2-[1-(Mercaptomethyl)cyclopropyl]acetic acid supplier

Name
2-[1-(Mercaptomethyl)cyclopropyl]acetic acid
EINECS 420-240-3
CAS No. 162515-68-6
Article Data10
CAS DataBase
Density 1.229 g/cm³
Solubility
Melting Point 42-45 °C
Formula C₆H₁₀O₂S
Boiling Point 290.1 °C at 760 mmHg
Molecular Weight 146.21
Flash Point 129.249 °C
Transport Information
Appearance off-white solid
Safety 22-26-36/37/39-45-61
Risk Codes 21/22-34-43-51/53-20/21/22
Molecular Structure
Hazard Symbols Xi
Synonyms 1-(Mercaptomethyl)cyclopropaneaceticacid;[1-(Mercaptomethyl)cyclopropyl]acetic acid;2-[1-(mercaptomethyl)cyclopropyl acetic acid;
PSA 76.10000
LogP 1.17110

Synthetic route

: 152922-73-1
2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
With water; potassium hydroxide at 0 - 20℃; for 3h;	93%
Stage #1: 2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester With methanol; sodium hydroxide; water at 70 - 80℃; for 2h; Stage #2: With hydrogenchloride; water at 40℃; pH=3.0 - ~ 4.0;

: 1314940-03-8
C6H9ClO2

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Stage #1: C6H9ClO2 With thiourea In water for 3h; Reflux; Stage #2: With sodium hydroxide In water for 2h; Reflux;	91.6%

: 1-(isothiuroniummethyl)cyclopropaneacetonitrile hydrobromide

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
With sodium hydroxide Reflux;	91.4%
Stage #1: 1-(isothiuroniummethyl)cyclopropaneacetonitrile hydrobromide With sodium hydroxide; water for 14h; Heating / reflux; Stage #2: With formic acid In water at -5 - 5℃; pH=3.5 - 4.0;	76.7%

: 1015076-74-0
C15H19NO2S

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Stage #1: C15H19NO2S With potassium hydroxide; water at 120℃; for 14h; Stage #2: With hydrogenchloride; water In diethyl ether Product distribution / selectivity;	80%
With water In tetrahydrofuran at 80℃; Product distribution / selectivity;	50%

: 152922-72-0
1-(Acetylthiomethyl)cyclopropaneacetonitrile

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide In toluene	11.99 g (82%)

: 855473-50-6
1-bromomethylcyclopropyl acetic acid methyl ester

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: copper(l) iodide / N,N-dimethyl-formamide / 50 - 60 °C 2: potassium carbonate; methanol / 6 h / Reflux 3: phosphorus tribromide / dichloromethane / 0 - 10 °C 4: acetonitrile / Reflux 5: sodium hydroxide / Reflux View Scheme

: 1-cyanomethylcyclopropyl acetic acid methyl ester

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate; methanol / 6 h / Reflux 2: phosphorus tribromide / dichloromethane / 0 - 10 °C 3: acetonitrile / Reflux 4: sodium hydroxide / Reflux View Scheme

: 152922-71-9
1-(hydroxymethyl)cyclopropaneacetonitrile

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus tribromide / dichloromethane / 0 - 10 °C 2: acetonitrile / Reflux 3: sodium hydroxide / Reflux View Scheme

: 39590-81-3
[1-(hydroxymethyl)cyclopropyl]methanol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: sulphate-doped anatase / tetrahydrofuran / 45 - 55 °C 2.1: isobutyric acid sodium salt / tetrahydrofuran / 10 - 20 °C / Inert atmosphere 2.2: 0.5 h 3.1: phosphorus tribromide / dichloromethane / 0 - 20 °C 4.1: copper(l) iodide / N,N-dimethyl-formamide / 50 - 60 °C 5.1: potassium carbonate; methanol / 6 h / Reflux 6.1: phosphorus tribromide / dichloromethane / 0 - 10 °C 7.1: acetonitrile / Reflux 8.1: sodium hydroxide / Reflux View Scheme

