1558-33-4

Basic information

• Product Name: Chloromethyldichloromethylsilane
• Synonyms: (CHLOROMETHYL)METHYLDICHLOROSILANE, WACKER QUALITY;ChloromethylmethyldichlorosilaneCMMCS;Dichloro(chloromethyl)methylsi;(CHLOROMETHYL)METHYLDICHLOROSILANE 97%;(Dichloromethylsilyl)chloromethane;(Chloromethyl)dichloromethylsilane, (Chloromethyl)methyldichlorosilane, Silane CMM1;(Chloromethyl)dichloromethylsilane, (Chloromethyl)methyldichlorosilane;Dichloro(methyl)(chloromethyl)silane
• CAS NO: 1558-33-4
• Molecular Formula: C₂H₅Cl₃Si
• Molecular Weight: 163.51
• EINECS: 216-319-5
• Product Categories: Dichlorosilanes;Si (Classes of Silicon Compounds);Si-Cl Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Alpha Silanes;Chloro Silanes
• Mol File: 1558-33-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 121-122 °C(lit.)
• Flash Point: 95 °F
• Appearance: Clear colorless to straw/Liquid
• Density: 1.284 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 18.6mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: 2-8°C
• Solubility: reacts
• Water Solubility: reacts
• BRN: 969205
• CAS DataBase Reference: Chloromethyldichloromethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Chloromethyldichloromethylsilane(1558-33-4)
• EPA Substance Registry System: Chloromethyldichloromethylsilane(1558-33-4)

Safety Data

• Hazard Codes: C
• Statements: 10-14-20-35-37-34
• Safety Statements: 26-36/37/39-45-8-16
• RIDADR: UN 2927 6.1/PG 2
• WGK Germany: 3
• RTECS: VV2160000
• F: 10
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1558-33-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear to straw liquid

InChI:InChI=1/C2H5Cl3Si/c1-6(4,5)2-3/h2H2,1H3

Synthetic route

dimethylsilicon dichloride (75-78-5) → chloromethylmethyldichlorosilane (1558-33-4)

Conditions	Yield
With chlorine Irradiation;	98%
With chlorine for 3h; Irradiation; visible light;	89%
With chlorine Irradiation.mit UV-Licht in der Dampfphase;

dimethylsilicon dichloride (75-78-5) → (dichloromethyl)methyldichlorosilane (1558-31-2) + chloromethylmethyldichlorosilane (1558-33-4)

Conditions	Yield
With chlorine for 15h; Heating; Irradiation;	A 8% B 89%
With SO2Cl2 In further solvent(s) boiling of (CH3)2SiCl2 and SO2Cl2 in bromobenzene in presence of dibenzoyl peroxide for a longer period of time;;
With SO2Cl2 In tetrachloromethane boiling of (CH3)2SiCl2 and SO2Cl2 in CCl4 in presence of dibenzoyl peroxide for a longer period of time;;
With SO2Cl2 In chlorobenzene boiling of (CH3)2SiCl2 and SO2Cl2 in chlorobenzene in presence of dibenzoyl peroxide for a longer period of time;;

dimethylsilicon dichloride (75-78-5) → (dichloromethyl)methyldichlorosilane (1558-31-2) + (Dichloro-methyl-silanyl)-methanesulfonyl chloride (77428-14-9) + chloromethylmethyldichlorosilane (1558-33-4)

Conditions	Yield
With yttrium(III) chloride; sulfuryl dichloride at 70℃; for 10h; Product distribution; Irradiation; other catalysts (HoCl3,TmCl3);	A 10% B 38% C 42%
With sulfuryl dichloride; copper dichloride at 50 - 70℃; Product distribution; Irradiation; various inorganic additives (chlorides and oxychlorides of 32 elements), effect of addition of S; effect of inorganic chlorides and oxychlorides on the photochemical reaction of methylchlorosilanes with SO2Cl2;	A 26 % Spectr. B 8 % Spectr. C 15 % Spectr.

diazomethane (186581-53-3, 908094-01-9) + Methyltrichlorosilane (75-79-6) → chloromethylmethyldichlorosilane (1558-33-4)

Conditions	Yield
copper In diethyl ether (CH3)SiCl3 and diazomethane in ether above -30°C with Cu powder as catalyst;;	12%
copper(II) sulfate In diethyl ether (CH3)SiCl3 and diazomethane in ether above -30°C with anhyd. CuSO4 as catalyst;;	12%
With diethyl ether; copper(II) sulfate
With diethyl ether; copper

octamethyltrisilane (3704-44-7) → chloro-trimethyl-silane (75-77-4) + Chloro(chloromethyl)dimethylsilane (1719-57-9) + dimethylsilicon dichloride (75-78-5) + chloromethylmethyldichlorosilane (1558-33-4)

