5344-90-1

Basic information

• Product Name: 2-Aminobenzylalcohol
• Synonyms: o-amino-benzylalcoho;o-Aminobenzylic alcohol;o-aminobenzylicalcohol;2-Aminobenzylalcohol(o-Aminobenzylalcohol);oABAIc;2-AMINOBENZYL ALCOHOL 98%;O-ACETAMINOPHENOL;2-Aminobenzene-1-methanol
• CAS NO: 5344-90-1
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• EINECS: 226-293-7
• Product Categories: Benzhydrols, Benzyl & Special Alcohols
• Mol File: 5344-90-1.mol
• Article Data: 140

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 162 °C15 mm Hg(lit.)
• Flash Point: 160°C/10mm
• Appearance: Beige to gray-brown/Crystalline Powder
• Density: 1.0877 (rough estimate)
• Vapor Pressure: 0.00253mmHg at 25°C
• Refractive Index: 1.4905
• Storage Temp.: 2-8°C
• PKA: 14.21±0.10(Predicted)
• Water Solubility: Very soluble in water.
• BRN: 1072211
• CAS DataBase Reference: 2-Aminobenzylalcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminobenzylalcohol(5344-90-1)
• EPA Substance Registry System: 2-Aminobenzylalcohol(5344-90-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DN3155000
• F: 8-10-23
• TSCA: Yes
• Hazardous Substances Data: 5344-90-1(Hazardous Substances Data)

Usage

Uses

2-Aminobenzyl alcohol was used in the synthesis of ethyl 2-hydroxymethylcarbanilate.

General Description

2-Aminobenzyl alcohol is oxidatively cyclised with an array of ketones in dioxane at 80°C in the presence of a ruthenium catalyst and KOH to give corresponding quinolines. It undergoes oxidation catalyzed by heterotrimetallic RuMnMn species on the hydrotalcite surface in the presence of O2 to yield 2-aminobenzaldehyde.

InChI:InChI=1/C7H9NO/c8-7-4-2-1-3-6(7)5-9/h1-4,9H,5,8H2

Synthetic route

2-Nitrobenzyl alcohol (612-25-9) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With hydrogen; palladium In methanol at 25℃; under 2327.2 Torr; for 4.5h;	100%
With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 24h; Autoclave;	99%
With sodium tetrahydroborate In water at 20℃; for 0.416667h; Green chemistry;	99%

anthranilic acid (118-92-3) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
Stage #1: anthranilic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: With water; sodium hydroxide In tetrahydrofuran	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;	94%

2-nitro-benzaldehyde (552-89-6) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With sodium tetrahydroborate In water at 50℃; Green chemistry;	100%
With sodium tetrahydroborate; copper In water at 80℃; for 0.0833333h; Green chemistry;	97%
With sodium tetrahydroborate In tetrahydrofuran; water at 26℃; for 0.0833333h;	96%

N-acetyl-O-acetyl-2-aminobenzyl alcohol (83326-80-1) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With methanol; potassium permanganate; trimethylsulphonium iodide at 25℃; under 760.051 Torr; chemoselective reaction;	96%

o-acetylamino-benzoic acid (89-52-1) → 2-Aminobenzyl alcohol (5344-90-1) + 2-acetamidobenzyl alcohol (20939-77-9)

Conditions	Yield
With hydrogenchloride; ytterbium In methanol for 0.166667h; Ambient temperature;	A 92% B 3%
With hydrogenchloride; samarium In methanol for 0.166667h; Ambient temperature;	A 87% B 8%
With potassium hydroxide; samarium diiodide In tetrahydrofuran; water for 0.0455556h; Ambient temperature;	A 55% B 4%

2-aminobenzyl methoxymethyl ether (263392-95-6) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
Stage #1: 2-aminobenzyl methoxymethyl ether With bromocatecholborane In dichloromethane at -78℃; demethoxymethylation; Stage #2: With acetic acid In dichloromethane at -78 - 20℃; Ring cleavage;	92%

2-(picolinamido)benzyl acetate → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; methanol; water at 50℃; for 24h;	85%
With ethanol; sodium hydroxide at 70℃;	85%

anthranilic acid nitrile (1885-29-6) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃;	83%

5-bromo-2-aminobenzoic acid methyl ester (52727-57-8) → 2-Aminobenzyl alcohol (5344-90-1) + (2-amino-5-bromophenyl)methanol (20712-12-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 25℃;	A n/a B 81%
With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 5h;	A n/a B 81%

2-carbomethoxyaniline (134-20-3) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran for 2h; Heating;	79%
With lithium aluminium tetrahydride In diethyl ether

3H-benzo[c][1,2]oxaborol-1-ol (5735-41-1) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;	74%

