947-42-2

Basic information

• Product Name: Diphenylsilanediol
• Synonyms: Diphenylsilanediol, min. 95%;Diphenylsilanediol,95%;Diphenylsilanediol,99%;Diphenylsilanediol,97%;Silanediol,1,1-diphenyl-;CD6150;Difenyl-dihydroxysilan;dihydroxydiphenyl-silan
• CAS NO: 947-42-2
• Molecular Formula: C₁₂H₁₂O₂Si
• Molecular Weight: 216.31
• EINECS: 213-427-4
• Product Categories: Si (Classes of Silicon Compounds);Silanols;Si-O Compounds;Phenyl Silanes;Organosilicon;Self Assembly&Contact Printing;Self-Assembly Materials;SilanesOrganometallic Reagents;Organometallic Reagents;organosilicon compounds
• Mol File: 947-42-2.mol
• Article Data: 46

Chemical Properties

• Melting Point: 144-147 °C
• Boiling Point: 353°C [760mmHg]
• Flash Point: 129 °F
• Appearance: white/Powder
• Density: 0.87
• Vapor Density: >1 (vs air)
• Vapor Pressure: 1.4E-05mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Flammables area
• PKA: 12.06±0.53(Predicted)
• Water Solubility: reacts
• Sensitive: Air & Light Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 2523445
• CAS DataBase Reference: Diphenylsilanediol(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenylsilanediol(947-42-2)
• EPA Substance Registry System: Diphenylsilanediol(947-42-2)

Safety Data

• Hazard Codes: F
• Statements: 11-10
• Safety Statements: 16-22-24/25-37-26
• RIDADR: UN 1325 4.1/PG 3
• WGK Germany: 1
• RTECS: VV3640000
• TSCA: Yes
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 947-42-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Diphenylsilanediol is used in Medicine field, electronics industry and polymer material.

Preparation

Diphenylsilanediol was obtained by controlled hydrolysis of diphenyldichlorosilane in the presence of aniline as acid acceptor and ethyl ether .

General Description

Diphenylsilanediol(DPSD) is an alkoxysilane that is used as a silane based precusor in the synthesis of organosiloxane based resins.

Flammability and Explosibility

Nonflammable

Purification Methods

Recrystallise it from CHCl3/methyl ethyl ketone. [Beilstein 16 IV 1523.]

InChI:InChI=1/C12H12O2Si/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H

Synthetic route

diphenylsilane (775-12-2) → diphenylsilanediol (947-42-2)

Conditions	Yield
With water In tetrahydrofuran at 20℃; for 0.5h;	99%
With oxygen In water; acetone at 30℃; under 760.051 Torr; for 0.333333h;	99%
With water; oxygen; hydroxyapatite-bound Ru In ethyl acetate at 80℃; for 9h;	98%

diphenylsilanol (5906-79-6) → diphenylsilanediol (947-42-2)

Conditions	Yield
With water; oxygen In tetrahydrofuran at 20℃; for 12h; Irradiation;	98%
With oxygen In tetrahydrofuran; water at 20℃; under 760.051 Torr; for 2h; Green chemistry;	96%
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In ethyl acetate; acetonitrile for 0.25h; Green chemistry;	78%
With dihydrogen peroxide; copper(II) oxide In acetonitrile at 45℃; for 3h; Irradiation;	98 %Chromat.

bis(benzyloxy)diphenylsilane (50870-65-0) → diphenylsilanediol (947-42-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 12h;	98%
With palladium-platinum; hydrogen In tetrahydrofuran at 20℃; for 1.5h; Concentration;	89%

diphenylsilane (775-12-2) → diphenylsilanediol (947-42-2) + hydrogen (1333-74-0)

Conditions	Yield
With water In acetone at 25℃; for 3h; Catalytic behavior;	A 97% B n/a
With water; silver nitrate at 24.84℃; for 0.416667h;	A 85% B 88%

diphenylsilyl dichloride (80-10-4) → diphenylsilanediol (947-42-2)

Conditions	Yield
With water In tert-Amyl alcohol; toluene at 10 - 12℃; for 0.166667h;	93%
With H2O In water; toluene addn. of a soln. of (C6H5)2SiCl2 in toluene to a heterogeneous mixt. of toluene, t-amylalc. and H2O;; sucking off; crystn. from warm 2-butanone/CHCl3;;	93%
With H2O In water; toluene addn. of a soln. of (C6H5)2SiCl2 in toluene to a heterogeneous mixt. of toluene, t-amylalc. and H2O;; sucking off; crystn. from warm 2-butanone/CHCl3;;	93%

diethoxydiphenylsilane (2553-19-7) → diphenylsilanediol (947-42-2)

