6940-80-3

Basic information

• Product Name: N-BENZYL-L-ALANINOL
• Synonyms: N-BENZYL-L-ALANINOL;(S)-2-(benzylaMino)propan-1-ol;(2S)-2-(benzylaMino)propan-1-ol;N-Bn-Ala-OL;(S)-2-[(Phenylmethyl)amino]-1-propanol
• CAS NO: 6940-80-3
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• Mol File: 6940-80-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 47-49 °C(Solv: cyclohexane (110-82-7); ligroine (8032-32-4))
• Boiling Point: 292.2 °C at 760 mmHg
• Flash Point: 120 °C
• Appearance: /
• Density: 1.02 g/cm³
• Vapor Pressure: 0.000848mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform; Methanol
• PKA: 14.59±0.10(Predicted)
• CAS DataBase Reference: N-BENZYL-L-ALANINOL(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-L-ALANINOL(6940-80-3)
• EPA Substance Registry System: N-BENZYL-L-ALANINOL(6940-80-3)

Safety Data

• Hazardous Substances Data: 6940-80-3(Hazardous Substances Data)

Usage

General Description

N-Benzyl-L-alaninol, also known as N-Benzylalaninol, is a chemical compound belonging to the class of alcohols. It is a chiral compound, meaning it has a non-superimposable mirror image, and is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. N-Benzyl-L-alaninol is often utilized in organic chemistry reactions as a chiral auxiliary for asymmetric synthesis, as well as a building block for the formation of various functionalized molecules. It has been studied for its potential use in medicinal chemistry and drug development, and is also used in the production of flavors and fragrances.

InChI:InChI=1/C10H15NO/c1-9(8-12)11-7-10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3/t9-/m0/s1

Synthetic route

N-benzoyl-L-alanine methyl ester (7244-67-9) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;	87%
With lithium aluminium tetrahydride In tetrahydrofuran for 3.5h; Reduction; Heating;
With lithium aluminium tetrahydride In tetrahydrofuran

(S)-Alaninol (2749-11-3) + benzaldehyde (100-52-7) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Stage #1: (S)-Alaninol; benzaldehyde In ethanol for 6h; Reflux; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 4h; Cooling with ice;	86%
With sodium tetrahydroborate In methanol at 0℃; for 1h;	84%
With sodium cyanoborohydride; acetic acid In methanol Ambient temperature;	75.3%

N-benzylalanine (7585-47-9, 40297-69-6, 65491-01-2) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Heating;	77%

N-benzoyl-L-alanine (2198-64-3) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With sodium hydroxide; sodium tetrahydroborate; sulfuric acid 1.) THF, ether, room temp., overnight 2.) reflux, 3 h; Yield given. Multistep reaction;
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating;
With lithium aluminium tetrahydride In tetrahydrofuran Heating;

(RS)-2-benzylaminopropanol (3217-09-2) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With L-Tartaric acid

N-benzyl-(S)-alanine (7585-47-9, 40297-69-6, 65491-01-2) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran for 24h;

L-alanin (56-41-7) + benzaldehyde (100-52-7) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multistep reaction;

(S)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-propan-1-ol (65943-49-9, 86941-35-7, 86941-38-0, 40916-81-2) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 2h;
With sodium tetrahydroborate In ethanol
With sodium tetrahydroborate In ethanol at 20℃; for 2h;
With sodium tetrahydroborate
With sodium tetrahydroborate In ethanol at 0℃;

bis(tetraethylammonium) carbonate + (S)-3-benzyl-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide (458560-71-9) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Stage #1: bis(tetraethylammonium) carbonate; (S)-3-benzyl-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide In acetonitrile Stage #2: With sulfuric acid	73 mg

benzaldehyde (100-52-7) + (E)-n-C6H13CH=CHZrCp2Cl → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C 2: sodium borohydride / ethanol / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 4 Angstroem molecular sieves 2: NaBH4 View Scheme

benzoyl chloride (98-88-4) + 6-t-butyl-12-p-tolyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / 1 h / 20 °C 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

benzoyl chloride (98-88-4) + tetrabutyl ammonium [Zn(2-thione-1,3-dithiole-4,5-dithiolate)2] → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / aq. K2CO3 / CHCl3 / 3 h / Heating 2: 87 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

benzaldehyde (100-52-7) + methylacetylene metal salt → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4 Angstroem molecular sieves / CH2Cl2 2: NaBH4 / ethanol View Scheme

benzaldehyde (100-52-7) + (C5H5)2(Cl)Zr{trans-CH=CH[CH2]4OSi(CH3)2(t-Bu)} → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / 4 h / Heating 2: NaBH4 / methanol / 2 h / 0 °C View Scheme

benzoyl chloride (98-88-4) + 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol bound on Rink resin → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / H2O; CHCl3 / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 3.5 h / Heating View Scheme

N-benzyl-L-alanine methyl ester (31022-10-3) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
With lithium aluminium tetrahydride In dichloromethane

benzaldehyde (100-52-7) → (S)-N-benzylalaninol (6940-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Reflux 2: sodium tetrahydroborate / ethanol / 0 °C View Scheme