Conditions	Yield
With tetrachloromethane; Perbenzoic acid; chlorine 1) 80 deg C, 18 h; 2) 5-10 deg C; Multistep reaction;

chlorine (7782-50-5) + dimethylsilicon dichloride (75-78-5) → (dichloromethyl)methyldichlorosilane (1558-31-2) + (trichloromethyl)methyldichlorosilane (4218-23-9) + chloromethylmethyldichlorosilane (1558-33-4) + dichloro-bis-chloromethyl-silane(?)

Conditions	Yield
at 24 - 40℃; UV-Licht.Irradiation;
at 24 - 40℃; UV-Licht.Irradiation;

dimethylsilicon dichloride (75-78-5) → (dichloromethyl)methyldichlorosilane (1558-31-2) + (trichloromethyl)methyldichlorosilane (4218-23-9) + chloromethylmethyldichlorosilane (1558-33-4)

Conditions	Yield
With chlorine In not given Irradiation (UV/VIS); (CH3)2SiCl2 and Cl2 at 20-40°C under irradiation of light;;
With Cl2 In not given Irradiation (UV/VIS); (CH3)2SiCl2 and Cl2 at 20-40°C under irradiation of light;;

dimethylhydrazone of the trimethylsilyl ester of benzoic acid (112746-60-8) + chloromethylmethyldichlorosilane (1558-33-4) → ((N-dimethylamino)benzimidato-N,O)(1-(1,1-dimethyl-2-benzoylhydrazonium)methyl-C,O)-methylsilicon(IV) chloride

Conditions	Yield
In hexane; chloroform at 20℃; for 168000h;	99%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + chloromethylmethyldichlorosilane (1558-33-4) → chloro-trimethyl-silane (75-77-4) + 1-Chloro-1-chloromethyl-1,3,3,3-tetramethyl-disilazane (135764-55-5)

Conditions	Yield
at 20℃; for 24h;	A n/a B 98%

ortho-phthalic acid bis(trimethylsilyl) ester (2078-22-0) + chloromethylmethyldichlorosilane (1558-33-4) → chloromethyl(methyl)silyl ortho-phthalate

Conditions	Yield
for 24h; Ambient temperature;	97%

chloromethylmethyldichlorosilane (1558-33-4) → methyl(chloromethyl)dihydrosilane (18165-20-3)

Conditions	Yield
With lithium aluminium tetrahydride In dibutyl ether under 0.8 - 3.8 Torr;	96%
With lithium aluminium tetrahydride In dibutyl ether at 25℃; for 6h; Inert atmosphere;	70%
Stage #1: chloromethylmethyldichlorosilane With lithium aluminium tetrahydride In dibutyl ether at 0 - 20℃; Stage #2: With hydrogenchloride for 0.5h; cooling;	40%
With lithium aluminium tetrahydride In dibutyl ether
With lithium aluminium tetrahydride

benzyl alcohol (100-51-6) + chloromethylmethyldichlorosilane (1558-33-4) → (chloromethyl)bis(benzyloxy)methylsilane (138380-14-0)

Conditions	Yield
In pentane 1) 0 deg C, 3 h 2) 23 deg C, 7 h;	96%

O,O'-bis-(trimethylsilyl)uracil (10457-14-4) + chloromethylmethyldichlorosilane (1558-33-4) → 1,3-bis[dichloro(methyl)silylmethyloxy]pyrimidine

Conditions	Yield
In chloroform at 20℃; for 48h; Inert atmosphere;	96%

isopropyl alcohol (67-63-0) + chloromethylmethyldichlorosilane (1558-33-4) → (chloromethyl)(diisopropoxy)methylsilane (2212-08-0)

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique;	95%
Stage #1: chloromethylmethyldichlorosilane With pyridine In di-isopropyl ether for 0.25h; Stage #2: isopropyl alcohol In di-isopropyl ether at 0 - 20℃;	80%

1-trimethylsiloxy-2,2,2-trifluoroacetone dimethylhydrazone (91152-82-8) + chloromethylmethyldichlorosilane (1558-33-4) → ((N-dimethylamino)trifluoroacetimidato-N,O)(1-((1,1-dimethyl-2-trifluoroacetyl)hydrazonium)methyl-C,O)-methylchlorosilicon(IV)

