5931-17-9

Basic information

• Product Name: 1,3-BIS(4-HYDROXYBUTYL)TETRAMETHYLDISILOXANE
• Synonyms: 1,3-BIS(HYDROXYBUTYL)TETRAMETHYLDISILOXANE;1,3-BIS(4-HYDROXYBUTYL)TETRAMETHYLDISILOXANE;1,3-BIS(4-HYDROXYBUTYL)-1,1,3,3-TETRA- METHYLDISILOXANE;1,3-Di(3-Hydroxylbutyl)-1,1,3,3-Tetramethyl-Disiloxane;Dihydroxybutyltetramethyldisiloxane;4,4μ-(1,1,3,3-Tetramethyldisiloxane-1,3-diyl)dibutan-1-ol;1,3-Bis(4-hydroxybutyl)-1,1,3,3-tetramethylpropanedisiloxane;4,4'-[Oxybis(dimethylsilanediyl)]bis(butane-1-ol)
• CAS NO: 5931-17-9
• Molecular Formula: C₁₂H₃₀O₃Si₂
• Molecular Weight: 278.54
• Product Categories: Si (Classes of Silicon Compounds);Siloxanes;Si-O Compounds
• Mol File: 5931-17-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 148 °C
• Flash Point: 110°C
• Appearance: Clear to straw liquid with mild odor
• Density: 0.95
• Vapor Pressure: 7.31E-05mmHg at 25°C
• Refractive Index: 1.4526 [25°C]
• PKA: 14.89±0.10(Predicted)
• CAS DataBase Reference: 1,3-BIS(4-HYDROXYBUTYL)TETRAMETHYLDISILOXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(4-HYDROXYBUTYL)TETRAMETHYLDISILOXANE(5931-17-9)
• EPA Substance Registry System: 1,3-BIS(4-HYDROXYBUTYL)TETRAMETHYLDISILOXANE(5931-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• TSCA: No
• Hazardous Substances Data: 5931-17-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H30O3Si2/c1-16(2,11-7-5-9-13)15-17(3,4)12-8-6-10-14/h13-14H,5-12H2,1-4H3

Synthetic route

4-(dimethylsiloxy)-1-butene (23483-24-1) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9)

Conditions	Yield
Stage #1: 4-(dimethylsiloxy)-1-butene With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; triethylamine In isopropyl alcohol at 90℃; for 10h; Stage #2: With hydrogenchloride; water at 90℃; for 10h;	86.37%
With sodium hydroxide

1,3-bis(4-trimethylsiloxybutyl)tetramethyldisiloxane (113425-96-0) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9)

Conditions	Yield
With methanol for 3h; Ambient temperature;	84%

4-acetoxy-n-butyldimethylchlorosilane (70761-34-1) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9)

Conditions	Yield
With acetic acid In water; toluene pH=2;	83.7%

2,2-Dimethyl-1-oxa-2-silacyclohexan (5833-47-6) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9)

Conditions	Yield
With potassium hydroxide; acetylene In water at 110℃; under 11250.9 Torr; for 3h;	50%
With hydrogenchloride; acetone

1,3-bis(4-trimethylsiloxybutyl)tetramethyldisiloxane (113425-96-0) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + δ-hydroxybutylpentamethyldisiloxane (74970-78-8)

Conditions	Yield
With hydrogenchloride In diethyl ether at 25℃; for 15h;	A 47% B 29%

2,2-Dimethyl-1-oxa-2-silacyclohexan (5833-47-6) + Hexamethyldisiloxane (107-46-0) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + δ-hydroxybutylpentamethyldisiloxane (74970-78-8)

Conditions	Yield
With potassium hydroxide; acetylene In water at 120℃; under 12000.9 Torr; for 4h;	A 3.5 g B 37%

tetrahydrofuran (109-99-9) + dimethylsilicon dichloride (75-78-5) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9)

Conditions	Yield
(i) MgBr2, Mg, (ii) aq. HCl; Multistep reaction;

2,2-Dimethyl-1-oxa-2-silacyclohexan (5833-47-6) + Trimethylsilanol (1066-40-6) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + δ-hydroxybutylpentamethyldisiloxane (74970-78-8)

Conditions	Yield
With hydrogenchloride at 90℃; for 2h;	A 1.1 g B n/a
With hydrogenchloride at 90℃; for 2h;	A n/a B 3.5 g

chloro(4-chlorobutoxy)dimethylsilane (1002-04-6) → 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium 2: aqueous HCl; acetone View Scheme

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + dimethoxy(methyl)phenylsilane (3027-21-2) → methanol (67-56-1) + hydroxybutyl-terminated polymethylsiloxane with fifty percent phenyl content

Conditions	Yield
With hydrogenchloride In water for 4.5h; Heating / reflux;	A n/a B 100%

4‐oxo‐4‐(prop‐2‐ynyloxy)butanoic acid + 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) → C26H42O9Si2 (1362107-86-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -20 - 20℃; Inert atmosphere;	76%

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) → C12H28I2OSi2 (1378236-10-2)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 0 - 20℃; for 1h;	70%

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + p-toluenesulfonyl chloride (98-59-9) → C26H42O7S2Si2 (933994-18-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 2h;	70%

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + 4-Carboxybenzaldehyde (619-66-9) → C28H38O7Si2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	67%

