3144-74-9

Basic information

• Product Name: CHLOROMETHYLDIMETHYLSILANE
• Synonyms: CHLOROMETHYLDIMETHYLSILANE;(chloromethyl)dimethyl-silan;ClCH2SiH(CH3)2;Dimethyl(chloromethyl)silane
• CAS NO: 3144-74-9
• Molecular Formula: C₃H₉ClSi
• Molecular Weight: 108.64
• EINECS: 221-556-2
• Product Categories: Organometallic Reagents;Organosilicon;Others;Chemical Synthesis;Organometallic Reagents
• Mol File: 3144-74-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 82-83 °C(lit.)
• Flash Point: 10 °F
• Appearance: /
• Density: 0.894 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.42(lit.)
• CAS DataBase Reference: CHLOROMETHYLDIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROMETHYLDIMETHYLSILANE(3144-74-9)
• EPA Substance Registry System: CHLOROMETHYLDIMETHYLSILANE(3144-74-9)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16-29-33
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3144-74-9(Hazardous Substances Data)

Usage

General Description

Chloromethyldimethylsilane is a chemical compound with the molecular formula C3H9ClSi. It is a colorless, flammable liquid with a pungent odor, and is commonly used as a reagent in organic synthesis and as a crosslinking agent in the production of silicones. It is also a key component in the production of silane coupling agents, which are used to improve adhesion and durability in various materials such as plastics, rubber, and coatings. Additionally, chloromethyldimethylsilane is used in the production of pharmaceuticals and agrochemicals, as well as in the manufacturing of specialty chemicals and electronic materials. Due to its reactive nature and potential health hazards, proper handling and storage of chloromethyldimethylsilane are required to ensure safe use in industrial and laboratory settings.

InChI:InChI=1/C3H8ClSi/c1-5(2)3-4/h3H2,1-2H3

Synthetic route

Chloro(chloromethyl)dimethylsilane (1719-57-9) → chloromethyldimethylsilane (3144-74-9)

Conditions	Yield
With lithium aluminium tetrahydride In dibutyl ether under 0.8 - 3.8 Torr;	92%
Stage #1: Chloro(chloromethyl)dimethylsilane With lithium aluminium tetrahydride; diethylene glycol dibutyl ether at 2 - 45℃; Inert atmosphere; Stage #2: With hydrogenchloride In water at 2 - 10℃; pH=< 2;	86%
With lithium aluminium tetrahydride In diethyl ether at 0℃;	78%

chloromethyldimethylsilane (3144-74-9) + C60H60O14Si10 → C72H96Cl4O14Si14

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 40℃; for 16h; Inert atmosphere; Schlenk technique;	99%

chloromethyldimethylsilane (3144-74-9) + 1,3,5-Tris-(1,1-diallyl-but-3-enyl)-benzene (152339-15-6) → 1,3,5-tris-{4-(chloromethyl-dimethyl-silanyl)-1,1-bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-butyl}-benzene

Conditions	Yield
With bis(η2:η2-1,3-divinyltetramethyl)platinum(0) In diethyl ether; xylene at 20℃; for 72h;	98%
chloroplatinic acid 1,1,3,3-tetramethyl-1,3-divinyldisiloxane complex at 20℃; for 24h;
Kartsted catalyst In diethyl ether at 20℃; for 13h;

chloromethyldimethylsilane (3144-74-9) + (1R,3S,7R,9S)-5,5,11,11-tetraallyl-1,3,7,9-tetraphenyl-2,4,6,8,10,12,13,14-octaoxa-1,3,5,7,9,11-hexasilatricyclo[7.3.1.13,7]tetradecane → 5,5,11,11-tetrakis(3-((chloromethyl)dimethylsilyl)propyl)-1,3,7,9-tetraphenyl-2,4,6,8,10,12,13,14-octaoxa-1,3,5,7,9,11-hexasilatricyclo[7.3.1.13,7]tetradecane

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 25 - 40℃; for 16h; Inert atmosphere;	95%

chloromethyldimethylsilane (3144-74-9) + 1-bromo-4-ethenyl-benzene (2039-82-9) → C11H16BrClSi (124789-74-8)

Conditions	Yield
dihydrogen hexachloroplatinate In toluene at 20℃;	94%

chloromethyldimethylsilane (3144-74-9) + 5-benzyloxy-1-pentyne (57618-47-0) → (5-(benzyloxy)pent-1-en-2-yl)(chloromethyl)dimethylsilane (1345668-23-6)

Conditions	Yield
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In acetone at 5℃; for 2h; Inert atmosphere; Cooling;	94%

chloromethyldimethylsilane (3144-74-9) + 4-triallylmethylphenol (224191-80-4) → 4-{4-(chloromethyl-dimethyl-silanyl)-1,1-bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-butyl}-phenol (387339-00-6)

