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Name	(S)-tert-Butanesulfinamide	EINECS	1312995-182-4
CAS No.	146374-27-8	Density	1.124 g/cm³
PSA	62.30000	LogP	1.97330
Solubility	N/A	Melting Point	97-101 °C
Formula	C₄H₁₁NOS	Boiling Point	220 °C at 760 mmHg
Molecular Weight	121.203	Flash Point	86.8 °C
Transport Information	N/A	Appearance	N/A
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	tert-Butylsulfinamide;2-Methyl-2-propanesulfinamide;1,1-Dimethylethyl sulfinamide;	Article Data	14

(S)-tert-Butanesulfinamide Synthetic route

: 31562-43-3
tert-butylsulfinyl chloride

: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With ammonium hydroxide aminolysis;	98%
With ammonia In 1,4-dioxane	71%
With ammonium hydroxide In tetrahydrofuran; ethyl acetate at 0 - 20℃; for 0.5h; Inert atmosphere;	71%

: (S,E)-2-methyl-N-(3-phenylpropylidene)propane-2-sulfinamide

A: 2-methyl-propane-2-sulfinic acid (2-benzyl-5-phenyl-pent-2-enylidene)-amide

B: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; phosphorus pentoxide In diethyl ether at 25℃; for 0.5h; aza-Mannich condensation;	A 50% B n/a

: 75-66-1
2-methylpropan-2-thiol

: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With methanol; [2,2]bipyridinyl; O-pivaloylhydroxylamine trifluoromethanesulfonate salt; iron(II) chloride In dichloromethane at 25℃; for 16h; Sealed tube;	50%

: 842121-02-2
C12H17NOS

A: 98-85-1, 13323-81-4
1-Phenylethanol

B: 3886-69-9
(R)-1-phenyl-ethyl-amine

C: 146374-27-8
S-tert-butylsulfinimide

D: 98-86-2
acetophenone

Conditions

Conditions	Yield
Stage #1: C12H17NOS With [RhCl2(p-cymene)]2; (1R,2S)-2-Amino-1,2-diphenylethanol; potassium hydroxide In isopropyl alcohol at 25℃; for 24h; Stage #2: With hydrogenchloride In methanol optical yield given as %ee; stereoselective reaction;	A n/a B 41% C n/a D n/a

: acetic acid 4-(2-methyl-propane-2-sulfinylimino)-butyl ester

A: acetic acid 7-acetoxy-3-[(2-methyl-propane-2-sulfinylimino)-methyl]-hept-3-enyl ester

B: acetic acid 7-acetoxy-3-[(2-methyl-propane-2-sulfinylimino)-methyl]-hept-3-enyl ester

C: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; phosphorus pentoxide In diethyl ether at 25℃; for 0.5h; Aza-Mannich condensation; Title compound not separated from byproducts;

: 2-methyl-N-octylidenepropane-2-sulfinamide

A: 2-methyl-propane-2-sulfinic acid (2-hexyl-dec-2-enylidene)-amide

B: 2-methyl-propane-2-sulfinic acid (2-hexyl-dec-2-enylidene)-amide

C: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; phosphorus pentoxide In diethyl ether at 25℃; for 0.5h; aza-Mannich condensation; Title compound not separated from byproducts;

: 2-methyl-propane-2-sulfinic acid (4-benzyloxy-butylidene)-amide

A: 2-methyl-propane-2-sulfinic acid [6-benzyloxy-2-(2-benzyloxy-ethyl)-hex-2-enylidene]-amide

B: 2-methyl-propane-2-sulfinic acid [6-benzyloxy-2-(2-benzyloxy-ethyl)-hex-2-enylidene]-amide

C: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; phosphorus pentoxide In diethyl ether at 25℃; for 0.5h; Aza-Mannich condensation; Title compound not separated from byproducts;

: (E)-(±)-N-butylidene-tert-butanesulfinamide

A: 2-methyl-propane-2-sulfinic acid (2-ethyl-hex-2-enylidene)-amide

B: 2-methyl-propane-2-sulfinic acid (2-ethyl-hex-2-enylidene)-amide

C: 146374-27-8
S-tert-butylsulfinimide

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; phosphorus pentoxide In diethyl ether at 25℃; for 0.5h; aza-Mannich condensation; Title compound not separated from byproducts;

: 842121-02-2
C12H17NOS

A: 98-85-1, 13323-81-4
1-Phenylethanol

B: 2627-86-3
(S)-1-phenyl-ethylamine

C: 3886-69-9
(R)-1-phenyl-ethyl-amine

D: 146374-27-8
S-tert-butylsulfinimide

E: 98-86-2
acetophenone

Conditions

Conditions	Yield
Stage #1: C12H17NOS With [RhCl2(p-cymene)]2; ethanolamine; potassium hydroxide In isopropyl alcohol at 25℃; for 15h; Stage #2: With hydrogenchloride In methanol optical yield given as %ee; stereoselective reaction;

...Expand

: 842121-02-2
C12H17NOS

A: 146374-27-8
S-tert-butylsulfinimide

B: 98-86-2
acetophenone

Conditions

Conditions	Yield
With [RhCl2(p-cymene)]2; ethanolamine; potassium hydroxide In isopropyl alcohol at 25℃; for 6h;

(S)-tert-Butanesulfinamide Chemical Properties

Systematic Name: 2-Methylpropane-2-sulfinamide
Synonyms of (S)-tert-Butanesulfinamide (CAS NO.146374-27-8): 2-Methylpropane-2-sulfinamide ; S-(-)-2-Methyl-2-propanesulfinamide
CAS NO: 146374-27-8
Molecular Formula: C₄H₁₁NOS
Molecular Weight: 121.2012
Molecular Structure:
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 39.52 Å²
Index of Refraction: 1.523
Molar Refractivity: 32.94 cm³
Molar Volume: 107.7 cm³
Surface Tension: 49.8 dyne/cm
Density: 1.124 g/cm³
Flash Point: 86.8 °C
Enthalpy of Vaporization: 45.64 kJ/mol
Boiling Point: 220 °C at 760 mmHg
Vapour Pressure: 0.116 mmHg at 25°C
Melting Point: 97-101 °C(lit.)
Appearance: white to light yellow crystal powder
SMILES: O=S(N)C(C)(C)C Copy
InChI: InChI=1/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m0/s1 Copy
InChIKey: CESUXLKAADQNTB-ZETCQYMHBT
Std. InChI: InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m0/s1 Copy Std. InChIKey: CESUXLKAADQNTB-ZETCQYMHSA-N
Product Categories of (S)-tert-Butanesulfinamide (CAS NO.146374-27-8): Sulphur Derivatives;API intermediates;CHIRAL CHEMICALS;Organic Building Blocks;Sulfonamides/Sulfinamides;Sulfur Compounds

(S)-tert-Butanesulfinamide Safety Profile

WGK Germany: 3

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