Yield

Multi-step reaction with 8 steps
1.1: sulphate-doped anatase / tetrahydrofuran / 45 - 55 °C
2.1: isobutyric acid sodium salt / tetrahydrofuran / 10 - 20 °C / Inert atmosphere
2.2: 0.5 h
3.1: phosphorus tribromide / dichloromethane / 0 - 20 °C
4.1: copper(l) iodide / N,N-dimethyl-formamide / 50 - 60 °C
5.1: potassium carbonate; methanol / 6 h / Reflux
6.1: phosphorus tribromide / dichloromethane / 0 - 10 °C
7.1: acetonitrile / Reflux
8.1: sodium hydroxide / Reflux
View Scheme

: 6-bromomethyl-5,7-dioxaspiro[2.5]octane

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: isobutyric acid sodium salt / tetrahydrofuran / 10 - 20 °C / Inert atmosphere 1.2: 0.5 h 2.1: phosphorus tribromide / dichloromethane / 0 - 20 °C 3.1: copper(l) iodide / N,N-dimethyl-formamide / 50 - 60 °C 4.1: potassium carbonate; methanol / 6 h / Reflux 5.1: phosphorus tribromide / dichloromethane / 0 - 10 °C 6.1: acetonitrile / Reflux 7.1: sodium hydroxide / Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1.1: isobutyric acid sodium salt / tetrahydrofuran / 10 - 20 °C / Inert atmosphere
1.2: 0.5 h
2.1: phosphorus tribromide / dichloromethane / 0 - 20 °C
3.1: copper(l) iodide / N,N-dimethyl-formamide / 50 - 60 °C
4.1: potassium carbonate; methanol / 6 h / Reflux
5.1: phosphorus tribromide / dichloromethane / 0 - 10 °C
6.1: acetonitrile / Reflux
7.1: sodium hydroxide / Reflux
View Scheme

: 142148-13-8
1-hydroxymethylcyclopropylacetic acid methyl ester

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: phosphorus tribromide / dichloromethane / 0 - 20 °C 2: copper(l) iodide / N,N-dimethyl-formamide / 50 - 60 °C 3: potassium carbonate; methanol / 6 h / Reflux 4: phosphorus tribromide / dichloromethane / 0 - 10 °C 5: acetonitrile / Reflux 6: sodium hydroxide / Reflux View Scheme

: C14H18O3

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium borohydride / tetrahydrofuran / 2 h / 20 °C 2.1: pyridine; triphenylphosphine; tetrachloromethane / 18 h / 75 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 5.1: thiourea / water / 3 h / Reflux 5.2: 2 h / Reflux View Scheme

: C14H20O3

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridine; triphenylphosphine; tetrachloromethane / 18 h / 75 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 4.1: thiourea / water / 3 h / Reflux 4.2: 2 h / Reflux View Scheme

: C14H19ClO2

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 3.1: thiourea / water / 3 h / Reflux 3.2: 2 h / Reflux View Scheme

: C6H11ClO

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 2.1: thiourea / water / 3 h / Reflux 2.2: 2 h / Reflux View Scheme

: C13H15ClO2

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / 5 h / 20 °C 2.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 3.1: thiourea / water / 3 h / Reflux 3.2: 2 h / Reflux View Scheme

: C9H19ClOSi

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / methanol / 2 h / 20 °C 2.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 3.1: thiourea / water / 3 h / Reflux 3.2: 2 h / Reflux View Scheme

: C13H17ClO

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C / 20686.5 Torr / Autoclave 2.1: trifluoroacetic acid; sodium nitrite / 5 h / 20 °C / Cooling with ice 3.1: thiourea / water / 3 h / Reflux 3.2: 2 h / Reflux View Scheme

: C12H11NOS

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 90℃; for 8h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	7.84 g

: 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 142522-28-9
cyclopentyl 3-{2-methoxy-4-[(o-tolylsulfonyl)carbamoyl]benzyl}-1-methyl-1H-indol-5-ylcarbamate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; Reagent/catalyst; Solvent;	98.8%

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: C6H9(2)HO2

Conditions

Conditions	Yield
With di-tert-butyl peroxide; water-d2; ethydiphenylphosphine oxide In dichloromethane at 20℃; for 10h; Irradiation; Green chemistry;	97%

