テトラメチルシラン

Tetramethylsilane

HCID 6396CAS 75-76-3

基本情報

標準SMILES
C[Si](C)(C)C
InChIKey
CZDYPVPMEAXLPK-UHFFFAOYSA-N
分子式
C4H12Si
平均分子量
88.22 g/mol
単同位体質量
88.07082692

名称と識別子

優先名称
Tetramethylsilane
IUPAC
tetramethylsilane
現地名
テトラメチルシラン
英語名
Tetramethylsilane
分子式
C4H12Si
分子量
88.22

名称と別名

TETRAMETHYLSILANE75-76-3Silane, tetramethyl-Tetramethyl silaneTetramethylsilicane41Y0RBG14QDTXSID9026423NSC-5210DTXCID206423CHEBI:85361Silicon tetramethylRefChem:188793
名称をさらに表示
テトラメチルシランメチルトリメチルシランテトラメチルシラン (99.9%)テトラメチルシラン (NMR用)テトラメチルシラン 溶液TMSTMS4MS(CH3)4SiSi(CH3)4TrialkylsilaneTetraMethylsilane, ACS reagent, NMR gradeCT2050DKSI045
200-899-1Silicon, tetramethyl-NSC 5210Tetramethyl-silaneEINECS 200-899-1UNII-41Y0RBG14QMFCD00008274UN2749

データベース識別子

CAS
75-76-3
PubChem CID
6396
DTXSID
DTXSID9026423
ChEMBL
CHEMBL68073
ChEBI
CHEBI:85361
UNII
41Y0RBG14Q
EC Number
200-899-1
Nikkaji
J2.258.481B、J35.910F

物性

構造計算による物性

極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
5

実験および物理化学的性質

LogPlog Kow = 3.24
Density · 2 件

0.641 g/cu cm at 25 °C

0.648 @25 °C

Color/FormVolatile liquid or gas
Solubility · 3 件

Insoluble in cold concentrated sulfuric acid; soluble in most organic solvents

Very soluble in ethanol and ether

In water, 19.6 mg/L at 25 °C

Flash Point-27 dec C (closed cup)
Boiling Point26.6 °C

物理化学的性質

融点
-99 °C · -99 °C (lit.)
沸点
26 · 26-28 °C (lit.)
比重(密度)
0.648 g/mL · 0.648 g/mL at 25 °C (lit.)
蒸気圧
11.66 psi · 11.66 psi ( 20 °C)
屈折率
20 · n20/D 1.358(lit.)
闪点
17 °F · −17 °F
化学的性質 · 1 件

化学的特性Tetramethylsilane (TMS) is the simplest tetraalkylsilane. It is a colorless, highly volatile liquid with a characteristic organometallic odor. TMS is chemically stable, insoluble in water, and soluble in most organic solvents.In nuclear magnetic resonance (NMR) spectroscopy, TMS is widely used as an internal standard for chemical shift measurements. Chemical shift is a relative value and is generally referenced to TMS, whose chemical shift is defined as 0 ppm. The protons in TMS experience a strong shielding effect, requiring a relatively high external magnetic field to achieve resonance. As a result, few compounds exhibit signals at a higher field than TMS, making it an ideal reference standard for NMR analysis.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H224 (99.2%): Extremely flammable liquid and vapor [Danger Flammable liquids];H302 (17.3%): Harmful if swallowed [Warning Acute toxicity, oral];H411 (23.6%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P210, P233, P240, P241, P242, P243, P264, P270, P273, P280, P301+P317, P303+P361+P353, P330, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 127 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 5 件

Chemical: Silane, tetramethyl-

Silane, tetramethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Silane, tetramethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 13-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14468

Tetramethylsilane: HSNO Approval: HSR005569 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.

Fire Potential · 2 件

A very dangerous fire hazard when exposed to heat or flame. Spontaneously flammable in air.

Tetramethylsilicane is spontaneously flammable in air. /Tetramethylsilicane/

Health Hazards · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

· May cause toxic effects if inhaled or absorbed through skin.;· Inhalation or contact with material may irritate or burn skin and eyes.;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

Hazards Summary · 1 件

Pyrophoric; No adverse effects observed in combined subchronic/reproductive/developmental inhalation study of rats at concentrations up to 5,000 ppm/6 hours/day; [HSDB] A mild irritant; Inhalation of vapor may cause nose, throat, and lung irritation and pose an asphyxiation hazard; Harmful by ingestion; [Air Products MSDS] See Diethylsilane.

