Isopropyl-beta-D-thiogalactopyranoside supplier

Name
Isopropyl-beta-D-thiogalactopyranoside
EINECS 206-703-0
CAS No. 367-93-1
Article Data15
CAS DataBase
Density 1.37 g/cm³
Solubility soluble in water
Melting Point 105 ºC
Formula C₉H₁₈O₅S
Boiling Point 438.4 ºC at 760 mmHg
Molecular Weight 238.305
Flash Point 219 ºC
Transport Information
Appearance white crystalline powder
Safety 23-24/25-36/37-22-36/37/39-27-26
Risk Codes 19-40-66-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Galactopyranoside,isopropyl 1-thio- (7CI);Galactopyranoside, isopropyl 1-thio-, b-D- (8CI);IPTG;Isopropyl 1-thio-b-D-galactopyranoside;Isopropyl thio-b-D-galactopyranoside;Isopropyl thio-b-D-galactoside;Isopropyl b-thiogalactopyranoside;Isopropyl b-thiogalactoside;
PSA 115.45000
LogP -1.07210

Synthetic route

: 55692-87-0
isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopiranoside

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; pH=10;	98%
With sodium methylate In methanol for 0.5h;	90%
With sodium methylate In methanol at 20℃; for 5h; pH=10;	81%

: 29587-08-4
2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-aethylxanthat

: 75-26-3
isopropyl bromide

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
With methanol; potassium carbonate at 60℃; for 5h; Reagent/catalyst; Temperature;	92%

: isopropylthio-6-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbonate)-β-D-galactopyranoside

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation;	75%

: 10257-28-0
D-Galactose

: 75-33-2
2-propanethiol

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Stage #1: D-Galactose; 2-propanethiol With aluminum (III) chloride; acetic anhydride at 5 - 10℃; Stage #2: With sodium methylate In methanol Reagent/catalyst;	74.3%

: 25878-60-8
D-galactose pentaacetate

: 75-33-2
2-propanethiol

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Stage #1: D-galactose pentaacetate; 2-propanethiol With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2h; Stage #2: With sodium methylate In methanol	45.2%

: 75-33-2
2-propanethiol

: 4163-60-4
β-D-galactose peracetate

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Stage #1: 2-propanethiol; β-D-galactose peracetate With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2h; Stage #2: With sodium methylate In methanol	45.2%

: 75-33-2
2-propanethiol

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
With potassium ethoxide Behandeln des Reaktionsprodukts mit Natriummethylat in Methanol;

: 4163-60-4
β-D-galactose peracetate

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / BF3*Et2O / CH2Cl2 / 1.5 h / 20 °C 2: 81 percent / CH3ONa / methanol / 5 h / 20 °C / pH 10 View Scheme
Multi-step reaction with 4 steps 1: thiourea; boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C 2: sodium metabisulfite / dichloromethane; water / Reflux 3: potassium carbonate / acetone / 20 °C 4: sodium methylate / methanol / 20 °C / pH 10 View Scheme

: 439-03-2, 439-04-3, 439-05-4, 2823-44-1, 2823-46-3, 3934-29-0, 4163-45-5, 20409-31-8, 23235-96-3, 51897-75-7, 51897-76-8, 51897-77-9, 57573-38-3, 62561-28-8, 126641-47-2, 4163-44-4
2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: BF3*OEt2 / CH2Cl2 / 0.17 h / Ambient temperature 2: 72 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

: 3947-62-4, 6207-76-7, 10343-06-3, 19235-21-3, 22554-70-7, 22860-22-6, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 47339-09-3
2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) NaH, Molekularsieb 4 A, 2) 0.1 M BF3*OEt2, Molekularsieb 4 A / 1) CH2Cl2, 30 min, RT, 2) CH2Cl2, 30 min, RT 2: 90 percent / 0.5 M CH3ONa / methanol / 0.5 h View Scheme

: 7296-64-2
β-D-galactopyranoside

: 75-33-2
2-propanethiol

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
With potassium acetate In acetic anhydride at 80℃;	0.5 kg

: 59-23-4
D-Galactose

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride / 0.2 h / 5 - 10 °C 2: sodium methylate / methanol View Scheme
Multi-step reaction with 3 steps 1: sodium acetate / 0.2 h / Reflux 2: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 5 °C 3: sodium methylate / methanol View Scheme

: S-tetraacetyl-β-D-galactosylisothiourea fluorine salt

: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium metabisulfite / dichloromethane; water / Reflux 2: potassium carbonate / acetone / 20 °C 3: sodium methylate / methanol / 20 °C / pH 10 View Scheme

: BEC-cIPTG

A: C15H17NO10

B: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Stage #1: BEC-cIPTG UV-irradiation; Stage #2: With water Enzymatic reaction;

: BEC-cIPTG

A: C11H7NO10(2-)*2Li(1+)