Conditions	Yield
With potassium hydroxide In potassium hydroxide (C6H5)2Si(OC2H5)2 and 5% aq. KOH at room temp. for 6 h; neutralization by acetic acid;;	88.1%
With KOH In potassium hydroxide aq. KOH; (C6H5)2Si(OC2H5)2 and 5% aq. KOH at room temp. for 6 h; neutralization by acetic acid;;	88.1%

bis(2-thienyl)diphenylsilane (18676-80-7) → diphenylsilanediol (947-42-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0℃; for 2h;	86%

pentaphenyldisilanecarboxylic acid (70096-32-1) → diphenylsilanediol (947-42-2) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With potassium hydroxide In ethanol; water for 48h; Ambient temperature;	A 30% B 55%

dichloro-diphenoxy-silane (3410-97-7) + phenylmagnesium bromide → diphenylsilanediol (947-42-2)

Conditions	Yield
With diethyl ether

1,1,3,3-tetraphenyldisiloxane-1,3-diol (1104-93-4) → diphenylsilanediol (947-42-2)

Conditions	Yield
With potassium hydroxide; acetic acid
In not given addn. of acid to a cold soln. of tetraphenyl-1,3-dioxydisiloxane in aq. KOH;;
Multi-step reaction with 2 steps 1: neat (no solvent) 2: KOH / ethanol View Scheme

phenylmagnesium bromide → diphenylsilanediol (947-42-2) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With tetrachlorosilane; diethyl ether

4-dimethylaminophenyllithium (13190-50-6) + diphenylsilyl dichloride (80-10-4) → diphenylsilanediol (947-42-2) + ph2(ph-4-Nme2)SiOH (1516-77-4)

Conditions	Yield
anschliessenden Hydrolysieren;

diphenylsilyl dichloride (80-10-4) + aqueous KOH-solution → diphenylsilanediol (947-42-2) + high-molecular diphenylsilicon oxide

Hexaphenyltrisiloxan-1,5-diol (1110-85-6) + alcoholic KOH-solution → diphenylsilanediol (947-42-2)

1,1,3,3-tetraphenyldisiloxane-1,3-diol (1104-93-4) + acetic acid (64-19-7) + KOH-solution → diphenylsilanediol (947-42-2)

chloro-phenoxy-diphenyl-silane (18557-45-4) + KOH-solution → diphenylsilanediol (947-42-2) + phenol (108-95-2)

piperidine (110-89-4) + 1,4-diethyl-1,1,2,2,3,3,4,4-octaphenyl-tetrasilane (18816-58-5) + furan-2,3,5(4H)-trione pyridine (1:1) → diphenylsilanediol (947-42-2) + hydrogen

piperidine (110-89-4) + octaphenyl-1,4-diphenoxytetrasilane (18827-40-2) + concentrated NaOH-solution → diphenylsilanediol (947-42-2) + phenol (108-95-2) + hydrogen

diphenylsilane (775-12-2) → diphenylsilanediol (947-42-2) + diphenylsilanol (5906-79-6)

Conditions	Yield
With bis(oxazoline derivative) oxorhenium(V); water In acetonitrile at 20℃; Title compound not separated from byproducts;
With [Re(O)(hoz)2][B(C6F5)4]; water In acetonitrile at 20℃; Kinetics; Temperature; Reagent/catalyst;

Triphenylsilyl chloride (76-86-8) → diphenylsilanediol (947-42-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / Li / tetrahydrofuran 2: 30 percent / 1 M KOH / ethanol; H2O / 48 h / Ambient temperature View Scheme

phenylmagnesium bromide → diphenylsilanediol (947-42-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; silicon tetrachloride 2: diluted KOH-solution View Scheme

Diphenyldibromsilan (4072-00-8) → diphenylsilanediol (947-42-2)

Conditions	Yield
With potassium hydroxide In potassium hydroxide very impure;;
With water In water very impure;;
With KOH In potassium hydroxide aq. KOH; very impure;;
With H2O In water very impure;;

(OC)4Mn(μ-SiPh2)(μ-H)Pt(PPh3)2 (118398-34-8) → tetracarbonylhydrido(triphenylphosphine)manganese (16925-29-4) + (OC)4Mn(μ-PPh2)(μ-H)PtPh(PPh3) (118398-37-1) + diphenylsilanediol (947-42-2)

