76-93-7

Basic information

• Product Name: Benzilic acid
• Synonyms: BENZILIC ACID extrapure;Benzilic acidDiphenylglycolic acid;TrospiuM Chloride Related CoMpound A;Trospium Chloride Related Compound A (20 mg) (Benzilic Acid) (Internationally Restricted Sales Item);BENZILIC ACID FOR SYNTHESIS 1 KG;BENZILIC ACID FOR SYNTHESIS 250 G;Benzeneacetic acid,a-hydroxy-a-phenyl-;Trospium Chloride Related Compound A (20 mg) (Benzilic Acid) (International Restricted Sales Item)
• CAS NO: 76-93-7
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24
• EINECS: 200-993-2
• Product Categories: Pharmaceutical Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organics
• Mol File: 76-93-7.mol
• Article Data: 51

Chemical Properties

• Melting Point: 149-151 °C(lit.)
• Boiling Point: 180 °C
• Flash Point: 180°C/22mm
• Appearance: White to cream-white/Powder
• Density: 1.28
• Vapor Pressure: 2.01E-07mmHg at 25°C
• Refractive Index: 1.5805 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 1.41g/l (experimental)
• PKA: pKa (25°): 3.036
• Water Solubility: 1.41 g/L (25 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• Merck: 14,1080
• BRN: 521402
• CAS DataBase Reference: Benzilic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Benzilic acid(76-93-7)
• EPA Substance Registry System: Benzilic acid(76-93-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 36-36/37/39-26
• WGK Germany: 3
• RTECS: DD2064000
• TSCA: Yes
• Hazardous Substances Data: 76-93-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Benzilic Acid is an impurity of Trospium (T892800), a tropine derivative with anticholinergic activity and a antiispasmodic agent.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 1631, 1964 DOI: 10.1021/jo01029a509

Safety Profile

Moderately toxic by subcutaneousroute. Slightly toxic by ingestion. When heated todecomposition it emits acrid smoke and irritating vapors.

Purification Methods

Crystallise benzilic acid from *benzene (ca 6mL/g), or hot H2O. [Beilstein 10 IV 1256.]

InChI:InChI=1/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16)/p-1

Synthetic route

benzophenone (119-61-9) + carbon dioxide (124-38-9) → Benzilic acid (76-93-7)

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile Electrochemical reaction; Irradiation;	98%
With Tetrapropylammonium chloride In acetonitrile at 20℃; under 760.051 Torr; for 10h; Electrochemical reaction;	90%
With potassium iodide In N,N-dimethyl-formamide Hg pool cathode, platinum plate anode, constant current of 2.5 nA/cm2;	86%
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃; electrochemical reaction;	75%
With tetrabutylammonium halide In N,N-dimethyl-formamide Ambient temperature; electrolysis, Mg anode;	70%

benzil (134-81-6) → Benzilic acid (76-93-7)

Conditions	Yield
With sodium hydroxide In ethanol; water for 0.5h; Heating;	97%
With water; sodium hydroxide In ethanol for 0.5h; Reflux;	97%
Stage #1: benzil With N-benzyl-trimethylammonium hydroxide at 40℃; for 4h; Stage #2: With hydrogenchloride In water pH=3;	92%

adiphenine (64-95-9) → Benzilic acid (76-93-7)

Conditions	Yield
With potassium hydroxide In methanol at 65℃;	92%

(Z)-1,2,4-triphenyl-2-butene-1,4-dione (13249-75-7) + 2-hydroxy-2-phenylacetophenone (119-53-9) → 1,2,4-triphenylbutane-1,4-dione (4441-01-4) + Benzilic acid (76-93-7) + benzil (134-81-6)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide for 2h; Mechanism; Ambient temperature; other reaction conditions, other substrates;	A 91% B n/a C n/a

benzaldehyde (100-52-7) → Benzilic acid (76-93-7)

Conditions	Yield
With C19H32N6O4(2+)*2Br(1-); sodium hydroxide In acetonitrile for 1.83333h; Catalytic behavior; Reagent/catalyst;	90%
Stage #1: benzaldehyde With oxygen; 1-butyl-3-methylimidazolium Tetrafluoroborate; potassium hydroxide at 60℃; for 0.416667h; Neat (no solvent); Microwave irradiation; Stage #2: With hydrogenchloride In water at 20℃;	74%

bromopropylate (18181-80-1) → Benzilic acid (76-93-7)

