132-27-4

Basic information

• Product Name: Sodium 2-biphenylate
• Synonyms: SODIUMBIPHENYL2-OLATE;SODIUM2-PHENYLPHENOL;SODIUMORTHO-PHENYLPHENOXIDE;SODIUM2-PHENYLPHENOXIDE;SODIUM2-BIPHENYLOL;Natrium-2-biphenylat;2-PHENYLPHENOL, SODIUM SALT TETRAHYDRATE, SYNTHESIS GRADE;Buffer solution, pH 8.00 (±0.01 @ 25°C), No Color, Specpure(R), NIST Traceable
• CAS NO: 132-27-4
• Molecular Formula: C₁₂H₉O*Na
• Molecular Weight: 192.19
• EINECS: 205-055-6
• Mol File: 132-27-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 59°C
• Boiling Point: 286°C
• Flash Point: 140.3 °C
• Appearance: Yellow/Liquid
• Density: 1,213 g/cm3
• Vapor Pressure: 1.2Pa at 20℃
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.9 (acid)
• Water Solubility: 1220 g kg-1 (35 °C)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,7304
• CAS DataBase Reference: Sodium 2-biphenylate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 2-biphenylate(132-27-4)
• EPA Substance Registry System: Sodium 2-biphenylate(132-27-4)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-37/38-41-50
• Safety Statements: 22-26-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: DV7750000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 132-27-4(Hazardous Substances Data)

Usage

Chemical Properties

light brown or beige solid

Uses

Antimicrobial additive in the manufacture of adhesives, leather, metalworking fluids, and textiles; preservative in automotive polishes, ceramic glazes, laundry starch, inks, floor wax emulsions; agricultural fungicide.

General Description

Beige flaky solid. pH of saturated solution in water: 12.0-13.5.

Air & Water Reactions

Soluble in water, yielding solutions with pHs of 12.0-13.5.

Reactivity Profile

Salts, basic, such as Sodium 2-biphenylate are generally soluble in water. The resulting solutions contain moderate concentrations of hydroxide ions and have pH's greater than 7.0. They react as bases to neutralize acids. These neutralizations generate heat, but less or far less than is generated by neutralization of the bases in reactivity group 10 (Bases) and the neutralization of amines. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Hazard

Possible carcinogen.

Fire Hazard

Flash point data for Sodium 2-biphenylate are not available, but Sodium 2-biphenylate is probably combustible.

Flammability and Explosibility

Notclassified

Safety Profile

Suspected carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Moderately toxic by ingestion.Experimental teratogenic and reproductive effects. Ahuman skin irritant. A severe skin irritant to experimentalanimals. When heated

Purification Methods

Crystallise the salt from acetone and dry it under vacuum at room temperature. [Beilstein 16 IV 4600.]

InChI:InChI=1/C12H10O.Na/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;/h1-9,13H;/q;+1

Synthetic route

2-Phenylphenol (90-43-7) → sodium 2-biphenylate (132-27-4)

Conditions	Yield
With sodium; benzene
With ethanol; sodium
With sodium hydroxide at 60℃;
With sodium hydroxide at 80 - 100℃;

dichlorobis(acetylacetonato)vanadium(IV) + sodium 2-biphenylate (132-27-4) → VCl(acetylacetonate)2(2-phenylphenoxide) (1161750-07-7)

Conditions	Yield
In tetrahydrofuran byproducts: NaCl; to Na-compd. in THF a suspension of V-compd. in THF added, molar ratio VCl2(acac)2:NaOAr 1:1, stirred for 3-4 h, refluxed for about 5 h; filtered, solv. removed in vac., treated repeatedly with Et2O and petroleum ether, dried in vac., recrystallized from THF, elem. anal.;	99%

dichlorobis(acetylacetonato)vanadium(IV) + sodium 2-biphenylate (132-27-4) → V(acetylacetonate)2(2-phenylphenoxide)2 (1161750-08-8)

