1871-57-4

Basic information

• Product Name: 2-(CHLOROMETHYL)ALLYLTRICHLOROSILANE
• Synonyms: METHALLYL DICHLORIDE;TRICHLORO[2-(CHLOROMETHYL)ALLYL]SILANE;1,3-Dichloro-2-methylenepropane;2-Chloromethyl-3-chloropropene;2-Methylene-1,3-dichloropropane;2-Methylenepropane-1,3-dichloride;3-chloro-2-(chloromethyl)-propen;3-Chloro-2-(chloromethyl)propene
• CAS NO: 1871-57-4
• Molecular Formula: C₄H₆Cl₂
• Molecular Weight: 125
• EINECS: 217-489-3
• Mol File: 1871-57-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 14 °C
• Boiling Point: 31 °C0.1 mm Hg(lit.)
• Flash Point: 98 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Density: 3.12 (vs air)
• Refractive Index: n20/D 1.484(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• Explosive Limit: 8.1%
• BRN: 1560178
• CAS DataBase Reference: 2-(CHLOROMETHYL)ALLYLTRICHLOROSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)ALLYLTRICHLOROSILANE(1871-57-4)
• EPA Substance Registry System: 2-(CHLOROMETHYL)ALLYLTRICHLOROSILANE(1871-57-4)

Safety Data

• Hazard Codes: T,Xi,F,N
• Statements: 14-34-36/37/38-25-10-36-50-23/25
• Safety Statements: 26-27-36/37/39-45-36-16-61-37/39
• RIDADR: UN 2987 8/PG 2
• WGK Germany: 3
• RTECS: UC7400000
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 1871-57-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

3-Chloro-2-chloromethyl-1-propene can be used in the synthesis of 2,11-bis(methylidene)spermine, an inhibitor of spermine oxidase and branched side chains of conjugated polymers. It can also be used in the intermolecular [2+2] photocycloaddition during the total synthesis of (?)-grandisol.

InChI:InChI=1S/C4H6Cl2/c1-4(2-5)3-6/h1-3H2

Synthetic route

3-chloro-2,2-bis(chloromethyl)propionic acid-1 (17831-70-8) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
at 205 - 215℃; Pyrolysis;	99%
With quinoline
at 200 - 220℃; in presence of quinoline the pyrolysis begins at 100 deg C.; Yield given;
at 210℃; Yield given;

1,3-dichloro-2-chloromethylpropane (66703-69-3) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene 70 deg C, 24 h; 190 deg C;	80%

5,5-dichloromethyl-2-thia-1,3-dioxane 2-oxide (2210-05-1) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
at 500℃; under 1 Torr; Inert atmosphere; Pyrolysis;	65%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With pyridine; thionyl chloride In dichloromethane for 3h; Reflux;	32%
With pyridine; thionyl chloride; chloroform

2,2-bis(chloromethyl)aziridine → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 5 - 50℃; for 5h; Large scale;	29.1%
With hydrogenchloride; sodium nitrite at 20 - 50℃; Ring cleavage; elimination;	85.0 g

quinoline (91-22-5) + 3-chloro-2,2-bis(chloromethyl)propionic acid-1 (17831-70-8) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

1,3-dichloro-2-methyl-propan-2-ol (597-32-0) → 1,3-dichloro-2-methylpropene (3375-22-2) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With sulfuric acid at 100℃; 1,3-dichloro-2-methyl-propene of uncertain stereochemical membership;

1,3-dichloro-2-methyl-propan-2-ol (597-32-0) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With sulfuric acid at 100℃;

1,2,3-trichloro-2-methylpropane (1871-58-5) → 1,3-dichloro-2-methylpropene (3375-22-2) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
at 450 - 460℃;

1-chloro-2,2-di(chloromethyl)-2-nitroethane (79437-10-8) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,3-dichloro-2-chloromethyl-1-propene (13245-65-3)

Conditions	Yield
With sodium amalgam

isobutene (115-11-7) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
beim Chlorieren;
With chlorine

3-Chloro-2-methylpropene (563-47-3) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With tetrachloromethane at 20 - 30℃; beim Chlorieren;
With sodium carbonate beim Chlorieren;

3-Chloro-2-methylpropene (563-47-3) → 1,3-dichloro-2-methylpropene (3375-22-2) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With chlorine