Conditions	Yield
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 96h;	87%

2-diphenylmethylene-1,3-benzodithiole (62217-32-7) → 1,2-benzenedisulfonyl dichloride (6461-76-3) + Benzilic acid (76-93-7)

Conditions	Yield
With chlorine In water; tert-butyl alcohol at 0 - 5℃; for 2h; Yields of byproduct given;	A n/a B 85%
With chlorine In water; tert-butyl alcohol at 0 - 5℃; for 2h; Yield given;	A n/a B 85%

[bis(acetoxy)iodo]benzene (3240-34-4) + methyl 2,2-diphenylacetate (3469-00-9) → Benzilic acid (76-93-7)

Conditions	Yield
With potassium hydroxide In water; benzene	75%

1,2-diphenyl-1,2-ethanediol (492-70-6, 655-48-1, 2325-10-2, 38270-73-4, 52340-78-0, 579-43-1) → Benzilic acid (76-93-7) + benzoic acid (65-85-0)

Conditions	Yield
Stage #1: 1,2-diphenyl-1,2-ethanediol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; Reagent/catalyst; Solvent; chemoselective reaction;	A 10% B 74%

phenyl benzyl ketone (451-40-1) → 4-chloro-aniline (106-47-8) + Benzilic acid (76-93-7) + benzoic acid (65-85-0)

Conditions	Yield
With nitrobenzene In potassium hydroxide; tert-butyl alcohol for 0.5h; Heating;	A 71% B 58% C 24%

2-hydroxy-2-phenylacetophenone (119-53-9) → Benzilic acid (76-93-7)

Conditions	Yield
With potassium hydroxide In ethanol; water at 100℃; for 1h; Temperature; Sealed tube;	70%
With potassium hydroxide
With potassium hydroxide at 100℃;

benzophenone (119-61-9) + carbon dioxide (124-38-9) → 1,1-Diphenylmethanol (91-01-0) + 2,2-diphenylacetic acid (117-34-0) + Benzilic acid (76-93-7)

Conditions	Yield
With ytterbium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide under 760 Torr; for 0.833333h; Ambient temperature;	A 12% B 4% C 61%
With ytterbium 1.) THF, HMPA, RT, 2.) RT, 1 atm, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

formic acid (64-18-6) + chloro(diphenyl)acetic acid (7475-56-1) → (formyloxy)diphenylacetic acid (133217-20-6) + Benzilic acid (76-93-7) + dimeric material

Conditions	Yield
In dichloromethane at 80℃; for 1h;	A 61% B 25% C n/a

benzophenone (119-61-9) + carbon dioxide (124-38-9) + triethylamine (121-44-8) → 1,1-Diphenylmethanol (91-01-0) + 1,1-diphenylpropane-1,2-diol (52183-00-3) + tetraphenylethane-1,2-diol (464-72-2) + Benzilic acid (76-93-7)

Conditions	Yield
With tetraethylammonium chloride; poly(p-phenylene) In N,N-dimethyl-formamide for 24h; Carboxylation; reduction; dimerization; Irradiation;	A 4% B 3% C 49% D 27%

1,1-Diphenylethylene (530-48-3) → Benzilic acid (76-93-7)

Conditions	Yield
With tert.-butylhydroperoxide; water; tetra-(n-butyl)ammonium iodide In acetonitrile at 90℃; for 12h;	45%

benzophenone (119-61-9) + carbon dioxide (124-38-9) → 2,2-diphenylacetic acid (117-34-0) + Benzilic acid (76-93-7)

Conditions	Yield
Stage #1: benzophenone With LiVH2 In tetrahydrofuran at 20℃; Stage #2: carbon dioxide In tetrahydrofuran Further stages.;	A 9% B 28%

benzophenone (119-61-9) + carbon dioxide (124-38-9) → 1,1-Diphenylmethanol (91-01-0) + tetraphenylethane-1,2-diol (464-72-2) + Benzilic acid (76-93-7)

