79-14-1

Basic information

• Product Name: Glycolic acid
• Synonyms: Aceticacid, hydroxy- (9CI);Glycolic acid (7CI,8CI);2-Hydroxyacetic acid;2-Hydroxyethanoic acid;GlyPure;GlyPure 70;GlyPure 99;Glycocide;Hydroxyaceticacid;Hydroxyethanoic acid;NSC 166;a-Hydroxyacetic acid
• CAS NO: 79-14-1
• Molecular Formula: C₂H₄O₃
• Molecular Weight: 76.05136
• EINECS: 201-180-5
• Mol File: 79-14-1.mol
• Article Data: 660

Chemical Properties

• Melting Point: 10℃
• Boiling Point: 265.6 °C at 760 mmHg
• Flash Point: 128.7 °C
• Appearance: Light yellow to amber liquid
• Density: 1.416 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Water Solubility: SOLUBLE
• CAS DataBase Reference: Glycolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Glycolic acid(79-14-1)
• EPA Substance Registry System: Glycolic acid(79-14-1)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R22:; R34:
• Safety Statements: S26:; S36/37/39:; S45:
• Hazardous Substances Data: 79-14-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)/p-1

Synthetic route

Glycolaldehyde (141-46-8) → glycolic Acid (79-14-1)

Conditions	Yield
With sodium chlorite; dimethyl sulfoxide In aq. phosphate buffer at 0 - 20℃; pH=4;	100%
With 5 % platinum on carbon In water at 80℃; under 7500.75 Torr; for 6h; Temperature; Time; Reagent/catalyst; Autoclave;	78%
With oxygen In water at 180℃; under 3750.38 Torr; for 1h; Autoclave;	50%

N-acetyl-N-nitrosoglycine → glycolic Acid (79-14-1) + acetic acid (64-19-7)

Conditions	Yield
With water at 25℃;	A 100% B 100%
With water-d2 at 25℃; Rate constant; Kinetics; half life; reactions of derivatives under var. conditions;	A 100% B 100%

glycolic acid methyl ester (96-35-5) → glycolic Acid (79-14-1)

Conditions	Yield
With water at 95 - 97℃; under 760.051 Torr; for 2h; Reactive distillation;	100%
With water; Candida rugosa lipase In aq. phosphate buffer at 45℃; for 30h; pH=7.2; Enzymatic reaction;
With water In methanol at 100℃;

formaldehyd (50-00-0) + carbon monoxide (201230-82-2) → glycolic Acid (79-14-1)

Conditions	Yield
With trifluorormethanesulfonic acid; acetic acid at 140℃; under 13689.1 - 52476.2 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Time; Reagent/catalyst; Concentration; Autoclave;	99.9%
With trifluorormethanesulfonic acid; acetic acid at 140℃; under 13689.1 - 52476.2 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Time; Reagent/catalyst; Concentration; Autoclave;	99.9%
With trifluorormethanesulfonic acid; acetic acid at 140℃; under 13689.1 - 52476.2 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Time; Reagent/catalyst; Concentration; Autoclave;	99.9%

ethylene glycol (107-21-1) → glycolic Acid (79-14-1)

Conditions	Yield
Stage #1: ethylene glycol With Rh(OTf)(trop2NH)(PPh3); water; cyclohexanone; sodium hydroxide at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere;	99%
Wird durch verschiedene Essigbakterien;
With ruthenium trichloride; N-Bromosuccinimide; perchloric acid; mercury(II) diacetate; acetic acid In water Thermodynamic data; Mechanism; Kinetics; ΔE(excit.), ΔS(excit.), ΔH(excit.), and ΔF(excit.);

glycolic acid ammonium salt (35249-89-9) → glycolic Acid (79-14-1)

Conditions	Yield
With water	98%
With sulfuric acid In water; 4-methyl-2-pentanone; kerosene at 25 - 75℃; for 0.5 - 1h; pH=2 - 3; Purification / work up;
With sulfuric acid In water; toluene at 25 - 75℃; for 0.5h; pH=2 - 3; Purification / work up;

Glyoxal (131543-46-9) → glycolic Acid (79-14-1)