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) → 2,2-Dimethyl-1-oxa-2-silacyclohexan (5833-47-6)

Hexamethyldisiloxane (107-46-0) + 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) → δ-hydroxybutylpentamethyldisiloxane (74970-78-8)

Conditions	Yield
With acetylene at 150℃; for 5h;	10 g

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + octamethylcyclotetrasiloxane (556-67-2) → poly(dimethylsiloxane) containing terminal 4-hydroxybutyl groups

Conditions	Yield
With sulfonic acid

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + divinyl carbonate (7570-02-7) → 1,3-bis-[(4-vinyloxycarbonyloxy)but-1-yl]tetramethyldisiloxane

Conditions	Yield
In xylene for 12h; Heating / reflux;

dimethyldimethoxysilan (1112-39-6) + 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + dimethoxy(diphenyl)silane (6843-66-9) → methanol (67-56-1) + poly(dimethylsiloxane-co-diphenylsiloxane)

Conditions	Yield
With hydrogenchloride; water for 2h; Heating / reflux;

dimethyldimethoxysilan (1112-39-6) + 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + dimethoxy(diphenyl)silane (6843-66-9) → methanol (67-56-1) + hydroxybutyl-terminated copolymer of dimethylsiloxane and diphenylsiloxane

Conditions	Yield
With hydrogenchloride In water for 2h; Heating / reflux;

dimethyldimethoxysilan (1112-39-6) + 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + dimethoxy(diphenyl)silane (6843-66-9) → hydroxybutyl-terminated copolymer of dimethylsiloxane and diphenylsiloxane with a 27:9 ratio of methyl/phenyl and a molecular weight of 4000

Conditions	Yield
Stage #1: dimethyldimethoxysilan; 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane; dimethoxy(diphenyl)silane With hydrogenchloride In water for 1h; Heating / reflux; Stage #2: In water for 1h; Heating / reflux;

dimethyldimethoxysilan (1112-39-6) + 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + dimethoxy(methyl)phenylsilane (3027-21-2) → hydroxybutyl-terminated copolymer of dimethylsiloxane and phenylmethylsiloxane with a 1:3 ratio of total methyl to phenyl attached to silicon and molecular weight of 4000

Conditions	Yield
Stage #1: dimethyldimethoxysilan; 1,3-bis(4-hydroxybutyl)tetramethyldisiloxane; dimethoxy(methyl)phenylsilane With hydrogenchloride In water for 1h; Heating / reflux; Stage #2: In water for 1h; Heating / reflux;

1,3-bis(4-hydroxybutyl)tetramethyldisiloxane (5931-17-9) + Propiolic acid (471-25-0) → C18H30O5Si2 (1197984-91-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -20℃;

Upstream product

• 70761-34-1 4-acetoxy-n-butyldimethylchlorosilane 
• 23483-24-1 4-(dimethylsiloxy)-1-butene 
• 109-99-9 tetrahydrofuran 
• 75-78-5 dimethylsilicon dichloride 
• 5833-47-6 2,2-Dimethyl-1-oxa-2-silacyclohexan 
• 1002-04-6 chloro(4-chlorobutoxy)dimethylsilane 
• 113425-96-0 1,3-bis(4-trimethylsiloxybutyl)tetramethyldisiloxane 
• 107-46-0 Hexamethyldisiloxane 
• 1066-40-6 Trimethylsilanol 

Downstream Products

• 933994-18-4 C₂₆H₄₂O₇S₂Si₂ 
• 67-56-1 methanol 
• 5833-47-6 2,2-Dimethyl-1-oxa-2-silacyclohexan 

Relevant articles and documents

A dog (d) for the preparation of hexamethyl disilane

The invention relates to a preparation method for hydroxypropyl (butyl) disiloxane. The preparation method comprises the following steps: (1) mixing an allyl alcohol salt-allyl alcohol mixed solution or an alkenyl butyl alcohol salt-alkenyl butyl alcohol mixed solution and hydrogen chlorosilane in an organic solvent, introducing inert gas, stirring the mixture to react, distilling the mixture and collecting a fraction to obtain an alcoholysis product; (2) adding a hydrosilylation catalyst and a co-catalyst into the alcoholysis product, stirring the mixture to react for 4-10 hours, and after reaction, naturally cooling the mixture to room temperature; and (3) adding a hydrochloric acid solution into the product obtained in the step (2), stirring the mixture and carrying out reflux reaction for 5-12 hours, after reaction, naturally cooling the mixture to room temperature, adjusting the pH to neutral, separating liquids to remove a lower solution, washing an organic phase by water to neutral, extracting the organic phase by an extraction agent, removing the extraction agent and drying the mixture to obtain the hydroxypropyl (butyl) disiloxane. The method provided by the invention is high in yield of target product, the highest yield of the alcoholysis product can reach 94.32%, and the highest yield of an addition-hydrolysate can reach 89.58%.

REACTION OF DIMETHYLSILAOXACYCLOHEXANE WITH METHACRYLIC ACID AND TRIETHYLSILANOL. SYNTHESIS OF METHACRYLOXYBUTYLDIMETHYL(TRIETHYLSILOXY)SILANE

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SYNTHESIS OF DIMETHYLORGANO(4-HYDROXYBUTYL)SILANES AND DIMETHYLORGANOSILANES

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