2469-55-8

Basic information

• Product Name: 1,3-Bis(3-aminopropyl)tetramethyldisiloxane
• Synonyms: 1,3-BIS(AMINOPROPYL)TETRAMETHYLDISILOXANE;1,3-BIS(3-AMINOPROPYL)-1,1,3,3-TETRAMETHYLDISILOXANE;1,3-BIS(3-AMINOPROPYL)TETRAMETHYLDISILOXANE;BIS(3-AMINOPROPYL)TETRAMETHYLDISILOXANE;BIS(AMINOPROPYL)TETRAMETHYLDISILOXANE;TETRAMETHYL-1,3-BIS(3-AMINOPROPYL)DISILOXANE;1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyl-disiloxan;1,3-bis(3-aminopropyl)tetramethyldislloxane
• CAS NO: 2469-55-8
• Molecular Formula: C₁₀H₂₈N₂OSi₂
• Molecular Weight: 248.51
• EINECS: 219-588-7
• Product Categories: Si (Classes of Silicon Compounds);Siloxanes;Si-O Compounds
• Mol File: 2469-55-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 132 °C11 mm Hg(lit.)
• Flash Point: 91°C
• Appearance: /
• Density: 0.901 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.27Pa at 20℃
• Refractive Index: n20/D 1.451
• Storage Temp.: 2-8°C
• PKA: 10.96±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• BRN: 1760876
• CAS DataBase Reference: 1,3-Bis(3-aminopropyl)tetramethyldisiloxane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(3-aminopropyl)tetramethyldisiloxane(2469-55-8)
• EPA Substance Registry System: 1,3-Bis(3-aminopropyl)tetramethyldisiloxane(2469-55-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-28-36/37/39-45-36/37/38
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• RTECS: JM9235000
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2469-55-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 2469-55-8 differently. You can refer to the following data:
1. 1,3-Bis(3-aminopropyl)tetramethyldisiloxane is an endcapper for the synthesis of aminopropyl-terminated silicone fluids and for the production of silicone-epoxy and silicone polyimide copolymers especially useful in electronics applications. A unique manufacturing process insures that It has only gamma - aminopropyl substitution and none of the beta isomer. This is expected to give better reactivity in copolymer synthesis and improved heat stability. 1,3-Bis(3-aminopropyl)tetramethyldisiloxane is an alkaline material due to its amine reactive groups. Care should be exercised in handling it to prevent contact with skin and eyes. Wear safety glasses with side shields and rubber gloves when handling.
2. 1,3-Bis(aminopropyl)tetramethyldisiloxane is used as a curing agent for epoxy molding compounds, which is utilized for high-reliability semiconductor devices. It is also used to prepare siloxane- urea copymers from 4,4?-diphenylmethane diisocyanate.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.

Synthetic route

methanol (67-56-1) + bis(trimethylsilylaminopropyl)tetramethyldisiloxane (151565-10-5) + bis(hexamethyldisilylaminopropyl)tetramethyldisiloxane (59384-10-0) → Hexamethyldisiloxane (107-46-0) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
for 2h; Product distribution / selectivity; Heating / reflux;	A n/a B 94.1%

bis(methylcarbamatopropyl)tetra-methyldisiloxane (1070740-24-7) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
Stage #1: bis(methylcarbamatopropyl)tetra-methyldisiloxane With water; sulfuric acid at 100℃; for 16h; Stage #2: With sodium hydroxide In water Product distribution / selectivity;	94%

bis(trimethylsilylaminopropyl)tetramethyldisiloxane (151565-10-5) + bis(hexamethyldisilylaminopropyl)tetramethyldisiloxane (59384-10-0) → Hexamethyldisiloxane (107-46-0) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
With water at 78 - 80℃; for 1h; Product distribution / selectivity;	A n/a B 92.7%

silyl carbamate + tetramethyldivinyldisiloxane (2627-95-4) + platinum (7440-06-4) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
chloroplatinic acid	84%