Conditions	Yield
In diethyl ether at 20℃; for 48h;	91%
chloroplatinic acid 1,1,3,3-tetramethyl-1,3-divinyldisiloxane complex In diethyl ether at 20 - 35℃; for 48h;	85%
chloroplatinic acid 1,1,3,3-tetramethyl-1,3-divinyldisiloxane complex In diethyl ether at 20 - 50℃; for 48h;	85%
With chloroplatinic acid 1,1,3,3-tetramethyl-1,3-divinyldisiloxane complex In tetrahydrofuran at 40℃; for 24h; Inert atmosphere;
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In diethyl ether at 20℃; for 24h;

chloromethyldimethylsilane (3144-74-9) + carbon dioxide (124-38-9) + diethylamine (109-89-7) → (chloromethyl)dimethylsilyl diethylcarbamate (64128-88-7)

Conditions	Yield
at 50℃; for 5h; N-siloxycarbonylation;	90.8%

chloromethyldimethylsilane (3144-74-9) + diethylamine (109-89-7) → (diethylaminomethyl)dimethylsilane

Conditions	Yield
In hexane for 10h; amination; Heating;	90.7%

chloromethyldimethylsilane (3144-74-9) + {Methyl-[2-(methyl-[2-(methyl-divinyl-silanyl)-ethyl]-{2-[tris-(2-{methyl-bis-[2-(methyl-divinyl-silanyl)-ethyl]-silanyl}-ethyl)-silanyl]-ethyl}-silanyl)-ethyl]-vinyl-silanyl}-ethene → C116H276Cl16Si29

Conditions	Yield
With platinum divinyltetramethyldisiloxane In tetrahydrofuran at 54℃; for 22h;	90%

chloromethyldimethylsilane (3144-74-9) + 1-(1,1-diallyl-but-3-enyl)-4-methylsulfanyl-benzene (289699-82-7) → 1-{4-(chloromethyl-dimethyl-silanyl)-1,1-bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-butyl}-4-methylsulfanyl-benzene (527698-51-7)

Conditions	Yield
In diethyl ether at 20℃; for 48h;	90%

chloromethyldimethylsilane (3144-74-9) + Allyl acetate (591-87-7) → 3-(chloromethyldimethylsilanyl)propyl ethanoate (499773-71-6)

Conditions	Yield
With dihydrogen hexachloroplatinate In tetrahydrofuran; isopropyl alcohol for 2h; Heating;	88%

chloromethyldimethylsilane (3144-74-9) + tetraallylsilane (1112-66-9) → 1-(chloromethyl-dimethyl-silanyl)-3-{tris-[3-(chloromethyl-dimethyl-silanyl)-propyl]-silanyl}-propane (441322-81-2)

Conditions	Yield
With Speier's catalyst In toluene at 60℃; for 5h; Inert atmosphere;	87%
With dihydrogen hexachloroplatinate In tetrahydrofuran at 70℃; for 12h;	76%
bis(tetrabutylammonium) hexachloroplatinate(IV) In dichloromethane at 45℃;

chloromethyldimethylsilane (3144-74-9) + allyl-trimethyl-silane (762-72-1) → (chloromethyl)dimethyl(3-(trimethylsilyl)propyl)silane (17891-75-7)

Conditions	Yield
platinum In tetrahydrofuran; toluene for 72h; Heating;	87%
With 1,3-di(η2-vinyl)-1.1.3.3-tetramethyldisiloxane platinum(0) In tetrahydrofuran; toluene Cooling with ice; Reflux; Inert atmosphere;	87%

chloromethyldimethylsilane (3144-74-9) + carbon dioxide (124-38-9) + diethyl amine hydrochloride (660-68-4) → (chloromethyl)dimethylsilyl diethylcarbamate (64128-88-7)

Conditions	Yield
at 60℃; for 10h; N-siloxycarbonylation;	86.9%

chloromethyldimethylsilane (3144-74-9) + 2,2-dimethyl-3-trimethylsilyl-1,3-oxazolidin-4-one → 2,2-dimethyl-3-(dimethylchlorosilylmethyl)-1,3-oxazolidin-4-one

Conditions	Yield
at 110 - 120℃; Substitution;	86%

chloromethyldimethylsilane (3144-74-9) + methyl vinyl ketone (78-94-4) → Chloromethyl-dimethyl-((Z)-1-methyl-propenyloxy)-silane

Conditions	Yield
HRh(PPh3)4 for 1.5h; Ambient temperature;	85%

chloromethyldimethylsilane (3144-74-9) + carbon dioxide (124-38-9) + diethylammonium diethylcarbamate (64882-07-1) → (chloromethyl)dimethylsilyl diethylcarbamate (64128-88-7)

Conditions	Yield
for 5h; dehydrocondensation; Heating;	84.6%

chloromethyldimethylsilane (3144-74-9) + (n-butylaminomethyl)dimethylmethoxysilane (53677-54-6) → [(chloromethyldimethylsilyl)butylaminomethyl]methoxydimethylsilane

Conditions	Yield
at 65℃; for 3h; dehydrocondensation;	84.6%

chloromethyldimethylsilane (3144-74-9) + carbon dioxide (124-38-9) + (n-butylaminomethyl)dimethylmethoxysilane (53677-54-6) → (chloromethyl)dimethylsilyl N-butyl-N-(methoxydimethylsilylmethyl)carbamate