Conditions	Yield
With water In not given byproducts: H2;	A <1 B n/a C n/a

diphenylsilyl dichloride (80-10-4) → 1,1,3,3-tetraphenyldisiloxane-1,3-diol (1104-93-4) + diphenylsilanediol (947-42-2)

Conditions	Yield
With H2O; NH3 In ammonia aq. ammonia=NH3;
With H2O In water

dichloro-diphenoxy-silane (3410-97-7) → diphenylsilanediol (947-42-2)

Conditions	Yield
With phenylmagnesium bromide In diethyl ether (C6H5O)2SiCl2 and C6H5MgBr in ether; addn. of ice and HCl;;
With C6H5MgBr In diethyl ether (C6H5O)2SiCl2 and C6H5MgBr in ether; addn. of ice and HCl;;
With phenylmagnesium bromide In diethyl ether (C6H5O)2SiCl2 and C6H5MgBr in ether; addn. of ice and HCl;;

Hexaphenyltrisiloxan-1,5-diol (1110-85-6) → diphenylsilanediol (947-42-2)

Conditions	Yield
With KOH In ethanol ppt. by addn. of CH3COOH;;

diphenylsilanediol (947-42-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 1,1,1,5,5,5-hexamethyl-3,3-diphenyltrisiloxane (797-77-3)

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	99%

1,3-Divinyl-1,1,3,3-tetramethyl-disilazan(germ.)=divinyltetramethyldisiloxane (7691-02-3) + diphenylsilanediol (947-42-2) → 1,5-divinyl-3,3-diphenyl-1,1,5,5-tetramethyltrisiloxane (18586-22-6)

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	99%

diphenylsilanediol (947-42-2) → disodium diphenylsilanediolate

Conditions	Yield
With sodium tert-isoamylate In pyridine; diethyl ether at -10 - 25℃; for 1.5h;	98%

tert.-butylhydroperoxide (75-91-2) + diphenylsilanediol (947-42-2) + triphenylantimony (603-36-1) → Sb2O4Si2(C6H5)10 + water (7732-18-5) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In 1,4-dioxane dissoln., cooling (5°C), soln. of peroxo compd. addn. under stirring, stirring (2 h), volatile product sepn. in cooled trap (reduced pressure); elem. anal.;	A 98% B 89% C 96%

diphenylsilanediol (947-42-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → diphenyl-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane (82172-57-4)

Conditions	Yield
In toluene at 20℃; for 0.5h; Green chemistry; chemoselective reaction;	98%

diphenylsilanediol (947-42-2) + 1,1,3,3-tetramethyldisilazane (15933-59-2) → 1,1,5,5-tetramethyl-3,3-diphenyl-trisiloxane (17875-55-7)

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	98%

trimethoxysilane (2487-90-3) + diphenylsilanediol (947-42-2) → C16H24O6Si3 (1544138-11-5)

Conditions	Yield
In benzene at 20℃; for 16h; Inert atmosphere;	97%
With magnesium hydroxide In methanol; toluene at 30℃; for 8h;

diphenylsilanediol (947-42-2) + 4-fluoroboronic acid (1765-93-1) → 4,8-bis(4-fluorophenyl)-2,2,6,6-tetraphenyl-1,3,5,7,2,6,4,8-tetraoxadisiladiborocane

Conditions	Yield
In toluene Dean-Stark; Reflux; Inert atmosphere;	97%
In toluene for 12h; Dean-Stark; Reflux;	86%

1,1,1,3,5,7,7,7-octamethyltetrasiloxane (16066-09-4) + diphenylsilanediol (947-42-2) → 1,1-diphenyl-3,5-bis-trimethylsiloxy-3,5-dimethylcyclotrisiloxane (188240-37-1)

Conditions	Yield
Stage #1: diphenylsilanediol With tris(pentafluorophenyl)borate In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; Inert atmosphere; Stage #2: 1,1,1,3,5,7,7,7-octamethyltetrasiloxane In 5,5-dimethyl-1,3-cyclohexadiene at 40 - 60℃; for 2h; Inert atmosphere;	96%

diphenylsilanediol (947-42-2) + tetraacetoxysilane (562-90-3) → 1,1,5,5-tetraacetoxy-3,3,7,7-tetraphenyl-1,3,5,7-cyclotetrasiloxane