: 1402070-72-7
C28H20ClNO3

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: {1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}-3-[2-(methoxycarbonyl)phenyl]-3-oxopropyl}sulfanyl)methyl]cyclopropyl}acetic acid

Conditions

Conditions	Yield
With C38H54FeN2O2(1+)*Cl(1-) In 1,2-dichloro-ethane at -5℃; for 39h;	96%

: C28H20ClNO3

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: {1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}-3-[2-(methoxycarbonyl)phenyl]-3-oxopropyl}sulfanyl)methyl]cyclopropyl}acetic acid

Conditions

Conditions	Yield
With C38H54ClFeN2O2 In 1,2-dichloro-ethane at -5℃; for 39h; enantioselective reaction;	96%

: 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 158966-92-8
montelukast

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With 3-ethyl-1-methyl-1H-imidazol-3-ium bromide In dimethyl sulfoxide at 10℃; for 0.0833333h; Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 10℃; for 0.166667h; Stage #3: 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol In dimethyl sulfoxide at 15 - 17℃; for 1h; Product distribution / selectivity;	93%

Yield

Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With 3-ethyl-1-methyl-1H-imidazol-3-ium bromide In dimethyl sulfoxide at 10℃; for 0.0833333h;
Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 10℃; for 0.166667h;
Stage #3: 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol In dimethyl sulfoxide at 15 - 17℃; for 1h; Product distribution / selectivity;

93%

: C70H109FN12O15

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: C76H119FN12O17S

Conditions

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 20℃; for 4h;	93%

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 21962-25-4
3-methylenepentanoic acid

Conditions

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In N,N-dimethyl-formamide	92%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	92%

: 1021952-71-5
(S)-2-(2-(3-(3-bromophenyl)-3-chloropropyl)phenyl)propan-2-ol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 1015076-82-0
(R)-2-(1-((1-(3-bromophenyl)-3-(2-(methoxycarbonyl)phenyl)propylthio)methyl)cyclopropyl)acetic acid

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (S)-2-(2-(3-(3-bromophenyl)-3-chloropropyl)phenyl)propan-2-ol In N,N-dimethyl-formamide at 20℃; for 48.5h; Stage #3: With tartaric acid In water; ethyl acetate; N,N-dimethyl-formamide pH=7; Product distribution / selectivity;	87.5%

: C13H6F4INO

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 2-(1-(((2-fluoro-5-((3,4,5-trifluorophenyl)carbamoyl)phenyl)thio)methyl)cyclopropyl)acetic acid

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 102℃; for 13h; Inert atmosphere; Sealed tube;	86%

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 807638-71-7
2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 577953-88-9
1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium t-butanolate In toluene at -3 - 10℃; for 1h; Inert atmosphere; Stage #2: 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol In tetrahydrofuran; toluene at -5 - 15℃; Stage #3: N-cyclohexyl-cyclohexanamine In tetrahydrofuran; ethyl acetate; toluene at 10 - 15℃; for 1h;	85.45%
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With n-butyllithium In tetrahydrofuran at -12.5℃; for 0.666667h; Stage #2: 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol In tetrahydrofuran at -2℃; for 3.5h; Stage #3: N-cyclohexyl-cyclohexanamine In isopropyl alcohol; acetonitrile at 29℃; for 15.5h; Product distribution / selectivity;

Yield

Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium t-butanolate In toluene at -3 - 10℃; for 1h; Inert atmosphere;
Stage #2: 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol In tetrahydrofuran; toluene at -5 - 15℃;
Stage #3: N-cyclohexyl-cyclohexanamine In tetrahydrofuran; ethyl acetate; toluene at 10 - 15℃; for 1h;

85.45%

Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With n-butyllithium In tetrahydrofuran at -12.5℃; for 0.666667h;
Stage #2: 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol In tetrahydrofuran at -2℃; for 3.5h;
Stage #3: N-cyclohexyl-cyclohexanamine In isopropyl alcohol; acetonitrile at 29℃; for 15.5h; Product distribution / selectivity;

...Expand

: C68H103F2N11O15

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: C74H113F2N11O17S

Conditions

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 20℃; for 4h;	81%

: C67H101F2N11O14

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: C73H111F2N11O16S

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; acetonitrile at 20℃; for 4h;	77%

