dimethyldichlorosilane

Dimethyldichlorosilane structural formula

Structural formula

Business number 01K3
Molecular formula C2H6Cl2Si
Molecular weight 129.06
label

Dichlorodimethylsilane,

dimethyl silicon dichloride,

Dimethyldichlorosilane,

dimethyldichlorosilane,

Dimethyldichlorosilane,

DMDCS,

Dow Corning® product Z-1219,

Elemental organic compounds

Numbering system

CAS number:75-78-5

MDL number:MFCD00000491

EINECS number:200-901-0

RTECS number:VV3150000

BRN number:605287

PubChem number:24867582

Physical property data

1. Characteristics: colorless fuming liquid with pungent odor. [1]

2. Melting point (?): <-70[2]

3. Boiling point (?) : 70.5[3]

4. Relative density (water = 1): 1.07[4]

5. Relative Vapor density (air=1): 4.45[5]

6. Saturated vapor pressure (kPa): 14.5 (20?)[6]

7. Critical pressure (MPa): 3.49[7]

8. Octanol/water partition coefficient: 2.24[8]

9. Flash point (?): -9 (CC); -16 (OC) [9]

10. Ignition Temperature (?): 398.9[10]

11. Explosion limit (%): 9.5[11]

12 .Lower explosion limit (%): 3.4[12]

13. Solubility: soluble in benzene and ether. [13]

Toxicological data

1. Skin/eye irritation

Standard Draize test: rabbit, skin contact: 20mg/24H; severity of reaction: moderate.

Standard Draize test: Rabbit, eye contact: 5 mg/24H; Severity of reaction: Severe.

2. Acute toxicity:

Rat oral LD50: 5660?L/kg; mouse inhalation LC50: 930ppm/4H; rat intraperitoneal LDLo: 10mg/kg; small Rat inhalation LC50: 300mg/m3/2H;

3. Acute toxicity[14] LC50: 4910mg /m3(rat inhalation, 4h)

4. Irritation [15]

Rabbit transdermal: 20mg (24h), moderate irritation.

Rabbit eye: 5mg (24h), severe irritation.

Ecological data

1. Ecotoxicity No data available

2. Biodegradability No data available

3 .Non-biodegradability No information available

Molecular structure data

1. Molar refractive index: 29.73

2. Molar volume (cm3/mol): 120

3. Isotonic specific volume (90.2K ): 247.7

4. Surface tension (dyne/cm): 18.1

5. Polarizability (10-24cm3): 11.78 p>

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 0

4. Number of rotatable chemical bonds: 0

5. Number of tautomers: none

6. Topological molecule polar surface area 0

7. Number of heavy atoms: 5

8. Surface charge: 0

9. Complexity: 30.6

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

1. This product is highly toxic. Irritating to respiratory tract and skin. After long-term exposure, symptoms such as nasal mucosa atrophy or bronchitis may occur. In addition, there are symptoms such as headache, drowsiness, weakness, and chest pain. Hydrogen chloride is released when it comes in contact with water, which is also irritating and corrosive, so special attention should be paid during operation. Rinse with plenty of water after contact with skin and eyes, equipment should be sealed, and operators should wear protective gear.

2. Stability[16] Stable

3. Incompatible substances[17] Strong oxidants, acids, alcohols, amines, strong bases

4. Conditions to avoid contact[18] Humid air, heat

5. Polymerization hazard[19] No polymerization

6. Decomposition products [20] Silicon oxide, hydrogen chloride

Storage method

Storage Precautions[21] Store in a cool, dry and well-ventilated warehouse. Keep away from fire and heat sources. The storage temperature should not exceed 37?. The packaging must be sealed and must not come into contact with air. They should be stored separately from oxidants, acids, alkalis, alcohols, etc. and avoid mixed storage. Use explosion-proof lighting and ventilation facilities. It is prohibited to use mechanical equipment and tools that are prone to sparks. The storage area should be equipped with emergency release equipment and suitable containment materials.

Synthesis method

(1) The direct method is now used in industry. During production, copper or copper salt is used as a catalyst to directly react methyl chloride with silicon powder at about 300°C. This is a complex heterogeneous reaction. The reaction mixture mainly contains dimethyldichlorosilane (75%), Monomethyltrichlorosilane (20-30%), trimethylmonochlorosilane (5%) and methyldichlorosilane; the boiling points of these components are 70°C, 66.4°C, 57.9°C and 41°C respectively , using an emulsification tower for separation. If necessary, its composition can be adjusted by changing operating conditions.