Conditions	Yield
In tetrahydrofuran byproducts: NaCl; to Na-compd. in THF a suspension of V-compd. in THF added, molar ratio VCl2(acac)2:NaOAr 1:2, stirred for 3-4 h, refluxed for about 5 h; filtered, solv. removed in vac., treated repeatedly with Et2O and petroleum ether, dried in vac., recrystallized from THF, elem. anal.;	99%

sodium 2-biphenylate (132-27-4) + Carbonic acid methyl ester (R)-1-methyl-allyl ester → 2-((R)-1-Methyl-allyloxy)-biphenyl

Conditions	Yield
With Wilkinson's catalyst; phosphorous acid trimethyl ester In tetrahydrofuran at 0 - 20℃; Etherification;	96%

sodium 2-biphenylate (132-27-4) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-([1,1'-biphenyl]-2-yl) N,N-dimethylcarbamothioate (10345-41-2)

Conditions	Yield
In N,N-dimethyl-formamide 1.) r.t., 2.) 80 deg C, 45 min;	86%
In N,N-dimethyl-formamide at 20 - 80℃; Alkylation;	86%

sodium 2-biphenylate (132-27-4) + cyclohexane-1,2-epoxide (286-20-4) → (+/-)-trans-2-(2-phenylphenoxy)cyclohexan-1-ol

Conditions	Yield
In water for 4h; Heating;	62%

carbon dioxide (124-38-9) + sodium 2-biphenylate (132-27-4) → 3-phenylsalicylic acid (304-06-3)

Conditions	Yield
at 190℃; under 15200 Torr; for 24h;	40%

cyclothiophosphazene (38595-77-6) + sodium 2-biphenylate (132-27-4) → 1-(Biphenyl-2-yloxy)-3,3,5,5-tetrachloro-1λ4,3λ5,5λ5-[1,2,4,6,3,5]thiatriazadiphosphinine (144514-50-1)

Conditions	Yield
In 1,4-dioxane at 15℃; for 2h;

sodium 2-biphenylate (132-27-4) + aniline (62-53-3) → 2-hydroxy-5-(phenylazo)biphenyl (79380-82-8)

Conditions	Yield
With hydrogenchloride; sodium nitrite 1.) 0 deg C, 2.) 0-2 deg C; Yield given. Multistep reaction;

ethanol (64-17-5) + sodium 2-biphenylate (132-27-4) + sodium monochloroacetic acid (3926-62-3) → ethyl (<1,1'-biphenyl>-2-yloxy)acetate (107352-46-5)

Conditions	Yield
(i) H2O, (ii) /BRN= 1718733/, H2SO4; Multistep reaction;

4-Bromodiphenyl ether (101-55-3) + sodium 2-biphenylate (132-27-4) → 1-(o-Phenyl-phenoxy)-4-phenoxy-benzol (3983-83-3)

Conditions	Yield
With copper at 275 - 300℃;

2-benzoylbenzoyl chloride (22103-85-1) + diethyl ether (60-29-7) + sodium 2-biphenylate (132-27-4) + benzene (71-43-2) → 2-benzoyl-benzoic acid biphenyl-2-yl ester + 3--3-phenyl-phthalide

sodium 2-biphenylate (132-27-4) + (hex-1-en-3-yl)methyl carbonate (83135-00-6) → 2-(1-propyl-allyloxy)-biphenyl + 2-[((E)-Hex-2-enyl)oxy]-biphenyl

Conditions	Yield
With Wilkinson's catalyst; phosphorous acid trimethyl ester In tetrahydrofuran at 0 - 20℃; Etherification; Title compound not separated from byproducts;
With Wilkinson's catalyst; phosphorous acid trimethyl ester In tetrahydrofuran at 0 - 20℃; Etherification; Title compound not separated from byproducts.;

sodium 2-biphenylate (132-27-4) + (2R*,3S*)-ethyl 3-chloro-2-morpholino-3-phenylpropionate → (2R,3R)-2-(Biphenyl-2-yloxy)-3-morpholin-4-yl-3-phenyl-propionic acid ethyl ester + (2S,3S)-3-(Biphenyl-2-yloxy)-2-morpholin-4-yl-3-phenyl-propionic acid ethyl ester

