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3221-15-6

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3221-15-6 Usage

Chemical Properties

clear colorless to light yellow liquid

Synthesis Reference(s)

Synthesis, p. 821, 1996 DOI: 10.1055/s-1996-4307

Check Digit Verification of cas no

The CAS Registry Mumber 3221-15-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,2 and 1 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 3221-15:
(6*3)+(5*2)+(4*2)+(3*1)+(2*1)+(1*5)=46
46 % 10 = 6
So 3221-15-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H5ClS/c4-1-3-2-5-3/h3H,1-2H2/t3-/m0/s1

3221-15-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(chloromethyl)thiirane

1.2 Other means of identification

Product number -
Other names Chloropropylene sulfide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3221-15-6 SDS

3221-15-6Synthetic route

epichlorohydrin
106-89-8

epichlorohydrin

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

Conditions
ConditionsYield
With ammonium thiocyanate; bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.416667h; Heating;99%
With tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate; ammonium thiocyanate In acetonitrile for 0.416667h; Heating;99%
With bismuth(III) chloride; ammonium thiocyanate In acetonitrile for 0.333333h; Heating;98%
N-(tert-butyl)-5-(chloromethyl)-1,3-oxathiolan-2-imine

N-(tert-butyl)-5-(chloromethyl)-1,3-oxathiolan-2-imine

A

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

B

Tert-butyl isocyanate
1609-86-5

Tert-butyl isocyanate

Conditions
ConditionsYield
In quinoline at 230℃;A 12%
B 81%
potassium thioacyanate
333-20-0

potassium thioacyanate

epichlorohydrin
106-89-8

epichlorohydrin

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

Conditions
ConditionsYield
With methanol
With methanol
thiourea
17356-08-0

thiourea

epichlorohydrin
106-89-8

epichlorohydrin

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

Conditions
ConditionsYield
With methanol
N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

epichlorohydrin
106-89-8

epichlorohydrin

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

Conditions
ConditionsYield
With benzene
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

epichlorohydrin
106-89-8

epichlorohydrin

A

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

B

3-chloro-2-hydroxypropyl thiocyanate
147194-24-9

3-chloro-2-hydroxypropyl thiocyanate

Conditions
ConditionsYield
With 2,6-bis[2-(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene In dichloromethane; acetonitrile at 70℃; for 1.25h;A n/a
B 78 % Chromat.
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

chloromethylthiirane-S-monooxide
29027-25-6

chloromethylthiirane-S-monooxide

Conditions
ConditionsYield
With water; fluorine; acetonitrile; propiononitrile In methanol at -78℃;95%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

3-methyl-8-bromoxanthine
93703-24-3

3-methyl-8-bromoxanthine

8-bromo-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
1005482-51-8

8-bromo-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 0 - 20℃;94.3%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

chloromethylthiirane-S,S-dioxide

chloromethylthiirane-S,S-dioxide

Conditions
ConditionsYield
With water; fluorine; acetonitrile In dichloromethane at -15 - 0℃;90%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

acetyl chloride
75-36-5

acetyl chloride

thioacetic acid S-(2-chloro-1-chloromethyl-ethyl) ester
16621-53-7

thioacetic acid S-(2-chloro-1-chloromethyl-ethyl) ester

Conditions
ConditionsYield
With CoCl2 In dichloromethane at 20℃; for 4h;81%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

2-chloro-1H-benzoimidazole
4857-06-1

2-chloro-1H-benzoimidazole

2-<1-(2-chlorobenzimidazolyl)>methyl-2,3-dihydrothiazolo<3,2-a>benzimidazole

2-<1-(2-chlorobenzimidazolyl)>methyl-2,3-dihydrothiazolo<3,2-a>benzimidazole

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Heating;80%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

acetic acid
64-19-7

acetic acid

A

2,5-bis(chloromethyl)-1,4-dithiane
61704-46-9

2,5-bis(chloromethyl)-1,4-dithiane

B

1-acetoxy-3-chloropropane-2-thiol
136197-48-3

1-acetoxy-3-chloropropane-2-thiol

Conditions
ConditionsYield
With lithium perchlorate In ethyl acetate Ambient temperature;A 80%
B 12%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

A

2,5-bis(chloromethyl)-1,4-dithiane
61704-46-9

2,5-bis(chloromethyl)-1,4-dithiane

B

1-acetoxy-3-chloropropane-2-thiol
136197-48-3

1-acetoxy-3-chloropropane-2-thiol

Conditions
ConditionsYield
With lithium perchlorate; acetic acid In ethyl acetate Ambient temperature;A 80%
B 12%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

phenylacetylene
536-74-3

phenylacetylene

1-chloro-3-(5-phenyl-1H-1,2,3-triazol-1-yl)propane-2-thiol

1-chloro-3-(5-phenyl-1H-1,2,3-triazol-1-yl)propane-2-thiol

Conditions
ConditionsYield
With sodium azide In water at 60℃; for 2.5h; Green chemistry; regioselective reaction;80%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

