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13154-24-0

13154-24-0

Identification

Synonyms:Silane,chlorotriisopropyl- (6CI,7CI,8CI);Chlorotriisopropylsilane;Chlorotris(1-methylethyl)silane;Triisopropylchlorosilane;Triisopropylsilylchloride;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Triisopropylchlorosilane
  • Packaging:25g
  • Price:$ 359
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Chlorotris(1-methylethyl)silane
  • Packaging:25g
  • Price:$ 80
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  • Manufacture/Brand:TRC
  • Product Description:Chlorotris(1-methylethyl)silane
  • Packaging:100g
  • Price:$ 225
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Triisopropylsilyl Chloride >95.0%(GC)
  • Packaging:250mL
  • Price:$ 558
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Triisopropylsilyl Chloride >95.0%(GC)
  • Packaging:25mL
  • Price:$ 102
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Triisopropylsilyl Chloride >95.0%(GC)
  • Packaging:5mL
  • Price:$ 38
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Tris(isopropyl)silyl chloride
  • Packaging:100 g
  • Price:$ 68
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Triisopropylsilyl chloride 97%
  • Packaging:50g
  • Price:$ 238
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Chlorotriisopropylsilane for synthesis. CAS 13154-24-0, molar mass 192.8 g/mol., for synthesis
  • Packaging:8145090050
  • Price:$ 259
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Triisopropylsilyl chloride 97%
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Relevant articles and documentsAll total 13 Articles be found

Kinetic and Theoretical Investigation of Iron(III)-Catalyzed Silane Chlorination

Savela, Risto,Grnman, Henrik,Sundelin, Heidi,Norrby, Per-Ola,Yu. Murzin, Dmitry,Leino, Reko

, p. 584 - 592 (2016)

A highly versatile, robust, and efficient methodology for chlorination of silanes, methoxysilanes and silanols using low loadings of FeCl3 or Fe(acac)3 as the catalyst in the presence of 1-1.5?equivalents of acetyl chloride as the chlorine source was recently developed. The aim of the present paper is to evaluate and derive the reaction mechanisms involved in this reaction by calculating substrates, intermediates, products, and selected transition states, as well as by employing mathematical modeling of the reaction kinetics. The results obtained required reconsideration of the originally proposed overall reaction mechanism. Based on the kinetic and molecular modeling, a new revised reaction mechanism was developed giving a very good correspondence between the experimental data and calculations.

Hexachloroethane: a highly efficient reagent for the synthesis of chlorosilanes from hydrosilanes

Pongkittiphan, Veerachai,Theodorakis, Emmanuel A.,Chavasiri, Warinthorn

, p. 5080 - 5082 (2009)

A new and efficient chlorination protocol is presented for the preparation of chlorosilanes from hydrosilanes. A variety of chlorinating agents in combination with palladium(II) chloride as the catalyst are examined. Among them, hexachloroethane is found to be the best choice, furnishing the desired product in good to quantitative yields under mild conditions. Various hydrosilanes are used as starting materials to explore the scope of this reaction.

-

Gilman, H.,Clark, R. N.

, p. 1499 - 1500 (1947)

-

Preparation of 1,1,3,3-tetraisopropyl-1,3-dichlorodisiloxane and triisopropylchlorosilane

Chawla, Ram,Larson, Gerald L.

, p. 3499 - 3501 (1999)

A facile, hydrochloric acid-free chlorination of silanes was developed. This allows for the elimination of siloxane bond cleavage and chlorination of carbon-hydrogen bonds during the chlorination of the Si-H bond.

Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

Fan, Xuanzi,Xiao, Pin,Jiao, Zeqing,Yang, Tingting,Dai, Xiaojuan,Xu, Wengang,Tan, Jin Da,Cui, Ganglong,Su, Hongmei,Fang, Weihai,Wu, Jie

supporting information, p. 12580 - 12584 (2019/08/16)

Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si?H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.