Conditions	Yield
In toluene at 20℃; for 48h;	95%

C8H21ClP2Si + LiCH2PMe2 (64065-06-1) + lithium diphenylphosphide (65567-06-8, 4541-02-0) + chloromethylmethyldichlorosilane (1558-33-4) → bis[(dimethylphosphino)methyl][(diphenylphosphino)methyl](methyl)-silane

Conditions	Yield
Stage #1: LiCH2PMe2; chloromethylmethyldichlorosilane In diethyl ether at -80℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: C8H21ClP2Si; lithium diphenylphosphide In tetrahydrofuran; hexane at -50 - -40℃; for 3h; Inert atmosphere; Schlenk technique;	95%

LiCH2PMe2 (64065-06-1) + lithium diphenylphosphide (65567-06-8, 4541-02-0) + chloromethylmethyldichlorosilane (1558-33-4) → bis[(dimethylphosphino)methyl][(diphenylphosphino)methyl](methyl)-silane

Conditions	Yield
Stage #1: LiCH2PMe2; chloromethylmethyldichlorosilane In diethyl ether at -80℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: lithium diphenylphosphide In tetrahydrofuran; diethyl ether; hexane at -50 - -40℃; for 3h; Inert atmosphere; Schlenk technique;	95%

1,1,3,3-Tetramethyldisiloxane (3277-26-7) + chloromethylmethyldichlorosilane (1558-33-4) → C6H19ClO2Si3 (144090-06-2)

Conditions	Yield
With water at 20℃;	94%

2,4,6-tris(trimethylsilyloxy)pyrimidine (31111-39-4) + chloromethylmethyldichlorosilane (1558-33-4) → 6-[(dichloro(methyl)silyl)methyl]-2-chloro-2-methyl-2H-[1,4,2]-oxazasilolo[4,5-c]pyrimidine-5,7(3H,6H)-dione

Conditions	Yield
In acetonitrile for 1h; Inert atmosphere; Heating;	94%

phenylmagnesium bromide + chloromethylmethyldichlorosilane (1558-33-4) → chloromethyl-methyl-diphenyl-silane (18407-40-4)

Conditions	Yield
In diethyl ether Heating;	93%

phenylmagnesium bromide (100-58-3) + chloromethylmethyldichlorosilane (1558-33-4) → chloromethyl-methyl-diphenyl-silane (18407-40-4)

Conditions	Yield
In tetrahydrofuran at 30 - 60℃; for 3h;	92.75%
In tetrahydrofuran for 12h; Reflux;	81%
In diethyl ether for 16.5h; Inert atmosphere; Reflux;	80%
In diethyl ether for 16h; Heating;	71%

2-methoxy-ethanol (109-86-4) + chloromethylmethyldichlorosilane (1558-33-4) → (chloromethyl)bis(2-methoxyethoxy)methylsilane (138380-15-1)

Conditions	Yield
In pentane at 23℃;	92%

caprolactam (105-60-2) + chloromethylmethyldichlorosilane (1558-33-4) → 1-[(Dichloro-methyl-silanyl)-methyl]-azepan-2-one

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In benzene for 1h; Heating;	92%
With thionyl chloride; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane 1.) C6H6, reflux, 1 h, 2.) H2O, 1 h, 3.) reflux, 1 h; Yield given. Multistep reaction;

5-chloro-2-tri-methylsilyloxy-pyridine (126856-30-2) + chloromethylmethyldichlorosilane (1558-33-4) → 1-dichloromethylsilylmethyl-5-chloropyrid-2-one

Conditions	Yield
In hexane for 7h; Alkylation; desilylation, rearrangement;	91%

phenylmagnesium bromide + chloromethylmethyldichlorosilane (1558-33-4) → chloro(chloromethyl)methyl(phenyl)silane (2632-83-9)

Conditions	Yield
In diethyl ether at 0 - 37℃;	90%
In diethyl ether Heating;	67%
In diethyl ether Grignard reaction; Heating;	67%

3-methoxy-2-trimethylsiloxypyridine (252980-61-3) + chloromethylmethyldichlorosilane (1558-33-4) → 1-dichloromethylsilylmethyl-3-methoxypyrid-2-one

Conditions	Yield
In hexane for 7h; Alkylation; desilylation, rearrangement;	90%

6-chloro-2-trimethylsiloxypyridine (252980-63-5) + chloromethylmethyldichlorosilane (1558-33-4) → 1-dichloromethylsilylmethyl-6-chloropyrid-2-one