Conditions	Yield
at 55℃; for 5h; N-siloxycarbonylation;	83.9%

chloromethyldimethylsilane (3144-74-9) + cyclohexenone (930-68-7) → Chloromethyl-(cyclohex-1-enyloxy)-dimethyl-silane

Conditions	Yield
HRh(PPh3)4 for 0.5h; Ambient temperature;	83%

chloromethyldimethylsilane (3144-74-9) + 4-hexen-3-one (2497-21-4, 50396-87-7, 50396-96-8, 130981-55-4, 25659-22-7) → Chloromethyl-((Z)-1-ethyl-but-1-enyloxy)-dimethyl-silane

Conditions	Yield
HRh(PPh3)4 for 10h; Ambient temperature;	83%

chloromethyldimethylsilane (3144-74-9) + diphenylphosphane (829-85-6) → ((dimethylsilyl)methyl)diphenylphosphane (86934-50-1)

Conditions	Yield
Stage #1: diphenylphosphane With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 3.5h; Inert atmosphere; Schlenk technique; Stage #2: chloromethyldimethylsilane In tetrahydrofuran; hexane at -40 - 20℃; Schlenk technique; Inert atmosphere;	83%

chloromethyldimethylsilane (3144-74-9) + ethyl (R)-3-(benzyloxy)hexanoate → (R)-(4-(benzyloxy)-2-methyleneheptyl)dimethylsilane

Conditions	Yield
Stage #1: chloromethyldimethylsilane With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: ethyl (R)-3-(benzyloxy)hexanoate With cerium(III) chloride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;	83%

chloromethyldimethylsilane (3144-74-9) + C56H52O14Si10 → C68H88Cl4O14Si14

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 40℃; for 16h; Inert atmosphere; Schlenk technique;	81%

diazoacetic acid ethyl ester (623-73-4) + chloromethyldimethylsilane (3144-74-9) → ethyl <(chloromethyl)dimethylsilyl>acetate (13950-54-4)

Conditions	Yield
Product distribution; multistep reaction; new method for synthesis of ethyl silylacetates;	80%
copper 1) 90 deg C, 2) 90 deg C; Yield given. Multistep reaction;

chloromethyldimethylsilane (3144-74-9) + 4,4-dimethylcyclohexenone (1073-13-8) → Chloromethyl-(4,4-dimethyl-cyclohex-1-enyloxy)-dimethyl-silane

Conditions	Yield
HRh(PPh3)4 for 4h; Ambient temperature;	80%

chloromethyldimethylsilane (3144-74-9) + 4-pentenyl acetate (1576-85-8) → 5-(chloromethyldimethylsilanyl)pentyl ethanoate (499773-73-8)

Conditions	Yield
With dihydrogen hexachloroplatinate In tetrahydrofuran; isopropyl alcohol for 2h; Heating;	80%

chloromethyldimethylsilane (3144-74-9) + 3-[Allyl-methyl-(3-{tris-[3-(diallyl-methyl-silanyl)-propyl]-silanyl}-propyl)-silanyl]-propene (175168-00-0) → 1-{bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-methyl-silanyl}-3-[tris-(3-{bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-methyl-silanyl}-propyl)-silanyl]-propane

Conditions	Yield
With Speier's catalyst In toluene at 60℃; for 5h; Inert atmosphere;	80%
With dihydrogen hexachloroplatinate In tetrahydrofuran Heating;	70%

chloromethyldimethylsilane (3144-74-9) + 1,1-dimethylhydrazine (57-14-7) → (N,N-dimethylhydrazinomethyl)dimethylsilane

Conditions	Yield
In hexane at 40℃; for 5h; Alkylation;	79.6%

Upstream product

• 1719-57-9 Chloro(chloromethyl)dimethylsilane 

Downstream Products

• 7393-55-7 Jodmethyl-dimethyl-silan 
• 2344-80-1 Chloromethyltrimethylsilane 
• 834-14-0 p-benzylanizole 
• 164169-58-8 dimethyl(6-phenylhex-5-ynyl)silane 
• 164169-57-7 dimethyl(5-phenylpent-4-ynyl)silane 
• 387339-00-6 4-{4-(chloromethyl-dimethyl-silanyl)-1,1-bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-butyl}-phenol 
• 86934-50-1 ((dimethylsilyl)methyl)diphenylphosphane 
• 1345668-23-6 (5-(benzyloxy)pent-1-en-2-yl)(chloromethyl)dimethylsilane 
• 1190781-37-3 (η5-Me3SiC5H4)Fe(CO)(PPh3)SiMe3 
• 1100051-53-3 (C₅(CH₃)5)Fe(C₅H₄(CH₂)11Si(CH₃)2CH₂OC₆H₄OH) 
• 124789-74-8 C₁₁H₁₆BrClSi 
• 252942-31-7 ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-2-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate 
• 527698-51-7 1-{4-(chloromethyl-dimethyl-silanyl)-1,1-bis-[3-(chloromethyl-dimethyl-silanyl)-propyl]-butyl}-4-methylsulfanyl-benzene 

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