(2) Grignard reagent method After long-term efforts, F.S. Kipping and his collaborators synthesized a large number of organosilicon compounds using the Grignard reagent method. Its characteristics are: the product has fewer components, can be used to prepare mixed hydrocarbyl silanes, can produce metal salts by-product, and can connect the same organic groups such as alkyl groups, alkenyl groups, aryl groups, etc. to silicon atoms to form monomers. The disadvantages are: it requires the use of flammable ether or other solvents, which not only consumes a lot of money, but is also flammable and explosive, making the production unsafe; the process steps are many and complex; the raw materials silicon tetrachloride and Grignard reagent are expensive and costly, and are not suitable For large-scale industrial production.

(3) Condensation method (substitution method) A method in which chlorosilane (mainly hydrogen-containing chlorosilane) reacts with hydrocarbons or halogenated hydrocarbons, and is condensed under high temperature or under the action of a catalyst to generate organochlorosilane. , also known as heat shrinkage method. Thinking of the condensation process as a process in which hydrogen or chlorine on the silane is replaced by a hydrocarbon group, the condensation method can also be called a substitution method.

(4) Disproportionation (redistribution) method refers to the method of using a certain catalyst to redistribute the substituents in silane to generate new organohalosilanes, so it is also called the redistribution method. Its outstanding advantage is that it can solve the imbalance problem in monomer production, realize comprehensive utilization and reduce production costs.

Purpose

1. Used in the manufacture of dimethyl silicone oil, silicone rubber and silicone resin.

2. Used as an intermediate in the manufacture of silicone resin. [22]

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2-furanmethanethiol

2-furanmethylthiol structural formula

Structural formula

Business number 02D3
Molecular formula C5H6OS
Molecular weight 114.07
label

furfuryl mercaptan,

2-Thiofuranmethanol,

coffee aldehyde,

Furfuryl mercaptan,

2-thio furan methanol,

Coffee aldehydes,

artificial flavors

Numbering system

CAS number:98-02-2

MDL number:MFCD00003254

EINECS number:202-628-2

RTECS number:LU2100000

BRN number:383594

PubChem number:24871755

Physical property data

1. Properties: colorless and transparent liquid with a very unpleasant odor.

2. Density (g/mL, 25?): 1.139

3. Relative vapor density (g/mL, air=1): Undetermined

4. Melting point (ºC): Undetermined

5. Boiling point (ºC, normal pressure): 155

6. Boiling point (ºC, kPa): Undetermined

7. Refractive index (n20/D): 1.5329

8. Flash point (ºC): 45

9. Specific rotation (º): Undetermined

p>

10. Autoignition point or ignition temperature (ºC): Not determined

11. Vapor pressure (mmHg, 55ºC): Not determined

12. Saturated vapor pressure (kPa, 25 ºC): 0 not determined

13. Heat of combustion (KJ/mol): not determined

14. Critical temperature (ºC): not determined

15. Critical pressure (KPa): Undetermined

16. Log value of oil-water (octanol/water) partition coefficient: Undetermined

17. Explosion upper limit (% , V/V): Undetermined

18. Lower explosion limit (%, V/V): Undetermined

19. Solubility: Insoluble in water, soluble in a variety of organic matter It is stable in solvents and dilute alkali solutions, and easily polymerizes in the presence of inorganic acids.

Toxicological data

1. Acute toxicity: mouse peritoneal cavity LD50: 100mg/kg; 2. Other multiple dose toxicity: rat oral TDLo: 2730 mg/kg/13W-C; 3. Reproductive toxicity: male rats 42 days before mating Oral TDLo: 1260 mg/kgSEX/DURATION;

Ecological data

Water hazard class 1 (German Regulation) (self-assessment via list) The substance is slightly hazardous to water.

Do not allow undiluted or large amounts of product to come into contact with groundwater, waterways or sewage systems.

Do not discharge materials into the surrounding environment without government permission.

Molecular structure data

1. Molar refractive index: 31.36

2. Molar volume (cm3/mol): 102.5

3.   Isotonic specific volume (90.2K): 249.9

4. Surface tension (dyne/cm): 35.2

5. Dielectric constant:

6. Even Polar distance (10-24cm3):

7. Polarizability: 12.43

Compute chemical data

1. Hydrophobic parameter calculation reference value (XlogP): 1.3

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 1

4. Number of rotatable chemical bonds: 1

5. Number of tautomers:

6. Topological molecular polar surface area (TPSA): 13.1

7. Number of heavy atoms: 7

8. Surface charge: 0

9. Complexity: 56

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters Number: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

Avoid contact with oxidants, reducing agents, alkalis, and alkali metals.