A method for synthesizing three silane isopropyl chloride

-

Paragraph 0028; 0029, (2017/01/12)

The invention relates to a high-strength triisopropyl chlorosilane synthesis method, and relates to the technical field of triisopropyl chlorosilane chemical synthesis. According to the invention, triisopropyl silane is subjected to a reaction with an oxidant, such that triisopropyl silanol is prepared, wherein the oxidant is at least any one selected from hydrogen peroxide, peracetic acid, potassium ferrate, potassium chlorate, sodium chlorate, sodium hypochlorite or potassium permanganate; triisopropyl silanol and hydrogen chloride gas are adopted as raw materials, and triisopropyl chlorosilane is prepared under a temperature condition of -5 DEG C to 5 DEG C. According to the invention, triisopropyl silanol is prepared by using triisopropyl silane and the oxidant. Triisopropyl silane can be quantitatively oxidized, no side reaction is caused, and the yield can reach 100%. The chlorination process is carried out under low temperature. Once hydrogen chloride delivery amount is controlled, triisopropyl chlorosilane hydrolysis can be effectively inhibited, and a yield can be higher than 99%.

Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans

Dunn, Jonathan,Dobbs, Adrian P.

, p. 7386 - 7414 (2015/08/24)

Abstract A detailed study on the synthesis and reactions of silylmethylcyclopropanes is reported. In their simplest form, these donor-only cyclopropanes undergo Lewis acid promoted reaction to give either cis- or trans-tetrahydrofurans, with the selectivity being reaction condition-dependant. The adducts themselves are demonstrated to be an important scaffold for structural diversification. The combination of a silyl-donor group in a donor-acceptor cyclopropane with novel acceptor groups is also discussed.

Iron-catalyzed chlorination of silanes

Savela, Risto,Zawartka, Wojciech,Leino, Reko

experimental part, p. 3199 - 3206 (2012/06/04)

A simple and highly efficient iron-catalyzed method for the chlorination of silanes has been developed. By use of 0.5-2% of the Fe(III)-based catalyst FeCl3 or Fe(acac)3 in the presence of 1-1.5 equiv of acetyl chloride as the chlorine donor, a large number of silanes, alkoxysilanes, and silanols were converted to the corresponding chlorosilanes in 50-93% yields. In contrast to earlier reported methods often suffering from expensive catalysts or use of stoichiometric metal salts, hazardous reagents, and reaction conditions, the presently described methodology allows benign reaction conditions and simple workup while using only catalytic amounts of a readily available and economically viable iron catalyst.

Process route upstream and downstream products

Process route

tri(iso-propyl)methoxysilane
33974-42-4

tri(iso-propyl)methoxysilane

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
With iron(III) chloride; acetyl chloride; In 1,2-dichloro-ethane; for 24h;
88%
With hydrogenchloride; In water; at 20 ℃; for 10h;
60%
With hydrogenchloride; at 24 ℃; for 2h;
98 % Chromat.
Multi-step reaction with 2 steps
1: 100 percent / aq. HCl / tetrahydrofuran / 65 °C
2: 95 percent / aq. HCl / 2 h / 24 °C
With hydrogenchloride; In tetrahydrofuran;
1-(triisopropylsilyl)oxybutane
75031-67-3

1-(triisopropylsilyl)oxybutane

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
With hydrogenchloride; In water; at 20 ℃; for 10h;
89%
With hydrogenchloride; In tetrahydrofuran; at 24 ℃; for 4h;
95 % Chromat.
triisopropylsilanol
17877-23-5

triisopropylsilanol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
With hydrogenchloride; at 24 ℃; for 2h;
95%
With iron(III) chloride; acetyl chloride; In 1,2-dichloro-ethane; for 2h;
84%
With hydrogenchloride; sodium sulfate; In water; at -5 - 5 ℃; for 2h;
191 g
(cyclopropylmethyl)triisopropylsilane