Conditions	Yield
With aluminum trihydroxide; water at 165℃; for 3h; Mechanism;	92%
With water at 99.84℃; for 18h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Sealed tube; Green chemistry;	91%
With alkali

glycolonitrile (107-16-4) → glycolic Acid (79-14-1)

Conditions	Yield
With sulfuric acid; water at 105 - 110℃; for 6h; Temperature;	92%
With water; microbial enzyme at 40℃; for 12h; Product distribution / selectivity;	10 - 99 %Chromat.
Stage #1: glycolonitrile With sulfuric acid In water for 2191.5h; pH=3; Stage #2: With sodium hydroxide pH=7; Stage #3: With water; microbial enzyme at 40℃; for 12h; Product distribution / selectivity;	99 %Chromat.
With nitrilase from Hoeflea phototrophica DFL-43; water In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 0.166667h; pH=8; Enzymatic reaction;

glycerol (56-81-5) → glycolic Acid (79-14-1) + glyceric acid (473-81-4) + dihydroxyacetone (96-26-4)

Conditions	Yield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;	A 8.9% B 89.9% C 6.8%
With oxygen In water at 80℃; under 7500.75 Torr; for 2h; pH=6.7; Reagent/catalyst; Autoclave;
With oxygen In water at 60℃; under 3750.38 Torr; for 24h; Catalytic behavior; Kinetics; Reagent/catalyst; Time; High pressure;	A 7.8 %Chromat. B 55.4 %Chromat. C 7.7 %Chromat.

benzyl glycolate (30379-58-9) → glycolic Acid (79-14-1)

Conditions	Yield
With hydrogen Hydrogenolysis;	88%

3-(α,α,α-trifluoro-m-tolyl)-4-isothiazolecarboxylic acid (68210-96-8) + chloroacetic acid ethyl ester (105-39-5) → glycolic Acid (79-14-1)

Conditions	Yield
With sodium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform; benzene	87%
With sodium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform; benzene	87%

POMP (7044-96-4) + carbon monoxide (201230-82-2) → glycolic Acid (79-14-1)

Conditions	Yield
With water; propionic acid at 140℃; under 52476.2 Torr; for 2h; Autoclave;	86%
With water; propionic acid at 140℃; under 52476.2 Torr; for 2h; Autoclave;	86%
With water; propionic acid at 140℃; under 52476.2 Torr; for 2h; Autoclave;	86%
With water; propionic acid at 140℃; under 52476.2 Torr; for 2h; Reagent/catalyst; Concentration; Autoclave;	86 %Chromat.

dihydroxyacetone (96-26-4) → formic acid (64-18-6) + glycolic Acid (79-14-1)

Conditions	Yield
With dihydrogen peroxide In neat (no solvent) at 25℃; for 24h; Catalytic behavior; Reagent/catalyst;	A n/a B 86%
With oxygen; vanadia In water at 79.84℃; under 2250.23 Torr; for 1h; Autoclave;	A 14 %Chromat. B 13 %Chromat.

potassium chloroacetate (7748-25-6) → glycolic Acid (79-14-1)

Conditions	Yield
With water at 150℃; for 5h;	85%

acetoxyacetic acid (13831-30-6) → glycolic Acid (79-14-1)

Conditions	Yield
With copper dichloride In methanol; water for 3h; Heating;	85%

N-nitrosoglycocholic acid (76757-85-2) → glycolic Acid (79-14-1) + cholic acid (81-25-4)

Conditions	Yield
With water at 37℃; Rate constant; Mechanism; pH 7.0 - 9.0;	A 85% B 50%

Cellobiose (13360-52-6) → glycolic Acid (79-14-1) + D-Fructose (57-48-7) + mannonic acid (642-99-9)

Conditions	Yield
With copper(II) oxide In water at 199.84℃; for 0.5h; Temperature; Inert atmosphere;	A n/a B n/a C 85%

Glycolaldehyde (141-46-8) → formic acid (64-18-6) + glycolic Acid (79-14-1) + Glyoxal (131543-46-9) + carbon dioxide (124-38-9) + acetic acid (64-19-7)

Conditions	Yield
With water; oxygen at 90℃; under 7500.75 Torr; for 8h; Catalytic behavior; Mechanism; Temperature; Pressure; Time; Reagent/catalyst;	A 80.5% B 4.2% C 6.2% D 2.6% E 0.3%