After dilution, it has the aroma of coffee and caramel, and when it is strong, it has an unpleasant sulfur-like smell. It is insoluble in water, soluble in a variety of organic solvents and dilute alkali solutions, and has stable properties. It is easy to polymerize in the presence of inorganic acids.

Storage method

Store in a cool, ventilated warehouse. Keep away from fire and heat sources. They should be stored separately from oxidants, reducing agents, alkalis, and food chemicals, and avoid mixed storage. It should not be stored for a long time to avoid deterioration. Use explosion-proof lighting and ventilation facilities. It is prohibited to use mechanical equipment and tools that are prone to sparks. The storage area should be equipped with emergency release equipment and suitable containment materials.

Synthesis method

Heat furfuryl alcohol, thiourea and 48% hydrobromic acid to reflux, add sodium hydroxide aqueous solution, acidify the aqueous layer after separation, extract and combine the ether layers with ether, dry and distill to obtain the desired product.

Purpose

Raw materials for preparing coffee and baking aroma. The dosage for candies and baked goods is 2×10-6. Dosage of soft drinks, iced foods, and frostings (5×10-7) ~ (7.8×10-7). The dosage of jelly and pudding is 10-7. Product quality: content ?99%.

It is used to prepare coffee, chocolate and other flavors and is an important edible spice. In the spice industry, this product can also be used to synthesize other spices containing furfuryl sulfur groups.

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Trimethylchlorosilane

Trimethylchlorosilane structural formula

Structural formula

Business number 01K2
Molecular formula C3H9ClSi
Molecular weight 108.64
label

Trimethylsilane chloride,

Trimethylmonochlorosilane,

Monochlorotrimethylsilane,

Trimethylsilyl chloride,

Chlorotrimethylsilane,

TMSCl,

Dow Corning® Z-1224,

TMCS,

Trimethylchlorosilane,

Trimethylsilyl chloride,

Cholrotrimethylsilane,

Elemental organic compounds

Numbering system

CAS number:75-77-4

MDL number:MFCD00000502

EINECS number:200-900-5

RTECS number:VV2710000

BRN number:1209232

PubChem number:24892952

Physical property data

1. Properties: colorless to light yellow transparent liquid with pungent odor. [18]

2. Melting point (?): -57.7[19]

3. Boiling point (?): 57[20]

4. Relative density (water = 1): 0.85[21]

5. Relative vapor Density (air=1): 3.8[22]

6. Saturated vapor pressure (kPa): 26.7 (20?)[23]

7. Critical pressure (MPa): 3.36[24]

8. Octanol/water partition coefficient: 2.48[25] sup>

9. Flash point (?): -18 (OC) [26]

10. Ignition temperature (?): 395[27]

11. Explosion upper limit (%): 6[28]

12. Explosion lower limit (%): 1.8[29]

13. Solubility: soluble in benzene, methanol, ether, and perchlorethylene. [30]

Toxicological data

1. Skin/eye irritation

Standard Draize test: rabbit, skin contact: 500?L; severity of reaction: moderate.

Standard Draize test: Rabbit, eye contact: 5 ?L; severity of reaction: moderate.

2. Acute toxicity: Oral LD50 in rats: 5660?L/kg; Inhaled LCLo in mice: 100mg/m3; Intraperitoneal LCLo in mice: 750mg/kg; Rabbit skin contact LD50: 1780?L/kg;

3. Chronic toxicity/carcinogenicity mice Intraperitoneal TCLo: 1000mg/kg/I;

4. Mutagenic microbial mice Salmonella typhi mutation: 1mg/plate;

5. Acute toxicity [31] LD50: 5660?l (4811mg)/kg (rat oral) ; 1780?l (1513mg)/kg (rabbit transdermal)

6. Irritation [32]

Rabbit transdermal Peel: 500?l, moderate irritation.

Rabbit eye: 5?l, moderate irritation.

7. Mutagenicity [33] Microbial mutagenicity: Salmonella typhimurium 1mg/dish.

Ecological data

Slightly hazardous to water, avoid contact of undiluted or large quantities of product with groundwater, waterways or sewage systems.

Molecular structure data

1. Molar refractive index: 29.51

2. Molar volume (cm3/mol): 125.1

3. Isotonic specific volume (90.2K ): 249.1

4. Surface tension (dyne/cm): 15.6

5. Polarizability (10-24cm3): 11.70 p>

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 0

4. Number of rotatable chemical bonds: 0

5. Number of tautomers: none

6. Topological molecule polar surface area 0

7. Number of heavy atoms: 5

8. Surface charge: 0

9. Complexity: 28.4

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

1. Stability[34] Stable

2. Incompatible substances[35] Strong acid, strong alkali, water

3. Conditions to avoid contact[36] Humid air

4. Polymerization hazard[37] No polymerization

5. Decomposition products[38] Hydrogen chloride

Storage method

Storage Precautions[39] Store in a cool, dry and well-ventilated warehouse. Keep away from fire and heat sources. The storage temperature should not exceed 37°C and the container should be kept sealed. They should be stored separately from acids, alkalis, etc., and avoid mixed storage. Use explosion-proof lighting and ventilation facilities. It is prohibited to use mechanical equipment and tools that are prone to sparks. The storage area should be equipped with emergency release equipment and suitable containment materials.