Conditions	Yield
In hexane for 7h; Alkylation; desilylation, rearrangement;	90%

chloro-trimethyl-silane (75-77-4) + 5,5-dimethylbarbituric acid (24448-94-0) + chloromethylmethyldichlorosilane (1558-33-4) → 1,3-bis[(dichloro(methyl)silyl)methyl]-5,5-dimethylpyrimidine-2,4,6-trione (1240207-51-5)

Conditions	Yield
Stage #1: chloro-trimethyl-silane; 5,5-dimethylbarbituric acid With triethylamine In diethyl ether Inert atmosphere; Reflux; Stage #2: chloromethylmethyldichlorosilane In chloroform for 16h; Inert atmosphere; Reflux;	90%

LiCH2PMe2 (64065-06-1) + chloromethylmethyldichlorosilane (1558-33-4) → C8H21ClP2Si

Conditions	Yield
In diethyl ether at -80℃; for 2h; Inert atmosphere; Schlenk technique;	90%

lithium diisopropylphosphide (21502-53-4) + LiCH2PMe2 (64065-06-1) + chloromethylmethyldichlorosilane (1558-33-4) → [(diisopropylphosphino)methyl]bis[(dimethylphosphino)methyl]-(methyl)silane

Conditions	Yield
Stage #1: LiCH2PMe2; chloromethylmethyldichlorosilane In diethyl ether at -80℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: lithium diisopropylphosphide In diethyl ether; hexane; N,N-dimethyl-formamide at -50 - -40℃; for 3h; Inert atmosphere; Schlenk technique;	90%

ortho-tolylmagnesium bromide (932-31-0) + chloromethylmethyldichlorosilane (1558-33-4) → (chloromethyl)(methyl)di-o-tolylsilane

Conditions	Yield
With silver nitrate In tetrahydrofuran at 20℃; for 2h;	90%

allylmagnesium bromide (2622-05-1) + chloromethylmethyldichlorosilane (1558-33-4) → diallyl(chloromethyl)methylsilane (83622-79-1) + Diallyl-but-3-enyl-methyl-silane

Conditions	Yield
With 3-chloroprop-1-ene In diethyl ether for 3h; Heating;	A 89.4% B 5.3%

chloromethylmethyldichlorosilane (1558-33-4) + phenol (108-95-2) → (chloromethyl)methyldiphenoxysilane

Conditions	Yield
Heating;	89%

isopropyl alcohol (67-63-0) + chloromethylmethyldichlorosilane (1558-33-4) → chloromethyl methyl isopropoxy chlorosilane (198066-58-9)

Conditions	Yield
With triethylamine In diethyl ether	89%
at 20℃; for 4h; Time; Cooling with ice; Inert atmosphere;	60.8%

1,3,4,6,7,8-hexahydro-1-trimethylsilyl-2H-pyrimido<1,2-a>pyrimidin (149758-20-3) + chloromethylmethyldichlorosilane (1558-33-4) → Dichloromethyl-(3,4,7,8-tetrahydro-2H,6H-pyrimido<1,2-a>pyrimidin-1-ylmethyl-C1N9)-silicium

Conditions	Yield
at 25℃;	88.5%

Upstream product

• 7782-50-5 chlorine 
• 75-78-5 dimethylsilicon dichloride 
• 186581-53-3 diazomethane 
• 75-79-6 Methyltrichlorosilane 
• 3704-44-7 octamethyltrisilane 

Downstream Products

• 18407-40-4 chloromethyl-methyl-diphenyl-silane 
• 2212-08-0 (chloromethyl)(diisopropoxy)methylsilane 
• 17878-12-5 dichloro-methyl-(3-methyl-benzyl)-silane 
• 17878-35-2 dichloro-methyl-(4-methyl-benzyl)-silane 
• 17922-28-0 dibenzyl-chloromethyl-methyl-silane 
• 2212-11-5 (chloromethyl)dimethoxymethylsilane 
• 2943-81-9 chloromethylmethyldiethylsilane 
• 2632-83-9 chloro(chloromethyl)methyl(phenyl)silane 
• 94671-34-8 1-chloromethyl-1-methyl-2,3,4,5-tetraphenyl-1-silacyclopentadiene 
• 18165-20-3 methyl(chloromethyl)dihydrosilane 
• 1615216-37-9 N-[chloro(chloromethyl)(methyl)silyl]-N-methylaniline 
• 1512854-02-2 rac-(chloromethyl)methyl(3-methylbut-2-en-1-yl)phenylsilane 
• 1512853-97-2 rac-(chloromethyl)(methyl)(2-methylprop-2-en-1-yl)(phenyl)silane 
• 125828-09-3 rac-allyl(chloromethyl)methylphenylsilane 

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