2-aminobenzyl methoxymethyl ether (263392-95-6) → 2-Aminobenzyl alcohol (5344-90-1) + 1,2-dihydro-4H-3,1-benzoxazine (59689-21-3)

Conditions	Yield
With bromocatecholborane In dichloromethane at -78 - 0℃; Cyclization; demethoxymethylation;	A 71% B 28%

2-iodobenzyl alcohol (5159-41-1) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With copper(I) oxide; sodium azide; L-proline In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere;	71%
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube;	47%

anthranil (271-58-9) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With potassium hydroxide; aluminum nickel In methanol for 0.7h;	65%

ortho-nitrobenzoic acid (552-16-9) → 2-Aminobenzyl alcohol (5344-90-1) + anthranilic acid (118-92-3)

Conditions	Yield
With hydrogenchloride; samarium In methanol for 0.166667h; Ambient temperature;	A 59% B 20%
With hydrogenchloride; ytterbium In methanol for 0.166667h; Ambient temperature;	A 27% B 48%

2-nitro-benzaldehyde (552-89-6) → 2-Aminobenzyl alcohol (5344-90-1) + anthranilic acid (118-92-3)

Conditions	Yield
With graphitic carbon nitride; hydrazine hydrate In water at 90℃; for 4h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;	A 56% B 44%

carbon monoxide (201230-82-2) + 2-Nitrobenzyl alcohol (612-25-9) → 2-Aminobenzyl alcohol (5344-90-1) + 1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one (13213-88-2) + 2-aminobenzaldehyde (529-23-7)

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; tetraethylammonium chloride In various solvent(s) at 170℃; under 45600 Torr; for 1h; Product distribution; other Pd catalyst; other cocatalyst; var. solvents, reaction time, pressure and temperatures; also substituted benzyl alcohols;	A 22% B 51% C 17%

2-[(1H-benzimidazol-2-ylsulfinyl)methyl]benzenamine (104340-34-3) → 2-Aminobenzyl alcohol (5344-90-1) + Benzimidazol-2-thiol (134469-07-1)

Conditions	Yield
With hydrogenchloride In water for 3h; Product distribution; Ambient temperature; other temp. and time; thiols added;	A 20.9% B 50.6%

o-acetylamino-benzoic acid (89-52-1) → 2-Aminobenzyl alcohol (5344-90-1) + 2-acetamidobenzyl alcohol (20939-77-9) + anthranilic acid (118-92-3)

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran for 0.0333333h; Ambient temperature;	A 9% B 28% C 37%

1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one (13213-88-2) + furan-2,3,5(4H)-trione pyridine (1:1) → 2-Aminobenzyl alcohol (5344-90-1)

2-Nitrobenzyl alcohol (612-25-9) + sodium ethanolate (141-52-6) → 2-Aminobenzyl alcohol (5344-90-1) + anthranil (271-58-9) + anthranilic acid (118-92-3) + 2-aminobenzaldehyde (529-23-7)

2-aminobenzaldehyde (529-23-7) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With nickel; decalin at 115 - 120℃; Hydrogenation;
With sodium tetrahydroborate In methanol at 0 - 20℃; for 0.5h;
Multi-step reaction with 2 steps 1: C84H108Cl2N10Pd2 / neat (no solvent) / 12 h / 60 °C / Glovebox 2: silica gel; methanol / 6 h / 60 °C View Scheme
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 25℃;

2-<2-(bromomethyl)phenyl>-1H-isoindole-1,3(2H)-dione (57365-06-7) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water for 6h; Heating;	30 mg

(E)-3-Hydroxy-3-(2-hydroxymethyl-phenylamino)-propen-1-ol anion → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With water In ethanol at 25℃; Rate constant; Mechanism;
With water; hydroxide In ethanol at 25℃; Rate constant;

4-methoxy-3-(o-nitrobenzyloxy)phenylacetic acid (129249-75-8) → 2-Aminobenzyl alcohol (5344-90-1) + homoisovanillic acid (1131-94-8)

Conditions	Yield
With hydrogenchloride; zinc In water; acetic acid at 5℃; for 5h;	A n/a B 0.23 g

2-nitro-benzaldehyde (552-89-6) → 2-Aminobenzyl alcohol (5344-90-1) + (2-(hydroxyamino)phenyl)methanol (41882-63-7) + 2-aminobenzaldehyde (529-23-7)

Conditions	Yield
In ethanol; water at 25℃; Rate constant; Mechanism; Product distribution; polarographic reduction; potential dependent rate constants kf,h, αna; pH = 1.81-11.00;

[2-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-carbamic acid tert-butyl ester → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With hydrogenchloride In ethyl acetate for 48h; Ambient temperature;	100 % Chromat.