Conditions	Yield
With cadmium(II) sulphide; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Irradiation;	A 26% B 23% C 11%
With triethylamine; lithium chloride; poly(p-phenylene) In N,N-dimethyl-formamide for 24h; Irradiation;	A 8 % Chromat. B 25% C 5%
With tetraethylammonium chloride; triethylamine; poly(p-phenylene) In N,N-dimethyl-formamide for 24h; Irradiation;	A 10% B 10% C 34 % Chromat.

bromo-diphenyl-acetic acid (7494-95-3) → azido-diphenyl-acetic acid (2571-41-7) + diphenyl ketene (525-06-4) + Benzilic acid (76-93-7)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide	A 25% B n/a C n/a

benzophenone (119-61-9) → Benzilic acid (76-93-7)

Conditions	Yield
With diethyl ether; carbon dioxide; sodium Zersetzung mit Wasser;

1-methyl-4-nitrosobenzene (623-11-0) + fluoro-diphenyl-acetic acid ethyl ester (427-47-4) → Benzilic acid (76-93-7)

Conditions	Yield
at 20℃;

benzoic acid ethyl ester (93-89-0) → Benzilic acid (76-93-7) + benzil (134-81-6)

Conditions	Yield
With ammonia; sodium

1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) → Benzilic acid (76-93-7)

Conditions	Yield
With potassium permanganate at 0℃;

hydroxy-diphenyl-acetaldehyde (4746-86-5) → Benzilic acid (76-93-7)

Conditions	Yield
With nitric acid

α-phenylimino-deoxybenzoin (4198-95-2) → anilino-diphenyl-acetic acid (1922-78-7) + Benzilic acid (76-93-7)

Conditions	Yield
at 170 - 180℃; in der Kalischmelze;
at 170 - 180℃; bei der Kalischmelze;

chloro(diphenyl)acetic acid (7475-56-1) + furan-2,3,5(4H)-trione pyridine (1:1) → Benzilic acid (76-93-7)

chloro(diphenyl)acetic acid (7475-56-1) → Benzilic acid (76-93-7)

Conditions	Yield
With sodium carbonate

N,N-diethyl-α-hydroxy-α-phenylbenzeneacetamide (10049-90-8) → Benzilic acid (76-93-7) + diethylamine (109-89-7)

Conditions	Yield
in der Alkalischmelze;

bromo-diphenyl-acetic acid (7494-95-3) → Benzilic acid (76-93-7)

Conditions	Yield
With water
With barium dihydroxide

α-ethoxy-benzoin; sodium salt → Benzilic acid (76-93-7)

Conditions	Yield
With ethanol

phenylmagnesium iodide (16002-63-4) + Ethyl oxalyl chloride (4755-77-5) → Benzilic acid (76-93-7)

Conditions	Yield
bei der Verseifung;

Benzilic acid (76-93-7) → benzophenone (119-61-9)

Conditions	Yield
With pyridine chromium peroxide In dichloromethane for 0.3h; Product distribution; Ambient temperature; effect of various chromium(VI) based oxidants;	100%
In acetic acid for 0.25h; Heating;	100%
With sodium hydroxide; copper(III) periodate for 0.05h; Heating; oxidative decarboxylation of α-hydroxy acids; var. α-hydroxy acids, also Cu(III) tellurate as oxidant;	95%

Benzilic acid (76-93-7) → 2,2-diphenylacetic acid (117-34-0)

Conditions	Yield
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 95℃; for 24h; Inert atmosphere;	99.3%
With triethylsilane; perchloric acid In dichloromethane; water at 40℃; for 20h;	94%
With phosphorus; iodine weiteres Reagens: wss. Phosphorsaeure;

methanol (67-56-1) + Benzilic acid (76-93-7) → methyl benzilate (76-89-1)

Conditions	Yield
With sulfuric acid; acetonitrile at 80 - 85℃; for 16 - 18h;	99%
With thionyl chloride at 0 - 75℃; for 12.0833h; Schlenk technique; Inert atmosphere; Reflux;	91%
With sulfuric acid

trimethylsilyl cyanide (7677-24-9) + Benzilic acid (76-93-7) → formylamino-diphenyl-acetic acid (183734-04-5)

Conditions	Yield
With sulfuric acid In acetic acid for 18h; Ambient temperature;	97%

2,2-dihydroxy-6-methyl-1,3,6,2-dioxazagermocane (148661-29-4) + Benzilic acid (76-93-7) → Ge{(OCH2CH2)2NCH3}{OC(C6H5)2C(O)O} (149236-31-7)

