5445-44-3

Basic information

• Product Name: O-BENZYL-DL-SERINE
• Synonyms: (+/-)-2-AMINO-3-BENZYLOXYPROPIONIC ACID;DL-SERINE BENZYL ESTER;H-DL-SER(BZL)-OH;BENZYL-DL-SERINE;O-BENZYL-DL-SERINE;3-benzyloxy-DL-alanine;O-BENZYL-DL-SERINE CRYSTALLINE;(+/-)-2-Amino-3-(benzyloxy)propionicacid~H-DL-Ser(Bzl)-OH
• CAS NO: 5445-44-3
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 226-650-7
• Mol File: 5445-44-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: ~227 °C (dec.)
• Boiling Point: 359℃
• Flash Point: 171℃
• Appearance: /
• Density: 1.217
• Vapor Pressure: 8.83E-06mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.10±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 3204905
• CAS DataBase Reference: O-BENZYL-DL-SERINE(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-DL-SERINE(5445-44-3)
• EPA Substance Registry System: O-BENZYL-DL-SERINE(5445-44-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5445-44-3(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

Uses

O-Benzyl-DL-serine is used as catalytic agent, petrochemical additive.

InChI:InChI=1/C10H13NO3/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

Upstream product

• 100-51-6 benzyl alcohol 
• 86522-27-2 benzyl 3-benzyloxy-2-chloropropanoate 
• 86522-28-3 benzyl 3-benzyloxy-2-chloropropanimidate 
• 119254-72-7 2-Azido-3-benzyloxy-propionic acid-benzyl ester 

Downstream Products

• 20806-39-7 N-(benzyloxycarbonyl)-O-benzylserine 
• 3062-02-0 O-benzyl-N-chloroacetyl-DL-serine 
• 104044-79-3 N-trifluoroacetyl-O-benzylserine 
• 78746-55-1 O-benzyl-DL-serine ethyl ester 
• 302-84-1 serin 
• 22831-98-7 4-benzyloxymethyl-oxazolidine-2,5-dione 
• 113933-16-7 2-bromo-3-(phenylmethoxy)propanoic acid methyl ester 
• 1075237-54-5 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-[1-(2-[7-(methyloxy)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-yl]-1-{[(phenylmethyl)oxy]methyl}ethyl)-4-piperidinyl]carbamate 
• 1075237-51-2 methyl 2-[4-((2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-{[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-3-[(phenylmethyl)oxy]propanoate 
• 1075237-52-3 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-[1-(2-hydroxy-1-{[(phenylmethyl)oxy]methyl}ethyl)-4-piperidinyl]carbamate 
• 1075237-53-4 1,1-dimethylethyl [1-(2-chloro-1-{[(phenylmethyl)oxy]methyl}ethyl)-4-piperidinyl]-(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)carbamate 
• 58178-57-7 O-benzyl-DL-serine ethyl ester; hydrochloride 

Relevant articles and documents

AMINO ACIDS; 13. INVESTIGATIONS ON THE SYNTHESIS OF DL-SERINE FROM α-HALOACRYLIC ACID DERIVATIVES

The alkoxide-catalyzed addition of alcohols 2 to α-chloroacrylonitrile (1) at -35 degC gives rise to 3-alkoxy-2-chloropropanenitriles 3; at 0-5 degC with excess 2 alkyl 3-alkoxy-2-chloropropanimidates 4 are obtained.The yields of 3 or 4 decrease with increasing pKa values of the alcohols 2.In the basecatalyzed addition of phenols 5 to 1, a temperature-dependent addition equilibrium is set up in which the position of equilibrium is shifted in favour of the addition products 6 with increasing pKa values of 5.The 3-alkoxy-2-chloropropanoates 8, which are readily accessible by hydrolysis of 4, react smoothly with sodium azide in the presence of a phase transfer catalyst to furnish the 3-alkoxy-2-azidopropanoates 10.Starting from benzyl 2-azido-3-benzyloxy-propanoate (10b), the specific syntheses of DL-serine (14), DL-serine hydrochloride (14*HCl), DL-serine methyl ester hydrochloride (13a*HCl), O-benzyl-DL-serine (12b), and O-benzyl-DL-serine benzyl ester hydrochloride (11b*HCl) are possible by variation of the hydrogenation conditions.