1,1,3,3-Tetramethyldisiloxane (3277-26-7) + 1-amino-2-propene (107-11-9) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
at 80 - 110℃; under 3750.38 Torr; for 6h; Concentration; Pressure; Temperature; Inert atmosphere;	80.56%

1,1,3,3-Tetramethyldisiloxane (3277-26-7) + allylaminotrimethylsilane → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 95 - 125℃; Inert atmosphere;	58%

allylamino-trimethyl-silane (10519-97-8) + 1,1,3,3-Tetramethyldisiloxane (3277-26-7) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
With dihydrogen hexachloroplatinate; ethanol

(3-aminopropyl)(ethoxy)dimethylsilane (18306-79-1) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
With potassium hydroxide

α,ω-Bis-(2-cyan-ethyl)-tetramethyldisiloxan (2603-88-5) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
With hydrogen; Co catalyst

chloropropyl(dimethyl)ethoxysilane (13508-63-9) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3 2: aqueous KOH View Scheme

(3-chloropropyl)dimethylchlorosilane (10605-40-0) → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
Multi-step reaction with 3 steps 2: NH3 3: aqueous KOH View Scheme

C28H40N2O5Si2 → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + coumarin (91-64-5)

Conditions	Yield
In methanol UV-irradiation;

C26H32N2O5Si2 → 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8)

Conditions	Yield
With hydrazine hydrate In ethanol at 70 - 110℃; for 4h; Inert atmosphere;	11.9 g

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + acrylic acid methyl ester (292638-85-8) → C26H52N2O9Si2 (1266558-39-7)

Conditions	Yield
In methanol at 50℃; for 48h;	99%
In methanol at 50℃; for 48h;	96%
In methanol at 50℃; for 48h; Michael condensation; Inert atmosphere;	95%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + acrylonitrile (107-13-1) → C22H40N6OSi2

Conditions	Yield
In methanol at 50℃; for 48h;	99%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → C26H40N2O5Si2

Conditions	Yield
In methanol; chloroform at 20℃; for 8h; Reflux;	98%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → nadic anhydride

Conditions	Yield
In N,N-dimethyl acetamide at 20℃; for 6h; Inert atmosphere;	97.2%

isatoic anhydride (118-48-9) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → 1,3-bis<3-(2-aminobenzamido)propyl>-1,1,3,3-tetramethyldisiloxane

Conditions	Yield
In ethanol for 2h; Ambient temperature;	96%

thiophosgene (463-71-8) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → 1,3-bis(3-isothiocyanatopropyl)-1,1,3,3-tetramethyldisiloxane

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 2.5h; Reflux;	95%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + salicylaldehyde (90-02-8) → C24H36N2O3Si2

Conditions	Yield
In methanol for 10h; Reflux;	95%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → bis((9H-fluoren-9-yl)methyl) ((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))dicarbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	95%

3,5-Dibromosalicylaldehyde (90-59-5) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → C24H32Br4N2O3Si2

Conditions	Yield
In dichloromethane at 20℃; for 1h;	95%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 2,3-dihydroxybenzaldehyde (24677-78-9) → C24H36N2O5Si2

Conditions	Yield
In dichloromethane at 20℃; for 1h;	95%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 3,5-dichlorosalicyclaldehyde (90-60-8) → C24H32Cl4N2O3Si2

Conditions	Yield
In dichloromethane at 20℃; for 1h; Kinetics;	95%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 4-methyl-benzaldehyde (104-87-0) → {3-[1,1,3,3-tetramethyl-3-(3-{[1-p-tolylmeth-(E)-ylidene]amino}propyl)disiloxanyl]propyl}-[1-p-tolylmeth-(E)-ylidene]amine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃;	92%

2-pyrrole aldehyde (1003-29-8) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → N,N'-bis(pyrrol-2-ylmethylene)tetramethyldisiloxane-1,3-bis(propanamine) (1421633-91-1)