Conditions	Yield
In ethanol; xylene addn. of Ge-compd. (abs. alcohol) to refluxing mixt. of org. ligand in EtOH and xylene over a period of 2 h, further refluxing for 1 h; concn. of soln., crystn. on standing; collecting, washing (benzene), drying in vac. over P2O5; elem. anal.;	96%

Benzilic acid (76-93-7) → chloro(diphenyl)acetic acid (7475-56-1)

Conditions	Yield
With acetyl chloride In dichloromethane	95%
With phosphorus pentachloride; benzene
With phosphorus trichloride

(1α, 5α, 6α)-6N-(3-azabicyclo [3.1.0] hexyl-3-benzyl)-2-chloro acetamide (712356-53-1) + Benzilic acid (76-93-7) → (1α, 5α, 6α)-1-[6N-(3-azabicyclo-[3.1.0] hexyl-3-benzyl)]-N-acetamido-2-cyclohexyl-2-hydroxy-2-phenylacetate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In xylene for 3h;	95%

dihydroxo(η3-2,2'-iminodiethoxo)germanium(IV) (143794-20-1) + Benzilic acid (76-93-7) → Ge{(OCH2CH2)2NH}{OC(C6H5)2C(O)O} (148661-56-7)

Conditions	Yield
In ethanol; xylene addn. of Ge-compd. (abs. alcohol) to refluxing mixt. of org. ligand in EtOH and xylene over a period of 2 h, further refluxing for 1 h; concn. of soln., crystn. on standing; collecting, washing (benzene), drying in vac. over P2O5; elem. anal.;	95%

n-butyldiethanolamine (102-79-4) + germanium dioxide + Benzilic acid (76-93-7) → (α-hydroxydiphenylaceto-O,O')(N-n-butyliminodiethanolato-N,O,O')germanium(IV) (162441-06-7)

Conditions	Yield
In ethanol; water; xylene refluxing (2 h); solvent removal, crystn. on cooling, filtn., drying (vac.); elem. anal.;	95%

Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide) (1201903-03-8) + Benzilic acid (76-93-7) → 2,5-dichloro-N-(2-{[(1R)-3-methyl-1-(5-oxo-4,4-diphenyl-1,3,2-dioxaborolan-2-yl)butyl]amino}-2-oxoethyl)benzamide (1201902-93-3)

Conditions	Yield
In ethyl acetate at 25 - 60℃;	95%

Benzilic acid (76-93-7) → 3,3,6,6-tetraphenyl-2,5-p-dioxanedione (467-32-3)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 85 - 90℃;	93%
With phosphorus pentaoxide
at 155 - 165℃; under 15 Torr;

3-diphenylpropyl amine (5586-73-2) + Benzilic acid (76-93-7) → C29H27NO2 (1061757-58-1)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	93%

ethyl 4-aminopiperidine-1-carboxylate (58859-46-4) + Benzilic acid (76-93-7) → N-(1-carboethoxy-4-piperidyl)-2-hydroxy-2,2-diphenylacetamide (160099-10-5)

Conditions	Yield
With 1,1'-carbonyldiimidazole In dichloromethane for 0.75h; Ambient temperature;	92.5%

Benzilic acid (76-93-7) + butyl glyoxalate (6295-06-3) → 2-(carbobutoxy)-5,5-diphenyl-1,3-dioxolan-4-one (78733-54-7)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	92.2%

diethyl germanium dichloride (13314-52-8) + Benzilic acid (76-93-7) → (C2H5)2GeCO2C(C6H5)2O (139415-85-3)

Conditions	Yield
With triethylamine In benzene byproducts: Et3NHCl; elem. anal.;	92%
With triethylamine In benzene (inert atm.); room temp. 2h; filtn., evapn., sublimation (195°C/760 mm Hg);	67%

germanium dioxide + Benzilic acid (76-93-7) + diisopropanolamine (110-97-4) → (α-hydroxydiphenylaceto-O,O')(iminodiisopropanolato-N,O,O')germanium(IV) (162441-07-8)

Conditions	Yield
In ethanol; water; xylene refluxing (2 h); solvent removal, crystn. on cooling, filtn., drying (vac.); elem. anal.;	92%

