC-ALPHA-BENZYL-4,6-O-BENZYLIDENE-MURAMIC ACID BENZYL-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE BOC-SER(BZL)-OSU BOC-THR(P-CHLORO-BZL)-OH DCHA

  • O-BENZYL-D-SERINOL
  • O-BENZYL-L-SERINOL
  • SERINOL(BZL)
  • (R)-(+)-2-AMINO-3-BENZYLOXY-1-PROPANOL
  • (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL
  • H-D-SER(BZL)-OL
  • H-SER(BZL)-OL
  • Serinol(Bzl)·HCl
  • (R)-(+)-2-Amino-3-benzyloxy-1-propanol,97%
  • (R)-(+)-2-AMino-3-benzyloxy-1-propanol, 98+%
  • (R)-2-Amino-3-(benzyloxy)propan-1-ol
  • H-Ser(Bzl)-ol.HCl
  • H-L-Ser(Bzl)-ol·HCl
  • L-Serinol(Bzl) hydrochloride
  • O-Benzyl-L-serinol hydrochloride≥ 98% (HPLC)
  • (2R)-(+)-2-Amino-3-(benzyloxy)propan-1-ol
  • 1-Propanol, 2-amino-3-(phenylmethoxy)-, (2R)-
  • (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL USP/EP/BP
  • (2R)-2-amino-3-phenylmethoxypropan-1-ol
  • (<i>R</i>)-(+)-2-Amino-3-benzyloxy-1-propanol
  • Ser(bzl)-OL.HCL
  • 58577-87-0
  • C6H5CH2OCH2CHNH2CH2OH
  • Amino Alcohols
  • Chiral Building Blocks
  • Asymmetric Synthesis
  • Organic Building Blocks
  • Amino Alcohols
  • Chiral Building Blocks
  • Organic Building Blocks