N-(4-chlorophenyl)cyanamide
13463-94-0

N-(4-chlorophenyl)cyanamide

C10H9ClN2S

C10H9ClN2S

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 48h;76%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

3-fluorophenylcyanamide
14213-18-4

3-fluorophenylcyanamide

N-(3-fluorophenyl)-N-(thietan-3-yl)cyanamide

N-(3-fluorophenyl)-N-(thietan-3-yl)cyanamide

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 48h;74%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

2-chloro-1H-benzoimidazole
4857-06-1

2-chloro-1H-benzoimidazole

1-(thietan-3-yl)-2-chlorobenzimidazole
136265-52-6

1-(thietan-3-yl)-2-chlorobenzimidazole

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 3h;73%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

3-Nitro-benzoic acid thietan-3-yl ester

3-Nitro-benzoic acid thietan-3-yl ester

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 60 - 70℃;73%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

1-phenylcyanamide
622-34-4

1-phenylcyanamide

N-phenyl-N-(thietan-3-yl)cyanamide

N-phenyl-N-(thietan-3-yl)cyanamide

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 48h;72%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

3,5-dibromotriazole
7411-23-6

3,5-dibromotriazole

2-bromo-5-(3,5-dibromo-1H-1,2,4-triazol-1-yl-methyl)-5,6-dihydro-1,3-thiazolo[3,2-b][1,2,4]triazole

2-bromo-5-(3,5-dibromo-1H-1,2,4-triazol-1-yl-methyl)-5,6-dihydro-1,3-thiazolo[3,2-b][1,2,4]triazole

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Heating;71%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

2-Fluoro-benzoic acid thietan-3-yl ester

2-Fluoro-benzoic acid thietan-3-yl ester

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 60 - 70℃;70%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

o-acetylamino-benzoic acid
89-52-1

o-acetylamino-benzoic acid

2-Acetylamino-benzoic acid thietan-3-yl ester

2-Acetylamino-benzoic acid thietan-3-yl ester

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 60 - 70℃;69%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

4-hydroxybenzaldehyde sodium salt
22666-84-8

4-hydroxybenzaldehyde sodium salt

4-(thietan-3-yloxy)benzaldehyde

4-(thietan-3-yloxy)benzaldehyde

Conditions
ConditionsYield
In methanol; water at 45 - 55℃; for 2h;69%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

4-Amino-2,6-dihydroxypyrimidine
873-83-6

4-Amino-2,6-dihydroxypyrimidine

6-(thietan-3-ylamino)pyrimidine-2,4(1H,3H)-dione

6-(thietan-3-ylamino)pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With potassium hydroxide In water at 50 - 55℃; for 2h;69%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

N-(4-bromophenyl)cyanamide
60592-84-9

N-(4-bromophenyl)cyanamide

C10H9BrN2S

C10H9BrN2S

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 48h;69%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

methanol
67-56-1

methanol

1-Chloro-2-(1-chloromethyl-2-methoxy-ethyldisulfanyl)-3-methoxy-propane
130258-47-8

1-Chloro-2-(1-chloromethyl-2-methoxy-ethyldisulfanyl)-3-methoxy-propane

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate for 0.66h; Heating;68%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone for 3.5h; Heating;45%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

sodium methylparaben
5026-62-0

sodium methylparaben

methyl 4-(thietane-3-yloxy)benzoate

methyl 4-(thietane-3-yloxy)benzoate

Conditions
ConditionsYield
In methanol; water at 45 - 55℃; for 2h;68%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

sodium n-hexyl xanthogenate

sodium n-hexyl xanthogenate

Dithiocarbonic acid O-hexyl ester S-thiiranylmethyl ester

Dithiocarbonic acid O-hexyl ester S-thiiranylmethyl ester

Conditions
ConditionsYield
In benzene at 70 - 80℃; for 3h;67%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

azelaic acid
123-99-9

azelaic acid

A

Nonanedioic acid mono-thietan-3-yl ester
122976-45-8

Nonanedioic acid mono-thietan-3-yl ester

B

Nonanedioic acid dithietan-3-yl ester
122976-44-7

Nonanedioic acid dithietan-3-yl ester

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water 1.) 1 h, 70 deg C, 2.) 8 h, 70 deg C;A 6%
B 65%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water 1.) 1 h, 70 deg C, 2.) 8 h, 70 deg C;A 6%
B 65%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

ethanol
64-17-5

ethanol

1-Chloro-2-(1-chloromethyl-2-ethoxy-ethyldisulfanyl)-3-ethoxy-propane
130258-48-9