(2-Chloro-1-chloromethyl-1-methyl-ethylselanyl)-benzene (81694-51-1) → 1,3-dichloro-2-methylpropene (3375-22-2) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In pyridine; dichloromethane 1.) -70 degC 2 h, 2.) R.T. overnight; Yield given;

isobutene (115-11-7) → 2-methylprop-1-enyl chloride (513-37-1) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,2-dichloro-2-methylpropane (594-37-6) + (E)-1,3-Dichloro-2-methyl-1-propene (35329-41-0) + (Z)-1,3-Dichloro-2-methyl-1-propene (35329-40-9) + 3-Chloro-2-methylpropene (563-47-3)

Conditions	Yield
With chlorine at 40 - 70℃; Product distribution; various conc.; further products;

3-Chloro-2-methylpropene (563-47-3) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + (E)-1,3-Dichloro-2-methyl-1-propene (35329-41-0) + (Z)-1,3-Dichloro-2-methyl-1-propene (35329-40-9)

Conditions	Yield
With chlorine monofluoride In chloroform in the dark; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3-Chloro-2-methylpropene (563-47-3) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,2,3-trichloro-2-methylpropane (1871-58-5) + (E)-1,3-Dichloro-2-methyl-1-propene (35329-41-0) + (Z)-1,3-Dichloro-2-methyl-1-propene (35329-40-9)

Conditions	Yield
With oxygen; phosphorus trichloride at 30℃;

tetrachloromethane (56-23-5) + chlorine (7782-50-5) + 3-Chloro-2-methylpropene (563-47-3) → 1,3-dichloro-2-methylpropene (3375-22-2) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,2,3-trichloro-2-methylpropane (1871-58-5)

Conditions	Yield
at 20 - 30℃;

1,1-bis-chloromethyl-ethanediyl sulfite → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4)

Conditions	Yield
With quartz at 500℃;

3-Chloro-2-methylpropene (563-47-3) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1ξ,3-dichloro-2-methyl-propene and 1,2,3-trichloro-2-methyl-propane

Conditions	Yield
With chlorine

2-methylprop-1-enyl chloride (513-37-1) + chlorine (7782-50-5) → 1,3-dichloro-2-methylpropene (3375-22-2) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,1,2-trichloro-2-methylpropane (29559-52-2) + 1,1,2,3-Tetrachlor-2-methylpropan (18963-01-4)

Conditions	Yield
unter Lichtausschluss;Produkt 5:3,3-Dichlor-2-methyl-propen;

1-chloro-2,2-di(chloromethyl)-2-nitroethane (79437-10-8) + sodium amalgam → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,3-dichloro-2-chloromethyl-1-propene (13245-65-3)

2-methylprop-1-enyl chloride (513-37-1) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + below/under light-exclusion

Conditions	Yield
With chlorine

5,5-dichloromethyl-2-thia-1,3-dioxane 2-oxide (2210-05-1) → formaldehyd (50-00-0) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + sulfur dioxide

Conditions	Yield
at 500℃; beim Leiten ueber Quarz;

1,2,3-trichloro-2-methylpropane (1871-58-5) → 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + trans-1.3-dichloro-2-methyl-propene-(1) + cis-1.3-dichloro-2-methyl-propene-(1)

Conditions	Yield
at 450 - 460℃;

sodium benzoate (532-32-1) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) → 1,3-dibenzoyl-(2-methylidene)-1,3-propanediol (39185-03-0)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 12h;	99%
In N,N-dimethyl-formamide for 4h; Heating;	73%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → C16H28O6 (1206187-88-3)

Conditions	Yield
Stage #1: (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol With 15-crown-5; sodium hydride In tetrahydrofuran; mineral oil at 40℃; Inert atmosphere; Stage #2: 2-chloromethyl-3-chloroprop-1-ene With 18-crown-6 ether; potassium iodide In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;	99%
Stage #1: (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol With 15-crown-5; sodium hydride In tetrahydrofuran at 50℃; for 1h; Stage #2: 2-chloromethyl-3-chloroprop-1-ene With 18-crown-6 ether; potassium iodide In tetrahydrofuran at 80℃; for 12h;	56%
Stage #1: (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol With 15-crown-5; sodium hydride In tetrahydrofuran; mineral oil at 40℃; Inert atmosphere; Stage #2: 2-chloromethyl-3-chloroprop-1-ene With 18-crown-6 ether; potassium iodide In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + methylphenylphosphine (6372-48-1) → (2-methylenepropane-1,3-diyl)bis(methylphenylphosphine sulfide)