L-Cysteine (52-90-4) + acetic acid (64-19-7) + Benzilic acid (76-93-7) → (R)-2-amino-3-((carboxydiphenyl-methyl)thio)propanoic acid

Conditions	Yield
With sulfuric acid at 40℃; for 3h;	92%

chloroacetonitrile (107-14-2) + Benzilic acid (76-93-7) → N-Chloroacetyldiphenylglycine (92874-63-0)

Conditions	Yield
With sulfuric acid; acetic acid at 20℃; for 5h; Ritter reaction;	91%

3-dimethylamino-2,2-dimethyl-2H-azirine (54856-83-6) + Benzilic acid (76-93-7) → 2-(2-Hydroxy-2,2-diphenylacetamido)-N,N,2-trimethylpropionamid (111492-15-0)

Conditions	Yield
In acetonitrile Ambient temperature;	90.5%

Benzilic acid (76-93-7) + 1,2-dibromomethane (74-95-3) → Hydroxy-diphenyl-acetic acid 2-hydroxy-2,2-diphenyl-acetoxymethyl ester (111008-65-2)

Conditions	Yield
With anion exchange resin for 5h; Heating;	90%

tert-butyl methyl ether (1634-04-4) + Benzilic acid (76-93-7) → methyl benzilate (76-89-1)

Conditions	Yield
With sulfuric acid Reflux; regioselective reaction;	90%

propan-1-ol (71-23-8) + Benzilic acid (76-93-7) → diphenyl-propoxy-acetic acid propyl ester (94686-44-9)

Conditions	Yield
With thionyl chloride for 10h; Product distribution / selectivity; Reflux;	90%

Benzilic acid (76-93-7) + carbonic acid dimethyl ester (616-38-6) → methyl benzilate (76-89-1)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.25h; Microwave irradiation; Reflux;	90%

Benzilic acid (76-93-7) + tantalum pentaethoxide (150747-55-0) → bis(benzilato)tantalum(V) ethoxide

Conditions	Yield
In benzene byproducts: ethanol; 10 h reflux, molar ratio of educts=1:2; ethanol recovered as azeotrope, elem. anal.;	88%

methanol (67-56-1) + galium(III) nitrate monohydrate + Benzilic acid (76-93-7) → [galium(III)(benzilate)2]*methanol monosolvate trihydrate

Conditions	Yield
at 60℃; for 2h; Reflux;	87%

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 427-47-4 fluoro-diphenyl-acetic acid ethyl ester 
• 93-89-0 benzoic acid ethyl ester 
• 16002-63-4 phenylmagnesium iodide 
• 4755-77-5 Ethyl oxalyl chloride 
• 93-59-4 Perbenzoic acid 
• 60-29-7 diethyl ether 
• 525-06-4 diphenyl ketene 
• 7475-56-1 chloro(diphenyl)acetic acid 
• 17356-08-0 thiourea 
• 451-40-1 phenyl benzyl ketone 
• 54556-98-8 propiverine hydrochloride 
• 119-61-9 benzophenone 
• 124-38-9 carbon dioxide 

Downstream Products

• 4398-62-3 benzilic acid-(2-pyrrolidino-ethyl ester) 
• 3567-12-2 [11C]-(+)-3-EPB 
• 4398-59-8 hydroxy-diphenyl-acetic acid 2-morpholin-4-yl-ethyl ester 
• 96354-74-4 N-(diphenylmethyl)pyridin-2-amine 
• 19962-66-4 2,5,5-triphenyl-[1,3]dioxolan-4-one 
• 603-54-3 N,N-diphenylurea 
• 102-07-8 bis(diphenyl)urea 
• 113650-82-1 benzilic acid-(3-dipropylamino-propylester); hydrochloride 
• 19503-55-0 2,2-diphenyl-2,2'-sulfanediyl-di-acetic acid 
• 29052-18-4 3,3-diphenyl-6-methyl-2(3H)-benzofuranone 
• 848436-09-9 (4-hydroxy-2-methyl-phenyl)-diphenyl-acetic acid 
• 858820-12-9 benzo[b]thiophen-3-yl-diphenyl-acetic acid 
• 52182-15-7 ethyl benzilate 
• 128887-44-5 Hydroxy-diphenyl-acetic acid 3-azepan-1-yl-propyl ester 

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