Conditions	Yield
In methanol at 20℃; for 3.16667h; Reflux;	91%

2-furancarbonyl chloride (527-69-5) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → C20H32N2O5Si2

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 24h; Cooling with ice;	90%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 2-hydroxy-5-methylbenzaldehyde (613-84-3) → C26H40N2O3Si2

Conditions	Yield
In ethanol; chloroform for 4h; Reflux;	90%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + benzenesulfonyl chloride (98-09-9) → N,N’-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))dibenzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	89%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 4-(diphenylamino)benzaldehyde (4181-05-9) → C48H54N4OSi2

Conditions	Yield
In dichloromethane at 20℃; for 24h; Molecular sieve;	86%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + C94H196N10O25Si10 → C166H388N26O25Si26

Conditions	Yield
In methanol at 50℃; for 168h;	81%
In methanol

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → C44H60N4O6Si4 (1272671-23-4)

Conditions	Yield
With zinc(II) acetate dihydrate In quinoline at 100 - 160℃; for 12h;	80%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + trimellitic Anhydride (552-30-7) → 1,3-bis(3-trimellitylimidopropyl)tetramethyldisiloxane (915101-62-1)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Reflux;	80%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + C26H52N2O9Si2 (1266558-39-7) → C62H148N10O9Si10

Conditions	Yield
In methanol at 50℃; for 168h;	80%
In methanol

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + isobutyryl chloride (79-30-1) → N,N′-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(propane-3,1-diyl))bis(2-methylpropanamide)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	80%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → 1,3-bis(3-ammoniumpropyl)tetramethyldisiloxane nitrate

Conditions	Yield
With copper(II) nitrate trihydrate; 4(5)formylimidazole In methanol; dichloromethane at 75℃; for 4h;	80%

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) + 2,4-Dihydroxybenzaldehyde (95-01-2) → C24H36N2O5Si2 (648441-58-1)

Conditions	Yield
In methanol for 10h; Reflux;	76.7%

5-Chloroisatoic anhydride (4743-17-3) + 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane (2469-55-8) → 1,3-bis<3-(5-chloro-2-aminobenzamido)propyl>-1,1,3,3-tetramethyldisiloxane

Conditions	Yield
In ethanol for 2h; Ambient temperature;	74%

Upstream product

• 10519-97-8 allylamino-trimethyl-silane 
• 3277-26-7 1,1,3,3-Tetramethyldisiloxane 
• 18306-79-1 (3-aminopropyl)(ethoxy)dimethylsilane 
• 13508-63-9 chloropropyl(dimethyl)ethoxysilane 
• 107-11-9 1-amino-2-propene 
• 1070740-24-7 bis(methylcarbamatopropyl)tetra-methyldisiloxane 
• 151565-10-5 bis(trimethylsilylaminopropyl)tetramethyldisiloxane 
• 59384-10-0 bis(hexamethyldisilylaminopropyl)tetramethyldisiloxane 
• 67-56-1 methanol 
• 2627-95-4 tetramethyldivinyldisiloxane 
• 7440-06-4 platinum 
• 10605-40-0 (3-chloropropyl)dimethylchlorosilane 
• 2603-88-5 α,ω-Bis-(2-cyan-ethyl)-tetramethyldisiloxan 

Downstream Products

• 648441-58-1 C₂₄H₃₆N₂O₅Si₂ 
• 349607-63-2 C₂₄H₃₆N₂O₃Si₂ 

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A supramolecular structure based on copper complex of 2,3-pyridinedicarboxylic acid and 1,3-bis(3-aminopropyl)tetramethyldisiloxane chlorohydrate07/13/2019

Having in mind the synthesis of a cooper complex with the product of condensation between an anhydride and a siloxane diamine as a new polydentate ligand, 2,3-pyridinedicarboxylic anhydride (PDCA) was treated first with 1,3-bis(3-aminopropyl)tetramethyldisiloxane (AP0) and then with cooper chlor...detailed

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