1-Chloro-2-(1-chloromethyl-2-ethoxy-ethyldisulfanyl)-3-ethoxy-propane

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate for 0.66h; Heating;65%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone for 5h; Heating;60%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

sodium isopropylxanthate
140-93-2

sodium isopropylxanthate

S-(1,2-epithiopropyl) isopropylxanthate

S-(1,2-epithiopropyl) isopropylxanthate

Conditions
ConditionsYield
In benzene at 70 - 80℃; for 3h;65%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

(2-chlorophenyl)cyanamide
45765-25-1

(2-chlorophenyl)cyanamide

N-(2-chlorophenyl)-N-(thietan-3-yl)cyanamide

N-(2-chlorophenyl)-N-(thietan-3-yl)cyanamide

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 48h;63%
2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

N-(4-methoxyphenyl)benzenesulphonamide
7471-26-3

N-(4-methoxyphenyl)benzenesulphonamide

N-(4-methoxyphenyl)-N-(thietan-3-yl)benzenesulfonamide

N-(4-methoxyphenyl)-N-(thietan-3-yl)benzenesulfonamide

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 10h;62%
(E)-3-(2-furanyl)-1-(2'-hydroxyphenyl)-2-propen-1-one
2875-23-2, 127089-57-0

(E)-3-(2-furanyl)-1-(2'-hydroxyphenyl)-2-propen-1-one

2-(chloromethyl)thiirane
3221-15-6

2-(chloromethyl)thiirane

(E)-3-(furan-2-yl)-1-(2-(thiiran-2-ylmethoxy)phenyl)prop-2-en-1-one

(E)-3-(furan-2-yl)-1-(2-(thiiran-2-ylmethoxy)phenyl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 70 - 80℃; for 20h;61.8%

3221-15-6Relevant articles and documents

Preparation, characterization and application of MgFe2O4/Cu nanocomposite as a new magnetic catalyst for one-pot regioselective synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles

Eisavi, Ronak,Naseri, Kazhal

, p. 13061 - 13076 (2021/04/22)

Magnesium ferrite magnetic nanoparticles were synthesized by a solid-state reaction of magnesium nitrate, hydrated iron(iii) nitrate, NaOH and NaCl salts and then calcined at high temperatures. In order to prevent oxidation and aggregation of magnesium ferrite particles, and also for preparing a new catalyst of supported copper on the magnetic surface, the MgFe2O4was covered by copper nanoparticles in alkaline medium. Magnetic nanoparticles of MgFe2O4/Cu were successfully obtained. The structure of the synthesized magnetic nanoparticles was identified using XRD, TEM, EDS, FT-IR, FESEM and VSM techniques. The prepared catalyst was used in the three component one-pot regioselective synthesis of 1,2,3-triazoles in water. The various thiiranes bearing alkyl, allyl and aryl groups with terminal alkynes, and sodium azide in the presence of the MgFe2O4/Cu nanocatalyst were converted to the corresponding β-thiolo/benzyl-1,2,3-triazoles as new triazole derivatives. The effects of different factors such as time, temperature, solvent, and catalyst amount were investigated, and performing the reaction using 0.02 g of catalyst in water at 60 °C was chosen as the optimum conditions. The recovered catalyst was used several times without any significant change in catalytic activity or magnetic property.

Green synthesis of thiiranes from epoxides catalyzed by magnetically separable CuFe2O4/Mg(OH)2 nanocomposite in water under benign conditions

Hassanzadeh, Shadi,Eisavi, Ronak,Abbasian, Mojtaba

, p. 240 - 255 (2019/01/30)

The magnetically separable CuFe2O4/Mg(OH)2 nanocomposite was prepared and characterized by FT-IR, XRD, SEM, EDS, and VSM techniques. The synthesized nanoparticles were used as a new and efficient heterogeneous catalyst for the conversion of various epoxides to the corresponding thiiranes with thiourea in water solvent at room temperature. The reactions were completed within 1–3.7 h to give thiiranes in 70–99% yields. The applied CuFe2O4/Mg(OH)2 nanocomposite was separated easily using an external magnet and reused for several times without any considerable loss of activity.

A green protocol for rapid and efficient conversion of epoxides to thiiranes using alumina immobilized thiourea at solvent-free conditions

Eisavi, Ronak,Zeynizadeh, Behzad

, p. 65 - 69 (2016/01/25)

Solvent-free conversion of various epoxides to the corresponding thiiranes was carried out successfully with alumina-immobilized thiourea at room temperature. The reactions were completed within 2-9 min to give thiiranes with 83-98% yields. The utilized alumina can be reused for several times without losing its activity.

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