C11H14N2O5S (85515-90-8) → glycolic Acid (79-14-1)

Conditions	Yield
With copper dichloride In methanol; water for 24h; Heating;	80%

glycerol (56-81-5) → glycolic Acid (79-14-1)

Conditions	Yield
With dihydrogen peroxide; zinc(II) oxide In water for 3h; Reagent/catalyst; UV-irradiation;	77%
With dihydrogen peroxide; yttrium(III) trifluoromethanesulfonate In acetonitrile at 70℃; for 12h;	16%
With dihydrogen peroxide

D-glucose (50-99-7) → glycolic Acid (79-14-1) + LACTIC ACID (849585-22-4)

Conditions	Yield
With oxygen In water at 180℃; under 13680.9 Torr; for 20h; Green chemistry;	A 23.3% B 76.7%

tartaric acid (87-69-4) → glycolic Acid (79-14-1) + (2E)-but-2-enedioic acid (110-17-8)

Conditions	Yield
With oxygen In water at 160℃; under 13680.9 Torr; for 10h; Reagent/catalyst;	A 27% B 73%

glycerol (56-81-5) → formic acid (64-18-6) + glycolic Acid (79-14-1) + acetic acid (64-19-7)

Conditions	Yield
With aluminium(III) triflate; dihydrogen peroxide In acetonitrile at 70℃; for 12h; Reagent/catalyst;	A 72% B 20% C 8%

D-glucose (50-99-7) → glycolic Acid (79-14-1) + LACTIC ACID (849585-22-4) + succinic acid (110-15-6)

Conditions	Yield
With oxygen In water at 180℃; under 7600.51 Torr; for 20h; Temperature; Pressure; Reagent/catalyst; Green chemistry;	A 15.5% B 71% C 13.5%

Cellobiose (13360-52-6) → glycolic Acid (79-14-1) + gluconic acid (526-95-4) + succinic acid (110-15-6) + oxalic acid (144-62-7) + acetic acid (64-19-7)

Conditions	Yield
With carbon nanotube supported gold nanoparticles (0.5 wt%); water; oxygen at 145℃; under 7500.75 Torr; for 3h;	A n/a B 70% C n/a D n/a E n/a

glycerol (56-81-5) → formic acid (64-18-6) + glycolic Acid (79-14-1) + Glyceraldehyde (56-82-6)

Conditions	Yield
With potassium hydroxide for 4h; Reagent/catalyst; Electrochemical reaction;	A 70% B 13% C 17%
With dihydrogen peroxide In water at 60℃; for 4h;

tartaric acid (87-69-4) → glycolic Acid (79-14-1) + LACTIC ACID (849585-22-4) + (2E)-but-2-enedioic acid (110-17-8)

Conditions	Yield
With oxygen In water at 160℃; under 13680.9 Torr; for 10h;	A 69% B 7% C 24%

Cellobiose (13360-52-6) → glycolic Acid (79-14-1) + D-glucose (50-99-7) + gluconic acid (526-95-4) + succinic acid (110-15-6) + oxalic acid (144-62-7) + acetic acid (64-19-7)

Conditions	Yield
With carbon nanotube supported gold nanoparticles (0.5 wt%); water; oxygen at 145℃; under 3750.38 Torr; for 3h;	A n/a B n/a C 68% D n/a E n/a F n/a

D-xylose (58-86-6) → glycolic Acid (79-14-1) + LACTIC ACID (849585-22-4)

Conditions	Yield
With water; Amberlite IRA400 at 50℃; for 2h; Product distribution / selectivity;	A n/a B 64%

glycerol (56-81-5) → 1,3-dioxolane-4-methanol (5464-28-8) + glycerol formal (4740-78-7) + glycolic Acid (79-14-1) + ethyl 2-hydroxyacetate (623-50-7) + diglycerol (627-82-7) + oxiranyl-methanol (556-52-5) + hydroxy-2-propanone (116-09-6) + acrolein (107-02-8)

Conditions	Yield
With pretreated aluminium vanadium phosphate In water at 280℃; under 760.051 Torr; Catalytic behavior; Activation energy; Reagent/catalyst; Temperature;	A n/a B n/a C n/a D n/a E n/a F n/a G n/a H 62%

