(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
(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
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
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.
N-Bromosuccinimide Price
- Product number
- 473758
- Product name
- (R)-(+)-2-Amino-3-benzyloxy-1-propanol
- Purity
- 97%
- Packaging
- 1g
- Price
- $105
- Updated
- 2023/06/20
- Product number
- A600205
- Product name
- (R)-(+)-2-Amino-3-benzyloxy-1-propanol
- Packaging
- 1g
- Price
- $95
- Updated
- 2021/12/16
- Product number
- 03219
- Product name
- O-Benzyl-L-serinolhydrochloride,≥98%(HPLC)
- Purity
- ≥98%(HPLC)
- Packaging
- 250MG
- Price
- $36.22
- Updated
- 2021/12/16
- Product number
- 03219
- Product name
- O-Benzyl-L-serinolhydrochloride,98%(HPLC)
- Purity
- 98%(HPLC)
- Packaging
- 1G
- Price
- $44.8
- Updated
- 2021/12/16
- Product number
- 03219
- Product name
- O-Benzyl-L-serinolhydrochloride,98%(HPLC)
- Purity
- 98%(HPLC)
- Packaging
- 5G
- Price
- $168
- Updated
- 2021/12/16
(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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View Lastest Price from (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL manufacturers
- 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
- 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
- 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