安全と保護具

Fire Fighting · 1 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.;LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· A vapor-suppressing foam may be used to reduce vapors.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· Use clean, non-sparking tools to collect absorbed material.;Large Spill;· Dike far ahead of liquid spill for later disposal.;· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

First Aid · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;Refer to the "General First Aid" section. Specific First Aid: Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. (ERG, 2024)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.
Fire Fighting Procedures · 4 件

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. ... Use water spray to cool unopened containers.

Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage Conditions · 1 件

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8 °C Over time, pressure may increase causing containers to burst. Handle and open container with care.

毒性情報

Body Burden · 1 件

Samples collected and analyzed during the period from July to December 1980 detected tetramethylsilane on 4 of 12 subjects' exhaled breath in Bayonne and Elizabeth, New Jersey (nine subjects) and Research Triangle Park, North Carolina (3 subjects). The subjects were workers in the chemical and oil industries as well as a sewage treatment plant worker(1).

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 44(SRC), determined from a structure estimation method(2), indicates that tetramethylsilane is expected to have very high mobility in soil(SRC). Volatilization of tetramethylsilane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.25 atm-cu m/mole(SRC), based upon its vapor pressure, 718 mm Hg(3), and water solubility, 19.6 mg/L(4). Tetramethylsilane is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 44(SRC), determined from a structure estimation method(2), indicates that tetramethylsilane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.25 atm-cu m/mole(SRC), derived from its vapor pressure, 718 mm Hg(4), and water solubility, 19.6 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.7 hours and 3.7 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 64(SRC), from a log Kow of 3.24(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetramethylsilane, which has a vapor pressure of 718 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tetramethylsilane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 days(SRC), calculated from its rate constant of 1.00X10-12 cu cm/molecule-sec at 25 °C(3). Tetramethylsilane does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOther Poison - Simple Asphyxiant
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tetramethylsilane can be estimated to be 44(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetramethylsilane is expected to have very high mobility in soil.

Artificial Pollution Sources · 1 件

Tetramethylsilane's production and use in chemical deposition of films of silicon carbide, as a 1H NMR primary reference standard(1), and as an additive to aviation fuel(2) may result in its release to the environment through various waste streams(SRC).

Environmental Bioconcentration · 1 件

An estimated BCF of 64 was calculated for tetramethylsilane(SRC), using a log Kow of 3.24(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

法規制情報

Regulatory Information · 5 件

Chemical: Silane, tetramethyl-

Silane, tetramethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Silane, tetramethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 13-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14468

Tetramethylsilane: HSNO Approval: HSR005569 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DHS Chemicals of Interest (COI) · 4 件

Tetramethylsilane

1

10000

Flammable chemical that can be released at a facility.

安全データ

F
10
wgk
3
tsca
TSCA listed
ridadr
UN 2749
hs_code
2931 90 00
risk_code
12-48/20/22-40-38-22

化学と産業

用途と製造

Uses · 4 件

Used as NMR reference standard, in semiconductor chemical vapor deposition, and for silylation of samples for GC analysis; [Merck Index] Used as an aviation fuel; [CAMEO] Used in semiconductor processing; [Air Products MSDS]

Semiconductor Manufacturing [Category: Industry]

In aviation fuel

Used in chemical deposition of films of silicon carbide; 1H NMR primary reference standard

U.S. Production · 4 件

2023: 1,000,000 - <2,500,000 lb;2022: 1,000,000 - <2,500,000 lb;2021: 1,000,000 - <2,500,000 lb;2020: 1,000,000 - <2,500,000 lb

Silane, tetramethyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7428]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Silane, tetramethyl-. Aggreated National Production Volume: 1 to < 10 million lbs.