ortho-nitrobenzoic acid (552-16-9) → 2-Aminobenzyl alcohol (5344-90-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating; Yield given;

cycloAmb-d4T-phosphormidate → 2-Aminobenzyl alcohol (5344-90-1) + 3'-deoxy-2',3'-didehydro-5'-O-dihydroxyphosphoryl thymidine (27646-59-9)

Conditions	Yield
With phosphate buffer at 37℃; pH=7.3; Kinetics; Hydrolysis;

2-Aminobenzyl alcohol (5344-90-1) + chloroacetyl chloride (79-04-9) → [2-(2-chloro-acetylamino)-phenyl]-methanol (189940-09-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%
With diethyl ether; benzene
With triethylamine In tetrahydrofuran	75.9 g (93%)
With triethylamine In tetrahydrofuran	75.9 g (93%)
With triethylamine In tetrahydrofuran	75.9 g (93%)

pyridine-4-carbaldehyde (872-85-5) + 2-Aminobenzyl alcohol (5344-90-1) → 2-Pyridin-4-yl-1,4-dihydro-2H-benzo[d][1,3]oxazine (134778-10-2)

Conditions	Yield
In ethanol for 2h; Ambient temperature;	100%

3-pyridinecarboxaldehyde (500-22-1) + 2-Aminobenzyl alcohol (5344-90-1) → 2-Pyridin-3-yl-1,4-dihydro-2H-benzo[d][1,3]oxazine (134778-04-4)

Conditions	Yield
In ethanol for 2h; Ambient temperature;	100%

2-Aminobenzyl alcohol (5344-90-1) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → N-(2-hydroxymethylphenyl)-4-methoxybenzenesulfonamide (601481-95-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	100%
With pyridine In dichloromethane at 20℃;
With pyridine In dichloromethane Reflux;
With pyridine In dichloromethane at 0 - 20℃; for 2h;
With pyridine In dichloromethane at 20℃; for 4h;

2-Aminobenzyl alcohol (5344-90-1) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → N-[2-(hydroxymethyl)phenyl]-4-nitrobenzene-1-sulfonamide (90312-01-9)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	100%
With pyridine In chloroform at 20℃; Inert atmosphere;	82%
With pyridine In dichloromethane for 1.5h;	70%

2-Aminobenzyl alcohol (5344-90-1) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C15H21BNO(1-)*H(1+)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃;	100%

furfural (98-01-1) + 2-Aminobenzyl alcohol (5344-90-1) → 2-(furan-2-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine (90284-37-0)

Conditions	Yield
In benzene Reflux; Dean-Stark;	100%
With magnesium sulfate In tetrahydrofuran at 50℃; for 10h;	48%
In methanol at 20℃; for 5h;
In acetonitrile at 80℃; for 2h;

2-Aminobenzyl alcohol (5344-90-1) + benzylamine (100-46-9) → 2-amino-N-benzylbenzamide (5471-20-5)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃;	100%
With iodine In ethanol Reflux;
In water at 40℃;

2-Aminobenzyl alcohol (5344-90-1) → 2-azidobenzyl alcohol (20615-76-3)

Conditions	Yield
Stage #1: 2-Aminobenzyl alcohol With hydrogenchloride; sodium nitrite In water at -5 - -3℃; for 0.0833333h; Stage #2: With sodium azide; sodium acetate In water at 0℃; for 2h; Further stages.;	99%
Stage #1: 2-Aminobenzyl alcohol With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 0.5h;	93%
Stage #1: 2-Aminobenzyl alcohol With hydrogenchloride In water at 0℃; Stage #2: With sodium nitrite In water for 0.166667h; Further stages;	73%

2-Aminobenzyl alcohol (5344-90-1) + 3-nitro-benzaldehyde (99-61-6) → 2-(3'-nitrophenyl)-1,2-dihydro-4H-3,1-benzoxazine (122483-63-0)

Conditions	Yield
With acetic acid at 20℃;	99%
In ethanol for 2h; Ambient temperature;	98%
at 110℃; for 0.166667h;	36%

2-Aminobenzyl alcohol (5344-90-1) + 4-nitrobenzaldehdye (555-16-8) → 2-(4'-nitrophenyl)-1,2-dihydro-4H-3,1-benzoxazine (82085-89-0)

Conditions	Yield
With acetic acid at 20℃;	99%
In ethanol for 2h; Ambient temperature;	98%
fusion of reagents mixture;

2-Aminobenzyl alcohol (5344-90-1) + acetophenone (98-86-2) → 2-Phenylquinoline (612-96-4)

Conditions	Yield
With benzophenone; potassium tert-butylate In 1,4-dioxane at 90℃; for 0.5h; Friedlaender synthesis; Inert atmosphere;	99%
With potassium hydroxide; Grubbs catalyst first generation In 1,4-dioxane at 80℃; for 1h;	97%
With potassium tert-butylate; Zn(2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline)Cl2; zinc In toluene at 90℃; for 10h; Reagent/catalyst;	97%