(cyclopropylmethyl)triisopropylsilane

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

triisopropylsilanol
17877-23-5

triisopropylsilanol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

ethyl (±)-trans-2-[(triisopropylsilyl)methyl]tetrahydrofuran-5-carboxylate

ethyl (±)-trans-2-[(triisopropylsilyl)methyl]tetrahydrofuran-5-carboxylate

Conditions
Conditions Yield
glyoxylic acid ethyl ester; With tin(IV) chloride; In dichloromethane; at -78 ℃; Inert atmosphere;
(cyclopropylmethyl)triisopropylsilane; In dichloromethane; at -78 - 0 ℃; Inert atmosphere;
With water; In dichloromethane; diastereoselective reaction; Inert atmosphere;
42%
11%
10%
(cyclopropylmethyl)triisopropylsilane

(cyclopropylmethyl)triisopropylsilane

tetrahydrofuran-2-carbaldehyde
7681-84-7

tetrahydrofuran-2-carbaldehyde

triisopropylsilanol
17877-23-5

triisopropylsilanol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

1-(tetrahydrofuran-2-yl)-2-[(triisopropylsilyl)methyl]but-3-en-1-ol

1-(tetrahydrofuran-2-yl)-2-[(triisopropylsilyl)methyl]but-3-en-1-ol

Conditions
Conditions Yield
With tin(IV) chloride; In dichloromethane; at 0 - 20 ℃; Optical yield = 57.143 %de; Inert atmosphere;
23%
26%
6%
(cyclopropylmethyl)triisopropylsilane

(cyclopropylmethyl)triisopropylsilane

t-butylglyoxal
4480-47-1

t-butylglyoxal

triisopropylsilanol
17877-23-5

triisopropylsilanol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

(±)-trans-2,2-dimethyl-1-{2-[(triisopropylsilyl)methyl]tetrahydrofuran-5-yl}propan-1-one

(±)-trans-2,2-dimethyl-1-{2-[(triisopropylsilyl)methyl]tetrahydrofuran-5-yl}propan-1-one

Conditions
Conditions Yield
t-butylglyoxal; With tin(IV) chloride; In dichloromethane; at 0 ℃; Inert atmosphere;
(cyclopropylmethyl)triisopropylsilane; In dichloromethane; at 0 ℃; for 3.5h; Inert atmosphere;
With water; In dichloromethane; diastereoselective reaction; Inert atmosphere;
5%
63%
26%
tetrachlorosilane
10026-04-7,53609-55-5

tetrachlorosilane

isopropyllithium
1888-75-1

isopropyllithium

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
In not given;
97%
In not given;
97%
In not given;
68%
In not given;
68%
chlorotriisopropylsilane
6485-79-6

chlorotriisopropylsilane

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
With hexachloroethane; palladium dichloride; at 20 ℃; for 1h; Cooling with ice;
99%
With iron(III) chloride; acetyl chloride; In dichloromethane;
93%
With tert-butylhypochlorite; at -10 ℃;
9.5 g
With hydrogenchloride; palladium on activated charcoal; at 25 ℃; for 3h;
chlorotriisopropylsilane; With iron(III) chloride; In dichloromethane; at 23 ℃; under 760.051 Torr;
With acetyl chloride; In dichloromethane; at 23 ℃; for 24h; under 760.051 Torr; Kinetics;
With dichloromethane; eosin y; at 20 ℃; for 60h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation; Green chemistry;
99 %Spectr.
isopropyllithium
1888-75-1

isopropyllithium

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
With tetrachlorosilane; Petroleum ether;
With tetrachlorosilane;
Me<sub>2</sub>CHOSi(CHMe<sub>2</sub>)3
56568-91-3

Me2CHOSi(CHMe2)3

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

Conditions
Conditions Yield
With hydrogenchloride; In tetrahydrofuran; at 50 ℃; for 4h;
98 % Chromat.

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