Synthesis method

1. Methyl chloride and silicon powder are directly synthesized in the next step catalyzed by cuprous chloride to generate a methylchlorosilane mixture, which can be purified by distillation to obtain trimethylchlorosilane and other monomers. Laboratory preparation can be made by reacting tetramethylsilane with acetyl chloride in the presence of aluminum trichloride.

2. Stir crude (or industrial product) trimethylchlorosilane with aluminum trichloride, aluminum tribromide or ferric hydroxide at 60°C for 10 minutes, and then distill to obtain pure product.

3. Methyl chloride and silicon powder are synthesized in one step at high temperatures above 300 to 550°C in the presence of cuprous chloride catalyst. The resulting methylchlorosilane mixture is purified by distillation to obtain trimethylchlorosilane.

4. Connect the 17.5g quad Methylsilane was quickly added to 26.5g of purified aluminum trichloride cooled in an ice-salt bath. While stirring, 16ml of acetyl chloride was added dropwise.
The dripping speed of acetyl chloride is preferably to maintain appropriate reflux. The dripping process is completed in 40 minutes. After the dripping is completed, the reaction is stirred for 1 hour and 20.8g of trimethylchlorosilane can be obtained by distillation. The response is:

Purpose

1. Used as an intermediate, hydrophobic agent, and analytical reagent in the manufacture of silicone oil.

2. Used as a gas chromatography derivatization reagent for the silanization of unhindered hydroxyl, amino and carboxyl groups. Also used in organic synthesis.

3. Silanization reagents for hydroxyl, amino and carbonyl groups. Used to prepare its volatile derivatives for gas chromatography analysis. Ketol condensation of esters, condensation cyclization of ? and ? monodioic acid esters, and acylation of malonate esters. Isosimilar acid esters are prepared from urethane. Preparation of enol silane ethers from carbonyl compounds. Preparation of enamines from ketones. Reductive silylation of aromatic rings, etc.

4. Trimethylchlorosilane is mostly used to synthesize silicon ether compounds and vinyl silane. It can also be used as a protective group for hydroxyl-containing compounds such as alcohols. In addition, it is also used in the synthesis of tert-butoxycarbonyl ( BOC) and other deprotection reactions.

As a protective group An important application of trimethylchlorosilane is as alcohols[1] and phenols[2] , terminal alkyne [3,4], etc., react to form compounds containing trimethylsilyl groups. In the reaction with alcohol compounds, TMSCl generates silicon ether compounds under the action of bases such as triethylamine, DMAP, etc. This method can be used to protect the alcoholic hydroxyl groups in primary, secondary, and tertiary alcohols (Formula 1)[ 1].

Under similar conditions, TMSCl also It can react with ketone compounds to generate enol ether compounds (formula 2)[5~7]. Trimethylsilyl is easily removed under the action of acid.

For terminal alkynes, in Under the action of lithium, zinc reagents, etc., terminal alkynes can directly interact with TMSCl to generate silane compounds (formula 3)[3,4].

Under the action of strong alkali, TMSCl It is also possible to introduce a trimethylsilyl group (formula 4)[8] on the aromatic ring.

Addition reaction With the participation of transition metal catalysts or triphenylphosphine, etc., epoxy compounds can directly react with TMSCl The reaction is ring-opening, and the product is an O-end-protected silicon ether compound. After removing the silicon group, an alcohol compound (formula 5) [9,10] can be obtained.

TMSCl can also be used with ?,?-unsaturated carbonyl compounds undergo 1,4-conjugate addition reaction (Formula 6)[11~14]. p>

Elimination reaction In the presence of TMSCl and a catalyst, epoxides or allyl alcohol derivatives can undergo deoxygenation reactions to generate carbon-carbon double bond compounds (formula 7)[15,16]

Formation of silyl vinyl accumulated dienes Under the action of transition metal catalysts, alkenes and alkynes can couple with TMSCl to generate accumulated dienes, which can be further oxidized to ?, ? -Unsaturated ketone (Formula 8)[17]

5. Used as an intermediate, hydrophobic agent, and analytical reagent in the manufacture of silicone oil. [40]

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