B: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium hydroxide; water / methanol / 1 h / 0 - 20 °C 2.1: UV-irradiation 2.2: Enzymatic reaction View Scheme

: BC-cIPTG

A: C11H7NO10(2-)*2Li(1+)

B: 367-93-1
isopropyl β-D-thiogalactopyranoside

Conditions

Conditions	Yield
Stage #1: BC-cIPTG UV-irradiation; Stage #2: With water Enzymatic reaction;

: 108-24-7
acetic anhydride

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 55692-87-0
isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopiranoside

Conditions

Conditions	Yield
With pyridine	100%
With pyridine at 20℃;	100%

: 1125-88-8
benzaldehyde dimethyl acetal

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: isopropyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h;	96%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 0 - 20℃;	82%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 20℃; pH=2 - 3;	82%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 824-94-2
p-methoxybenzyl chloride

: C41H50O9S

Conditions

Conditions	Yield
Stage #1: isopropyl β-D-thiogalactopyranoside With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 23℃; for 17h; Schlenk technique; Inert atmosphere;	95%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1273157-53-1
isopropyl 1-thio-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranoside

Conditions

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide In acetonitrile at 20℃; for 0.5h; regioselective reaction;	92%
With pyridine at 0 - 20℃; for 14h; Inert atmosphere;	88.1%
With pyridine at 23℃;	84%
With pyridine at 20℃; for 16h;

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: isopropylthio 3-O-(4-nitrobenzenesulfonyl)-β-D-galactopyranoside

Conditions

Conditions	Yield
With 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 20h; regioselective reaction;	88%

: 100-39-0
benzyl bromide

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 440652-81-3
isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	85%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 98-88-4
benzoyl chloride

: isopropyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With pyridine; dmap at 20℃; Concentration;	85%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 98-59-9
p-toluenesulfonyl chloride

: isopropylthio 3-O-(4-toluenesulfonyl)-β-D-galactopyranoside

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 18h; regioselective reaction;	84%

: 39234-86-1
3,5-bis(trifluoromethyl)benzenesulfonyl chloride

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: isopropylthio 3-O-(3,5-bis(trifluoromethyl)benzenesulfonyl)-β-D-galactopyranoside

Conditions

Conditions	Yield
With 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 20h; regioselective reaction;	82%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 106-95-6
allyl bromide

: 847225-60-9
(2R,3S,4S,5R,6S)-4-Allyloxy-2-hydroxymethyl-6-isopropylsulfanyl-tetrahydro-pyran-3,5-diol

Conditions

Conditions	Yield
Stage #1: isopropyl β-D-thiogalactopyranoside In methanol for 2h; Heating; Stage #2: allyl bromide With tetra-(n-butyl)ammonium iodide In toluene at 60℃; for 24h;	79%

: 1125-88-8
benzaldehyde dimethyl acetal

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 936549-98-3
C16H22O5S

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane; water for 2h;	79%

: 712-97-0
6-nitro-1,3-benzodioxole-5-carbaldehyde

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: NP-cIPTG

Conditions

Conditions	Yield
With sulfuric acid In dimethyl sulfoxide at 0 - 20℃;	78%
With sulfuric acid In dimethyl sulfoxide at 0 - 20℃; for 24h;	21%

: 100-39-0
benzyl bromide

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: isopropyl 3-O-benzyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
Stage #1: isopropyl β-D-thiogalactopyranoside With di(n-butyl)tin oxide In methanol; toluene for 4h; Reflux; Stage #2: benzyl bromide With tetrabutylammomium bromide In toluene at 70℃; for 5h; regioselective reaction;	78%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 98-88-4
benzoyl chloride

: 615570-19-9
3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside

Conditions

Conditions	Yield
With pyridine at -10℃;	70%
With pyridine at 0℃; Concentration;	0.98 g

: 54769-36-7
N-benzoyloxybenzotriazole

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 615570-19-9
3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 10h; regioselective reaction;	69%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 7087-68-5
N-ethyl-N,N-diisopropylamine

A: C9H18O8S2*C8H19N

B: C9H18O11S3*2C8H19N

Conditions

Conditions	Yield
With sulfur trioxide trimethylamine complex; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In acetonitrile at 60℃; for 3h; Inert atmosphere;	A 69% B 24%

...Expand

: tert-butyl (1-phenylprop-2-yn-1-yl) carbonate

: 367-93-1
isopropyl β-D-thiogalactopyranoside

A: (2S,3R,4S,5R,6R)-2-(isopropylthio)-6-((((R)-1-phenylprop-2-yn-1-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

B: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(isopropylthio)-4-(((S)-1-phenylprop-2-yn-1-yl)oxy)tetrahydro-2H-pyran-3,5-diol

Conditions

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; R,R-C5H3N(C3H3NOPh)2; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran Molecular sieve; Inert atmosphere; Sealed tube;	A n/a B 66%