Conditions	Yield
Stage #1: diphenylsilanediol; tetraacetoxysilane In acetonitrile at 25℃; for 1h; Stage #2: diphenylsilanediol In acetonitrile at 25℃; for 24h;	95%

tetramethyldivinyldisiloxane (2627-95-4) + diphenylsilanediol (947-42-2) → 1,5-divinyl-3,3-diphenyl-1,1,5,5-tetramethyltrisiloxane (18586-22-6)

Conditions	Yield
With toluene-4-sulfonic acid In hexane at 70 - 80℃; for 2h; Reagent/catalyst; Inert atmosphere; Green chemistry;	94.6%

diphenylsilanediol (947-42-2) + 3-Aminophenylboronic acid (30418-59-8) → (NH2C6H4BO)2((C6H5)2SiO)2

Conditions	Yield
In toluene Condensation; Heating;	94%
In toluene byproducts: H2O; under N2; Ph2Si(OH)2 added to m-NH2C6H4B(OH)2 (molar ratio 1:1) in toluene; heated to reflux in Dean-Stark apparatus; elem. anal.;	94%

diphenylsilanediol (947-42-2) + trimethylsilylacetylene (1066-54-2) → 1,1,1,5,5,5-hexamethyl-3,3-diphenyltrisiloxane (797-77-3)

Conditions	Yield
With potassium hexamethylsilazane In acetonitrile at 40℃; for 0.5h; Inert atmosphere; Green chemistry; chemoselective reaction;	94%

[(HC(CMeN(2,6-i-Pr2C6H3))2)AlH2] (278608-73-4) + diphenylsilanediol (947-42-2) → [HC(CMeN(2,6-iPr2C6H3))2AlHO]2SiPh2 (1410247-90-3)

Conditions	Yield
In toluene at 20℃; for 72h; Schlenk technique; Inert atmosphere;	93.5%

diphenylsilanediol (947-42-2) → ({Sr[O(SiPh2O)2](H2O)(NH3)}n)

Conditions	Yield
With ammonia; water; strontium In toluene	93%

butylboronic acid (4426-47-5) + diphenylsilanediol (947-42-2) → 4,8-dibutyl-2,2,6,6-tetraphenyl-[1,3,5,7,2,6,4,8]tetroxadisiladiborocane

Conditions	Yield
In toluene Condensation; Heating;	93%
In toluene byproducts: H2O; under N2; Ph2Si(OH)2 added to C4H9B(OH)2 (molar ratio 1:1) in toluene; heated to reflux in Dean-Stark apparatus; elem. anal.;	93%

diphenylsilanediol (947-42-2) → octaphenylcyclotetrasiloxane (546-56-5)

Conditions	Yield
With triethylamine In toluene	92.1%
at 140 - 180℃;
With acetyl chloride

diphenylsilanediol (947-42-2) + 2-Methoxyphenylboronic acid (5720-06-9) → 4,8-bis-(2-methoxy-phenyl)-2,2,6,6-tetraphenyl-[1,3,5,7,2,6,4,8]tetroxadisiladiborocane

Conditions	Yield
In toluene Condensation; Heating;	92%

diphenylsilanediol (947-42-2) + 2-Methylphenylboronic acid (16419-60-6) → (CH3C6H4BO)2((C6H5)2SiO)2 (261720-27-8)

Conditions	Yield
In toluene byproducts: H2O; under N2; Ph2Si(OH)2 added to o-MeC6H4B(OH)2 (molar ratio 1:1) in toluene; heated to reflux in Dean-Stark apparatus; elem. anal.;	92%

diphenylsilanediol (947-42-2) + naphthalene-2-boronic acid (32316-92-0) → 4,8-di(naphthalen-2-yl)-2,2,6,6-tetraphenyl-1,3,5,7,2,6,4,8-tetraoxadisiladiborocane

Conditions	Yield
In toluene for 12h; Dean-Stark; Reflux;	92%

2,3-dimethyl-2,3-butane diol (76-09-5) + diphenylsilanediol (947-42-2) + boric acid (11113-50-1) → diphenyl-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane (82172-57-4)

Conditions	Yield
In toluene byproducts: H2O; inert atmosphere; refluxing (8 h); evapn., hexanes addn., filtering, pptn. on concg. (-22°C, severalh); elem. anal.;	90.1%
In benzene byproducts: H2O; azeotropic dehydration with C6H6, molar ratio of H3BO3:Ph2Si(OH)2:diol=2:1:2, under reflux; elem. anal.;

diphenylsilanediol (947-42-2) → 1,1,3,3,5,5-hexaphenylcyclotrisiloxane (512-63-0)