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃; for 12h; Substitution; Title compound not separated from byproducts.;

sodium 2-biphenylate (132-27-4) + Carbonic acid methyl ester (R)-1-methyl-allyl ester → 2-((R)-1-Methyl-allyloxy)-biphenyl + 2-((S)-1-Methyl-allyloxy)-biphenyl

Conditions	Yield
With Wilkinson's catalyst; phosphorous acid trimethyl ester In tetrahydrofuran at 0 - 20℃; Etherification;

sodium 2-biphenylate (132-27-4) → 2-isopropoxybiphenyl-3-carbaldehyde (478942-83-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: LiAlH4 / tetrahydrofuran / Heating 4: MnO2 / diethyl ether / 12 h / 20 °C View Scheme

sodium 2-biphenylate (132-27-4) → 2-isopropoxy-3-vinyl-1,1'-biphenyl (478942-85-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: LiAlH4 / tetrahydrofuran / Heating 4: MnO2 / diethyl ether / 12 h / 20 °C 5: tBuOK / diethyl ether / 0.17 h / 0 °C View Scheme

sodium 2-biphenylate (132-27-4) → (2-isopropoxy-biphenyl-3-yl)-methanol (566162-85-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

sodium 2-biphenylate (132-27-4) → C16H15(2)HO2

Conditions	Yield
Multi-step reaction with 4 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: 94 percent / LiAlD4 / tetrahydrofuran / Heating 4: MnO2 / diethyl ether / 12 h / 20 °C View Scheme

sodium 2-biphenylate (132-27-4) → C17H17(2)HO

Conditions	Yield
Multi-step reaction with 5 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: 94 percent / LiAlD4 / tetrahydrofuran / Heating 4: MnO2 / diethyl ether / 12 h / 20 °C 5: tBuOK / diethyl ether / 0.17 h / 0 °C View Scheme

sodium 2-biphenylate (132-27-4) → C16H16(2)H2O2 (566162-88-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: 94 percent / LiAlD4 / tetrahydrofuran / Heating View Scheme

sodium 2-biphenylate (132-27-4) → 2-isopropoxy-biphenyl-3-carboxylic acid isopropyl ester (566162-84-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C View Scheme

sodium 2-biphenylate (132-27-4) → [1,1′-biphenyl]-2-yl(methyl)sulfane (19813-75-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH; H2O / 2.33 h / 110 °C View Scheme
Multi-step reaction with 4 steps 1: 86 percent / dimethylformamide / 1.) r.t., 2.) 80 deg C, 45 min 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH / H2O / 2.33 h / 110 °C View Scheme

sodium 2-biphenylate (132-27-4) → 2-phenylbenzenethiol (2688-96-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 86 percent / dimethylformamide / 1.) r.t., 2.) 80 deg C, 45 min 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating View Scheme

sodium 2-biphenylate (132-27-4) → S-<2-Diphenylyl>-dimethylthiocarbaminat (16241-17-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C View Scheme
Multi-step reaction with 2 steps 1: 86 percent / dimethylformamide / 1.) r.t., 2.) 80 deg C, 45 min 2: 0.58 h / 264 - 282 °C View Scheme

sodium 2-biphenylate (132-27-4) → 2-<(trifluoromethyl)sulfinyl>biphenyl (129922-49-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C View Scheme
Multi-step reaction with 5 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 76 percent / NaH / dimethylformamide / 3 h / 50 °C 5: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C View Scheme
Multi-step reaction with 7 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH; H2O / 2.33 h / 110 °C 5: 82 percent / Cl2 / CCl4 / 20 °C / Irradiation 6: 86 percent / Et3N*3HF / 9 h / 180 °C 7: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C View Scheme

sodium 2-biphenylate (132-27-4) → 2-<(trifluoromethyl)thio>biphenyl (129922-51-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C View Scheme
Multi-step reaction with 4 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 76 percent / NaH / dimethylformamide / 3 h / 50 °C View Scheme
Multi-step reaction with 6 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH; H2O / 2.33 h / 110 °C 5: 82 percent / Cl2 / CCl4 / 20 °C / Irradiation 6: 86 percent / Et3N*3HF / 9 h / 180 °C View Scheme

sodium 2-biphenylate (132-27-4) → Umemoto's reagent (129946-88-9)