: 287930-77-2
(S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 158966-92-8
montelukast

Conditions

Conditions	Yield
Stage #1: (S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -15 - -10℃; Inert atmosphere; Stage #2: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium methylate In tetrahydrofuran; methanol; 4-methyl-2-pentanone at -15 - 20℃;	68.55%
Stage #1: (S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -15 - -10℃; Inert atmosphere; Stage #2: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium methylate In tetrahydrofuran; methanol; 4-methyl-2-pentanone at -15 - 20℃;

: 1021952-71-5
(S)-2-(2-(3-(3-bromophenyl)-3-chloropropyl)phenyl)propan-2-ol

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 1015076-80-8
(1-{1-(R)-(3-bromophenyl)-3-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (S)-2-(2-(3-(3-bromophenyl)-3-chloropropyl)phenyl)propan-2-ol In N,N-dimethyl-formamide at 20℃; for 48.5h; Stage #3: With tartaric acid In water; ethyl acetate; N,N-dimethyl-formamide pH=7; Product distribution / selectivity;	67.8%

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: Methanesulfonic acid (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[3-iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-propyl ester

: (1-{(R)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[3-iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With n-butyllithium In tetrahydrofuran; hexane at -22 - 0℃; for 0.25h; Metallation; Stage #2: Methanesulfonic acid (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[3-iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-propyl ester In tetrahydrofuran; hexane at -22 - 0℃; for 2h; Substitution;	66%

: 1015076-81-9
(S)-methyl 2-(3-(3-bromophenyl)-3-methylsulfonyloxypropyl)benzoate

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 1015076-82-0
(R)-2-(1-((1-(3-bromophenyl)-3-(2-(methoxycarbonyl)phenyl)propylthio)methyl)cyclopropyl)acetic acid

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium methylate In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: (S)-methyl 2-(3-(3-bromophenyl)-3-methylsulfonyloxypropyl)benzoate In tetrahydrofuran at -15 - 10℃; for 6.5h; Inert atmosphere;	61.1%

: 880769-25-5
methyl 2-[(3S)-[3-[(2E)-(7-chloro quinolin-2-yl)ethenyl]phenyl]-3-chloropropyl]benzoate

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 2-(3(R)-(1-carboxymethyl-cyclopropylmethylsulfanyl)-3-{3-[2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester dicyclohexyl-amine

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium hydride In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Stage #2: methyl 2-[(3S)-[3-[(2E)-(7-chloro quinolin-2-yl)ethenyl]phenyl]-3-chloropropyl]benzoate In N,N-dimethyl-formamide at -5 - 0℃; for 25h; Stage #3: N-cyclohexyl-cyclohexanamine In ethyl acetate at 20 - 25℃; for 37.5h;	52.8%

...Expand

: methyl 2-[(3S)-[3-[(2E)-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-chloropropyl]benzoate

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 2-(3(R)-(1-carboxymethyl-cyclopropylmethylsulfanyl)-3-{3-[2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester dicyclohexyl-amine

Conditions

Conditions	Yield
Stage #1: methyl 2-[(3S)-[3-[(2E)-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-chloropropyl]benzoate; 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium hydride In N,N-dimethyl-formamide at -5 - 0℃; Inert atmosphere; Stage #2: N-cyclohexyl-cyclohexanamine In ethyl acetate at 20 - 45℃;	52.8%

...Expand

: 880769-28-8
2-(2-(3(S)-chloro-3-(3-(2-(7-chloro-2-quinolinyl)-(E)ethenyl)phenyl)propyl)phenyl)-2-propanol

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 577953-88-9
1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt