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-N-benzylalaninol (6940-80-3) → (S)-[N-benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid (873197-15-0)

Conditions	Yield
With potassium carbonate In water; toluene at 20 - 65℃; for 21h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	89%
With potassium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 12h;	76%

(S)-N-benzylalaninol (6940-80-3) → (2S)-Benzyl-(1-hydroxy-2-propyl)aminoacetonitrile

Conditions	Yield
With formaldehyd; sodium hydrogensulfite In water	99%

(S)-N-benzylalaninol (6940-80-3) + methyl vinyl ketone (78-94-4) → (S)-(+)-5-benzyl-7-hydroxy-6-methyl-5-azaheptanone-2 (167905-80-8)

Conditions	Yield
In chloroform for 24h; Ambient temperature;	98%

(S)-N-benzylalaninol (6940-80-3) + acetic anhydride (108-24-7) → C12H17NO2 (1013663-94-9)

Conditions	Yield
With silica-supported phosphomolybdic acid at 20℃; for 0.166667h;	97%

(S)-N-benzylalaninol (6940-80-3) + chloroacetyl chloride (79-04-9) → N-Benzyl-2-chloro-N-((S)-2-hydroxy-1-methyl-ethyl)-acetamide (118948-07-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	95%

1,3,5-Trioxan (110-88-3) + (S)-N-benzylalaninol (6940-80-3) + phenylacetylene (536-74-3) → (S)-2-[benzyl(3-phenylprop-2-yn-1-yl)amino]propan-1-ol

Conditions	Yield
With copper(l) chloride In toluene at 100℃; for 0.666667h; Microwave irradiation; Inert atmosphere;	93%

(S)-N-benzylalaninol (6940-80-3) + 3-Chloro-2-methylpropene (563-47-3) → (S)-(+)-3-benzyl-2,5-dimethyl-3-aza-5-hexen-1-ol

Conditions	Yield
With potassium carbonate In water at 62℃; for 24h;	92%

(R)-(-)-epichlorohydrin (51594-55-9) + (S)-N-benzylalaninol (6940-80-3) → ((2S,5S)-4-benzyl-5-methylmorpholin-2-yl)methanol

Conditions	Yield
Stage #1: (R)-(-)-epichlorohydrin; (S)-N-benzylalaninol With lithium perchlorate In toluene at 20℃; for 16h; Stage #2: With methanol; sodium hydroxide In toluene at 20℃; for 36h;	92%

(S)-N-benzylalaninol (6940-80-3) + 1,3-dichloro-2-(phenylsulfonyl)propane (90838-45-2) → (S)-2-[(2-Benzenesulfonyl-allyl)-benzyl-amino]-propan-1-ol (214911-98-5)

Conditions	Yield
With triethylamine In tetrahydrofuran	89%

(4S,5R)-4-trityloxymethyl-3-oxa-1-azabicyclo[3.1.0]hexan-2-one + (S)-N-benzylalaninol (6940-80-3) → (4R,5S)4-((benzyl((S)-1-hydroxypropan-2-yl)amino)methyl)-5-(trityloxymethyl)oxaazolidin-2-one

Conditions	Yield
In dichloromethane at 20℃; for 24h; Inert atmosphere;	89%

(S)-N-benzylalaninol (6940-80-3) → (R)-1-<(Phenylmethyl)amino>-2-propanol (162240-94-0)

Conditions	Yield
Stage #1: (S)-N-benzylalaninol With triethylamine; trifluoroacetic anhydride In tetrahydrofuran at 120℃; for 12h; Sealed tube; Inert atmosphere; Microwave irradiation; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere; stereospecific reaction;	88%

3-bromo-1,1-diphenyl-1-propene (4801-15-4) + (S)-N-benzylalaninol (6940-80-3) → (S)-(+)-2-[N-Benzyl-N-(3,3-diphenyl-2-propen-1-yl)]amino-1-propanol (221876-44-4)

Conditions	Yield
With potassium carbonate In water at 20℃; for 24h; Alkylation;	87%

(4R,5S)-4-trityloxymethyl-3-oxa-1-azabicyclo[3.1.0]hexan-2-one (1333501-65-7) + (S)-N-benzylalaninol (6940-80-3) → (4S,5R)4-((benzyl((S)-1-hydroxypropan-2-yl)amino)methyl)-5-(trityloxymethyl)oxazolidin-2-one

Conditions	Yield
In dichloromethane at 20℃; for 24h; Inert atmosphere;	85%

(S)-N-benzylalaninol (6940-80-3) + N,N-diethyl-α,α-difluorobenzylamine (90238-20-3) → (S)-N-benzyl-N-(2-fluoro-1-methylethyl)benzamide

Conditions	Yield
at 100℃; for 0.166667h; microwave irradiation;	84%

(S)-N-benzylalaninol (6940-80-3) + Cinnamyl bromide (4392-24-9) → (S)-(+)-2-(N-Benzyl-N-cinnamyl)amino-1-propanol (221876-43-3)