...Expand

: tert-butyl (1-phenylprop-2-yn-1-yl) carbonate

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: (2S,3R,4S,5R,6R)-2-(isopropylthio)-6-((((R)-1-phenylprop-2-yn-1-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
With 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran at 20℃; for 6h; Molecular sieve; Inert atmosphere; Sealed tube;	65%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 312-94-7
2-trifluoromethylbenzoyl chloride

: 3,5-dihydroxy-2-(hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-4-yl 2-(trifluoromethyl)benzoate

Conditions

Conditions	Yield
With 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 48h; regioselective reaction;	62%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 7087-68-5
N-ethyl-N,N-diisopropylamine

A: C9H18O8S2*C8H19N

B: C9H18O8S2*C8H19N

C: C9H18O11S3*2C8H19N

Conditions

Conditions	Yield
With sulfur trioxide trimethylamine complex; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In acetonitrile at 60℃; for 3h; Inert atmosphere;	A 58% B 6% C 18%

...Expand

: 4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzylaldehyde diethyl acetal

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: BEC-cIPTG

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 20h;	45%

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 77-76-9
2,2-dimethoxy-propane

: isopropyl 3,4-O-(1-methylethylidene)-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In acetone at 20℃;	40%
With camphor-10-sulfonic acid In acetonitrile at 20℃; for 1h; Inert atmosphere;

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 98-88-4
benzoyl chloride

: isopropyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With pyridine at -10℃; for 3h;	40%

: 1337923-38-2
4,6-dimethoxy-1,3,5-triazin-2-yl α-N-acetylglucosaminide

: 367-93-1
isopropyl β-D-thiogalactopyranoside

: 1352031-32-3
i-propyl 1-thio-4-O-(2-acetamido-2-deoxy-α-glucopyranosyl)-β-galactopyranoside

Conditions

Conditions	Yield
With Bacteroides thetaiotaomicron VPI5482 α-N-acetylglucosaminidase B1 at 37℃; for 1h; pH=6.5; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;	29%

Isopropyl-beta-D-thiogalactopyranoside Specification

The Isopropyl-β-D-thiogalactopyranoside , with appearance of white crystalline powder, belongs to the classes of (1) Substrates ; (2) 13C & 2H Sugars ; (3) Biochemistry ; (4) Galactose ; (5) Glycosides ; (6) Sugars ; (7) Thioglycosides ; (8) Enzyme substrates ; (9) Carbohydrates & Derivatives ; (10) Carbohydrates . Besides its cas registry number of 367-93-1, it also has other registry number which is 30323-26-3. Its BRN registry number is 4631. Its systematic name is called propan-2-yl 1-thio-beta-D-galactopyranoside . And its IUPAC name is called (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol . This chemical is stable but incompatible with strong oxidizing agents.

Physical properties about this chemical are: (1) # of Rule of 5 Violations: 0 ; (2) ACD/BCF (pH 5.5): 1 ; (3) ACD/BCF (pH 7.4): 1 ; (4) ACD/KOC (pH 5.5): 6.7 ; (5) ACD/KOC (pH 7.4): 6.7 ; (6) #H bond acceptors: 5 ; (7) #H bond donors: 4 ; (8) #Freely Rotating Bonds: 7 ; (9) Polar Surface Area: 71.45 Å² ; (10) Index of Refraction: 1.577 ; (11) Molar Refractivity: 57.43 cm³ ; (12) Molar Volume: 173 cm³ ; (13) Surface Tension: 63.9 dyne/cm ; (14) Density: 1.37 g/cm³ ; (15) Flash Point: 219 °C ; (16) Enthalpy of Vaporization: 80.25 kJ/mol ; (17) Boiling Point: 438.4 °C at 760 mmHg ; (18) Vapour Pressure: 1.58E-09 mmHg at 25°C ; (19) Melting point: 105 oC ; (20) Alpha: -31 °(c=1, water).

When you are using this chemical, please be cautious about it as the following:
The Isopropyl-β-D-thiogalactopyranoside should be stored at the temperature of -20°C. This chemical is irritating to eyes, respiratory system and skin. It may form explosive peroxides. Repeated exposure may cause skin dryness or cracking. It also has limited evidence of a carcinogenic effect. If you will use this material, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. Do not breathe gas, fumes, vapor, spray, and dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After use it, take off immediately all contaminated clothing.

You can still convert the following datas into molecular structure:
(1) SMILES:S(C(C)C)[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)CO;
(2) InChI:InChI=1/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9+/m1/s1;
(3) InChIKey:BPHPUYQFMNQIOC-NXRLNHOXBD

Product Name

Isopropyl-beta-D-thiogalactopyranoside

Synthetic route

Isopropyl-beta-D-thiogalactopyranoside Specification

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