...Expand

glycolic Acid (79-14-1) + 4-methyl-1,2-diaminobenzene (496-72-0) → (5-methyl-1H-benzimidazole-2-yl)methanol (20034-02-0)

Conditions	Yield
With hydrogenchloride In water for 3h; Reflux;	100%
With hydrogenchloride In water for 6h; Reflux;	83%
With phosphoric acid at 130℃; for 3h;	72%

glycolic Acid (79-14-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester (67226-76-0)

Conditions	Yield
With pyridine for 2h; Ambient temperature;	100%
With 1H-imidazole In N,N-dimethyl-formamide for 10h; Ambient temperature;	97%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	95%

glycolic Acid (79-14-1) + N-phenylsulfinylamine (222851-56-1) → glycolanilide (4746-61-6)

Conditions	Yield
at 25℃; for 8h;	100%
In acetonitrile at 20℃; Inert atmosphere;	53.6%

glycolic Acid (79-14-1) + N-(4-chloro-phenyl)-sulfur imide oxide (13165-68-9, 52867-11-5) → glycolic acid-(4-chloro-anilide) (21919-09-5)

Conditions	Yield
at 25℃; for 6h;	100%

glycolic Acid (79-14-1) + FR901469 hydrochloride → C73H118N14O25

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%

2,2′-bis(pyrazolyl)-ethylamine + glycolic Acid (79-14-1) → C10H13N5O2

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;	100%

glycolic Acid (79-14-1) + 4-methoxy-1,2-phenylenediamine (102-51-2) → (5-methoxy-1H-benzimidazole-2-yl)-methanol (20033-99-2)

Conditions	Yield
With hydrogenchloride In water Reflux;	100%
With hydrogenchloride In water for 6h; Reflux;	51%
Stage #1: glycolic Acid; 4-methoxy-1,2-phenylenediamine With hydrogenchloride In water for 16h; Heating / reflux; Stage #2: With sodium hydroxide In water
With hydrogenchloride In water for 6h; Reflux;
With hydrogenchloride In water at 100℃; for 6h;

glycolic Acid (79-14-1) + piperidine-4-carboxylic acid benzyl ester hydrochloride → benzyl 1-glycoloylpiperidine-4-carboxylate (945955-09-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 12h;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 48h;	57%

glycolic Acid (79-14-1) + meloxicam (71125-38-7) → meloxicam glycolic acid (1174325-97-3)

Conditions	Yield
In chloroform for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

glycolic Acid (79-14-1) + 3-(4-chlorophenyl)-1H-pyrazol-5-amine (78583-81-0) → N-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-2-hydroxyacetamide (1160285-30-2)

Conditions	Yield
In toluene at 110℃; for 48h; Inert atmosphere;	100%

glycolic Acid (79-14-1) + 4,6,4',6'-tetrachloro-2,2'-(3,6-dioxa-octane-1,8-diyldioxy)-bis-[1,3,5]triazine (36394-85-1) → C16H16Cl2N6O10(2-)*2Na(1+)

Conditions	Yield
Stage #1: glycolic Acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2h; Stage #2: 4,6,4',6'-tetrachloro-2,2'-(3,6-dioxa-octane-1,8-diyldioxy)-bis-[1,3,5]triazine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;	100%

glycolic Acid (79-14-1) + (R)-6-chloro-5-fluoro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-N-(piperidin-3-yl)pyrimidin-4-amine → 2-((3R)-3-{[6-chloro-5-fluoro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-yl]amino} piperidin-1-yl)-2-oxoethanol

Conditions	Yield
Stage #1: (R)-6-chloro-5-fluoro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-N-(piperidin-3-yl)pyrimidin-4-amine With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: glycolic Acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4.5h;	100%

glycolic Acid (79-14-1) + C25H33NO9 → C23H31NO9

Conditions	Yield
Stage #1: C25H33NO9 With tetrakis(triphenylphosphine) palladium(0); N,N-Dimethyltrimethylsilylamine In chloroform at 20℃; for 2h; Inert atmosphere; Stage #2: glycolic Acid With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 2h;	100%

glycolic Acid (79-14-1) + C47H58N2O14 → 1-allyl-2-glycolylamino-6-O-benzyl-4-O-(3’-O-benzyl-4’,6’-O-benzylidene-2’-deoxy-2’-ethylamino-β-D-glucopyranosyl)-2-deoxy-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-α-D-glucopyranoside