Conditions	Yield
Multi-step reaction with 8 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 7: 79 percent / H2SO4*SO3 / CH2Cl2 / 1.5 h / 20 °C 8: 92 percent / acetonitrile / 1.5 h / 60 °C View Scheme
Multi-step reaction with 7 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 76 percent / NaH / dimethylformamide / 3 h / 50 °C 5: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 6: 79 percent / H2SO4*SO3 / CH2Cl2 / 1.5 h / 20 °C 7: 92 percent / acetonitrile / 1.5 h / 60 °C View Scheme
Multi-step reaction with 9 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH; H2O / 2.33 h / 110 °C 5: 82 percent / Cl2 / CCl4 / 20 °C / Irradiation 6: 86 percent / Et3N*3HF / 9 h / 180 °C 7: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 8: 79 percent / H2SO4*SO3 / CH2Cl2 / 1.5 h / 20 °C 9: 92 percent / acetonitrile / 1.5 h / 60 °C View Scheme

sodium 2-biphenylate (132-27-4) → 5-(trifluoromethyl)-5H-dibenzo[b,d]thiophenium-3-sulfonate (160656-62-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 7: 84 percent / H2SO4*SO3 / CH2Cl2 / 20 h / 0 - 42 °C View Scheme
Multi-step reaction with 8 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 7: 79 percent / H2SO4*SO3 / CH2Cl2 / 1.5 h / 20 °C 8: H2SO4*SO3 / CH2Cl2 / 17 h / 42 °C View Scheme
Multi-step reaction with 6 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 76 percent / NaH / dimethylformamide / 3 h / 50 °C 5: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 6: 84 percent / H2SO4*SO3 / CH2Cl2 / 20 h / 0 - 42 °C View Scheme

sodium 2-biphenylate (132-27-4) → 2-<(Trichloromethyl)thio>biphenyl (220156-12-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH; H2O / 2.33 h / 110 °C 5: 82 percent / Cl2 / CCl4 / 20 °C / Irradiation View Scheme
Multi-step reaction with 5 steps 1: 86 percent / dimethylformamide / 1.) r.t., 2.) 80 deg C, 45 min 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: 92 percent / NaOH / H2O / 2.33 h / 110 °C 5: 82 percent / Cl2 / CCl4 / 1.75 h / 0 °C / Irradiation View Scheme

Upstream product

• 90-43-7 2-Phenylphenol 

Downstream Products

• 160656-62-2 5-(trifluoromethyl)-5H-dibenzo[b,d]thiophenium-3-sulfonate 
• 129946-88-9 Umemoto's reagent 
• 129922-49-2 2-<(trifluoromethyl)sulfinyl>biphenyl 
• 304-06-3 3-phenylsalicylic acid 
• 3983-83-3 1-(o-Phenyl-phenoxy)-4-phenoxy-benzol 
• 79380-82-8 2-hydroxy-5-(phenylazo)biphenyl 
• 144514-50-1 1-(Biphenyl-2-yloxy)-3,3,5,5-tetrachloro-1λ⁴,3λ⁵,5λ⁵-[1,2,4,6,3,5]thiatriazadiphosphinine 
• 79380-72-6 2,3-dihydro-5-methoxy-6-phenylbenzofuran-2-one 
• 60987-03-3 2,3-dihydro-5-hydroxy-6-phenylbenzofuran-2-one 
• 79380-81-7 2-methoxy-5-(phenylazo)biphenyl 
• 56970-26-4 6-methoxy-[1,1’-biphenyl]-3-amine 

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