Conditions	Yield
With potassium carbonate In water at 20℃; for 24h; Alkylation;	80%

4-bromo-trans-crotonic acid ethyl ester (37746-78-4) + (S)-N-benzylalaninol (6940-80-3) → ethyl (S)-(+)-5-benzyl-7-hydroxy-6-methyl-5-aza-2-heptenoate

Conditions	Yield
With potassium carbonate In water at 60℃; for 48h;	79%

(S)-N-benzylalaninol (6940-80-3) + (4R,5R)-5-(methoxycarbonyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid (67812-33-3) → N-benzyl-N'-[(1S)-2-hydroxy-1-methylethyl]-(2R,3R)-2,3-di-isopropylidenetartramic acid methyl ester (250137-68-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 25℃; for 12h; Acylation;	76%

(S)-N-benzylalaninol (6940-80-3) + p-toluenesulfonyl chloride (98-59-9) → (S)-N-benzyl-2-(p-tolylsulfonyl-amino)propanol (209266-15-9)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.333333h;	74%

(S)-N-benzylalaninol (6940-80-3) + (+/-)-(R,S)-2,3-di-O-isopropylidenetartaric acid monomethyl ester → N-benzyl-N'-[(1S)-2-hydroxy-1-methylethyl]-(2R,3S)/(2S,3R)-2,3-di-isopropylidenetartramic acid methyl ester (250137-72-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 25℃; for 12h; Acylation;	69%

(S)-N-benzylalaninol (6940-80-3) + cyanomethyl bromide (590-17-0) → (S)-N-benzyl-N-cyanomethyl-2-aminopropan-1-ol (152673-15-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	68%
With potassium carbonate In acetonitrile for 2.5h; Heating;	68%
With potassium carbonate In acetonitrile

3,4-dihydro-2H-pyran (110-87-2) + (S)-N-benzylalaninol (6940-80-3) → C15H23NO2 (1097211-32-9)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 25℃; for 17h;	66%

(S)-N-benzylalaninol (6940-80-3) → N-benzyl-N-(2-chloro-1-methylethyl)amine hydrochloride

Conditions	Yield
With thionyl chloride In chloroform for 2h; Heating;	60%
With thionyl chloride In chloroform for 2h; Chlorination; Heating;

(S)-N-benzylalaninol (6940-80-3) → N-benzyl-2-bromo-1-methylethylammonium bromide

Conditions	Yield
With hydrogen bromide; phosphorus tribromide	60%

(S)-N-benzylalaninol (6940-80-3) + copper(II) acetate monohydrate (6046-93-1) → C24H38Cu2N2O8

Conditions	Yield
In methanol at 80℃; for 4h;	45%

(S)-N-benzylalaninol (6940-80-3) → (S)-3-benzyl-4-methyl-1,2,3-oxathiazolidine-2-oxide (458560-69-5)

Conditions	Yield
With thionyl chloride; triethylamine In dichloromethane at -78 - 20℃;	44%
With pyridine; thionyl chloride In tetrahydrofuran
With 1H-imidazole; thionyl chloride; triethylamine In dichloromethane

(S)-N-benzylalaninol (6940-80-3) + rac-3-bromocyclohexene (1521-51-3) → (2S,3'R/S)-2-[N-benzyl-(cyclohexen-3'-yl)amino]propan-1-ol

Conditions	Yield
In diethyl ether for 48h; Ambient temperature;	26%

Upstream product

• 7585-47-9 N-benzyl-(S)-alanine 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 31022-10-3 N-benzyl-L-alanine methyl ester 
• 7585-47-9 N-benzylalanine 
• 52724-28-4 bis(tetraethylammonium) carbonate 
• 458560-71-9 (S)-3-benzyl-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide 
• 65943-49-9 (S)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-propan-1-ol 
• 7244-67-9 N-benzoyl-L-alanine methyl ester 
• 56-41-7 L-alanin 
• 2749-11-3 (S)-Alaninol 
• 3217-09-2 2-(benzylamino)-1-propanol 
• 2198-64-3 N-benzoyl-L-alanine 

Downstream Products

• 122764-74-3 6-methyl-9,10-didehydro-ergoline-8β-carboxylic acid-[benzyl-((S)-β-hydroxy-isopropyl)-amide] 
• 2749-11-3 (S)-Alaninol 
• 118948-07-5 N-Benzyl-2-chloro-N-((S)-2-hydroxy-1-methyl-ethyl)-acetamide 
• 221876-44-4 (S)-(+)-2-[N-Benzyl-N-(3,3-diphenyl-2-propen-1-yl)]amino-1-propanol 
• 172034-96-7 2-{[Benzyl-((S)-2-hydroxy-1-methyl-ethyl)-amino]-methyl}-acrylic acid ethyl ester 
• 873197-15-0 (S)-[N-benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid 
• 1013663-94-9 C₁₂H₁₇NO₂ 
• 162240-94-0 (R)-1-<(Phenylmethyl)amino>-2-propanol 
• 119128-21-1 (5S)-5-methyl-4-(phenylmethyl)-3-morpholinone 

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