Conditions	Yield
Stage #1: C47H58N2O14 With tetrakis(triphenylphosphine) palladium(0); N,N-Dimethyltrimethylsilylamine In chloroform at 20℃; for 2h; Inert atmosphere; Stage #2: glycolic Acid With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 2h;	100%

glycolic Acid (79-14-1) + 4-(benzyloxy)-5-chlorobenzene-1,2-diamine → N-(2-amino-4-(benzyloxy)-5-chlorophenyl)-2-hydroxyacetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 2h;	100%

glycolic Acid (79-14-1) + 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3) → C14H20BNO4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 36h;	100%

glycolic Acid (79-14-1) + tris(4-aza-2-hydroxydecyl)amine → tris(4-aza-2,6-dihydroxy-4-hexyl-5-oxohexyl)amine

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene	99.7%

glycolic Acid (79-14-1) + H-Gpn-OH (60142-96-3) → C9H17NO2*C2H4O3

Conditions	Yield
In neat (no solvent) for 0.25h; Green chemistry;	99.3%

2-(N,N-dimethylamino)ethanol (108-01-0) + glycolic Acid (79-14-1) → N,N-dimethylethanolammonium glycolate (176158-74-0)

Conditions	Yield
In ethanol	99%

glycolic Acid (79-14-1) + ethanolamine (141-43-5) → (4,5-dihydrooxazol-2-yl)methanol (22375-00-4)

Conditions	Yield
In xylene for 6h; Heating / reflux;	99%

glycolic Acid (79-14-1) + N-[4-(4-amino-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl)-2-fluorophenyl]-N'-[2-fluoro-5-(trifluoromethyl)phenyl]urea (939965-82-9) → N-4-[4-amino-7-(1-glycoloylpiperidin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-fluorophenyl-N'-[2-fluoro-5-(trifluoromethyl)phenyl]urea (939965-86-3)

Conditions	Yield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 17h;	99%

glycolic Acid (79-14-1) + 3-chloro-aniline (108-42-9) → N-(3-chlorophenyl)-2-hydroxyacetamide

Conditions	Yield
at 130℃; for 5h; Inert atmosphere;	99%

(morpholinomethyl)hydrosilane (5625-96-7) + glycolic Acid (79-14-1) → 5-(morpholin-4-iomethyl)-2,7-dioxo-1,4,6,9-tetraoxa-5-silaspiro[4,4]nonan-5-uide (1138348-24-9)

Conditions	Yield
In dichloromethane at 20℃; for 0.25h; Solvent;	99%

glycolic Acid (79-14-1) + (R)-5-bromo-2-(3-methylpiperazin-1-yl)pyrimidine dihydrochloride → (R)-1-(4-(5-bromopyrimidin-2-yl)-2-methylpiperazin-1-yl)-2-hydroxyethanone

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide for 1.5h;	99%
With triethylamine; HATU In N,N-dimethyl-formamide for 4h;	87%

glycolic Acid (79-14-1) → acetic acid (64-19-7)

Conditions	Yield
With hydrogen; propionic acid; sodium iodide at 220℃; under 20686.5 Torr; for 1h;	99%

Upstream product

• 124-38-9 CARBON DIOXIDE 
• 96-35-5 Methyl glycolate 
• 74-90-8 HYDROGEN CYANIDE 
• 143-33-9 Sodium cyanide 

Downstream Products

• 337508-58-4 1H-BENZIMIDAZOLE-2-CARBONYL CHLORIDE HYDROCHLORIDE 
• 2849-93-6 2-Benzimidazolecarboxylic acid 
• 79-11-8 Chloroacetic acid 
• 53164-05-9 Acemetacin 
• 96-35-5 Methyl glycolate 
• 87-51-4 Indole-3-acetic acid 
• 73250-68-7 Mefenacet 
• 13831-31-7 Acetoxyacetyl chloride 
• 15571-58-1 2-ethylhexyl 10-ethyl-4,4-dioctyl-7-oxo-8-oxa-3,5-dithia-4-stannatetradecanoate 
• 4856-97-7 1H-Benzimidazole-2-methanol 

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