2-Aminobenzyl alcohol (5344-90-1) + para-methylacetophenone (122-00-9) → 2-(4-methylphenyl)quinoline (24667-94-5)

Conditions	Yield
With benzophenone; potassium tert-butylate In 1,4-dioxane at 90℃; for 0.5h; Friedlaender synthesis; Inert atmosphere;	99%
With potassium hydroxide; benzophenone; [Ru(DMSO)4]Cl2 In 1,4-dioxane at 80℃;	96%
With potassium hydroxide; benzophenone; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) In 1,4-dioxane at 80℃; for 24h;	96%

2-Aminobenzyl alcohol (5344-90-1) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 1,2-dihydrobenzo[c]acridine (16600-51-4)

Conditions	Yield
With benzophenone; potassium tert-butylate In 1,4-dioxane at 90℃; for 0.5h; Friedlaender synthesis; Inert atmosphere;	99%
With potassium hydroxide; benzophenone; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) In 1,4-dioxane at 80℃; for 24h;	98%
With lithium tert-butoxide In toluene at 110℃; for 12h; Inert atmosphere;	94%

2-Aminobenzyl alcohol (5344-90-1) + methyl 2-naphthyl ketone (93-08-3) → 2-naphthalen-2-yl-quinoline (47077-29-2)

Conditions	Yield
With potassium hydroxide; Grubbs catalyst first generation In 1,4-dioxane at 80℃; for 1h;	99%
With lithium tert-butoxide In toluene at 110℃; for 12h; Inert atmosphere;	93%
With dichloro[1,3‐diethyl(5,6‐dimethyl)benzimidazolin‐2‐ylidene](benzene)ruthenium (II); sodium hydroxide In toluene at 105℃; for 8h;	90%

2-Aminobenzyl alcohol (5344-90-1) + pentan-3-one (96-22-0) → 2-ethyl-3-methylquinoline (27356-52-1)

Conditions	Yield
With benzophenone; potassium tert-butylate In 1,4-dioxane at 90℃; for 0.5h; Friedlaender synthesis; Inert atmosphere;	99%
With potassium hydroxide; benzophenone; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) In 1,4-dioxane at 80℃; for 24h;	96%
Stage #1: 2-Aminobenzyl alcohol; pentan-3-one With potassium hydroxide; copper dichloride In 1,4-dioxane at 20℃; Stage #2: With oxygen In 1,4-dioxane Reflux;	75%

2-Aminobenzyl alcohol (5344-90-1) + 2-Methoxyacetophenone (579-74-8) → 2-(2-methoxyphenyl)quinoline (72195-25-6)

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 1h;	99%
With potassium hydroxide; palladium diacetate In toluene at 100℃; for 20h;	87%
With caesium carbonate In toluene at 120℃; for 10h; Schlenk technique; Inert atmosphere;	85%

2-Aminobenzyl alcohol (5344-90-1) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → 1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one (13213-88-2)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	99%

Upstream product

• 13213-88-2 1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one 
• 612-25-9 2-Nitrobenzyl alcohol 
• 141-52-6 sodium ethanolate 
• 552-89-6 2-nitro-benzaldehyde 
• 7664-93-9 sulfuric acid 
• 118-92-3 anthranilic acid 
• 529-23-7 o-aminobenzaldehyde 
• 91-17-8 decalin 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 57365-06-7 2-<2-(bromomethyl)phenyl>-1H-isoindole-1,3(2H)-dione 
• 83326-80-1 N-acetyl-O-acetyl-2-aminobenzyl alcohol 
• 1885-29-6 anthranilic acid nitrile 
• 18982-54-2 o-bromobenzyl alcohol 

Downstream Products

• 82085-87-8 2-(4'-methoxyphenyl)-1,2-dihydro-4H-3,1-benzoxazine 
• 62460-63-3 2-(4-methoxy-phenyl)-4H-benzo[d][1,3]oxazine 
• 225-11-6 benz[a]acridine 
• 85796-90-3 3-<(2-Hydroxymethyl)anilino>-2-cyclohexen-1-on 
• 115975-86-5 3-(2-hydroxymethylanilino)-3-phenylprop-2-enenitrile 
• 85796-89-0 3-<(2-Hydroxymethyl)anilino>-5,5-dimethyl-2-cyclohexen-1-on 
• 127558-16-1 (Z)-3-(2-Hydroxymethyl-phenylamino)-propenal 
• 127558-22-9 (E)-3-(2-Hydroxymethyl-phenylamino)-propenal 
• 68847-33-6 2-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]phenylamine 
• 95-53-4 o-toluidine 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 170699-86-2 C₂₀H₂₃N₃O₄ 
• 164226-32-8 2-(tert-butyloxycarbonyl)aminobenzyl alcohol 

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