Conditions	Yield
With sulfuric acid In ethyl acetate for 96h; Product distribution; other reagents and solvents, var. temp.;	90%
With toluene-4-sulfonic acid In water for 168000h;	70%
With toluene-4-sulfonic acid for 4.91667h;	49%

diphenylsilanediol (947-42-2) + m-nitrobenzene boronic acid (13331-27-6) → 4,8-bis-(3-nitro-phenyl)-2,2,6,6-tetraphenyl-[1,3,5,7,2,6,4,8]tetroxadisiladiborocane

Conditions	Yield
In toluene Condensation; Heating;	90%
In toluene byproducts: H2O; under N2; Ph2Si(OH)2 added to m-NO2C6H4B(OH)2 (molar ratio 1:1) in toluene; heated to reflux in Dean-Stark apparatus; elem. anal.;	90%

bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5) + diphenylsilanediol (947-42-2) → {(C5H5)2Zr(OSi(C6H5)2O)}2

Conditions	Yield
In diethyl ether byproducts: CH4; Ar-atmosphere; addn. of equimolar amt. of silanol to metal complex (0°C); evapn., addn. of toluene and hexane, filtration, crystn. (refrigerator, 2 days); elem. anal.;	90%

bis(cyclopentadienyl)hafnium dimethyl + diphenylsilanediol (947-42-2) → {(C5H5)2Hf(OSi(C6H5)2O)}2

Conditions	Yield
In diethyl ether byproducts: CH4; Ar-atmosphere; addn. of equimolar amt. of silanol to metal complex (0°C); evapn., addn. of toluene and hexane, filtration, crystn. (refrigerator, 2 days);	90%

Upstream product

• 80-10-4 diphenylsilyl dichloride 
• 110-89-4 piperidine 
• 18816-58-5 1,4-diethyl-1,1,2,2,3,3,4,4-octaphenyl-tetrasilane 
• 4072-00-8 Diphenyldibromsilan 
• 2553-19-7 diethoxydiphenylsilane 
• 118398-34-8 (OC)4Mn(μ-SiPh2)(μ-H)Pt(PPh3)2 
• 3410-97-7 dichloro-diphenoxy-silane 
• 1110-85-6 Hexaphenyltrisiloxan-1,5-diol 
• 512-63-0 1,1,3,3,5,5-hexaphenylcyclotrisiloxane 
• 5906-79-6 diphenylsilanol 
• 50870-65-0 bis(benzyloxy)diphenylsilane 
• 775-12-2 diphenylsilane 
• 6843-66-9 dimethoxy(diphenyl)silane 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 1000-00-6 1,3-dimethyl-1,1,3,3-tetraethyldisiloxane 
• 18817-04-4 1,1,5,5-tetraethyl-1,5-dimethyl-3,3-diphenyl-trisiloxane 
• 797-77-3 1,1,1,5,5,5-hexamethyl-3,3-diphenyltrisiloxane 
• 1693-48-7 1,1,5,5-tetramethyl-3,3,7,7-tetraaphenylcyclotetrasiloxane 
• 18845-87-9 1,1,1,5,5,5-hexa-sec-butoxy-3,3-diphenyl-trisiloxane 
• 56764-47-7 C₁₄H₁₆Cl₄O₂Si₃ 
• 56764-60-4 C₁₈H₂₂Cl₂O₂Si₃ 
• 64793-15-3 2,2,6,6-Tetraethoxy-4,4,8,8-tetraphenyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocane 
• 56764-48-8 C₁₆H₁₆Cl₄O₂Si₃ 
• 65197-32-2 1,5-dichloro-1,1,5,5-tetramethyl-3,3-diphenyltrisiloxane 
• 67059-36-3 3,3-Dimethyl-1,1,5,5-tetraphenyl-1,5-trisiloxandiol 
• 15040-12-7 2.2.4.4-Tetramethyl-6.6-diphenyl-1.5-dioxa-3-aza-cyclohexasilan 
• 18919-31-8 1,1,1,5,5,5-hexaethyl-3,3-diphenyltrisiloxane 
• 1693-51-2 1,1,3,3-tetramethyl-5,5-diphenylcyclotrisiloxane 

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