Conditions

Conditions	Yield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium hydride In N,N-dimethyl-formamide at -5℃; for 1h; Stage #2: 2-(2-(3(S)-chloro-3-(3-(2-(7-chloro-2-quinolinyl)-(E)ethenyl)phenyl)propyl)phenyl)-2-propanol In N,N-dimethyl-formamide at -5 - 0℃; for 13h; Stage #3: N-cyclohexyl-cyclohexanamine In ethyl acetate at 20 - 22℃; for 1.75h;	40.5%
Stage #1: 2-(2-(3(S)-chloro-3-(3-(2-(7-chloro-2-quinolinyl)-(E)ethenyl)phenyl)propyl)phenyl)-2-propanol; 1-(sulfanylmethyl)cyclopropaneacetic acid With sodium hydride In N,N-dimethyl-formamide at -5 - 0℃; Inert atmosphere; Stage #2: N-cyclohexyl-cyclohexanamine In ethyl acetate at 20 - 45℃; Product distribution / selectivity;	40.5%

...Expand

: 538-51-2
benzylidene phenylamine

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 6,7-diphenyl-5-thia-7-azaspiro[2.6]nonan-8-one

Conditions

Conditions	Yield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In 2-methyltetrahydrofuran at 20℃; Inert atmosphere; Cooling;	24%

: C73H112FN13O17

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: C79H122FN13O19S

Conditions

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 20℃; for 15h;	17%

: 1197374-12-1
[1-[(R)-1-(3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]-phenyl)-3-(2-isopropenylphenyl)propylsulfanylmethyl]cyclopropyl]acetic acid dicyclohexylamine salt

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 1351973-24-4
C41H44ClNO4S2

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 25 - 45℃; for 26h;	12.4%

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 186353-01-5
Methanesulfonic acid (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-2-methoxymethoxy-1-methyl-ethyl)-phenyl]-propyl ester

: 184764-27-0
(1-{(R)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-2-methoxymethoxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid

Conditions

Conditions	Yield
With n-butyllithium 1.) THF, 0 deg C, 30 min, 2.) THF, -15 deg C, overnight; Yield given. Multistep reaction;

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 184764-00-9
Butane-1-sulfonic acid (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-((S)-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-ethyl ester

: {1-[(R)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-((S)-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid

Conditions

Conditions	Yield
With n-butyllithium 1.) THF, 0 deg C, 15 min, 2.) THF, 4 deg C, 16 h; Yield given. Multistep reaction;

: 162515-68-6
1-(sulfanylmethyl)cyclopropaneacetic acid

: 184764-64-5
Butane-1-sulfonic acid (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-((R)-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-ethyl ester

: {1-[(R)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-((R)-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid

Conditions

Conditions	Yield
With n-butyllithium 1.) THF, 0 deg C, 15 min, 2.) THF, 4 deg C, 16 h; Yield given. Multistep reaction;

2-[1-(Mercaptomethyl)cyclopropyl]acetic acid Specification

The systematic name of Cyclopropaneaceticacid, 1-(mercaptomethyl)- is [1-(sulfanylmethyl)cyclopropyl]acetic acid. With the CAS registry number 162515-68-6, it is also named as [1-(Mercaptomethyl)cyclopropyl]acetic acid; 2-(1-(mercaptomethyl)cyclopropyl)acetic acid. The product's categories are carboxylic acids, organic acids, (intermediate of montelukast), metal isotopes, sulfur & selenium compounds and ring systems. It is off-white solid which is irritative. And it is used as an intermediate of Montelukast.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 10; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.538; (12)Molar Refractivity: 37.222 cm3; (13)Molar Volume: 118.981 cm3; (14)Polarizability: 14.756 10-24cm3; (15)Surface Tension: 56.787 dyne/cm; (16)Enthalpy of Vaporization: 58.251 kJ/mol; (17)Vapour Pressure: 0.001 mmHg at 25°C.

People can use the following data to convert to the molecule structure. SMILES: O=C(O)CC1(CS)CC1; InChI: InChI=1/C6H10O2S/c7-5(8)3-6(4-9)1-2-6/h9H,1-4H2,(H,7,8); InChIKey: VFAXPOVKNPTBTM-UHFFFAOYAL. Cyclopropaneaceticacid, 1-(mercaptomethyl)- has many suppliers, such as Nantong Chem-land Co., Ltd. and Shanghai Qiao Chemical Science Co., Ltd..

Product Name

2-[1-(Mercaptomethyl)cyclopropyl]acetic acid

Synthetic route

2-[1-(Mercaptomethyl)cyclopropyl]acetic acid Specification

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