Conditions	Yield
Stage #1: 2-chloromethyl-3-chloroprop-1-ene; methylphenylphosphine With [((R)-MeO-BiPHEP)(1,2-bis(dimethylphosphino)ethane)Ru(H)][BPh4]; sodium tert-pentoxide In tetrahydrofuran at 23℃; for 1.5h; Inert atmosphere; Stage #2: With borane-THF In tetrahydrofuran at 23℃; for 0.5h; Inert atmosphere; enantioselective reaction;	99%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1-Hexadecanol (36653-82-4) → C36H72O2

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran Reflux;	99%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + propargyl alcohol (107-19-7) → 5-methylenenona-2,7-diyne-1,9-diol

Conditions	Yield
With copper(l) iodide; potassium carbonate; sodium iodide In acetone for 17h; Reflux;	99%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + benzyl alcohol (100-51-6) → 2-methylenepropane-1,3-bisbenzyl ether (27441-79-8)

Conditions	Yield
Stage #1: 2-chloromethyl-3-chloroprop-1-ene; benzyl alcohol With sodium hydride In tetrahydrofuran for 0.5h; Cooling with ice; Stage #2: With 15-crown-5 In tetrahydrofuran for 14h; Reflux;	98%
Stage #1: benzyl alcohol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-chloromethyl-3-chloroprop-1-ene In N,N-dimethyl-formamide at 20℃; Further stages.;	97%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;	88%
With sodium hydride 1.) THF, 2.) a) room temperature, overnight, b) reflux, 5 h; Yield given. Multistep reaction;

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,5-bis(carboxyethyl)glycoluril (161146-03-8) → 6-Methylene-1,4-dioxo-hexahydro-2,3,4a,7a-tetraaza-cyclopenta[cd]indene-2a,7b-dicarboxylic acid diethyl ester

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide	98%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + N,N-methylenediacetamide (3852-14-0) → 5-exomethylene-1,3-diacetyl-1,3-diazacyclohexane (261508-08-1)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 72h; Alkylation; Thermolysis;	98%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1-Decanol (112-30-1) → 1-(2-((decyloxy)methyl)allyloxy)decane (1259928-12-5)

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran for 20.25h; Reflux;	98%
With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere;	74%
With 15-crown-5; sodium hydride In tetrahydrofuran Reflux;

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + methyl 4,6-O-benzylidene-α-D-galactopyranoside (64552-06-3) → methyl 4,6-O-(S)-benzylidene-2,3-O-(2-methylidene-1,3-propylene)-α-D-galactopyranoside (1263386-75-9)

Conditions	Yield
With 18-crown-6 ether; potassium hydroxide In tetrahydrofuran at 5 - 20℃;	98%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + C28H58O3 → C60H120O6

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran Reflux;	98%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + n-eicosanol (629-96-9) → C44H88O2

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran Reflux;	98%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + para-tert-butylphenol (98-54-4) → C24H32O2 (206653-69-2)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	97%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + (Nk-)4[G-3]-ol (245071-36-7) → (Nk-)4[G-4]-methylallyl chloride (268567-74-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran	97%

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) → methyl 14-cyclohexyl-7-methylene-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (886042-33-7)

Conditions	Yield
Stage #1: 3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-chloromethyl-3-chloroprop-1-ene In N,N-dimethyl-formamide at 20℃;	97%
Stage #1: 3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 2-chloromethyl-3-chloroprop-1-ene In N,N-dimethyl-formamide at 20℃; for 1h;	70%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1,5-anhydro-4,6-O-(R)-benzylidene-D-glucitol (65391-44-8) → 1,5-anhydro-4,6-O-(R)-benzylidene-2,3-O-(2-methylidene-1,3-propylene)-D-glucitol (1263386-76-0)