Industry UsesPlating agent;Intermediate
Methods of ManufacturingBy Grignard reaction of silicon tetrachloride and methylmagnesium chloride.
General Manufacturing Information · 2 件

All Other Basic Organic Chemical Manufacturing;All Other Chemical Product and Preparation Manufacturing;Electrical Equipment, Appliance, and Component Manufacturing;All Other Basic Inorganic Chemical Manufacturing

Silane, tetramethyl-: ACTIVE

応用分野 · 6 件

解説C4H12Si(88.23).(CH3)4Si.略称TMS.反応活性な官能基を含まないもっとも簡単な有機ケイ素化合物.実験室的合成法の一つは,乾燥したジブチルエーテル中で調整した臭化メチルマグネシウムに,クロロトリメチルシランまたは四塩化ケイ素を加える.生成したテトラメチルシランを充填塔を用いて2回精留精製する.無色の揮発性液体.融点-99.0 ℃,沸点26.54 ℃.d2040.6480.n20D1.3591.水に不溶.石油臭がある.1H NMRスペクトル測定に化学シフトの内部基準物質として用いられ,TMSのシグナルは,化学シフトのδ値で0.000 ppm(四塩化炭素溶液)と決められている.森北出版「化学辞典(第2版)

用途プロトンNMRにおける標準物質。

用途核磁気共鳴分光法の標準品。半導体応用 (化学気相成長法)

使用NMR reference standard. In semiconductor applications (chemical vapor deposition). Tetramethylsilane (TMS) is used as a chemical shift reference for proton, carbon-13, and silicon-29 analysis in organic solvents and is given 0 as its chemical shift position.

一般的な説明Tetramethylsilane appears as a colorless, mildly acidic volatile liquid. A serious fire hazard. Mildly toxic by ingestion. Emits acrid smoke and fumes when heated to high temperatures. Less dense than water and insoluble in water, but soluble in most organic solvents. Used as an aviation fuel and as an internal standard for nmr analytical instruments.

使用用途テトラメチルシランは主に、1H、13C、29Siを用いる核磁気共鳴分光法 (NMR分光法) の内部標準物質や、化学気相成長 (CVD) におけるや炭化ケイ素の前駆体材料などに用いられます。テトラメチルシランのNMRピークは低周波数側に大きくシフトします。これは、テトラメチルシランのケイ素原子は炭素原子よりも電気陰性度が低く、水素原子・炭素原子を強く遮蔽化するためです。 つまり、有機化合物一般の試料ピークとは干渉しません。そのため、テトラメチルシランのシングレットピークはδ 0.0と定義されています。また、化学的に反応性に乏しく揮発性が高く、NMR測定後に簡単に除去することができることも利点です。NMRで標準物質として用いる場合は特に、空気中の水分を吸わせないよう、開封・使用時は手早く行わなくてはいけません。結果に影響を与えてしまう恐れがあります。 もう一つの用途である化学気相成長 (CVD) とは、様々な物質の薄膜を形成する蒸着法の一つです。石英などで出来た反応管内で加熱した基板物質上に、目的とする薄膜の成分を含む原料ガスを供給し、基板表面あるいは気相での化学反応により膜を堆積します。この方法においては、テトラメチルシランは二酸化ケイ素や炭化ケイ素のです。どちらの化合物になるかは、その成長条件に依存します。

調製方法 · 3 件

製造方法At present, the synthesis method of Tetramethylsilane mainly comprises two methods, namely, tetrachlorosilane or tetraethoxysilane is reacted with methyl magnesium iodide to prepare the tetramethylsilane. The second one is prepared by reacting chloromethane and silicon powder in the presence of copper catalyst and then carrying out fine fractionation.

合成方法テトラメチルシランを実験室で合成するための方法の一つは、乾燥したジブチルエーテル中で調製した臭化メチルマグネシウムに、クロロトリメチルシランまたはを加える方法です。この方法で生成したテトラメチルシランは一般的に充填塔を用いて2回精留精製されます。

純化方法Distil it from conc H2SO4 (after shaking with it) or LiAlH4, through a 5ft vacuum-jacketed column packed with glass helices into an ice-cooled condenser, then percolate it through silica gel to remove traces of halide. [Beilstein 4 IV 3875.]

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補足説明

定義ChEBI: Tetramethylsilane is an organosilicon compound that is silane in which the hydrogens have been replaced by methyl groups.

関連反応

4 件

関連ノート

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