Conditions	Yield
With 18-crown-6 ether; potassium hydroxide In tetrahydrofuran at 5 - 20℃;	97%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside (71117-36-7) → methyl 4,6-O-(S)-benzylidene-2,3-O-(2-methylidene-1,3-propylene)-β-D-galactopyranoside (1263386-73-7)

Conditions	Yield
With 18-crown-6 ether; potassium hydroxide In tetrahydrofuran at 5 - 20℃;	97%

1-octadecanol (112-92-5) + 2-chloromethyl-3-chloroprop-1-ene (1871-57-4) → 1-(2-Octadecyloxymethyl-allyloxy)-octadecane

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran Reflux;	97%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + sodium thiomethoxide (5188-07-8) → 3-methylsulfanyl-2-methylsulfanylmethylprop-1-ene (96694-05-2)

Conditions	Yield
With cetyltributylphosphonium bromide In water for 6h; Ambient temperature;	96%

Upstream product

• 91-22-5 quinoline 
• 17831-70-8 3-chloro-2,2-bis(chloromethyl)propionic acid-1 
• 597-32-0 1,3-dichloro-2-methyl-propan-2-ol 
• 1871-58-5 1,2,3-trichloro-2-methylpropane 
• 3513-81-3 2-(Hydroxymethyl)allyl alcohol 
• 79437-10-8 1-chloro-2,2-di(chloromethyl)-2-nitroethane 
• 115-11-7 isobutene 
• 563-47-3 3-Chloro-2-methylpropene 
• 66703-69-3 1,3-dichloro-2-chloromethylpropane 
• 81694-51-1 (2-Chloro-1-chloromethyl-1-methyl-ethylselanyl)-benzene 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 513-37-1 2-methylprop-1-enyl chloride 
• 2210-05-1 5,5-dichloromethyl-2-thia-1,3-dioxane 2-oxide 

Downstream Products

• 6142-73-0 methylene cyclopropane 
• 3513-81-3 2-(Hydroxymethyl)allyl alcohol 
• 78948-04-6 3-(Trichlorosilyl)-2-<(trichlorosilyl)methyl>-1-propene 
• 854813-60-8 2-phenoxymethyl-prop-2-ene-1-sulfonic acid 
• 16601-92-6 α,α-Bis-<2.5-dichlor-phenoxy>-isobuten, (1.3-Bis-<2.5-dichlor-phenoxy>-2-methylen-propan) 
• 1522-96-9 1,3-bis(4-chlorophenoxy)-2-methylenepropane 
• 14470-71-4 3,6-Dimethylen-cycloheptanon 
• 4982-20-1 1,4-dimethylidenecyclohexane 
• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 16615-75-1 1,1-bis<(2-methylphenoxy)methyl>ethene 
• 2726-33-2 1,3-bis(2,4-dichlorophenoxy)-2-methylenepropane 
• 3716-14-1 3-phenoxy-2-(phenoxymethyl)propene 
• 96694-03-0 (E)-3-Hydroxy-5-methyl-1-phenyl-1,5-hexadiene 
• 115413-92-8 5-methyl-1-phenyl-5-hexen-3-ol 

Relevant articles and documents

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Improved Preparations of 3-Chloro-2-(chloromethyl)-1-propene and 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane: Intermediates in the Synthesis of Propellane

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3-chloro-2-chloromethyl propylene, preparation method and application thereof

The invention relates to 3-chloro-2-chloromethyl propene, a preparation method and application thereof. The preparation method comprises the step that 1, 3-dichloroacetone is subjected to a carbonization reaction under the action of a catalyst to obtain 3-chloro-2-chloromethyl propene. According to the invention, 1, 3-dichloroacetone serves as a raw material and is subjected to a carbonization reaction under the action of a catalyst to obtain a product 3-chloro-2-chloromethyl propene in one step, wherein the raw materials are easy to obtain, the steps are simple, a large amount of wastewater is not generated in the preparation process, the method is environment-friendly, the yield of the final product is high and can reach 51-65%, and the 3-chloro-2-chloromethyl propylene can be applied to the synthesis of bridged ring compounds.

COMPOUNDS

The present invention features compounds of formula (I): and salts thereof, pharmaceutical compositions comprising said compounds, and uses of such compounds in treating or preventing viral infections, such as HCV infections, and diseases associated with such infections.